KR20170094714A - Compound and organic electronic device using the same - Google Patents

Abstract

The present invention relates to a compound and an organic electronic device including the same. The present invention comprises: hydrogen; heavy hydrogen; a halogen group; a cyano group; an ester group; a carbonyl group; a substituted or non-substituted alkyl group; a substituted or non-substituted cyclo-alkyl group; a substituted or non-substituted alkoxy group; a substituted or non-substituted alkenyl group; a substituted or non-substituted aryl group; or a substituted or non-substituted heteroaryl group.

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.

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,

X is O, S or SO ₂ ,

Ar ₁ is a substituted or unsubstituted C ₆ to C ₄₀ aryl group,

At least one of R ₁ to R ₈ is any one selected from the following formulas (2) to (9), and the others are the same or different and each independently hydrogen; heavy hydrogen; A halogen group; A nitro group; Cyano; An ester group; A carbonyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

 (2)

(3)

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

(7)

[Chemical Formula 8]

[Chemical Formula 9]

In the above formulas 2 to 9,

Ar ₃ is the same or different and each independently represents a substituted or unsubstituted C ₁₀ to C ₆₀ aryl group; Or a substituted or unsubstituted C ₂ to C ₆₀ heteroaryl group,

Ar ₃ 'and Ar ₃ "are the same or different and each independently represents a substituted or unsubstituted C ₆ to C ₆₀ aryl group; Or a substituted or unsubstituted C ₂ to C ₆₀ heteroaryl group,

R is hydrogen; heavy hydrogen; A halogen group; A nitro group; Cyano; 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,

n is an integer of 0 to 4, and when n is an integer of 2 or more, plural Rs are the same or different,

m is an integer of 0 to 5, and when m is an integer of 2 or more, plural Rs are the same or different,

p is an integer of 0 to 7, and when p is an integer of 2 or more, plural Rs 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).

According to one embodiment of the present invention, the compound represented by Formula 1 includes S, O, and N, which are typical electron donors, and thus has an electron-rich core structure. In addition, due to the unique three-dimensional arrangement of the cores such as phenothiazine and phenoxazine, the amorphous form has a low crystallinity, which prevents the element from deteriorating due to the heat generated during manufacture or operation of the device, . ≪ / RTI >

In addition, heterocyclic groups containing N atoms are often used as electron acceptors because of their high electron affinity. By using these substituents as a green light emitting layer, an electron transporting layer and an electron injecting layer, it is possible to achieve the maximum efficiency by balancing holes and electrons in an OLED device.

According to one embodiment of the present disclosure, phenothiazine 5,5-dioxide can be prepared by oxidizing phenothiazine. In this case, by shortening the UV wavelength, (Blue shift) and can be used for blue light emission, hole transport layer, and electron suppression layer.

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

및

는 연결되는 부위를 의미한다.In the present specification,

And

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

In the present specification, the carbon number of the carbonyl group is not particularly limited, but is preferably 1 to 50 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

In the present specification, the number of carbon atoms of the ester group is not particularly limited, but is preferably 1 to 50 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.

In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 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 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, the alkoxy group may be linear, branched or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 20 carbon atoms. Specific examples include methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, N-hexyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, But is 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, 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 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.

According to an exemplary embodiment of the present disclosure, X is O, S, and SO _2.

According to one embodiment of the present disclosure, X is O.

According to one embodiment of the present disclosure, X is S.

According to an exemplary embodiment of the present disclosure, X is SO _2.

According to one embodiment of the present disclosure, Ar ₁ is a substituted or unsubstituted C ₆ to C ₄₀ aryl group.

According to one embodiment of the present invention, Ar ₁ is 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 triphenyl group , A substituted or unsubstituted pyrene group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted chrysenyl group, or a substituted or unsubstituted fluorenyl group.

According to one embodiment of the present invention, Ar ₁ is phenyl, biphenyl, terphenyl, naphthyl, triphenyl, pyrene, anthracenyl,

According to one embodiment of the present invention, Ar ₁ is a naphthyl group in which a phenyl group, biphenyl group, or naphthyl group is substituted or unsubstituted.

According to one embodiment of the present invention, Ar ₁ is a phenyl group, a biphenyl group, or a naphthyl group substituted with a naphthyl group.

According to one embodiment of the present disclosure, Ar ₁ is a naphthyl group substituted with a phenyl group.

