KR20170113340A - Compound and organic electronic device comprising 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 and an organic electronic device including the compound.

This application claims the benefit of Korean Patent Application No. 10-2016-0037220, filed on March 28, 2016, to the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference.

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,

Q is a condensed polycyclic aromatic group having 10 to 30 carbon atoms; Or a monocyclic or polycyclic heterocyclic group,

L ₁ and L ₂ are the same or different and are each independently 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 alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

R ₁ to R ₃ are the same or different and each independently hydrogen; heavy hydrogen; A halogen group; Cyano; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

a is an integer of 1 to 4,

b is an integer of 1 to 4,

c is an integer of 1 to 4,

When a is 2 or more, two or more R < ₁ > s are the same or different from each other,

When b is 2 or more, two or more R < ₂ &_gt; s are the same or different from each other,

When c is 2 or more, two or more R ₃ are the same or different from each other.

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).

The compound of Formula 1 may have properties suitable for use as an organic material layer used in an organic light emitting device by introducing various substituents into the core structure. Specifically, it is as follows.

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; Arylphosphine groups; Phosphine oxide groups; An aryl group; Silyl group; And a heterocyclic 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 >

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 50. 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 cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and specifically includes cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, But are not limited to, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert- butylcyclohexyl, cycloheptyl, Do not.

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 30 carbon atoms. Specific examples of the monocyclic aryl group include, but are not limited to, a phenyl group, a biphenyl group, a terphenyl group, a quaterphenyl group, and the like.

When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited. And preferably has 6 to 30 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 50 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.

In the present specification, the heterocycle may be selected from the examples of the above-mentioned cycloalkyl group, aryl group or heteroaryl group except monosubstituted, monocyclic or polycyclic, aliphatic or aromatic or condensed form thereof . 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 condensed polycyclic aromatic group means an aromatic hydrocarbon ring and includes, for example, naphthylene, anthracene, phenanthrene, pyrene and the like, but is not limited thereto.

In the present specification, the monocyclic or polycyclic heterocyclic group means a ring containing at least one of N, O, or S atoms as a hetero atom, and includes, for example, pyridine, pyrimidine, pyridazine, triazine, Thiopyran, diazine, or pyrazine. Examples of the heteroaryl group include, but are not limited to, the above-mentioned heteroaryl 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.

In one embodiment of the present specification, Q is a condensed polycyclic aromatic group having 10 to 30 carbon atoms; Or a monocyclic or polycyclic heterocyclic group.

In one embodiment of the present disclosure, Q is substituted or unsubstituted naphthylene.

In one embodiment of the present disclosure, Q is substituted or unsubstituted phenanthrene.

In one embodiment of the present disclosure, Q is naphthylene.

In one embodiment of the present disclosure, Q is phenanthrene.

In one embodiment of the present disclosure, L ₁ and L ₂ are the same or different from each other, and are each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group.

In one embodiment of the present specification, L ₁ and L ₂ are substituted or unsubstituted phenylene groups.

In one embodiment of the present disclosure, L ₁ and L ₂ are phenylene groups.

In one embodiment of the present specification, L ₁ and L ₂ are substituted or unsubstituted biphenylene groups.

In one embodiment of the present specification, L ₁ and L ₂ are biphenylene groups.

In one embodiment of the present specification, Ar ₁ and Ar ₂ are the same or different and are each independently a substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

In one embodiment of the present specification, Ar ₁ and Ar ₂ are the same or different and each independently represents a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted N-containing heteroaryl group.

In one embodiment of the present specification, Ar ₁ and Ar ₂ are the same or different and each independently represents a substituted or unsubstituted aryl group having 10 to 30 carbon atoms; Or a heteroaryl group containing 3 or less substituted or unsubstituted N atoms.

In one embodiment of the present specification, Ar ₁ and Ar ₂ are the same or different and each independently represents an aryl group having 10 to 30 carbon atoms; Or a heteroaryl group containing 3 or less of N substituted or unsubstituted with an aryl group.

