KR101896151B1 - Compound and organic electronic device using the same - Google Patents

Abstract

The present disclosure relates to compounds and organic electronic devices comprising them.

Description

BACKGROUND OF THE INVENTION 1. Field of the Invention [0001] The present invention relates to a compound,

The present disclosure relates to compounds and organic electronic devices comprising them.

A representative example of the organic electronic device is an organic light emitting device. In general, organic light emission phenomenon refers to a phenomenon in which an organic material is used to convert electric energy into light energy. An organic light emitting device using an organic light emitting phenomenon generally has a structure including an anode, a cathode, and an organic material layer therebetween. Here, in order to increase the efficiency and stability of the organic light emitting device, the organic material layer may have a multi-layer structure composed of different materials and 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, electrons are injected into the organic layer in the cathode, excitons are formed when injected holes and electrons meet, When it falls back to the ground state, the light comes out.

Development of new materials for such organic light emitting devices has been continuously required.

International Patent Application Publication No. 2003-012890

The present specification intends to provide a compound and an organic electronic device including the same.

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

[Chemical Formula 1]

In Formula 1,

L is a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,

Ar ₁ and Ar ₂ are the same or different and each independently represents a substituted or unsubstituted aryl group,

R ₁ to R ₁₇ are the same or different and each independently hydrogen; heavy hydrogen; A halogen group; Cyano; A substituted or unsubstituted C ₁ to C ₁₀ alkyl group; Or a substituted or unsubstituted C ₆ to C ₁₀ aryl group, which may be bonded to adjacent groups to form a ring.

Also, the present specification discloses a plasma display panel comprising a first electrode; A second electrode facing the first electrode; And at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the above-described compound.

The compound according to one embodiment of the present invention is used in an organic electronic device including an organic light emitting device to lower the driving voltage of the organic electronic device, improve the light efficiency, and improve the lifetime characteristics of the device by the thermal stability of the compound. have.

1 shows an organic electronic device 10 according to an embodiment of the present invention.
2 shows an organic electronic device 11 according to another embodiment of the present invention.

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

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

According to one embodiment of the present invention, the compound represented by Formula 1 has a core structure in which diphenylfluorene is substituted with an arylamine at an ortho position. By having the core structure, it has higher efficiency and longer life than the structure in which the arylamine is substituted at the meta position or the para position. In particular, it exhibits more than 10% improvement in efficiency over compounds in other directions, and its lifetime is equal to or better than that of conventional materials. In general, the higher the efficiency, the shorter the lifetime. However, the compound of the present invention has an advantage that the lifetime of the compound of the present invention is equal to or higher than that of the conventional materials, even though the efficiency is increased.

Examples of substituents herein are described below, but are not limited thereto.

는 연결되는 부위를 의미한다.In the present specification,

Refers to the connected area.

The term "substituted" means that the hydrogen atom bonded to the carbon atom of the compound is replaced with another substituent, and the substituted position is not limited as long as the substituent is a substitutable position, , Two or more substituents may be the same as or different from each other.

As used herein, the term " substituted or unsubstituted " A halogen group; Cyano; A nitro group; A hydroxy group; A carbonyl group; An ester group; Imide; An amino group; An alkyl group; A cycloalkyl group; An alkenyl group; An amine group; Phosphine oxide groups; An aryl group; Silyl group; And a heteroaryl group containing at least one of N, O, S, Se and Si atoms, or wherein at least two of the substituents exemplified above are substituted with a substituent to which they are connected, Quot; means < / RTI > 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, examples of the halogen group include fluorine, chlorine, bromine, and 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. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec- N-pentyl, 3-dimethylbutyl, 2-ethylbutyl, heptyl, n-hexyl, Cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethyl Heptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl and the like.

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, when the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 6 to 25 carbon atoms. Specific examples of the monocyclic aryl group include a phenyl group, a biphenyl group, a terphenyl group, and the like, but are not limited thereto.

When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited. And preferably has 10 to 24 carbon atoms. Specific examples of the polycyclic aryl group include naphthyl, anthracenyl, phenanthryl, pyrenyl, perylenyl, klychenyl, fluorenyl, and the like.

In the present specification, the fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.

,

,

,

,

,

등이 될 수 있으나, 이에 한정되는 것은 아니다.When the fluorenyl group is substituted,

,

,

,

,

,

And the like, but the present invention is not limited thereto.

In the present specification, the heteroaryl group is a heterocyclic group and is a heterocyclic group containing at least one of N, O, S, Si and Se. The number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms. Examples of the heteroaryl group include a thiophene group, a furane group, a furyl group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, a bipyridyl group, a pyrimidyl group, A pyridazinyl group, a pyrazinopyrazinyl group, an isoquinoline group, an isoquinolinyl group, an isoquinolinyl group, an isoquinolinyl group, an isoquinolinyl group, an isoquinolyl group, A benzothiazole group, a benzothiophene group, a dibenzothiophene group, a benzofuranyl group, a phenanthroline group, a thiazolyl group, a thiazolyl group, a thiazolyl group, An isoxazolyl group, an oxadiazolyl group, a thiadiazolyl group, a benzothiazolyl group, and a dibenzofuranyl group, but is not limited thereto.