According to one embodiment of the present disclosure, Ar ₁ is a naphthyl group.

According to one embodiment of the present invention, Ar ₁ is a phenyl group, a biphenyl group, or a terphenyl group in which a naphthyl group is substituted or unsubstituted.

According to one embodiment of the present invention, Ar ₁ is a phenyl group, a biphenyl group, or a terphenyl group substituted with a naphthyl group.

According to one embodiment of the present disclosure, Ar ₁ is a terphenyl group substituted with a phenyl group.

According to one embodiment of the present disclosure, Ar ₁ is a terphenyl group.

According to one embodiment of the present invention, Ar ₁ is a phenanthrenyl group in which a phenyl group, biphenyl group, or naphthyl group is substituted or unsubstituted.

According to one embodiment of the present invention, Ar ₁ is a phenanthrenyl group substituted with a phenyl group, a biphenyl group, or a naphthyl group.

According to one embodiment of the present invention, Ar ₁ is a phenanthrenyl group substituted with a phenyl group.

According to one embodiment of the present disclosure, Ar ₁ is a phenanthrenyl group.

According to one embodiment of the present invention, Ar ₁ is an anthracenyl group in which a phenyl group, biphenyl group, or naphthyl group is substituted or unsubstituted.

According to one embodiment of the present disclosure, Ar ₁ is an anthracenyl group substituted with a phenyl group, a biphenyl group, or a naphthyl group.

According to one embodiment of the present disclosure, Ar ₁ is an anthracenyl group substituted with a phenyl group.

According to one embodiment of the present disclosure, Ar ₁ is an anthracenyl group.

According to one embodiment of the present invention, Ar ₁ is a fluorenyl group in which a phenyl group, a biphenyl group, or a naphthyl group is substituted or unsubstituted.

According to one embodiment of the present invention, Ar ₁ is a phenyl group, a biphenyl group, or a fluorenyl group substituted with a naphthyl group.

According to one embodiment of the present disclosure, Ar ₁ is a fluorenyl group substituted with a phenyl group.

According to one embodiment of the present disclosure, Ar < ₁ > is a fluorenyl group.

According to one embodiment of the present invention, at least one of R ₁ to R ₈ is any one selected from the following formulas (2) to (9), and the others are the same or different and each independently hydrogen; heavy hydrogen; A halogen group; A nitro group; Cyano; An ester group; A carbonyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

(2)

(3)

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

(7)

[Chemical Formula 8]

[Chemical Formula 9]

In the above formulas 2 to 9,

Ar ₃ is the same or different and each independently represents a substituted or unsubstituted C ₁₀ to C ₆₀ aryl group; Or a substituted or unsubstituted C ₂ to C ₆₀ heteroaryl group,

Ar ₃ 'and Ar ₃ "are the same or different and each independently represents a substituted or unsubstituted C ₆ to C ₆₀ aryl group; Or a substituted or unsubstituted C ₂ to C ₆₀ heteroaryl group,

R is hydrogen; heavy hydrogen; A halogen group; A nitro group; Cyano; 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,

n is an integer of 0 to 4, and when n is an integer of 2 or more, plural Rs are the same or different,

m is an integer of 0 to 5, and when m is an integer of 2 or more, plural Rs are the same or different,

p is an integer of 0 to 7, and when p is an integer of 2 or more, plural Rs are the same or different from each other.

According to one embodiment of the present invention, at least one of R ₁ to R ₈ is any one selected from the above formulas (2) to (9), and the remainder is hydrogen.

According to one embodiment of the present disclosure, Ar ₃ , Ar ₃ ', and Ar ₃ "are the same or different and each independently a substituted or unsubstituted C ₁₀ to C ₆₀ aryl group.

According to one embodiment of the present invention, Ar ₃ is a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted triphenyl group, a substituted or unsubstituted pyrene A substituted or unsubstituted anthracenyl group, a substituted or unsubstituted chrysenyl group, or a substituted or unsubstituted fluorenyl group.

According to one embodiment of the present invention, Ar ₃ is biphenyl, terphenyl, naphthyl, triphenyl, pyrene, anthracenyl,

According to one embodiment of the present specification, Ar ₃ is a biphenyl group in which a phenyl group, biphenyl group, or naphthyl group is substituted or unsubstituted.

