KR20140063428A - Amine compound and organic light emitting device using the same - Google Patents

Abstract

Provided in the present invention relates to a novel compound significantly improving the life, efficiency, electrochemical stability, and thermal stability of an organic light emitting device, and an organic light emitting device having the compound contained in an organic compound layer. The novel compound according to the present invention is represented by the following chemical formula 1, which can be used as an organic compound layer material, especially a hole injection material and/or a hole transport material, and can have low drive voltage and improve the luminous efficiency and/or life characteristics when being used for an organic light emitting device.

Description

[0001] The present invention relates to an amine compound and an organic light-

The present invention relates to an amine compound and an organic light emitting device including the same.

The present application claims the benefit of Korean Patent Application No. 10-2012-0129756 filed on November 15, 2012 with the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference.

The organic light emission phenomenon is one example in which current is converted into visible light by an internal process of a specific organic molecule. The principle of organic luminescence phenomenon is as follows.

When an organic layer is positioned between the anode and the cathode, when a voltage is applied between the two electrodes, electrons and holes are injected into the organic layer from the cathode and the anode, respectively. Electrons and holes injected into the organic material layer recombine to form an exciton, and the exciton falls back to the ground state to emit light. An organic light emitting device using such a principle may be generally composed of an organic material layer including a cathode, an anode, and an organic material layer disposed therebetween, for example, a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer.

As a material used in an organic light emitting device, a pure organic material or a complex in which an organic material and a metal form a complex is mostly used. Depending on the application, a hole injecting material, a hole transporting material, a light emitting material, an electron transporting material, . As the hole injecting material and the hole transporting material, an organic material having a p-type property, that is, an organic material that is easily oxidized and electrochemically stable at the time of oxidation, is mainly used. On the other hand, as an electron injecting material or an electron transporting material, an organic material having an n-type property, that is, an organic material that is easily reduced and electrochemically stable when being reduced is mainly used. As the light emitting layer material, a material having both a p-type property and an n-type property, that is, a material having both a stable form in oxidation and in a reduced state is preferable, and a material having a high luminous efficiency for converting an exciton into light desirable.

In addition to the above, it is preferable that the material used in the organic light emitting device further has the following properties.

First, the material used in the organic light emitting device is preferably excellent in thermal stability. This is because joule heating occurs due to the movement of charges in the organic light emitting device. NPB, which is mainly used as a hole transporting layer material, has a glass transition temperature of 100 ° C or less, which makes it difficult to use in an organic light emitting device requiring a high current.

Secondly, in order to obtain a highly efficient organic light emitting device capable of driving at a low voltage, holes or electrons injected into the organic light emitting element should be smoothly transferred to the light emitting layer, and injected holes and electrons should not escape from the light emitting layer. For this purpose, the material used in the organic light emitting device should have an appropriate band gap and a HOMO or LUMO energy level. In the case of PEDOT: PSS used as a hole transport material in the organic light emitting device manufactured by the solution coating method, since the LUMO energy level is lower than the LUMO energy level of the organic material used as the light emitting layer material, There is a difficulty.

In addition, materials used in organic light emitting devices should have excellent chemical stability, charge mobility, and interface characteristics with electrodes or adjacent layers. That is, the material used in the organic light emitting device should have little deformation of the material due to moisture or oxygen. In addition, by having appropriate hole or electron mobility, it is necessary to maximize the formation of excitons by balancing the density of holes and electrons in the light emitting layer of the organic light emitting device. For the stability of the device, the interface between the electrode and the electrode including the metal or metal oxide should be improved.

Accordingly, there is a need in the art to develop organic materials having the above-mentioned requirements.

Korean Patent Publication No. 10-2006-0050915

Accordingly, the present inventors intend to provide a novel amine compound and an organic light emitting device containing the same.

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

[Chemical Formula 1]

In Formula 1,

Ar ₁ To Ar < ₃ > are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted aryl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted carbazole group; Or a substituted or unsubstituted heterocyclic group containing at least one of N, O and S atoms,

At least one of Ar ₁ to Ar ₃ in Formula 1 is substituted with the following Formula 2,

(2)

L is a direct bond; A substituted or unsubstituted arylene group; A substituted or unsubstituted alkenylene group; A substituted or unsubstituted carbazolylene group; A substituted or unsubstituted heterocyclic group containing at least one of N, O and S atoms; Or a substituted or unsubstituted fluorenylene group,

Y is a substituted or unsubstituted nitrogen-containing heterocyclic group.

In addition, in the organic light-emitting device according to the present invention, at least one layer of the organic material layer includes at least one layer selected from the group consisting of the compounds represented by Chemical Formula 1 And a compound represented by formula (I): < EMI ID = 1.0 >

The compounds of the present invention can be used as an organic material layer material, particularly a hole injecting material and / or a hole transporting material in an organic light emitting device, and can improve a low driving voltage, a light efficiency and / or a lifetime Do.