,

,

,

등이 될 수 있으나, 이에 한정되는 것은 아니다.In the present specification, the condensed structure may be a structure in which an aromatic carbon-hydrogen ring is condensed with the substituent. For example, as a condensation ring of benzimidazole

,

,

,

And the like, but the present invention is not limited thereto.

As used herein, the term "adjacent" means that the substituent is a substituent substituted on an atom directly connected to the substituted atom, a substituent stereostructically closest to the substituent, or another substituent substituted on the substituted atom . For example, two substituents substituted at the ortho position in the benzene ring and two substituents substituted at the same carbon in the aliphatic ring may be interpreted as "adjacent" groups to each other.

In the present specification, the adjacent groups bonded to each other to form a ring means that adjacent groups are bonded to each other to form a 5-membered to 8-membered hydrocarbon ring or a 5-to 8-membered heterocyclic ring as described above , Monocyclic or polycyclic, and may be aliphatic, aromatic, or condensed forms thereof, but is not limited thereto.

As used herein, the hydrocarbon ring or heterocycle may be selected from the examples of cycloalkyl groups, aryl groups or heterocyclic groups described above, except monovalent, and may be monocyclic or polycyclic, aliphatic or aromatic, or a condensed form thereof Yes. But is not limited thereto.

In the present specification, the aromatic ring group may be monocyclic or polycyclic, and may be selected from the examples of the aryl group except that it is not monovalent.

In the present specification, the 2- to 4-valent aromatic ring group may be monocyclic or polycyclic, meaning that the aryl group has 2 to 4 bonding positions, that is, 2 to 4 bonds. The description of the aryl group described above can be applied, except that these are each 2 to 4 groups.

In the present specification, an arylene group means a divalent group having two bonding positions in an aryl group. The description of the aryl group described above can be applied except that each of these is 2 groups.

In the present specification, the heteroarylene group means that the heteroaryl group has two bonding positions, that is, divalent. The description of the above-mentioned heteroaryl groups can be applied, except that they are each 2 groups.

According to one embodiment of the present disclosure, L is a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group.

According to one embodiment of the present invention, L is a direct bond or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms.

According to one embodiment of the present invention, L is a direct bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted naphthylene group.

According to one embodiment of the present disclosure, L is a direct bond or a phenylene group, a biphenylene group, or a naphthylene group.

According to one embodiment of the present disclosure, Ar ₁ and Ar ₂ are the same or different and are each independently a substituted or unsubstituted aryl group.

According to one embodiment of the present invention, Ar ₁ and Ar ₂ are substituted or unsubstituted aryl groups having 1 to 30 carbon atoms.

According to one embodiment of the present invention, Ar ₁ and Ar 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, A substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted pyrene group, or a substituted or unsubstituted fluorenyl group.

According to one embodiment of the present invention, Ar ₁ and Ar ₂ are the same or different from each other and each independently represents a phenyl group, a biphenyl group, a terphenyl group, a triphenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, Fluorenyl group.

According to one embodiment of the present invention, Ar ₁ and Ar ₂ are the same or different and are each independently a phenyl group substituted or unsubstituted with an alkyl group, cyano group, silyl group, or carbazole group.

According to one embodiment of the present invention, Ar ₁ and Ar ₂ are the same or different and are each independently a phenyl group substituted with a carbamoyl group substituted with a methyl group, an ethyl group, a cyano group, a silyl group, or a phenyl group.

According to one embodiment of the present invention, Ar ₁ and Ar ₂ are the same or different from each other and are each independently a phenyl group.

According to one embodiment of the present invention, Ar ₁ and Ar ₂ are the same or different and each independently a biphenyl group in which an alkyl group, cyano group, silyl group, or carbazole group is substituted or unsubstituted.

According to one embodiment of the present invention, Ar ₁ and Ar ₂ are the same or different and each independently a biphenyl group substituted with a carbamoyl group substituted with a methyl group, an ethyl group, a cyano group, a silyl group, or a phenyl group.

According to one embodiment of the present invention, Ar ₁ and Ar ₂ are the same or different and are each independently a biphenyl group.

According to one embodiment of the present invention, Ar ₁ and Ar ₂ are the same or different and are each independently a naphthyl group substituted or unsubstituted with an alkyl group, a cyano group, a silyl group, or a carbazole group.

According to one embodiment of the present invention, Ar ₁ and Ar ₂ are the same or different and each independently a naphthyl group substituted with a carbamoyl group substituted with a methyl group, an ethyl group, a cyano group, a silyl group, or a phenyl group.

According to one embodiment of the present invention, Ar ₁ and Ar ₂ are the same or different and are each independently a naphthyl group.

According to one embodiment of the present invention, Ar ₁ and Ar ₂ are the same or different from each other, and each independently represents a substituted or unsubstituted fluorenyl group having an alkyl group, a cyano group, a silyl group, an aryl group, or a carbazole group.

According to one embodiment of the present invention, Ar ₁ and Ar ₂ are the same or different and each independently represents a substituted or unsubstituted carbazole group substituted with a methyl group, an ethyl group, a cyano group, a silyl group, a phenyl group, Orrenyl group.

According to one embodiment of the present disclosure, Ar ₁ and Ar ₂ are the same or different from each other, and each independently is a fluorenyl group.

According to one embodiment of the present invention, Ar ₁ and Ar ₂ are the same or different and each independently a substituted or unsubstituted phenanthrenyl group.