In one embodiment of the present specification, Ar ₁ and Ar ₂ are the same or different and each independently represents a substituted or unsubstituted pyridine group, a substituted or unsubstituted pyrimidine group, a substituted or unsubstituted triazine group, a substituted Or an unsubstituted triphenylene group or a substituted or unsubstituted carbazole group.

In one embodiment of the present specification, Ar ₁ and Ar ₂ are the same or different and each independently represents a pyridine group substituted or unsubstituted with an aryl group, a pyrimidine group substituted or unsubstituted with an aryl group, A substituted triazine group, a triphenylene group or a carbazole group.

In one embodiment of the present specification, Ar ₁ is a pyridine group in which the aryl group is substituted or unsubstituted.

In one embodiment of the present specification, Ar ₁ is a pyridine group in which the phenyl group is substituted or unsubstituted.

In one embodiment of the present specification, Ar < ₁ > is a pyridine group.

In one embodiment of the present specification, Ar ₁ is a pyrimidine group in which the aryl group is substituted or unsubstituted.

In one embodiment of the present specification, Ar ₁ is a pyrimidine group in which the phenyl group is substituted or unsubstituted.

In one embodiment of the present specification, Ar ₁ is a triazine group in which the aryl group is substituted or unsubstituted.

In one embodiment of the present specification, Ar ₁ is a triazine group in which the phenyl group is substituted or unsubstituted.

In one embodiment of the present specification, Ar ₁ represents a substituted or unsubstituted triphenylene group; Or a substituted or unsubstituted carbazole group.

In one embodiment of the present specification, Ar ₁ is a carbazole group.

In another embodiment, Ar ₁ is a triphenylene group.

In one embodiment of the present specification, Ar ₂ is a pyridine group in which the aryl group is substituted or unsubstituted.

In one embodiment of the present specification, Ar ₂ is a pyridine group in which the phenyl group is substituted or unsubstituted.

In one embodiment of the present specification, Ar ₂ is a pyridine group.

In one embodiment of the present specification, Ar ₂ is a pyrimidine group in which the aryl group is substituted or unsubstituted.

In one embodiment of the present specification, Ar ₂ is a pyrimidine group in which the phenyl group is substituted or unsubstituted.

In one embodiment of the present specification, Ar ₂ is a triazine group in which the aryl group is substituted or unsubstituted.

In one embodiment of the present specification, Ar ₂ is a triazine group in which the phenyl group is substituted or unsubstituted.

In one embodiment of the present specification, Ar ₂ represents a substituted or unsubstituted triphenylene group; Or a substituted or unsubstituted carbazole group.

In one embodiment of the present specification, Ar ₂ is a carbazole group.

In another embodiment, Ar ₂ is a triphenylene group.

In one embodiment of the present specification, R ₁ to R ₃ are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; Cyano; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

In one embodiment of the present disclosure, R ₁ to R ₃ are the same or different and each independently hydrogen.

In one embodiment of the present invention, the formula (1) may be represented by the following formula (1-A) or (1-B).

[Chemical Formula 1-A]

[Chemical Formula 1-B]

In the above formulas (1-A) and (1-B)

Q, L ₁ , L ₂ , Ar ₂ , R ₁ to R ₃ , and a to c are the same as defined in Formula 1,

At least one of X ₁ to X ₃ is N and the others are the same or different and are each independently N or CR,

At least one of X ₄ to X ₆ is N and the others are the same or different and are each independently N or CR,

Ar ₃ to Ar ₆ are the same or different and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

In one embodiment of the present specification, Ar ₃ to Ar ₆ are the same or different from each other, and each independently hydrogen; Or a substituted or unsubstituted aryl group.

In another embodiment, Ar ₃ to Ar ₆ are the same or different and are each independently selected from the group consisting of hydrogen; Or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

In another embodiment, Ar ₃ to Ar ₆ are the same or different and are each independently selected from the group consisting of hydrogen; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In another embodiment, Ar ₃ to Ar ₆ are the same or different and are each independently selected from the group consisting of hydrogen; Or an aryl group having 6 to 30 carbon atoms.

In another embodiment, Ar ₃ to Ar ₆ are the same or different and are each independently selected from the group consisting of hydrogen; Or a phenyl group.

In one embodiment of the present disclosure, R is hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

In yet another embodiment, R is hydrogen.