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 shows an example of an organic light emitting element comprising a substrate 1, an anode 2, a hole injecting layer 5, a hole transporting layer 6, a light emitting layer 7, an electron transporting layer 8 and a cathode 4 It is.

In the present specification, Y may be a pyridine group of nitrogen.

In the present specification, the formula (2) may be represented by the following formula (2-1).

 [Formula 2-1]

In Formula 2-1,

L is the same as defined in Chemical Formula 2,

n is an integer of 0 to 4,

Wherein R < _{a >} is a substituted or unsubstituted aryl group.

In one embodiment of the present invention, L in Formula 2-1 may be bonded to the N and para positions of the pyridine group.

In one embodiment of the present invention, L in Formula 2-1 may be bonded to the N of the pyridine group at the ortho position.

The compound represented by the formula (1) in the present specification can be represented by the following formula (3-1) or (3-2).

 [Formula 3-1]

 [Formula 3-2]

In the above Formulas (3-1) and (3-2)

Ar ₂ , Ar ₃ and L are the same as defined in formulas (1) and (2)

R ₁ and R _{2, which} may be the same or different, are each independently a substituted or unsubstituted aryl group.

In one embodiment of the present invention, Ar ₁ to Ar ₃ are the same or different from each other and each independently represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, An unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted perylenyl group, a substituted or unsubstituted tetracenyl group , A substituted or unsubstituted fluorenyl group, a substituted or unsubstituted acenaphthacenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluoranthene, a substituted or unsubstituted phenanthroline group, A substituted or unsubstituted thiophene group, a substituted or unsubstituted furan group, a substituted or unsubstituted pyrrole group, a substituted or unsubstituted imidazole group, a substituted or unsubstituted thiazole group, a substituted or unsubstituted furan group, A substituted or unsubstituted thiazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted bipyridyl group, a substituted or unsubstituted thiazine group, a substituted or unsubstituted thiazole group, A substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinoline group, a substituted or unsubstituted indole group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted pyrazinyl group, A substituted or unsubstituted benzothiazole group, a substituted or unsubstituted benzothiophene group, a substituted or unsubstituted benzothiazole group, a substituted or unsubstituted benzothiazole group, a substituted or unsubstituted benzothiophene group, a substituted or unsubstituted benzothiophene group, A dibenzothiophene group, a substituted or unsubstituted benzofuranyl group, and a substituted or unsubstituted dibenzofuranyl group.

In one embodiment of the present specification, Ar ₁ and Ar ₂ are the same or different from each other and each independently represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, An unsubstituted terphenyl group, or a substituted or unsubstituted fluorenyl group.

In one embodiment of the present specification, R ₁ and R ₂ are the same or different and each independently represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, An unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted perylenyl group, a substituted or unsubstituted tetracenyl group , A substituted or unsubstituted fluorenyl group, a substituted or unsubstituted acenaphenyl group, a substituted or unsubstituted triphenylene group, and a substituted or unsubstituted fluoranthene group.

In one embodiment of the present invention, R 1 and R 2 are the same or different and are each independently a substituted or unsubstituted phenyl group or a substituted or unsubstituted biphenyl group.

In one embodiment of the present specification, L is a substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylene group; Or a substituted or unsubstituted fluorenylene group.

Illustrative examples of such substituents are set forth below, but are not limited thereto.

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 20. Specific examples include, but are not limited to, methyl, ethyl, propyl, isopropyl, butyl, t-butyl, pentyl, hexyl and heptyl.

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. Specific examples thereof include, but are not limited to, an alkenyl group substituted with an aryl group such as a stilbenyl group or a styrenyl group.

In the present specification, the alkoxy group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30.

The length of the alkyl, alkenyl, and alkoxy groups contained in the compound does not affect the conjugation length of the compound but affects the application of the compound to the organic light emitting device, for example, vacuum deposition or solution coating. The number of carbon atoms is not particularly limited.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and particularly preferably a cyclopentyl group and a cyclohexyl group.

In the present specification, the aryl group may be monocyclic or polycyclic, and the number of carbon atoms is not particularly limited, but is preferably 6 to 60. [ Specific examples of the aryl group include monocyclic aromatic and naphthyl groups such as phenyl group, biphenyl group, triphenyl group, terphenyl group and stilbene group, anthracenyl group, phenanthrenyl group, pyrenyl group, perylenyl group, tetracenyl group, A cyclic aromatic group such as a fluorenyl group, an acenaphthacenyl group, a triphenylene group, and a fluoranthene group, but is not limited thereto.