According to one embodiment of the present invention, Ar ₁ and Ar ₂ are the same or different and are each independently a phenanthrenyl group.

According to one embodiment of the present invention, Ar ₁ and Ar ₂ are the same or different and are each independently a substituted or unsubstituted triphenylene group.

According to one embodiment of the present invention, Ar ₁ and Ar ₂ are the same or different and are each independently a triphenylene group.

According to one embodiment of the present disclosure, R ₁ to R ₁₇ are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; Cyano; A substituted or unsubstituted C ₁ to C ₁₀ alkyl group; Or a substituted or unsubstituted C ₆ to C ₁₀ aryl group, which may be bonded to adjacent groups to form a ring.

According to one embodiment of the present disclosure, R ₁ to R ₁₇ are the same or different and each independently represents hydrogen, deuterium, a halogen group, a cyano group, a C ₁ to C ₁₀ alkyl group, a C ₆ to C ₁₀ aryl group And may form a ring by bonding to adjacent groups.

According to one embodiment of the present invention, R ₁ to R ₁₇ are the same or different from each other, and each independently represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted naphthyl group.

According to one embodiment of the present invention, R ₁ to R ₁₇ are the same or different from each other and are each independently a phenyl group, a biphenyl group, or a naphthyl group.

According to one embodiment of the present invention, R ₁ to R ₁₇ are the same or different from each other and are each independently a phenyl group.

According to one embodiment of the present invention, R ₁ to R ₁₇ may be the same or different from each other, and may be independently bonded to adjacent groups to form a ring.

According to one embodiment of the present disclosure, R ₁ to R ₁₇ are the same or different and are each independently hydrogen.

According to one embodiment of the present invention, Ar ₁ and Ar ₂ may be selected from the following structural formulas of Groups 1 and 2, but are not limited thereto.

[Group 1]

[Group 2]

According to one embodiment of the present invention, the compound represented by Formula 1 may be selected from the following structural formulas, but is not limited thereto.

The compound according to one embodiment of the present specification can be produced by a production method described below. Exemplary examples are described below in the preparation examples, but substituents can be added or removed as needed, and the position of the substituent can be changed. In addition, based on techniques known in the art, starting materials, reactants, reaction conditions, and the like can be changed.

For example, the compound of Formula 1 can be prepared as shown in Reaction Scheme 1 below. Substituent groups may be attached by methods known in the art, and the type, position, or number of substituent groups may be varied according to techniques known in the art. A concrete manufacturing method will be described later.

 [Reaction Scheme 1]

[Reaction Scheme 2]

In the above Reaction Schemes 1 and 2, L, Ar ₁ , and Ar ₂ are the same as defined in Formula 1 above. In the above reaction scheme 2, L is a direct bond, but the present invention is not limited thereto.

Further, the present invention provides an organic electronic device comprising the above-mentioned compounds.

In one embodiment of the present disclosure, the first electrode; A second electrode facing the first electrode; And at least one organic compound layer provided between the first electrode and the second electrode, wherein at least one of the organic compound layers includes the compound.

When a member is referred to herein as being "on " another member, it includes not only a member in contact with another member but also another member between the two members.

Whenever a component is referred to as "comprising ", it is understood that it may include other components as well, without departing from the other components unless specifically stated otherwise.

The organic material layer of the organic electronic device in this specification may have a single layer structure, but may have a multi-layer structure in which two or more organic material layers are stacked. For example, as a representative example of the organic electronic device of the present invention, the organic light emitting device may have a structure including a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, an electron injecting layer, etc. as an organic material layer. However, the structure of the organic electronic device is not limited thereto and may include a smaller number of organic layers.

According to one embodiment of the present invention, the organic electronic device may be selected from the group consisting of an organic light emitting device, an organic phosphor device, an organic solar cell, an organic photoconductor (OPC), and an organic transistor.

Hereinafter, the organic light emitting device will be described.

In one embodiment of the present invention, the organic layer includes a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer includes the compound.

In one embodiment of the present invention, the organic layer includes an electron blocking layer, and the electron blocking layer includes the compound.

In one embodiment of the present invention, the organic material layer is a hole transporting layer or an electron blocking layer, and the organic electronic device is one or more layers selected from the group consisting of a hole transporting layer, a hole injecting layer, .

In one embodiment of the present invention, the organic layer further includes a hole injection layer or a hole transport layer containing a compound having an arylamino group, a carbazolyl group or a benzocarbazolyl group in addition to the organic compound layer containing the compound.

In one embodiment of the present invention, the organic light emitting device includes a first electrode; A second electrode facing the first electrode; And a light emitting layer provided between the first electrode and the second electrode; At least one of the two or more organic layers includes two or more organic layers disposed between the light emitting layer and the first electrode or between the light emitting layer and the second electrode. In one embodiment of the present invention, the two or more organic layers may be selected from the group consisting of an electron transport layer, an electron injection layer, a layer that simultaneously transports electrons and electrons, and a hole blocking layer.

In one embodiment of the present invention, the organic layer further includes a hole injection layer or a hole transport layer containing a compound having an arylamino group, a carbazolyl group or a benzocarbazolyl group in addition to the organic compound layer containing the compound.