In one embodiment of the present invention, the formula (1) may be represented by any one of the following formulas (2) to (5).

(2)

(3)

[Chemical Formula 4]

[Chemical Formula 5]

In the above formulas 2 to 5,

L ₁ , L ₂ , Ar ₁ , Ar ₂ , R ₁ to R ₃ , and a to c are the same as defined in the above formula (1)

R ₄ and R ₅ are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; Cyano; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

d is an integer of 1 to 6,

e is an integer of 1 to 8,

When d is 2 or more, two or more R < ₄ > s are the same or different from each other,

When e is 2 or more, R ₅ of 2 or more are the same or different from each other.

In one embodiment of the present disclosure, R ₄ and R ₅ are the same or different and are each independently hydrogen.

According to one embodiment of the present invention, the compound of Formula 1 may be any one selected from the following structural formulas.

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.

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 to be understood that the component may include other components as well, without departing from the scope of the present invention.

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 light emitting layer, and the light emitting layer includes the compound.

In another embodiment, the organic layer includes a light emitting layer, the light emitting layer includes a host material, and the host material includes the compound.

The host material includes 50% by weight to 99% by weight, preferably 60% by weight to 95% by weight, and more preferably 80% by weight to 90% by weight with respect to the total luminescent layer material.

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 transporting layer or an electron injecting layer, and the electron transporting layer or the electron injecting 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 light emitting element is a hole injection layer, a hole transport layer, A light emitting layer, an electron transporting layer, an electron injecting layer, a hole blocking layer, and an electron blocking layer.

The organic compound layer containing the compound includes the compound as a host and can be used in combination with an iridium (Ir) dopant.

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 material layer includes two or more electron transporting layers, and at least one of the two or more electron transporting layers includes the above compound. Specifically, in one embodiment of the present specification, the compound may be contained in one of the two or more electron transporting layers, and may be included in each of two or more electron transporting layers.

In addition, in one embodiment of the present specification, when the compound is contained in each of the two or more electron transporting layers, the materials other than the above compounds may be the same or different from each other.

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.

When the organic compound layer containing the compound of Formula 1 is an electron transporting layer, the electron transporting layer may further include an n-type dopant. As the n-type dopant, those known in the art can be used, and for example, a metal or a metal complex can be used. According to an example, the electron transport layer containing the compound of Formula 1 may further include LiQ.

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.

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 electron blocking layer is a layer which can prevent the holes injected from the hole injection layer from entering the electron injection layer through the light emitting layer to improve the lifetime and efficiency of the device. If necessary, And may be formed in an appropriate portion between the injection layers.

The light emitting material of the light emitting layer 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 high 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.

Examples of the dopant material include an aromatic amine derivative, a styrylamine compound, a boron complex, a fluoranthene compound, and a metal complex. Specific examples of the aromatic amine derivatives include condensed aromatic ring derivatives having substituted or unsubstituted arylamino groups, and examples thereof include pyrene, anthracene, chrysene, and peripherrhene having an arylamino group. Examples of the styrylamine compound include substituted or unsubstituted Wherein at least one aryl vinyl group is substituted with at least one aryl vinyl group, and at least one substituent selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group is substituted or unsubstituted. Specific examples thereof include, but are not limited to, styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like. Examples of the metal complex include iridium complex, platinum complex, and the like, but are not limited thereto.

The electron transporting material of the electron transporting layer is a layer that transports electrons from the electron injecting layer to the electron transporting layer and transports electrons from the cathode to the light emitting layer. This large material 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 having a low work function followed by an aluminum layer or a 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 represented by Formula 1 may be included in an organic solar cell or an organic transistor in addition to an organic light emitting device.

The 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.

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 >

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

(1) Preparation of compound of formula 1B

Potassium carbonate (118.8 g, 859.62 mmol) was added with stirring to 1000 ml of acetonitrile in 500 ml of water with stirring under nitrogen atmosphere, to which was added 4-chlorophenyl) (4-hydroxyphenyl) methanone (Compound 1A, 100.0 g, 429.81 mmol) . Then, 1-butanesulfonyl fluoride (194.8 g, 644.72 mmol) was added slowly while heating with a water bath. The reaction was then terminated after about 1 hour of reaction. After completion of the reaction, the temperature was lowered to room temperature, and the water layer and the organic layer were separated. The organic layer was distilled under reduced pressure to prepare Compound 1B (210 g, 95%).