In the present specification, the heterocyclic group is a hetero ring group containing O, N or S as a heteroatom, 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 thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, a bipyridyl group, a triazine group, , A quinolinyl group, an isoquinoline group, an indole group, a carbazole group, a benzoxazole group, a benzimidazole group, a benzothiazole group, a benzocarbazole group, a benzothiophene group, a dibenzothiophene group, a benzofuranyl group, (phenanthroline), dibenzofuranyl group, and the like, but are not limited thereto.

In the present specification, the heteroaromatic ring group containing N may be at least one selected from the group consisting of pyrrole, imidazole, thiazole, oxazole, oxadiazole, triazole, pyridyl, bipyridyl, triazinyl, acridyl, Anthraquinone group, anthraquinone group, anthraquinonyl group, an isoquinoline group, an indole group, a carbazole group, a benzoxazole group, a benzimidazole group, a benzothiazole group, a benzocarbazole group and a phenanthroline group.

In the present specification, the heterocyclic group may be selected from the above-mentioned examples of the heterocyclic group.

In the present specification, examples of the halogen group include fluorine, chlorine, bromine or iodine.

,

등이 있다. In the present specification, a fluorenyl group is a structure in which two ring organic compounds are connected via one atom,

,

.

,

등이 있다. In the present specification, a fluorenyl group includes a structure of an open fluorenyl group, wherein an open fluorenyl group is a structure in which one ring compound is disconnected in a structure in which two ring compounds are connected through one atom, For example,

,

.

In the present specification, the aryl group in the aryloxy group, the arylthioxy group, the arylsulfoxy group and the aralkylamine group is the same as the aforementioned aryl group.

In the present specification, the alkyl group in the alkylthio group, alkylsulfoxy group, alkylamine group, and aralkylamine group is the same as the alkyl group described above.

In the present specification, an arylene group, an alkenylene group, a fluorenylene group, a carbazolylene group and a heterorene group are each a divalent group of an aryl group, an alkenyl group, a fluorenyl group and a carbazole group. The description of the above-mentioned aryl group, alkenyl group, fluorenyl group and carbazole group can be applied, except that these are two groups each.

The term "substituted or unsubstituted" A halogen group; An alkyl group; An alkenyl group; An alkoxy group; A cycloalkyl group; Silyl group; An arylalkenyl group; An aryl group; An aryloxy group; An alkyloxy group; An alkylsulfoxy group; Arylsulfoxy group; Boron group; A heterocyclic group; Carbazole group; An aryl group; A fluorenyl group; A nitrile group; A nitro group; A heterocyclic group containing at least one of a hydroxyl group and at least one of N, O and S atoms, or has no substituent group.

The present specification provides a novel tertiary arylamine compound represented by formula (1). Such a compound can be used as an organic material layer in an organic light emitting device due to its structural specificity.

In one embodiment of the present invention, at least one of Ar &_lt; ₁ > to Ar &_lt; ₃ >

Specifically, Ar ₁ to Ar ₃ May be the formula (2). In this case, the other two may be a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group.

In another example, Ar ₁ to Ar ₃ Lt; 2 > may be the formula (2). In this case, the other may be a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group.

In another example, Ar ₁ To Ar ₃ All of which may be of the formula (2).

In another example, any one of Ar ₁ to Ar ₃ may be the formula (2-1). In this case, the other two may be a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group.

In another example, Ar ₁ to Ar ₃ Two of which may be the same or different, and each independently may be the formula (2-1). In this case, the other may be a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group.

In another example, Ar ₁ to Ar ₃ may be the same as or different from each other, and each independently may be a formula (2-1).

In one embodiment of the present specification, among Ar ₁ to Ar ₃ in the general formula (1), those which are not represented by the general formula (2) may be a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group.

Specifically, Ar ₁ to Ar ₃ May be the formula (2) or (2-1). In this case, the other two may be the same or different and each independently represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted terphenyl group, Lt; / RTI > may be an unsubstituted fluorenyl group.

In another example, two of Ar ₁ to Ar ₃ may be the same as or different from each other, and each independently may be a formula (2) or (2-1). In this case, the other one may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted triphenyl group, or a substituted or unsubstituted fluorenyl group.

In another example, among Ar ₁ to Ar ₃ , a group other than Formula 2 and Formula 2-1 may be a phenyl group, a biphenyl group, a naphthyl group, a triphenyl group, or a fluorenyl group.

In another embodiment, R _a in formula (2-1), R ₁ and R ₂ in formulas (3-1) and (3-2) are substituted or unsubstituted aryl groups.

Specifically, R _a in formula (2-1) is a substituted or unsubstituted phenyl group or a substituted or unsubstituted biphenyl group.

In another example, R _a in formula (2-1) is a phenyl group or _a biphenyl group.