In another embodiment, the organic light emitting device may be a normal type organic light emitting device in which an anode, at least one organic layer, and a cathode are sequentially stacked on a substrate.

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

1 illustrates a structure of an organic light emitting diode 10 in which a first electrode 30, a light emitting layer 40, and a second electrode 50 are sequentially stacked on a substrate 20. 1 is an exemplary structure of an organic light emitting diode according to an embodiment of the present invention, and may further include another organic layer.

2 shows a structure in which a first electrode 30, a hole injecting layer 60, a hole transporting layer 70, an electron blocking layer 80, a light emitting layer 40, an electron transporting layer 90, 100 and a second electrode 50 are sequentially laminated on a transparent substrate 100. In this case, 2 is an exemplary structure according to an embodiment of the present invention, and may further include another organic layer.

In such a structure, the compound may be included in at least one of the hole injecting layer, the hole transporting layer, and the electron blocking layer.

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 includes the compound of the present invention, i.e., the compound.

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.

 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, i.e., the compound represented by 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.

In addition to such a method, an organic light emitting device may be fabricated by sequentially depositing an organic material layer and a cathode material on a substrate from a cathode material (International Patent Application Publication No. 2003/012890). However, the manufacturing method is not limited thereto.

In one embodiment of the present invention, the first electrode is an anode and the second electrode is a cathode.

In another embodiment, 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 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.

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 (HOMO) of the hole injecting material be 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.

The hole transport layer is a layer that transports holes from the hole injection layer to the light emitting layer. The hole transport material is a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer. The 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; Polymers of poly (p-phenylenevinylene) (PPV) series; 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 heterocycle-containing compounds include compounds, dibenzofuran derivatives, ladder furan compounds , Pyrimidine derivatives, 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 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 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 layer 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 the 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 complex compound and a nitrogen-containing five-membered ring derivative, 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- hydroxyquinolinato) gallium, bis (10- Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8- quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) (2-naphtholato) gallium, and the like, But is not limited thereto.

The hole blocking layer prevents holes from reaching the cathode, and may be formed under the same conditions as those of the hole injection layer. Specific examples thereof include, but are not limited to, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes and the like.

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.

In one embodiment of the present invention, the compound may be included in an organic solar cell or an organic transistor in addition to the organic light emitting device.

The compound 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 phosphorescent devices, organic solar cells, organic photoconductors, organic transistors and the like. For example, the organic solar cell may include a cathode, an anode, and a photoactive layer disposed between the anode and the cathode, and the photoactive layer may include the compound.

Hereinafter, the present invention will be described in detail by way of examples with reference to the drawings. However, the embodiments according to the present disclosure can be modified in various other forms, and the scope of the present specification is not construed as being limited to the embodiments described below. Embodiments of the present disclosure are provided to more fully describe the present disclosure to those of ordinary skill in the art.

< Example >

< Manufacturing example  1>

9-phenyl-9H-fluorene (15.0 g, 37.87 mmol) and diphenylamine (7.04 g, 41.66 mmol) were added to a 500 ml round bottom flask in a nitrogen atmosphere, (Tert-butylphosphine) palladium (0.19 g, 0.38 mmol) was added thereto, followed by heating and stirring for 2 hours. The temperature was lowered to room temperature, and the salt was removed by filtration. The xylene was concentrated under reduced pressure and the residue was subjected to column chromatography with tetrahydrofuran: hexane = 1: 10 to prepare Compound 1 (15.61 g, yield: 85%).

MS [M + H] &lt; ⁺ &gt; = 486

< Manufacturing example  2>

9-phenyl-9H-fluorene (15.0 g, 37.87 mmol) and N-phenyl- [1,1'-biphenyl] -4- Amine (10.21 g, 41.66 mmol) was completely dissolved in 200 ml of xylene and sodium tert-butoxide (4.73 g, 49.23 mmol) was added and bis (tri-tert-butylphosphine) palladium , 0.38 mmol), and the mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, and the salt was removed by filtration. The xylene was concentrated under reduced pressure and the residue was subjected to column chromatography with tetrahydrofuran: hexane = 1: 10 to prepare Compound 2 (17.42 g, yield: 81%).

MS [M + H] &lt; ⁺ &gt; = 562

< Manufacturing example  3>

9-phenyl-9H-fluorene (15.0 g, 37.87 mmol), di [(1,1'-biphenyl) -4-yl) Amine (13.37 g, 41.66 mmol) was completely dissolved in 200 ml of xylene and sodium tert-butoxide (4.73 g, 49.23 mmol) was added and bis (tri-tert-butylphosphine) palladium , 0.38 mmol) were added thereto, followed by heating and stirring for 5 hours. The temperature was lowered to room temperature, and the salt was removed by filtration. Xylene was concentrated under reduced pressure, and the residue was subjected to column chromatography with tetrahydrofuran: hexane = 1: 6 to obtain Compound 3 (21.67 g, yield: 88%).

MS [M + H] &lt; ⁺ &gt; = 638

< Manufacturing example  4>

9-phenyl-9H-fluorene (15.0 g, 37.87 mmol), N - ([1,1'-biphenyl] -4- ) -9,9-dimethyl-9H-fluorene-2-amine (13.37 g, 41.66 mmol) was completely dissolved in 200 ml of xylene and sodium tert-butoxide (4.73 g, 49.23 mmol) , And bis (tri-tert-butylphosphine) palladium (0.19 g, 0.38 mmol) were added thereto, followed by heating and stirring for 3 hours. The temperature was lowered to room temperature, and the salt was removed by filtration. Xylene was concentrated under reduced pressure, and the residue was subjected to column chromatography with tetrahydrofuran: hexane = 1: 7 to prepare Compound 4 (22.45 g, yield: 87%).