According to one embodiment of the present invention, Ar ₃ is a biphenyl group substituted with a phenyl group, a biphenyl group, or a naphthyl group.

According to one embodiment of the present disclosure, Ar ₃ is a biphenyl group.

According to one embodiment of the present invention, Ar ₃ is a terphenyl group in which a phenyl group, a biphenyl group, or a naphthyl group is substituted or unsubstituted.

According to one embodiment of the present disclosure, Ar ₃ is a phenyl group, a biphenyl group, or a terphenyl group substituted with a naphthyl group.

According to one embodiment of the present disclosure, Ar ₃ is a terphenyl group substituted with a phenyl group.

According to one embodiment of the present disclosure, Ar ₃ is a terphenyl group.

According to one embodiment of the present invention, Ar ₃ is a naphthyl group in which a phenyl group, biphenyl group, or naphthyl group is substituted or unsubstituted.

According to one embodiment of the present invention, Ar ₃ is a phenyl group, a biphenyl group, or a naphthyl group substituted with a naphthyl group.

According to one embodiment of the present disclosure, Ar ₃ is a naphthyl group substituted with a phenyl group.

According to one embodiment of the present disclosure, Ar ₃ is a naphthyl group.

According to one embodiment of the present invention, Ar ₃ is a triphenyl group in which a phenyl group, biphenyl group, or naphthyl group is substituted or unsubstituted.

According to one embodiment of the present invention, Ar ₃ is a phenyl group, a biphenyl group, or a triphenyl group substituted with a naphthyl group.

According to one embodiment of the present disclosure, Ar ₃ is a triphenyl group substituted with a phenyl group.

According to one embodiment of the present disclosure, Ar ₃ is a triphenyl group.

According to one embodiment of the present specification, Ar ₃ is an anthracenyl group in which a phenyl group, biphenyl group, or naphthyl group is substituted or unsubstituted.

According to one embodiment of the present disclosure, Ar ₃ is an anthracenyl group substituted with a phenyl group, a biphenyl group, or a naphthyl group.

According to one embodiment of the present disclosure, Ar ₃ is an anthracenyl group substituted with a phenyl group.

According to one embodiment of the present disclosure, Ar ₃ is an anthracenyl group.

According to one embodiment of the present invention, Ar ₃ is a chrysiphenyl group in which a phenyl group, biphenyl group, or naphthyl group is substituted or unsubstituted.

According to one embodiment of the present disclosure, Ar ₃ is a chrysenyl group substituted with a phenyl group, a biphenyl group, or a naphthyl group.

According to one embodiment of the present disclosure, Ar < ₃ > is a chrysenyl group substituted with a phenyl group.

According to one embodiment of the present disclosure, Ar ₃ is a chrysenyl group.

According to one embodiment of the present invention, Ar ₃ is a fluorenyl group in which a phenyl group, a biphenyl group, or a naphthyl group is substituted or unsubstituted.

According to one embodiment of the present invention, Ar ₃ is a phenyl group, a biphenyl group, or a fluorenyl group substituted with a naphthyl group.

According to one embodiment of the present disclosure, Ar ₃ is a fluorenyl group substituted with a phenyl group.

According to one embodiment of the present disclosure, Ar ₃ is a fluorenyl group.

According to one embodiment of the present disclosure, Ar ₃ is a substituted or unsubstituted C ₂ to C ₆₀ heteroaryl group.

According to one embodiment of the present disclosure, Ar ₃ is substituted or unsubstituted dibenzofuran, or substituted or unsubstituted dibenzothiophene.

According to one embodiment of the present disclosure, Ar ₃ is dibenzofuran, or dibenzothiophene.

According to one embodiment of the present invention, Ar ₃ 'and Ar ₃ "are the same or different and are each independently a substituted or unsubstituted phenyl group, or a substituted or unsubstituted naphthyl group.

According to one embodiment of the present disclosure, Ar ₃ 'and Ar ₃ "are the same or different from each other, and are each independently a phenyl group or a naphthyl group.

According to one embodiment of the present disclosure, R is hydrogen; heavy hydrogen; A halogen group; A nitro group; Cyano; 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.

According to one embodiment of the present disclosure, R is selected from the group consisting of hydrogen; heavy hydrogen; Or a C ₁ to C ₂₀ alkyl group.