In another example, R ₁ and R ₂ in formula (3-1) are the same or different from each other and are each independently a phenyl group or a biphenyl group.

In another example, R ₁ and R ₂ in the formula (3-2) are the same or different from each other and are each independently a phenyl group or a biphenyl group.

 In another embodiment, L in formulas (2), (2-1), (3-1) and (3-2) is a substituted or unsubstituted aryl group.

In another embodiment, L is a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted fluorenylene group.

In another example, L is a phenylene group, a biphenylene group or a fluorenylene group.

In another embodiment, the groups other than the groups represented by formulas (2) and (2-1) among Ar ₁ to Ar ₃ may be naphthyl groups.

In another embodiment, it may be connected to N in formula (1) and to any one of positions 1 to 3, 6, 7 to 10 of the following naphthyl group.

In another example, the N in formula (1) may be linked to the 3, 6, 7 or 10 positions of the following naphthyl groups.

In another example, the N in formula (1) can be linked to the position of 1, 2, 8 or 9 of the naphthyl group below.

The compound of the formula (1) is preferably exemplified by the following compounds, but the range of the compounds of the present invention is not limited by the following compounds.

The compound of formula (1) may be prepared based on the preparation examples described below.

In this specification, compounds represented by the general formula (1) other than the compounds 1 to 20 can be prepared by bonding a brominated - (L) - (Y) and an amine group substituted with a boronic acid.

The compound of Formula 1 may be prepared by introducing various substituents into the core structure of which the core structure is a tertiary arylamine and at least one of the substituents of the tertiary amine is a heterocyclic group containing N, It is possible to have properties suitable for use as the organic layer used in the organic EL device.

The conjugation length of the compound and the energy band gap are closely related. Specifically, the longer the conjugation length of the compound, the smaller the energy bandgap. As described above, since the core of the compound of Formula 1 contains limited conjugation, it has a large energy band gap.

In this specification, compounds having various energy bandgaps can be synthesized by introducing various substituent groups at positions of Ar ₁ to Ar ₃ of the core structure having a large energy band gap as described above. Usually, it is easy to control the energy band gap by introducing a substituent to a core structure having a large energy band gap. However, when the core structure has a small energy band gap, it is difficult to control the energy band gap by introducing a substituent. In this specification, the HOMO and LUMO energy levels of a compound can be controlled by introducing various substituents at the positions of Ar ₁ to Ar ₃ of the core structure.

Further, by introducing various substituents into the core structure having the above structure, it is possible to synthesize a compound having the intrinsic characteristics of the substituent introduced. For example, by introducing a substituent mainly used for a hole injecting layer material, a hole accepting material, a light emitting layer material, and an electron transporting layer material used in manufacturing an organic light emitting device into the core structure, a material satisfying the conditions required in each organic layer is synthesized .

 Since the compound of Formula 1 contains an amine structure in the core structure, it can have an appropriate energy level as a hole injecting and / or hole transporting material in the organic light emitting device. In this specification, a compound having an appropriate energy level according to a substituent among the compounds of Formula 1 is selected and used in an organic light emitting device, thereby realizing a device having a low driving voltage and a high light efficiency.

 In addition, by introducing various substituents, especially hydrogen or deuterium, into the core structure, it is possible to finely control the energy band gap, while improving the characteristics at the interface between the organic materials, .

On the other hand, the compound of formula (1) has a high glass transition temperature (T _g ) and is excellent in thermal stability. This increase in thermal stability is an important factor in providing drive stability to the device.

 The present invention also provides an organic light emitting device using the compound of formula (1).

In one embodiment of the present disclosure, the organic light emitting device may have a structure including a first electrode, a second electrode, and an organic layer disposed therebetween.

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 in this specification may have a structure including a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and an electron injecting layer as an organic material layer. However, the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers.

Therefore, in another embodiment of the present disclosure, the organic material layer of the organic light emitting device may include at least one of a hole injecting layer, a hole transporting layer, and a layer simultaneously injecting holes and transporting holes, Layer may contain a compound represented by the above formula (1).

 In addition, the organic material layer may include a light emitting layer, and the light emitting layer may include a compound represented by the general formula (1).

 The organic material layer may include at least one of an electron transport layer, an electron injection layer, and a layer that simultaneously transports electrons and electron injection, and at least one of the layers may include a compound represented by Formula 1 .

 In the organic compound layer having such a multi-layer structure, the compound represented by Formula 1 may be included in a light emitting layer, a layer that simultaneously transports and injects holes, a layer that simultaneously transports light and emits light, or a layer that simultaneously transports electrons and emits light have.

The organic light emitting device of the present invention may have a structure as shown in FIGS. 1 and 2 in the state of implementation, but the present invention is not limited thereto.