MS [M + H] &lt; ⁺ &gt; = 678

< Manufacturing example  5>

9-phenyl-9H-fluorene (15.0 g, 37.87 mmol), N - ([1,1'-biphenyl] -4- ) - [1,1'-biphenyl] -2-amine (13.37g, 41.66mmol) was completely dissolved in 200ml of xylene, sodium tert-butoxide (4.73g, 49.23mmol) Bis (tri-tert-butylphosphine) palladium (0.19 g, 0.38 mmol) was added and the mixture was heated with stirring for 4 hours. The temperature was lowered to room temperature, and the salt was removed by filtration. Xylene was concentrated under reduced pressure, and the residue was subjected to column chromatography with tetrahydrofuran: hexane = 1: 9 to prepare Compound 5 (19.12 g, yield: 81%).

MS [M + H] &lt; ⁺ &gt; = 638

< Manufacturing example  6>

9-phenyl-9H-fluorene (15.0 g, 37.87 mmol), N - ([1,1'-biphenyl] -4- ) -9,9-dimethyl-9H-fluoren-2-amine (13.37 g, 41.66 mmol) was completely dissolved in 200 ml of xylene and sodium tert-butoxide (4.73 g, 49.23 mmol) , And bis (tri-tert-butylphosphine) palladium (0.19 g, 0.38 mmol) were added thereto, followed by heating and stirring for 6 hours. The temperature was lowered to room temperature, and the salt was removed by filtration. Xylene was concentrated under reduced pressure, and the residue was subjected to column chromatography with tetrahydrofuran: hexane = 1: 12 to prepare Compound 6 (18.62 g, yield: 71%).

MS [M + H] &lt; ⁺ &gt; = 678

< Manufacturing example  7>

(15.0 g, 37.87 mmol), (4-diphenylamino) phenylboronic acid (13.14 g, 45.44 mmol) were added to a 500 ml round bottom flask under a nitrogen atmosphere. mmol) was completely dissolved in 200 ml of tetrahydrofuran, and 2M potassium carbonate aqueous solution (100 ml) was added. Tetrakis- (triphenylphosphine) palladium (1.31 g, 1.14 mmol) was added and the mixture was heated with stirring for 2 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 300 ml of ethanol to obtain Compound 7 (18.85 g, yield: 89%).

MS [M + H] &lt; ⁺ &gt; = 562

< Manufacturing example  8>

Phenyl) -9H-fluorene (15.0 g, 37.87 mmol) and 4- (biphenyl-4-yl (phenyl) amino) phenyl (16.59 g, 45.44 mmol) was completely dissolved in 300 ml of tetrahydrofuran, then 2M potassium carbonate aqueous solution (150 ml) was added, tetrakis- (triphenylphosphine) palladium (1.31 g, 1.14 mmol) Lt; / RTI &gt; The temperature was lowered to room temperature, and the water layer was removed. The organic layer was dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from ethyl acetate (300 ml) to obtain Compound 8 (21.55 g, yield: 88%).

MS [M + H ] ⁺ = 638

< Manufacturing example  9>

9-phenyl-9H-fluorene (15.0 g, 37.87 mmol) and 4 - ((dibiphenyl-4-yl) amino) phenylboron were added to a 500 ml round bottom flask under a nitrogen atmosphere. (Triphenylphosphine) palladium (1.31 g, 1.14 mmol) was added thereto, and the mixture was stirred for 4 hrs. Lt; / RTI &gt; The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from ethyl acetate (300 ml) to obtain Compound 9 (25.71 g, yield: 93%).

MS [M + H] &lt; ⁺ &gt; = 714

< Manufacturing example  10>

9-phenyl-9H-fluorene (15.0 g, 37.87 mmol) and 4- ([l, l'-biphenyl] -4- (21.86, 45.44 mmol) was completely dissolved in 300 ml of tetrahydrofuran, followed by addition of 2M aqueous potassium carbonate solution (150 ml), tetrakis (triphenylphosphine) palladium - (triphenylphosphine) palladium (1.31 g, 1.14 mmol) was added thereto, followed by heating and stirring for 4 hours. The temperature was lowered to room temperature, and the water layer was removed. The organic layer was dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from ethyl acetate (300 ml) to obtain Compound 10 (25.48 g, yield: 89%).

MS [M + H] &lt; ⁺ &gt; = 754

< Manufacturing example  11>

(15.0 g, 37.87 mmol), 4 - ([1,1'-biphenyl] -2- (2-bromophenyl) (20.04 g, 45.44 mmol) in tetrahydrofuran was completely dissolved in 300 ml of tetrahydrofuran, followed by addition of 2M aqueous potassium carbonate solution (150 ml), tetrakis (triphenylphosphine) palladium - (triphenylphosphine) palladium (1.31 g, 1.14 mmol) was added thereto, followed by heating and stirring for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from ethyl acetate (300 ml) to prepare the above compound 11 (23.53 g, yield: 84%).