According to one embodiment of the present disclosure, R is selected from the group consisting of hydrogen; heavy hydrogen; Or a methyl group.

According to one embodiment of the present disclosure, R is hydrogen.

According to one embodiment of the present invention, the formula (1) may be represented by any one of the following formulas (1-1) to (1-3).

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

In Formulas 1-1 to 1-3, Ar ₁ and R ₁ to R ₈ are the same as defined in Formula 1.

According to one embodiment of the present invention, at least one of R ₃ and R ₆ is represented by any one of the formulas (2) to (9).

According to one embodiment of the present invention, R ₃ is represented by any one of the formulas (2) to (9).

According to one embodiment of the present invention, R ₆ is represented by any one of formulas (2) to (9).

According to one embodiment of the present invention, R ₃ and R ₆ are represented by any one of formulas (2) to (9).

According to one embodiment of the present invention, at least one of R ₁ to R ₈ is any one selected from the following formulas (2-1) to (8-1) and (9).

[Formula 2-1]

[Formula 3-1]

[Formula 4-1]

[Formula 5-1]

[Formula 6-1]

[Formula 7-1]

[Formula 8-1]

[Chemical Formula 9]

The definition of Ar ₃ , Ar ₃ ', Ar ₃ ", R, n, m and p in the above formulas (2-1) to (8-1) is the same as defined in the above formula (1).

According to one embodiment of the present invention, the compound represented by 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.

For example, the compound of formula (1) can be prepared into a core structure as shown in following general formulas (1) and (2). 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.

 [Formula 1]

[Formula 2]

Specifically, the above-mentioned formula 1 is illustrated in the middle of the reaction to couple a substituent at the position of R ₃ or R ₆ in the core structure of Formula 1, said Formula 2, R ₃ and R in the core structure of Formula 1 ₆ , but the present invention is not limited thereto, and the kind and position of the substituent group can be changed if necessary. A concrete manufacturing method will be described later.

If necessary, substituents such as the above formulas (2) to (9) may be bonded. For example, a compound corresponding to the general formulas (2) to (7) can be produced through the additional reaction of the general formula (1-1) shown below in the structure of the general formula (1).

 [Formula 1-1]

In the general formula 1-1, X, Ar ₁ , and Ar _{3 are} the same as defined in the general formula (1). In the general formula 1-1, the substituents 2 'to 7' can be used to synthesize the structures of 2 "to 7" corresponding to the general formulas 2 to 7 of the present specification.

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. For example, substituents may be connected as shown in the general formulas 1, 2, and 1-1, 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 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 typical example of the organic electronic device of the present invention, the organic light emitting device has a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, an electron blocking 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 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.

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.

1 및 일반식 2는 상기 화학식 1의 코어 구조에서 여러 위치에 치환기를 결합시키는 중간반응이며, 이하에서 제조예 및 실험예를 통하여 본 명세서의 합성예를 상세하게 설명한다.In the general formula

1 and Formula 2 are intermediate reactions in which substituents are bonded at various positions in the core structure of Formula 1. The synthesis examples of the present specification will be described in detail in the following Preparation Examples and Experimental Examples.

< Example >

< Manufacturing example  1> Preparation of the following compound 1-1

Compound A was prepared in the same manner as in the above Formula 1 using X = S in the above-mentioned Formula 1 and using chlorobenzene as Ar ₁ -Cl. The compound A (15.5 g, 57 mmol) and 2-bromo-1,10-phenanthroline (25.14 g, 63 mmol) were completely dissolved in tetrahydrofuran (300 ml), 2M aqueous potassium carbonate solution (120 ml) Tetraquistriphenylphosphinopalladium (198 mg, 2 mmol) was added and the mixture was heated with stirring for 2 hours. After the temperature was lowered to room temperature and the reaction was terminated, the potassium carbonate solution was removed and the white solid was filtered. The filtered white solid was washed once with ethyl acetate and once with ethanol to give Compound 1-1 (23.5 g, yield 88%).