 1 shows a structure of an organic light emitting device in which a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4 are sequentially laminated. In such a structure, the compound may be included in the light emitting layer (3).

2 shows an organic light emitting device in which a substrate 1, an anode 2, a hole injecting layer 5, a hole transporting layer 6, a light emitting layer 7, an electron transporting layer 8 and a cathode 4 are sequentially laminated Structure is illustrated. In such a structure, the compound may be contained in at least one of the hole injection layer 5, the hole transport layer 6, the light emitting layer 7, and the electron transport layer 8.

The organic light emitting device of the present invention can be manufactured by materials and methods known in the art, except that one or more of the organic layers include the compound of the present invention, i.e., the compound of the above formula (1).

 For example, the organic light emitting device of the present invention can be manufactured by sequentially laminating a first electrode, an organic material layer, and a second electrode on a substrate. At this time, by using a PVD (physical vapor deposition) method such as a sputtering method or an e-beam evaporation method, a metal or a metal oxide having conductivity or an alloy thereof is deposited on the substrate to form a positive electrode Forming an organic material layer including a hole injecting layer, a hole transporting layer, a light emitting layer and an electron transporting layer thereon, 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 of Formula 1 may be formed into an organic material layer by a solution coating method as well as a vacuum evaporation method in the production of an organic light emitting device. Here, the solution coating method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating and the like, but is not limited thereto.

As the anode material, a material having a large work function is preferably used so that hole injection can be smoothly conducted into the organic material layer. Specific examples of the cathode material that can be used in the present invention 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); ZnO: Al or SNO _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 magnesium, calcium, 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 are not limited thereto.

As the hole injecting material, it is preferable that the highest occupied molecular orbital (HOMO) of the hole injecting material is between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injecting material include metal porphyrin, oligothiophene, arylamine-based organic materials, hexanitrile hexaazatriphenylene-based organic materials, quinacridone-based organic materials, and perylene- , Anthraquinone, polyaniline and polythiophene-based conductive polymers, but the present invention is not limited thereto.

As the hole transporting material, a material capable of transporting holes from the anode or the hole injecting layer to the light emitting layer and having high mobility to holes 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 benzoxazole, benzothiazole and benzimidazole series; Polymers of poly (p-phenylenevinylene) (PPV) series; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited thereto.

As the electron transporting material, a material capable of transferring electrons from the cathode well into the light emitting layer, which is suitable for electrons, is suitable. Specific examples include an Al complex of 8-hydroxyquinoline; Complexes containing Alq ₃ ; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited thereto.

The organic light emitting device according to the present invention may be of a top emission type, a back emission type, or a both-side emission type, depending on the material used.

The compounds according to the present invention can act on a principle similar to that applied to organic light emitting devices in organic electronic devices including organic solar cells, organic photoconductors, organic transistors and the like.

The method for preparing the compound of Formula 1 and the preparation of the organic light emitting device using 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.

< Synthetic example  1> Preparation of the compound represented by the compound 1

[Compound 1]

(1) Preparation of Compound (1)

(12.95 g, 35.46 mmol) and potassium carbonate (K ₂ CO ₃ ) (13.3 g, 35.46 mmol) were added to a solution of 4-bromo-3,5-diphenylpyridine 96.7 mmol) was dissolved in tetrahydrofuran (THF) (300 ml) H ₂ O (100 ml) and heated to 50 ° C. And then tetrakis (triphenylphosphine) palladium _{(Pd (PPh 3) 4)} , (0.74g, 0.64mmol) was added, and the mixture was refluxed for 12 hours. After cooling to room temperature, the water layer was removed. Magnesium sulfate (MgSO ₄ ) was added to the organic layer, followed by filtration. Concentrated, and then purified by column chromatography to obtain Compound 1 (15 g, yield 84%).

MS: [M + H] &lt; ⁺ &gt; = 551

< Synthetic example  2> Preparation of a compound represented by Compound 2

[Compound 2]

(1) Preparation of compound 2

Biphenyl] -4-yl) amino) - [1,1'-biphenyl] -4,5-diphenylpyridine (10 g, 32.2 mmol) dissolve 4-yl) boronic acid (18.3g, 35.46mmol) and potassium carbonate _{(K 2 CO 3) (13.3g} , 96.7mmol) in tetrahydrofuran _{(THF) (300ml) H 2} O (100ml), 50 ℃ Lt; / RTI &gt; And then tetrakis (triphenylphosphine) palladium _{(Pd (PPh 3) 4)} , (0.74g, 0.64mmol) was added, and the mixture was refluxed for 12 hours. After cooling to room temperature, the water layer was removed. Magnesium sulfate (MgSO ₄ ) was added to the organic layer, followed by filtration. Concentrated, and then purified by column chromatography to obtain Compound 2 (20 g, yield 88%).