MS [M + H] &lt; ⁺ &gt; = 714

< Manufacturing example  12>

(15.0 g, 37.87 mmol), 4 - ([1,1'-biphenyl] -2- (2-bromophenyl) (21.86, 45.44 mmol) was completely dissolved in 300 ml of tetrahydrofuran, followed by addition of 2M aqueous potassium carbonate solution (150 ml), tetrakis (triphenylphosphine) palladium - (triphenylphosphine) palladium (1.31 g, 1.14 mmol) was added thereto, followed by heating and stirring for 4 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from ethyl acetate (300 ml) to give Compound 12 (25.48 g, yield: 89%).

MS [M + H] &lt; ⁺ &gt; = 754

< Manufacturing example  13>

Benzo [c] fluorene (15.0 g, 33.63 mmol) and N-phenyl- [1,1'-biphenyl ] -4-amine (9.06 g, 36.99 mmol) was completely dissolved in 250 ml of xylene and sodium tert-butoxide (4.20 g, 43.72 mmol) Palladium (0.17 g, 0.34 mmol) was added thereto, followed by heating and stirring for 3 hours. The temperature was lowered to room temperature, and the salt was removed by filtration. The xylene was concentrated under reduced pressure, and the residue was subjected to column chromatography with tetrahydrofuran: hexane = 1: 6 to obtain Compound 13 (19.55 g, yield: 84%).

MS [M + H] &lt; ⁺ &gt; = 612

< Manufacturing example  14>

Benzo [c] fluorene (15.0 g, 33.63 mmol) and 9,9-dimethyl-N-phenyl-9H- (9.06 g, 36.99 mmol) was completely dissolved in 250 ml of xylene and sodium tert-butoxide (4.20 g, 43.72 mmol) was added, and bis (tri-tert-butylphosphine ) Palladium (0.17 g, 0.34 mmol) was added thereto, followed by heating and stirring for 5 hours. The temperature was lowered to room temperature, and the salt was removed by filtration. Xylene was concentrated under reduced pressure, and the residue was subjected to column chromatography with tetrahydrofuran: hexane = 1: 7 to prepare Compound 14 (17.41 g, yield: 78%).

MS [M + H] &lt; ⁺ &gt; = 652

< Manufacturing example  15>

Phenyl-9H-indino [l, 2- l] phenanthrene (15.0 g, 33.06 mmol) and N-phenyl- [l, Biphenyl] -4-amine (8.91 g, 36.37 mmol) was dissolved in 250 ml of xylene and sodium-tert-butoxide (3.18 g, 43.72 mmol) -Butylphosphine) palladium (0.16 g, 0.33 mmol) were added thereto, and the mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, and the salt was removed by filtration. The xylene was concentrated under reduced pressure and the residue was subjected to column chromatography with tetrahydrofuran: hexane = 1: 6 to prepare Compound 15 (19.55 g, yield: 84%).

MS [M + H] &lt; ⁺ &gt; = 662

< Experimental Example  1>

<Experimental Example 1-1>

A glass substrate coated with a thin ITO (indium tin oxide) film having a thickness of 100 nm was immersed in distilled water containing detergent and washed with ultrasonic waves. In this case, Fischer Co. was used as a detergent, and distilled water filtered by a filter of Millipore Co. was used as distilled water. 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, and methanol, dried, and then transported to a plasma cleaner. Further, the substrate was cleaned using oxygen plasma for 5 minutes, and then the substrate was transported by a vacuum evaporator.

On this ITO transparent electrode, hexanitrile hexaazatriphenylene (HAT) of the following formula was thermally vacuum deposited to a thickness of 50 nm to form a hole injection layer.

[LINE]

N-phenylamino] biphenyl (NPB) (300 Å) was vacuum-deposited on the hole injection layer to form a hole transport layer, which is a material for transporting holes, and the following compound 4-4'-bis [N- (1-naphthyl) Respectively.

[NPB]

Subsequently, the following compound 1 was vacuum deposited on the hole transport layer to a thickness of 100 ANGSTROM to form an electron blocking layer.

[Compound 1]

Subsequently, BH and BD were vacuum deposited on the electron blocking layer to a film thickness of 30 nm at a weight ratio of 25: 1 to form a light emitting layer.

[BH]

[BD]

[ET1]

[LiQ]

The compound ET1 and the compound LiQ (Lithium Quinolate) were vacuum deposited on the light emitting layer at a weight ratio of 1: 1 to form an electron injecting and transporting layer having a thickness of 30 nm. Lithium fluoride (LiF) and aluminum having a thickness of 200 nm were sequentially deposited on the electron injecting and transporting layer to form a cathode.

Was maintained at a vapor deposition rate of 0.4 to 0.07nm / sec for organic material in the above process, the lithium fluoride of the cathode was maintained at the deposition speed of 0.03nm / sec, aluminum is 0.2nm / sec, the degree of vacuum upon deposition ⅹ10 2 ^{- 7} to 5 x ¹⁰ &lt; ^-6 &gt; torr. Thus, an organic light emitting device was fabricated.

<Experimental Example 1-2>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that Compound 2 was used instead of Compound 1 in Experimental Example 1-1.

<Experimental Example 1-3>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that Compound 3 was used instead of Compound 1 in Experimental Example 1-1.