MS [M + H] &lt; ⁺ &gt; = 454

< Manufacturing example  2> Preparation of the following compounds 1-2

Compound B was prepared in the same manner as in the general formula 1 using X = S in the general formula 1 and 2-chloronaphthalene as Ar ₁ -Cl. The compound B (12.5 g, 43 mmol) and 2-chloro-4- (naphthalen-2-yl) quinazoline (21.38 g, 47 mmol) were completely dissolved in tetrahydrofuran (500 ml), and 2M aqueous potassium carbonate solution (240 ml) Tetrakistriphenylphosphinopalladium (249 mg, 2 mmol) was added thereto, followed by heating and stirring for 8 hours. After the temperature was lowered to room temperature and the reaction was terminated, the potassium carbonate solution was removed and the white solid was filtered. The filtered white solid was washed once with ethyl acetate and once with ethanol to give Compound 1-2 (18.75 g, yield 75%).

MS [M + H] &lt; ⁺ &gt; = 580

< Manufacturing example  3> Preparation of the following compounds 1-3

The compound A (10.0 g, 30 mmol) and 2-chloro-4- (dibenzo [b, d] furan-2-yl) quinazoline (13.41 g, 33 mmol) were completely dissolved in 600 ml of tetrahydrofuran, Potassium carbonate aqueous solution (280 ml) was added, and tetrakistriphenylphosphinopalladium (176 mg, 2 mmol) was added thereto, followed by heating and stirring for 8 hours. After the temperature was lowered to room temperature and the reaction was terminated, the potassium carbonate solution was removed and the white solid was filtered. The filtered white solid was washed with 300 ml of ethyl acetate to prepare the compound 1-3 (15.64 g, yield 90%).

MS [M + H] &lt; ⁺ &gt; = 569

< Manufacturing example  4> Preparation of the following compounds 1-4

The procedure of Production Example 1 was repeated except that (4-bromophenyl) diphenylphosphine oxide was used in place of 2-bromo-1,10-phenanthroline in Preparation Example 1, Compound 1-4 was prepared.

MS [M + H] &lt; ⁺ &gt; = 552

< Manufacturing example  5> Preparation of the following compounds 1-5

In the same manner as in the above Production Example 1, except that 2-bromobenzo [d] oxazole was used instead of 2-bromo-1,10-phenanthroline, the compound 1- 5.

MS [M + H] &lt; ⁺ &gt; = 393

< Manufacturing example  6> Preparation of the following compounds 1-6

Compound C was prepared in the same manner as in the general formula 1 using X = O in the above general formula 1 and chlorobenzene as Ar ₁ -Cl. The compound C (11.8 g, 37 mmol) and 2-bromo-1- (naphthalen-2-yl) -1H- benzo [d] imidazole (15.52 g, 40 mmol) were completely dissolved in 300 ml of tetrahydrofuran 2M aqueous potassium carbonate solution (140 ml) was added, tetrakis triphenylphosphinopalladium (212 mg, 2 mmol) was added, and the mixture was heated with stirring for 3 hours. After the temperature was lowered to room temperature and the reaction was terminated, the potassium carbonate solution was removed and the white solid was filtered. The filtered white solid was washed with 400 ml of ethyl acetate to give the above compound 1-6 (17.85 g, yield 86%).

MS [M + H] &lt; ⁺ &gt; = 502

< Manufacturing example  7> Preparation of the following compounds 1-7

Compound D was prepared in the same manner as in the general formula 1 using X = O in the above general formula 1 and 4-bromobiphenyl as Ar ₁ -Br. The compound D (10.42 g, 36 mmol) and 2-bromo-1- (naphthalen-2-yl) -1H- benzo [d] imidazole (18.22 g, 40 mmol) were completely dissolved in 300 ml of tetrahydrofuran 2M aqueous potassium carbonate solution (140 ml) was added, and tetrakistriphenylphosphinopalladium (208 mg, 2 mmol) was added thereto, followed by heating and stirring for 7 hours. After the temperature was lowered to room temperature and the reaction was terminated, the potassium carbonate solution was removed and the white solid was filtered. The filtered white solid was washed with 400 ml of ethyl acetate to prepare the above compound 1-7 (17.45 g, yield 82%).

MS [M + H] &lt; ⁺ &gt; = 590

< Manufacturing example  Preparation of the following compounds 1-8

Compound E was prepared in the same manner as in the general formula 1 using X = O in the above general formula 1 and 2-chloronaphthalene as Ar ₁ -Cl. Benzo [d] imidazole (20.96 g, 48 mmol) was added to a solution of the compound E (15.11 g, 44 mmol) and 2-chloro-1- (dibenzo [b, d] thiophen- (600 ml), 2M potassium carbonate aqueous solution (280 ml) was added, tetrakis triphenylphosphinopalladium (253 mg, 2 mmol) was added, and the mixture was heated and stirred for 8 hours. After the temperature was lowered to room temperature and the reaction was terminated, the potassium carbonate solution was removed and the white solid was filtered. The filtered white solid was washed with 300 ml of ethyl acetate to give the above compound 1-8 (24.05 g, yield 89%).