(2) Preparation of formula 1C

The compound 1B (210.2 g, 408.36 mmol), bis (pinacolato) diboron (103.7 g, 408.36 mmol) and potassium acetate (120.2 g, 1225.08 mmol) were mixed in a nitrogen atmosphere and 1000 ml of tetrahydrofuran And heated with stirring. [1,1'-bis (diphenylphosphino) ferrocene] dichloropalladium (II) (1.8 g, 2.45 mmol) was added under reflux and the mixture was heated and stirred for 24 hours. After completion of the reaction, the temperature was lowered to room temperature and then filtered. Water was poured into the filtrate, extracted with chloroform, and the organic layer was dried over anhydrous magnesium sulfate. After distillation under reduced pressure, recrystallization from ethanol gave Compound 1C (100.0 g, 72%).

(3) Preparation of intermediate 1

The compound 1C (39.0 g, 145.67 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (compound 1D, 50.0 g, 145.67 mmol) were added to 300 ml of tetrahydrofuran in a nitrogen atmosphere, Followed by stirring and refluxing. Then, potassium carbonate (60.4 g, 437.02 mmol) was dissolved in 200 ml of water, and the mixture was sufficiently stirred. Tetraquistriphenylphosphinopalladium (5.0 g, 4.37 mmol) was added thereto. After 12 hours of reaction, the temperature was lowered to room temperature and filtered. The filtrate was extracted with chloroform and water, and then the organic layer was dried with magnesium sulfate. The organic layer was then distilled under reduced pressure and recrystallized using ethyl acetate. The resulting solid was filtered and dried to give Intermediate 1 (52.2 g, 80%).

< Synthetic example  2 > - Preparation of the compound represented by Intermediate 2

Compound 2A (30.0 g, 105.94 mmol) was added to 500 mL of anhydrous tetrahydrofuran and cooled to -78 ° C. Then, n-butyllithium (50.9 mL, 127.13 mmol) was slowly added dropwise over 30 minutes while stirring, and then reacted for 1 hour. Then, the intermediate 1 (28.5 g, 63.57) was put into a solid state, slowly warmed to room temperature, and reacted for 4 hours. After completion of the reaction by pouring water after the reaction, the water layer and the organic layer were separated, and the organic layer was distilled under reduced pressure to obtain the compound 2B. The resultant was added to 500 ml of acetic acid, and 1 to 2 drops of sulfuric acid was added thereto while stirring, followed by refluxing. After reacting for 2 hours, the resulting solid was filtered, and the filtrate was again dissolved in chloroform. After neutralization and extraction with water saturated with calcium carbonate, the organic layer was dried with magnesium sulfate. The organic layer was then distilled under reduced pressure and recrystallized using ethanol. The resulting solid was filtered and dried to give Intermediate 2 (26.2 g, 65%).

< Synthetic example  3> - Preparation of compound represented by Compound 1

In a nitrogen atmosphere, the intermediate 2 (10.0 g, 15.77 mmol), carbazole (Compound 3A, 3.2 g, 18.92 mmol) and sodium t-butoxide (1.8 g, 18.92 mmol) were added to 100 ml of xylene and stirred and refluxed. Then, bis (tri-tert-butylphosphine) palladium (0.2 g, 0.47 mmol) was added thereto. After 8 hours of reaction, the temperature was lowered to room temperature and filtered. The filtrate was extracted with chloroform and water, and then the organic layer was dried with magnesium sulfate. The organic layer was then distilled under reduced pressure and recrystallized using ethyl acetate. The resulting solid was filtered and dried to give Compound 1 (8.4 g, 71%).