MS: [M + H] &lt; ⁺ &gt; = 703

< Synthetic example  3> Preparation of compound represented by Compound 3

[Compound 3]

(1) Preparation of Compound 3

Phenyl-1-naphthylamino) biphenylboronic acid (14.7 g, 35.46 mmol) and potassium carbonate (K ₂ CO ₃ ) (13.3 g, 96.7 mmol) was dissolved in tetrahydrofuran (THF) (300 ml) H ₂ O (100 ml) and heated to 50 ° C. And then tetrakis (triphenylphosphine) palladium _{(Pd (PPh 3) 4)} , (0.74g, 0.64mmol) was added, and the mixture was refluxed for 12 hours. After cooling to room temperature, the water layer was removed. Magnesium sulfate (MgSO ₄ ) was added to the organic layer, followed by filtration. Concentrated, and then purified by column chromatography to obtain Compound 3 (12 g, yield 62%).

MS: [M + H] &lt; ⁺ &gt; = 601

< Synthetic example  4> Preparation of the compound represented by the compound 9

[Compound 9]

(1) Preparation of Compound 9

(14.3 g, 35.46 mmol) and potassium carbonate (K ₂ CO ₃ ) (13.3 g, 96.7 mmol) were added to a solution of 4-bromo-3,5-diphenylpyridine mmol) was dissolved in tetrahydrofuran (THF) (300 ml) H ₂ O (100 ml) and heated to 50 ° C. And then tetrakis (triphenylphosphine) palladium _{(Pd (PPh 3) 4)} , (0.74g, 0.64mmol) was added, and the mixture was refluxed for 12 hours. After cooling to room temperature, the water layer was removed. Magnesium sulfate (MgSO ₄ ) was added to the organic layer, followed by filtration. Concentrated, and then purified by column chromatography to obtain Compound 9 (10 g, yield 53%).

MS: [M + H] &lt; ⁺ &gt; = 591

< Synthetic example  5> Preparation of the compound represented by the compound 11

[Compound 11]

(1) Preparation of Compound 11

(12.95 g, 35.46 mmol) and potassium carbonate (K ₂ CO ₃ ) (13.3 g, 35.46 mmol) were added to a solution of 4- (diphenylamino) biphenylboronic acid 96.7 mmol) was dissolved in tetrahydrofuran (THF) (300 ml) H ₂ O (100 ml) and heated to 50 ° C. And then tetrakis (triphenylphosphine) palladium _{(Pd (PPh 3) 4)} , (0.74g, 0.64mmol) was added, and the mixture was refluxed for 12 hours. After cooling to room temperature, the water layer was removed. Magnesium sulfate (MgSO ₄ ) was added to the organic layer, followed by filtration. Concentrated, and then purified by column chromatography to obtain Compound 11 (13 g, yield 73%).

MS: [M + H] &lt; ⁺ &gt; = 551

< Synthetic example  6> Preparation of the compound represented by the compound 12

[Compound 12]

(1) Preparation of Compound (12)

Biphenyl] -4-yl) amino) - [1,1'-biphenyl] -4,4'-diphenylpyridine (10 g, 32.2 mmol) (19.6 g, 35.46 mmol) and potassium carbonate (K ₂ CO ₃ ) (13.3 g, 96.7 mmol) were dissolved in tetrahydrofuran (THF) (300 ml) H ₂ O (100 ml) Lt; / RTI &gt; And then tetrakis (triphenylphosphine) palladium _{(Pd (PPh 3) 4)} , (0.74g, 0.64mmol) was added, and the mixture was refluxed for 12 hours. After cooling to room temperature, the water layer was removed. Magnesium sulfate (MgSO ₄ ) was added to the organic layer, followed by filtration. Concentrated, and then purified by column chromatography to obtain Compound 12 (16 g, yield 71%).

MS: [M + H] &lt; ⁺ &gt; = 703

< Synthetic example  7> Compound To 14  Preparation of indicated compounds

[Compound 14]

(1) Preparation of Compound 14

Phenyl-1-naphthylamino) biphenylboronic acid (14.7 g, 35.46 mmol) and potassium carbonate (K ₂ CO ( ₂ ml) ₃ ) (13.3 g, 96.7 mmol) was dissolved in tetrahydrofuran (THF) (300 ml) H ₂ O (100 ml) and heated to 50 ° C. And then tetrakis (triphenylphosphine) palladium _{(Pd (PPh 3) 4)} , (0.74g, 0.64mmol) was added, and the mixture was refluxed for 12 hours. After cooling to room temperature, the water layer was removed. Magnesium sulfate (MgSO ₄ ) was added to the organic layer, followed by filtration. Concentrated, and then purified by column chromatography to obtain Compound 14 (12 g, yield 62%).