MS [M + H] &lt; ⁺ &gt; = 619

< Manufacturing example  Preparation of the following compounds 1-9

Except that 2-chloro-1,10-phenanthroline was used in place of 2-bromo-1- (naphthalen-2-yl) -1H- The compound 1-9 was prepared in the same manner as in the preparation of the compound 1-9.

MS [M + H] &lt; ⁺ &gt; = 514

< Manufacturing example  Preparation of the following compounds 1-10

Except that (4-bromophenyl) diphenylphosphine oxide was used in place of 2-bromo-1- (naphthalen-2-yl) -1H- The compound 1-10 was prepared in the same manner as in the production of the compound 1-10.

MS [M + H] &lt; ⁺ &gt; = 612

< Manufacturing example  Preparation of the following compound 1-11

Except that 2-bromobenzo [d] oxazole was used instead of 2-bromo-1- (naphthalen-2-yl) -1H- The compound 1-11 was prepared in the same manner as the preparation method.

MS [M + H] &lt; ⁺ &gt; = 469

< Manufacturing example  Preparation of the following compound 1-12

In step 1 of the above general formula 1, X = SO ₂ and 2Naphthyl-Br as Ar ₁ -Br can be used to obtain the above compound F. The compound F (12.5 g, 40 mmol) and 2-chloro-4- (naphthalen-2-yl) quinazoline (21.38 g, 43 mmol) were completely dissolved in tetrahydrofuran (500 ml), and 2M aqueous potassium carbonate solution (240 ml) Tetraquistriphenylphosphinopalladium (262 mg, 2.1 mmol) was added thereto, followed by heating with stirring for 5 hours. After the temperature was lowered to room temperature and the reaction was terminated, the potassium carbonate solution was removed and the white solid was suspended. The filtered white solid was washed once with ethyl acetate and once with ethanol to give Compound 1-12 (17.54 g, yield 72%).

MS [M + H] &lt; ⁺ &gt; = 612

< Manufacturing example  Preparation of the following compound 1-13

In the above general formula 1 step 1, the compound G can be obtained by using Phenyl-Br with X = SO ₂ and Ar ₁ -Br. The compound G (16.15 g, 33.43 mmol) and 2-chloro-4- (dibenzo [b, d] furan-2-yl) quinazoline (10.00 g, 30.41 mmol) were completely dissolved in 300 ml of tetrahydrofuran Then, 2M aqueous potassium carbonate solution (150 ml) was added, tetrakistriphenylphosphinopalladium (161 mg, 0.3 mmol) was added, and the mixture was stirred with heating for 3 hours. After the temperature was lowered to room temperature and the reaction was terminated, the potassium carbonate solution was removed and the white solid was suspended. The filtered white solid was washed once with ethyl acetate and once with ethanol to give the compound 1-13 (16.47 g, yield 82%).

MS [M + H] &lt; ⁺ &gt; = 601

< Manufacturing example  Preparation of the following compound 1-14

In the same manner as in the above Production Example 13 except that 2-bromo-1,10-phenanthroline was used instead of 2-chloro-4- (naphthalen-2-yl) quinazoline, To give the above compound 1-14.

MS [M + H] &lt; ⁺ &gt; = 486

< Manufacturing example  Preparation of the following compounds 1-15

The same procedure as in the above Production Example 13 was conducted except that (4-bromophenyl) diphenylphosphine oxide was used in place of 2-chloro-4- (naphthalen-2-yl) quinazoline To give the above compound 1-15.

MS [M + H] &lt; ⁺ &gt; = 584

< Manufacturing example  Preparation of the following compounds 1-16

In the same manner as in the above Production Example 13 except for using 2-bromobenzo [d] oxazole instead of 2-chloro-4- (naphthalen-2-yl) quinazoline, Compound 1-16 was prepared.