MS: [M + H] &lt; + &gt; = 764

< Synthetic example  4> - Preparation of the compound represented by the compound 2

The intermediate 2 (10.0 g, 15.77 mmol) and the compound 4A (6.7 g, 18.92 mmol) were added to 200 ml of 1,4-dioxane in a nitrogen atmosphere, followed by stirring and refluxing. After dissolving potassium phosphate (10.0 g, 47.31 mmol) in 50 ml of water and stirring well, bis (dibenzylidineacetone) palladium (0.3 g, 0.47 mmol) and tricyclohexylphosphine (0.3 mg, 0.95 mmol) Respectively. After 18 hours of reaction, the temperature was lowered to room temperature and filtered. The filtrate was extracted with chloroform and water, and then the organic layer was dried with magnesium sulfate. The organic layer was then distilled under reduced pressure and recrystallized using ethyl acetate. The resulting solid was filtered and dried to give Compound 2 (8.3 g, 64%).

MS: [M + H] &lt; + &gt; = 826

< Synthetic example  5> - Preparation of the compound represented by the compound 3

(Intermediate 2) (Compound 5A) (Compound 3)

The intermediate 2 (10.0 g, 15.77 mmol) and the compound 5A (3.8 g, 18.92 mmol) were added to 200 ml of 1,4-dioxane in a nitrogen atmosphere, followed by stirring and refluxing. Then, potassium phosphate (10.0 g, 47.31 mmol) was dissolved in 50 ml of water and the mixture was thoroughly stirred. Then bis (dibenzylidineacetone) palladium (0.3 g, 0.47 mmol) and tricyclohexylphosphine (0.3 mg, 0.95 mmol) Respectively. After 18 hours of reaction, the temperature was lowered to room temperature and filtered. The filtrate was extracted with chloroform and water, and then the organic layer was dried with magnesium sulfate. The organic layer was then distilled under reduced pressure and recrystallized using ethyl acetate. The resulting solid was filtered and dried to give Compound 3 (7.9 g, 67%).

MS: [M + H] &lt; + &gt; = 752

< Synthetic example  6> - Preparation of the compound represented by the compound 4

(1) Preparation of intermediate 3

(THF) was prepared by mixing intermediate 2 (30.0 g, 47.31 mmol), bis (pinacolato) diboron (compound 6A, 13.2 g, 52.04 mmol) and potassium acetate (13.9 g, 141.92 mmol) And heated with stirring. (0.8 g, 1.42 mmol) and tri (cyclohexyl) phosphin (0.8 g, 2.84 mmol) were added to the solution under reflux and 24 [ Lt; / RTI &gt; for 1 hour. After completion of the reaction, the temperature was lowered to room temperature and then filtered. Water was poured into the filtrate, extracted with chloroform, and the organic layer was dried over anhydrous magnesium sulfate. After distillation under reduced pressure, the product was recrystallized from ethanol to obtain Intermediate 3 (26.4 g, 77%).

(2) Preparation of Compound 4

The compound 6B (5.0 g, 18.75 mmol) and the intermediate 3 (15.0 g, 20.62 mmol) were dissolved in 150 ml of tetrahydrofuran in a nitrogen atmosphere, followed by stirring and refluxing. Then, potassium carbonate (7.8 g, 56.24 mmol) was dissolved in 200 ml of water, and the mixture was sufficiently stirred. Tetraquistriphenylphosphinopalladium (0.6 g, 0.56 mmol) was added thereto. After 6 hours of reaction, the temperature was lowered to room temperature and filtered. The filtrate was extracted with chloroform and water, and then the organic layer was dried with magnesium sulfate. The organic layer was then distilled under reduced pressure and recrystallized using ethyl acetate. The resulting solid was filtered and dried to give Compound 4 (9.0 g, 55%).

MS: [M + H] &lt; + &gt; = 830

< Synthetic example  7> - Compound To 5  Preparation of indicated compounds

Compound 7A (5.0 g, 18.75 mmol) and Intermediate 3 (15.0 g, 20.62 mmol) were added to 150 ml of tetrahydrofuran in a nitrogen atmosphere, followed by stirring and refluxing. Then, potassium carbonate (7.8 g, 56.24 mmol) was dissolved in 200 ml of water, and the mixture was sufficiently stirred. Tetraquistriphenylphosphinopalladium (0.6 g, 0.56 mmol) was added thereto. After 6 hours of reaction, the temperature was lowered to room temperature and filtered. The filtrate was extracted with chloroform and water, and then the organic layer was dried with magnesium sulfate. The organic layer was then distilled under reduced pressure and recrystallized using ethyl acetate. The resulting solid was filtered and dried to give Compound 5 (6.8 g, 44%).