MS: [M + H] &lt; ⁺ &gt; = 601

< Synthetic example  8> Preparation of the compound represented by Compound 20

[Compound 20]

(1) Preparation of Compound 20

(14.3 g, 35.46 mmol) and potassium carbonate (K ₂ CO ₃ ) (13.3 g, 96.7 mmol) were added to a solution of 4- (diphenylamino) fluoroboronic acid mmol) was dissolved in tetrahydrofuran (THF) (300 ml) H ₂ O (100 ml) and heated to 50 ° C. And then tetrakis (triphenylphosphine) palladium _{(Pd (PPh 3) 4)} , (0.74g, 0.64mmol) was added, and the mixture was refluxed for 12 hours. After cooling to room temperature, the water layer was removed. Magnesium sulfate (MgSO ₄ ) was added to the organic layer, followed by filtration. Concentrated, and then purified by column chromatography to obtain Compound 20 (12 g, yield 63%).

MS: [M + H] &lt; ⁺ &gt; = 591

< Example  1>

A glass substrate (corning 7059 glass) coated with ITO (indium tin oxide) to a thickness of 1000 Å was immersed in distilled water and dissolved with ultrasonic waves. As a detergent, a product of Fischer Co. was used, and as distilled water, distilled water which was secondly filtered with a filter of Millipore Co. was used. The ITO was washed for 30 minutes and then washed twice with distilled water and ultrasonically cleaned for 10 minutes. After the distilled water was washed, it was ultrasonically washed with a solvent of isopropyl alcohol, acetone, methanol and dried.

Hexanitrile hexaazatriphenylene (HAT) of the following chemical formula was thermally vacuum deposited on the prepared ITO transparent electrode to a thickness of 500 Å to form a hole injection layer. Compound 1 (400 Å) synthesized in Preparation Example 1, which is a hole transport material, was vacuum-deposited thereon, and a host H1 and a dopant D1 compound were vacuum deposited as a light emitting layer to a thickness of 300 Å. The E1 compound (300 ANGSTROM) was then thermally vacuum deposited sequentially by electron injecting and transporting layers. A 12 Å thick lithium fluoride (LiF) layer and a 2000 Å thick aluminum layer were successively deposited on the electron transport 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 Å / sec, the deposition rate of lithium fluoride of 0.2 Å / sec and the deposition rate of aluminum of 3 to 7 Å / sec were maintained.

[LINE]

[H1] [D1]

 [E1]

< Example  2>

The same experiment was conducted as in Example 1 except that Compound 2 was used instead of Compound 1 synthesized in Production Example as a hole transport layer.

< Example  3>

The same experiment was conducted as in Example 1 except that Compound 3 was used instead of Compound 1 synthesized in Production Example as a hole transport layer.

< Example  4>

The same experiment was conducted as in Example 1 except that Compound 9 was used instead of Compound 1 synthesized in Production Example as a hole transport layer.

< Example  5>

The same experiment was conducted as in Example 1 except that Compound 11 was used instead of Compound 1 synthesized in Production Example as a hole transport layer.

< Example  6>

The same experiment was conducted as in Example 1 except that Compound 12 was used instead of Compound 1 synthesized in Production Example as a hole transport layer.

< Example  7>

The same experiment was conducted as in Example 1 except that Compound 14 was used instead of Compound 1 synthesized in Production Example as a hole transport layer.

< Example  8>

The same experiment was conducted as in Example 1 except that Compound 20 was used instead of Compound 1 synthesized in Production Example as a hole transport layer.

&Lt; Comparative Example 1 &

The same experiment was conducted as in Example 1 except that HT1 was used instead of Compound 1 synthesized in Production Example as a hole transport layer.

[HT1]

< Comparative Example  2>

In the above example, the hole transport layer was tested in the same manner except that NPB was used in place of the compound 1 synthesized in Production Example.

[NPB]

Table 1 shows the results of the experiment of the organic light emitting device manufactured by using each compound as the hole transporting layer material as in Examples 1 to 8, Comparative Examples 1 and 2.

Experimental Example
(50 mA / cm ² ) The hole transport layer (HTL)
compound Voltage (V) Efficiency (cd / A) Comparative Example 1 HT1 6.25 5.98 Comparative Example 2 NPB 6.21 5.87 Example 1 Compound 1 6.21 7.11 Example 2 Compound 2 6.22 7.12 Example 3 Compound 3 6.15 7.18 Example 4 Compound 9 6.11 7.15 Example 5 Compound 11 6.14 6.90 Example 6 Compound 12 6.18 6.97 Example 7 Compound 14 6.05 7.01 Example 8 Compound 20 6.01 6.97

As can be seen from Table 1, the organic light emitting device manufactured by using the compound of the present invention as a hole transporting layer material exhibits excellent characteristics in terms of efficiency, driving voltage, and stability as compared with the case of using a conventional material.