MS [M + H] &lt; ⁺ &gt; = 425

< Manufacturing example  Preparation of the following compounds 1-17

In the above general formula 2 step 1, the compound G can be obtained by using Phenyl-Br with X = O and Ar ₁ -Br. After completely dissolving the compound G (50.21 g, 95 mmol) and (4-bromophenyl) diphenylphosphine oxide (11.78 g, 43 mmol) in tetrahydrofuran (300 ml), 2M aqueous potassium carbonate solution (120 ml) Tetraquistriphenylphosphinopalladium (250 mg, 2 mmol) was added thereto, followed by heating and stirring for 3 hours. After the temperature was lowered to room temperature and the reaction was terminated, the potassium carbonate solution was removed and the white solid was filtered. The filtered white solid was washed with 450 ml of ethyl acetate to give the above compound 1-17 (25.15 g, yield 91%).

MS [M + H] &lt; ⁺ &gt; = 668

< Manufacturing example  Preparation of the following compounds 1-18

In the same manner as in the above Production Example 17, except that 2-bromobenzo [d] thiazole was used instead of (4-bromophenyl) diphenylphosphine oxide, the compound 1-18 .

MS [M + H] &lt; ⁺ &gt; = 526

< Experimental Example  1>

The glass substrate coated with ITO (indium tin oxide) thin film with a thickness of 1,000 Å 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 chemical formula was thermally vacuum deposited to a thickness of 500 Å to form a hole injection layer.

[LINE]

The following compound N - ([1,1'-biphenyl] -4-yl) -9,9-dimethyl-N- (4- (9- Yl) phenyl) -9H-fluorene-2-amine: HTL (400 ANGSTROM) was vacuum deposited to form a hole transport layer.

[HTL]

Subsequently, the following BH and BD were vacuum deposited on the hole transport layer at a weight ratio of 25: 1 at a thickness of 300 ANGSTROM to form a light emitting layer.

[BH]

[BD]

[LiQ]

Compound 1-1 prepared in Preparation Example 1 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 300 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, the degree of vacuum upon deposition ⅹ10 2 ^-7 To 5 x 10 &lt; ^-6 &gt; torr, thereby fabricating an organic light emitting device.

 < Experimental Example  2>

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

 < Experimental Example  3>

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

< Experimental Example  4>

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

< Experimental Example  5>

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

< Experimental Example  6>

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

< Experimental Example  7>

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

< Experimental Example  8>

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

< Experimental Example  9>

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

< Experimental Example  10>

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

< Experimental Example  11>

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

< Experimental Example  12>

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

< Experimental Example  13>

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

< Experimental Example  14>

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

< Experimental Example  15>

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

< Experimental Example  16>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 1-16 was used instead of Compound 1-1 in Experimental Example 1.

< Experimental Example  17>

An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that Compound 1-17 was used instead of Compound 1-1 in Experimental Example 1.

< Experimental Example  18>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 1-18 was used instead of Compound 1-1 in Experimental Example 1.

< Comparative Example  1>

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

[ET1]

< Comparative Example  2>

An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that the compound of ET2 was used instead of the compound 1-1 in Experimental Example 1.

[ET2]

< Comparative Example  3>

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

[ET3]

< Comparative Example  4>

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

[ET4]

< Comparative Example  5>

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

[ET5]

< Comparative Example  6>

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

[ET6]

The results shown in Table 1 were obtained when current was applied to the organic luminescent devices manufactured by Experimental Examples 1 to 18 and Comparative Examples 1 to 6.