MS: [M + H] &lt; + &gt; = 831

< Example >

< Experimental Example  1-1>

A glass substrate (corning 7059 glass) coated with ITO (indium tin oxide) to a thickness of 1000 Å was placed in distilled water in which dispersant was dissolved and ultrasonically cleaned. The detergent was a product of Fischer Co. The distilled water was supplied by Millipore Co. Distilled water, which was secondly filtered with a filter of the product, was used. After the ITO was washed for 30 minutes, ultrasonic washing was repeated 10 times with distilled water twice. After the distilled water was washed, ultrasonic washing was performed in the order of isopropyl alcohol, acetone, and methanol solvent, followed by drying.

Hexanitrile hexaazatriphenylene was thermally vacuum deposited on the prepared ITO transparent electrode to a thickness of 500 Å to form a hole injection layer. HT1 (400 Å), which is a hole transporting 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. Compound 1 prepared in Synthesis Example 3 and LiQ (Lithium Quinolate) were vacuum deposited on the light emitting layer at a weight ratio of 1: 1 to form an electron injection and transport layer having a thickness of 350 Å. Lithium fluoride (LiF) and aluminum were deposited to a thickness of 2000 Å on the electron injecting and transporting layer sequentially to form a cathode.

Was maintained at a vapor deposition rate of 0.4 to 0.7Å / sec for organic material in the above process, the lithium fluoride of the cathode was 0.3Å / sec, aluminum is deposited at a rate of 2Å / sec, During the deposition, a vacuum 2 × 10 ^{- 7} to 5 x 10 &lt; ^-6 &gt; torr to manufacture an organic light emitting device.

< 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 as the electron transporting layer 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 as the electron transporting layer 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 as the electron transporting layer 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 as the electron transport layer in Experimental Example 1-1.

< Experimental Example  2-1>

The glass substrate coated with ITO (indium tin oxide) film with a thickness of 1,500 Å was immersed in distilled water containing detergent and washed with ultrasonic waves. At this time, a Fischer Co. product was used as a detergent, and distilled water, which was filtered with 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.

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.

N, N-bis- (1-naphthalenyl) -N, N-bis-phenyl- (1,1- biphenyl) -4,4- diamine compound of the following structure was deposited on the hole injection layer to a thickness of 400 Å The hole transport layer was formed by thermal vacuum deposition.

Subsequently, Compound 1 prepared in Synthesis Example 3 was deposited on the hole transport layer to a thickness of 300 ANGSTROM as a host and 10 wt% of Ir (ppy) ₃ dopant to form a light emitting layer. The following electron transport material was vacuum deposited on the light emitting layer to a thickness of 200 Å to form an electron injection and transport layer.

Lithium fluoride (LiF) and aluminum were deposited to a thickness of 12 Å on the electron injection and transport layer sequentially to form a cathode.

In the above process, the deposition rate of the organic material was maintained at 0.4 to 0.7 Å / sec, the deposition rate of lithium fluoride at the cathode was 0.3 Å / sec and the deposition rate of aluminum was maintained at 2 Å / sec. ^-7 to 5 × 10 ^- to maintain the ⁸ torr, it was produced in the organic light emitting device.

< Experimental Example  2-2>

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

< Experimental Example  2-3>

An organic light emitting device was fabricated in the same manner as in Experimental Example 2-1, except that Compound 3 was used instead of Compound 1 as the light emitting layer in Experimental Example 2-1.

< Experimental Example  2-4>

An organic light emitting device was fabricated in the same manner as in Experimental Example 2-1, except that Compound 4 was used instead of Compound 1 as the light emitting layer in Experimental Example 2-1.

< Experimental Example  2-5>

An organic light emitting device was fabricated in the same manner as in Experimental Example 2-1, except that Compound 5 was used instead of Compound 1 as the light emitting layer in Experimental Example 2-1.