<Experimental Example 1-4>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that Compound 4 was used instead of Compound 1 in Experimental Example 1-1.

<Experimental Example 1-5>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that Compound 5 was used instead of Compound 1 in Experimental Example 1-1.

<Experimental Example 1-6>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that Compound 6 was used instead of Compound 1 in Experimental Example 1-1.

<Experimental Example 1-7>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 7 was used instead of Compound 1 in Experimental Example 1-1.

<Experimental Example 1-8>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that Compound 8 was used instead of Compound 1 in Experimental Example 1-1.

<Experimental Example 1-9>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that Compound 9 was used instead of Compound 1 in Experimental Example 1-1.

<Experimental Example 1-10>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that Compound 10 was used instead of Compound 1 in Experimental Example 1-1.

<Experimental Example 1-11>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that Compound 11 was used instead of Compound 1 in Experimental Example 1-1.

<Experimental Example 1-12>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that Compound 12 was used instead of Compound 1 in Experimental Example 1-1.

<Experimental Example 1-13>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that Compound 13 was used instead of Compound 1 in Experimental Example 1-1.

<Experimental Example 1-14>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that Compound 14 was used instead of Compound 1 in Experimental Example 1-1.

<Experimental Example 1-15>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that Compound 15 was used instead of Compound 1 in Experimental Example 1-1.

&Lt; Comparative Example 1-1 >

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that Compound EB1 was used instead of Compound 1 in Experimental Example 1-1.

[EB1]

&Lt; Comparative Example 1-2 >

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that the following compound EB2 was used in place of Compound 1 in Experimental Example 1-1.

[EB2]

&Lt; Comparative Example 1-3 >

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that Compound EB3 was used instead of Compound 1 in Experimental Example 1-1.

[EB3]

&Lt; Comparative Example 1-4 >

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that Compound EB4 was used instead of Compound 1 in Experimental Example 1-1.

[EB4]

&Lt; Comparative Example 1-5 >

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that Compound EB5 was used in place of Compound 1 in Experimental Example 1-1.

[EB5]

When current was applied to the organic light-emitting devices manufactured by Experimental Examples 1-1 to 1-15 and Comparative Examples 1-1 to 1-5, the results shown in Table 1 were obtained.

division compound
(Electron blocking layer) Voltage
(V @ 10 mA / cm ² ) efficiency
(cd / A @ 10mA / cm 2) life span
(T95) Experimental Example 1-1 Compound 1 3.79 6.65 76 Experimental Example 1-2 Compound 2 3.64 6.75 72 Experimental Example 1-3 Compound 3 3.75 6.66 73 Experimental Examples 1-4 Compound 4 3.96 6.31 75 Experimental Examples 1-5 Compound 5 3.93 6.42 79 Experimental Example 1-6 Compound 6 3.82 6.47 74 Experimental Example 1-7 Compound 7 3.80 6.51 86 Experimental Examples 1-8 Compound 8 3.87 6.35 88 Experimental Examples 1-9 Compound 9 3.86 6.34 81 Experimental Example 1-10 Compound 10 3.85 6.31 85 Experimental Example 1-11 Compound 11 3.85 6.33 87 Experimental Example 1-12 Compound 12 3.81 6.32 88 Experimental Example 1-13 Compound 13 3.89 6.30 76 Experimental Example 1-14 Compound 14 3.89 6.50 70 Experimental Example 1-15 Compound 15 3.84 6.52 72 Comparative Example 1-1 EB1 4.73 5.41 21 Comparative Example 1-2 EB2 4.83 5.21 16 Comparative Example 1-3 EB3 4.63 4.81 42 Comparative Example 1-4 EB4 4.53 4.71 43 Comparative Example 1-5 EB5 5.03 4.51 46

As shown in Table 1, when compared with the organic light emitting device manufactured using the compound of the present invention as an electron blocking layer and the organic light emitting device of Comparative Examples 1-1 to 1-5, And exhibits excellent characteristics in terms of efficiency, driving voltage and / or stability of the organic light emitting device.

Specifically, the compound of the present invention has a structure in which an arylamine is substituted at the ortho position with diphenylfluorene, so that a compound having a higher efficiency than a structure in which an arylamine is substituted at a meta position or a para position And long life. That is, the device characteristics of ortho>> meta> para in terms of efficiency and ortho> para> meta in terms of life can be seen. The diamine type Comparative Example 1-5 is an electron blocking layer and its characteristics are very poor.

< Experimental Example  2>

&Lt; Experimental Examples 2-1 to 2-15 >

The same experiment was performed except that TCTA was used as an electron blocking layer in Experimental Example 1 and the compounds of Experimental Examples 1-1 to 1-15 were used instead of NPB as a hole transporting layer.

&Lt; Comparative Example 2-1 >

An organic luminescent device was fabricated in the same manner as in Experimental Examples 2-1 to 2-15 except that HT1 compound was used as a hole transport layer in Experimental Examples 2-1 to 2-15.

[HT1]

&Lt; Comparative Example 2-2 &

An organic light emitting device was fabricated in the same manner as in Experimental Examples 2-1 to 2-15 except that HT2 compounds were used as the hole transport layer in Experimental Examples 2-1 to 2-15.