Claims (13)

A compound represented by the following formula (1):
[Chemical Formula 1]

In formula (1)
Ar ₁ To Ar &lt; ₃ &gt; are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted aryl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted carbazole group; Or a substituted or unsubstituted heterocyclic group containing at least one of N, O and S atoms
At least one of Ar ₁ to Ar ₃ in Formula 1 is substituted with the following Formula 2,
(2)

L is a direct bond; A substituted or unsubstituted arylene group; A substituted or unsubstituted alkenylene group; A substituted or unsubstituted carbazolylene group; A substituted or unsubstituted heterocyclic group containing at least one of N, O and S atoms; Or a substituted or unsubstituted fluorenylene group,
Y is a substituted or unsubstituted nitrogen-containing heterocyclic group. [2] The compound according to claim 1, wherein the compound represented by Formula 2 is represented by Formula 2-1:
[Formula 2-1]

In Formula 2-1,
L is the same as defined in Chemical Formula 2,
n is an integer of 0 to 4,
R _a is a substituted or unsubstituted aryl group. The compound according to claim 1, wherein the compound represented by Formula 1 is represented by Formula 3-1 or Formula 3-2:
[Formula 3-1]

[Formula 3-2]

In the above Formulas (3-1) and (3-2)
Ar ₂ , Ar ₃ and L are the same as defined in formulas (1) and (2)
R ₁ and R _{2, which} may be the same or different, are each independently a substituted or unsubstituted aryl group. The method of claim 2,
L is a substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylene group; Or a substituted or unsubstituted fluorenylene group. [4] The compound according to claim 3, wherein R ₁ and R ₂ are the same or different from each other and each independently represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, Substituted or unsubstituted phenanthrenyl groups, substituted or unsubstituted pyrenyl groups, substituted or unsubstituted perylenyl groups, substituted or unsubstituted tetracenyl groups, substituted or unsubstituted phenanthrenyl groups, substituted or unsubstituted pyrenyl groups, substituted or unsubstituted tetracenyl groups, A substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted acenaphenyl group, a substituted or unsubstituted triphenylene group, and a substituted or unsubstituted fluoranthene group. 2. The compound according to claim 1, wherein Ar &lt; _{1 &gt;} To Ar ₃ are the same or different from each other and each independently represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthra A substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted perylenyl group, a substituted or unsubstituted tetracenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted pyrazinyl group, A substituted or unsubstituted phenanthroline group, a substituted or unsubstituted thiophene group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluoranthene group, a substituted or unsubstituted phenanthroline group, a substituted or unsubstituted thiophene group, A substituted or unsubstituted aryl group, a substituted furan group, a substituted or unsubstituted pyrrole group, a substituted or unsubstituted imidazole group, a substituted or unsubstituted thiazole group, a substituted or unsubstituted oxazole group, Substituted or unsubstituted pyrazole groups, substituted or unsubstituted pyridyl groups, substituted or unsubstituted bipyridyl groups, substituted or unsubstituted triazine groups, substituted or unsubstituted acridyl groups, substituted or unsubstituted pyrazole groups, substituted or unsubstituted pyrazole groups, A substituted or unsubstituted quinolinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinoline group, a substituted or unsubstituted indole group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted benzoxazole group, A substituted or unsubstituted benzothiazole group, a substituted or unsubstituted benzothiazole group, a substituted or unsubstituted benzothiazole group, a substituted or unsubstituted benzothiophene group, a substituted or unsubstituted benzothiazole group, a substituted or unsubstituted benzothiazole group, A benzofuranyl group, and a substituted or unsubstituted dibenzofuranyl group. The compound according to claim 1, wherein the compound of formula (1) is one of the following compounds:

. An organic light emitting device comprising at least one organic compound layer including a first electrode, a second electrode, and a light emitting layer disposed between the first electrode and the second electrode, wherein at least one of the organic compound layers is a compound of any one of claims 1 to 7 And a compound according to any one of claims 1 to 3. 9. The organic light emitting device according to claim 8, wherein the organic layer comprises a hole transporting layer, and the hole transporting layer comprises the compound. 9. The organic light emitting device according to claim 8, wherein the organic layer includes a hole injection layer, and the hole injection layer comprises the compound. [Claim 9] The organic light emitting device according to claim 8, wherein the organic material layer includes a hole injection layer and a hole transport layer at the same time, and the hole injection layer and the hole transport layer simultaneously contain the compound. 9. The organic light emitting device according to claim 8, wherein the organic material layer includes an electron injection layer and an electron transport layer, and the electron injection layer or electron transport layer comprises the compound. 9. The organic light emitting device according to claim 8, wherein the light emitting layer comprises the compound.

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