< Comparative Example  1-1>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that the compound of ET1 was used instead of the compound 1 in Experimental Example 1-1.

< Comparative Example  1-2>

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

[ET2]

< Comparative Example  1-3>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that the compound of Formula 1 and ET3 were used in Experimental Example 1-1.

[ET3]

< Comparative Example  1-4>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that the compound of ET4 was used in place of Compound 1 in Experimental Example 1-1.

[ET4]

< Comparative Example  1-5>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that the compound of ET5 was used instead of the compound 1 in Experimental Example 1-1.

[ET5]

Experimental Example 1-1 to 1-5 and Comparative Examples 1-1 to compare the current density of the organic light emitting element 10 mA / cm ² prepared using each compound as the electron injecting and transporting layer as in the Example 1-5 (LT ₉₈ ) at a current density of 20 mA / cm ² , which was 98% of the initial luminance, was measured. The results are shown in Table 1 below.

< Comparative Example  2-1>

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

[EM2]

< Comparative Example  2-2>

An organic light emitting device was fabricated in the same manner as in Experimental Example 2-1, except that the compound of Formula 3 was used instead of the compound of Formula 1 in Experimental Example 2-1.

[ET3]

< Comparative Example  2-3>

An organic light emitting device was fabricated in the same manner as in Experimental Example 2-1, except that the compound of Formula 4 was used instead of the compound of Formula 1 in Experimental Example 2-1.

[ET4]

< Comparative Example  2-4>

An organic light emitting device was fabricated in the same manner as in Experimental Example 2-1, except that the compound of ET6 was used in place of the compound of Formula 1 in Experimental Example 2-1.

[ET6]

The organic light-emitting devices prepared using the respective compounds as the light-emitting layer materials as in Experimental Examples 2-1 to 2-5 and Comparative Examples 2-1 to 2-4 were driven at a current density of 10 mA / cm &lt; ^{2 &} The efficiency was measured and the time to reach 98% of initial luminance (LT ₉₈ ) was measured at a current density of 20 mA / cm ² . The results are shown in Table 1 below.

Experimental Example
(at 10 mA / cm 2) compound Voltage
(V @ 10 mA / cm 2) Current efficiency
(cd / A @ 10mA / cm2) Color coordinates
(x, y) Life Time 95% at 20mA / cm2 Experimental Example 1-1 Compound 1 3.81 6.80 (0.134, 0.133) 130 Experimental Example 1-2 Compound 2 3.70 7.05 (0.134, 0.133) 80 Experimental Example 1-3 Compound 3 3.90 6.75 (0.134, 0.133) 120 Experimental Examples 1-4 Compound 4 3.60 7.10 (0.134, 0.133) 75 Experimental Examples 1-5 Compound 5 3.64 7.22 (0.134, 0.133) 70 Experimental Example 2-1 Compound 1 (doping 10%) 4.10 66.5 (0.445, 0.543) 70 EXPERIMENTAL EXAMPLE 2-2 Compound 2 (doping 10%) 4.20 62.4 (0.450, 0.539) 60 Experimental Example 2-3 Compound 3 (doping 10%) 4.22 60.8 (0.448, 0.544) 80 Experimental Example 2-4 Compound 4 (doping 10%) 4.14 64.2 (0.455, 0.535) 77 Experimental Example 2-5 Compound 5 (doping 10%) 4.24 64.2 (0.455, 0.535) 90 Comparative Example 1-1 ET1 3.90 5.30 (0.134, 0.133) 120 Comparative Example 1-2 ET2 3.90 7.00 (0.132, 0.134) 5 Comparative Example 1-3 ET3 3.86 6.00 (0.133, 0.135) 60 Comparative Example 1-4 ET4 3.70 7.00 (0.134, 0.133) 25 Comparative Example 1-5 ET5 3.63 7.20 (0.134, 0.133) 40 Comparative Example 2-1 EM2 (doping 10%) 4.22 62.4 (0.452, 0.549) 33 Comparative Example 2-2 ET3 (doping 10%) 4.23 60.8 (0.447, 0.534) 42 Comparative Example 2-3 ET4 (doping 10%) 4.10 64.2 (0.454, 0.565) 19 Comparative Example 2-4 ET6 (doping 10%) 5.22 30.5 (0.452, 0.549) 5

As can be seen from the above Table 1, in the case of the organic light emitting device prepared by using the compound of the present invention as an electron transporting layer material, ET3 to ET5, which are similar to the structures of the compounds 1, 2 and 5 but are not condensation structures, And it shows excellent characteristics in terms of efficiency and lifetime. In addition, it can be seen that the current efficiency is superior to that of Comparative Example 1-1, which does not have the core structure of the present invention, in Examples 1-1 to 1-5.