 [HT2]

&Lt; Comparative Example 2-3 >

An organic light emitting device was fabricated in the same manner as in Experimental Examples 2-1 to 2-15, except that the compound of HT3 described below was used as the hole transport layer in Experimental Examples 2-1 to 2-15.

 [HT3]

&Lt; Comparative Example 2-4 &

An organic light emitting device was fabricated in the same manner as in Experimental Examples 2-1 to 2-15 except that HT4 compounds described below were used as the hole transport layer in Experimental Examples 2-1 to 2-15.

 [HT4]

&Lt; Comparative Example 2-5 &

An organic light emitting device was fabricated in the same manner as in Experimental Examples 2-1 to 2-15 except that HT5 compound was used as a hole transport layer in Experimental Examples 2-1 to 2-15.

 [HT5]

When currents were applied to the organic light emitting devices fabricated by Experimental Examples 2-1 to 2-15 and Comparative Examples 2-1 to 2-5, the results shown in Table 2 were obtained.

division compound
(Hole transport layer) Voltage
(V @ 10 mA / cm ² ) efficiency
(cd / A @ 10mA / cm 2) life span
(T95) Experimental Example 2-1 Compound 1 4.79 7.65 96 EXPERIMENTAL EXAMPLE 2-2 Compound 2 4.64 7.75 92 Experimental Example 2-3 Compound 3 4.75 7.66 93 Experimental Example 2-4 Compound 4 4.96 7.31 95 Experimental Example 2-5 Compound 5 4.93 7.42 99 Experimental Examples 2-6 Compound 6 4.82 7.47 94 Experimental Example 2-7 Compound 7 4.80 7.51 106 Experimental Examples 2-8 Compound 8 4.87 7.35 108 Experimental Examples 2-9 Compound 9 4.86 7.34 101 Experimental Example 2-10 Compound 10 4.85 7.31 105 Experimental Example 2-11 Compound 11 4.85 7.33 107 Experimental Examples 2-12 Compound 12 4.81 7.32 108 Experimental Example 2-13 Compound 13 4.89 7.30 96 Experimental Example 2-14 Compound 14 4.89 7.50 90 Experimental Example 2-15 Compound 15 4.84 7.52 92 Comparative Example 2-1 HT1 5.73 6.41 41 Comparative Example 2-2 HT2 5.83 6.21 36 Comparative Example 2-3 HT3 5.63 5.81 62 Comparative Example 2-4 HT4 5.53 5.71 63 Comparative Example 2-5 HT5 6.03 5.51 66

As shown in Table 2, the organic light emitting device manufactured using the compound of the present invention as a hole transporting layer shows characteristics superior to those of Comparative Examples 2-1 to 2-5 in terms of efficiency, driving voltage and / or stability . In addition, as in the results of Table 1 using the compound of the present invention as an electron blocking layer, ortho >> meta> para, and ortho> para> (meta) can be seen.

From the results of Tables 1 and 2, it can be confirmed that the compounds of the present invention are applicable not only to electron blocking ability but also to hole transporting ability and applicable to organic light emitting devices.

While the present invention has been described with reference to the preferred embodiments (the electron blocking layer and the hole transport layer), the present invention is not limited thereto and can be variously modified within the scope of the claims and the detailed description of the invention And this also belongs to the category of invention.

10, 11: Organic light emitting device
20: substrate
30: first electrode
40: light emitting layer
50: second electrode
60: Hole injection layer
70: hole transport layer
80: electron blocking layer
90: electron transport layer
100: electron injection layer

Claims (9)

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

In Formula 1,
L is a direct bond; Or an arylene group,
Ar ₁ and Ar ₂ are the same or different and are each independently selected from the group consisting of deuterium, a halogen group, an alkyl group, a cyano group, a silyl group, a trimethylsilyl group, an aryl group, a dibenzothiophene group, a dibenzofurane group, An aryl group which is substituted or unsubstituted with at least one of a carbazole group and a carbazole group,
R ₁ to R ₉ are each hydrogen,
R ₁₀ to R ₁₇ are each hydrogen or may combine with adjacent groups to form a ring. The method according to claim 1,
L is a direct bond; A phenylene group; Biphenylene group; Or a naphthylene group. A compound according to claim 1, wherein Ar ₁ and Ar ₂ are to be, which can be selected from among the group of the formula 1 and 2.
[Group 1]

[Group 2]

The compound according to claim 1, wherein the compound represented by Formula 1 is any one selected from the following structural formulas:

A first electrode; A second electrode facing the first electrode; And at least one organic compound layer provided between the first electrode and the second electrode, wherein at least one of the organic compound layers comprises a compound according to any one of claims 1 to 4. 2. The organic electronic device according to claim 1, Electronic device. The organic electronic device according to claim 5, wherein the organic material layer includes a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer comprises the compound. The organic electronic device according to claim 5, wherein the organic layer comprises an electron blocking layer, and the electron blocking layer comprises the compound. [6] The organic electroluminescent device according to claim 5, wherein the organic material layer is a hole transporting layer or an electron blocking layer, and the organic electronic device further comprises one or more layers selected from the group consisting of a hole transporting layer, Organic electronic device. The organic electronic device according to claim 5, wherein the organic electronic device is selected from the group consisting of an organic light emitting device, an organic phosphorescent device, an organic solar cell, an organic photoconductor (OPC), and an organic transistor.

Images