In addition, it can be seen that the organic light emitting device manufactured by using the compound of the present invention as a light emitting layer material exhibits excellent characteristics particularly in terms of lifetime as compared with the materials of Comparative Examples 2-1 to 2-4.

While the present invention has been particularly shown and described with reference to exemplary embodiments thereof, it is to be understood that the invention is not limited to the disclosed exemplary embodiments, and that various changes and modifications may be made therein without departing from the spirit and scope of the 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 (12)

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

In Formula 1,
Q is a condensed polycyclic aromatic group having 10 to 30 carbon atoms; Or a monocyclic or polycyclic heterocyclic group,
L ₁ and L ₂ are the same or different and are each independently 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 alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
R ₁ to R ₃ are the same or different and each independently hydrogen; heavy hydrogen; A halogen group; Cyano; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
a is an integer of 1 to 4,
b is an integer of 1 to 4,
c is an integer of 1 to 4,
When a is 2 or more, two or more R &lt; ₁ &gt; s are the same or different from each other,
When b is 2 or more, two or more R &lt; ₂ &_gt; s are the same or different from each other,
When c is 2 or more, two or more R ₃ are the same or different from each other. The method according to claim 1,
Ar ₁ or Ar ₂ is a substituted or unsubstituted pyridine group; A substituted or unsubstituted pyrimidine group; A substituted or unsubstituted carbazole group; A substituted or unsubstituted triphenylene group; Or a substituted or unsubstituted triazine group. The compound according to claim 1, wherein the compound represented by Formula 1 is represented by Formula 1-A or 1-B:
[Chemical Formula 1-A]

[Chemical Formula 1-B]

In the above formulas (1-A) and (1-B)
Q, L ₁ , L ₂ , R ₁ to R ₃ , Ar ₂ and a to c are the same as defined in Formula 1,
At least one of X ₁ to X ₃ is N and the others are the same or different and are each independently N or CR,
At least one of X ₄ to X ₆ is N and the others are the same or different and are each independently N or CR,
R is hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
Ar ₃ to Ar ₆ are the same or different and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group. The compound according to claim 1, wherein the compound represented by Formula 1 is represented by any one of the following Formulas 2 to 5:
(2)

(3)

[Chemical Formula 4]

[Chemical Formula 5]

In the above formulas 2 to 5,
L ₁ , L ₂ , Ar ₁ , Ar ₂ , R ₁ to R ₃ , and a to c are the same as defined in the above formula (1)
R ₄ and R ₅ are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; Cyano; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
d is an integer of 1 to 6,
e is an integer of 1 to 8,
When d is 2 or more, two or more R &lt; ₄ &gt; s are the same or different from each other,
When e is 2 or more, R ₅ of 2 or more are the same or different from each other. The compound according to claim 1, wherein the compound of formula (1) is any one selected from the following compounds:

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 5. 2. The organic electronic device according to claim 1, Electronic device. The organic electronic device according to claim 6, wherein the organic layer includes a light emitting layer, and the light emitting layer comprises the compound. 7. The organic electronic device according to claim 6, 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 6, wherein the organic layer includes an electron injection layer or an electron transport layer, and the electron transport layer or the electron injection layer comprises the compound. 7. The organic electronic device according to claim 6, wherein the organic layer includes an electron blocking layer or a hole blocking layer, and the electron blocking layer or the hole blocking layer comprises the compound. 7. The organic electroluminescent device according to claim 6, wherein the organic electronic device is a hole injection layer, a hole transport layer, An electron injection layer, an electron transport layer, an electron blocking layer, and a hole blocking layer. The organic electronic device according to claim 6, 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.

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