division compound Voltage
(V @ 10 mA / cm ² ) efficiency
(cd / A @ 10mA / cm 2) Color coordinates
(x, y) Experimental Example 1 Compound 1-1 3.86 5.04 (0.138, 0.126) Experimental Example 2 Compound 1-2 3.75 5.15 (0.139, 0.124) Experimental Example 3 Compound 1-3 3.85 5.51 (0.138, 0.127) Experimental Example 4 Compound 1-4 3.77 5.22 (0.137, 0.125) Experimental Example 5 Compound 1-5 3.83 5.19 (0.136, 0.126) Experimental Example 6 Compound 1-6 3.82 5.18 (0.136, 0.127) Experimental Example 7 Compound 1-7 3.84 5.27 (0.136, 0.125) Experimental Example 8 Compound 1-8 3.85 5.51 (0.138, 0.127) Experimental Example 9 Compound 1-9 3.77 5.22 (0.137, 0.122) Experimental Example 10 Compound 1-10 3.83 5.19 (0.136, 0.127) Experimental Example 11 Compound 1-11 3.82 5.18 (0.136, 0.127) Experimental Example 12 Compound 1-12 3.85 5.51 (0.138, 0.126) Experimental Example 13 Compound 1-13 3.77 5.22 (0.137, 0.125) Experimental Example 14 Compound 1-14 3.83 5.19 (0.136, 0.127) Experimental Example 15 Compound 1-15 3.82 5.18 (0.136, 0.127) Experimental Example 16 Compound 1-16 3.77 5.22 (0.137, 0.125) Experimental Example 17 Compound 1-17 3.83 5.19 (0.136, 0.127) Experimental Example 18 Compound 1-18 3.76 5.25 (0.136, 0.126) Comparative Example 1 ET1 4.42 3.85 (0.136, 0.130) Comparative Example 2 ET2 4.38 3.94 (0.136, 0.126) Comparative Example 3 ET3 4.20 4.09 (0.135, 0.125) Comparative Example 4 ET4 4.19 4.26 (0.135, 0.130) Comparative Example 5 ET5 4.25 4.24 (0.135, 0.125) Comparative Example 6 ET6 4.34 4.11 (0.135, 0.127)

As shown in Table 1, when Examples 1 to 18 and Comparative Examples 1 to 6 are compared, when Ar ₁ is an alkyl group (Comparative Example 2 and Comparative Example 4), a linking group (Comparative Example 1, Comparative Example 3, and Comparative Example 5), it was confirmed that the compounds of the present invention are superior in electron transporting and injecting ability and applicable to organic light emitting devices.

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, but, on the contrary, is intended to cover various modifications and equivalent arrangements included within the spirit and scope of the appended claims. .

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 (13)

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

In Formula 1,
X is O, S or SO ₂ ,
Ar ₁ is a substituted or unsubstituted C ₆ to C ₄₀ aryl group,
At least one of R ₁ to R ₈ is any one selected from the following formulas (2) to (9), and the others are the same or different and each independently hydrogen; heavy hydrogen; A halogen group; A nitro group; Cyano; An ester group; A carbonyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
(2)

(3)

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

(7)

[Chemical Formula 8]

[Chemical Formula 9]

In the above formulas 2 to 9,
Ar ₃ is the same or different and each independently represents a substituted or unsubstituted C ₁₀ to C ₆₀ aryl group; Or a substituted or unsubstituted C ₂ to C ₆₀ heteroaryl group,
Ar ₃ 'and Ar ₃ "are the same or different and each independently represents a substituted or unsubstituted C ₆ to C ₆₀ aryl group; Or a substituted or unsubstituted C ₂ to C ₆₀ heteroaryl group,
R is hydrogen; heavy hydrogen; A halogen group; A nitro group; Cyano; 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,
n is an integer of 0 to 4, and when n is an integer of 2 or more, plural Rs are the same or different,
m is an integer of 0 to 5, and when m is an integer of 2 or more, plural Rs are the same or different,
p is an integer of 0 to 7, and when p is an integer of 2 or more, plural Rs are the same or different from each other. The compound according to claim 1, wherein the formula (1) is represented by any one of the following formulas (1-1) to (1-3):
[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

In Formulas 1-1 through 1-3,
The definitions of Ar ₁ and R ₁ to R ₈ are the same as those defined in the above formula (1). The method according to claim 1,
And at least one of R ₃ and R ₆ is any one selected from the above formulas (2) to (9). The compound according to claim 1, wherein at least one of R ₁ to R ₈ is any one selected from the following formulas (2-1) to (8-1) and (9)
[Formula 2-1]

[Formula 3-1]

[Formula 4-1]

[Formula 5-1]

[Formula 6-1]

[Formula 7-1]

[Formula 8-1]

[Chemical Formula 9]

In the above formulas (2-1) to (8-1) and (9)
Ar ₃ , Ar ₃ ', Ar ₃ ", R, n, m and p are the same as defined in formula (1). The method according to claim 1,
Ar ₁ represents a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted triphenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted pyrene A substituted or unsubstituted anthracenyl group, a substituted or unsubstituted chrysenyl group, or a substituted or unsubstituted fluorenyl group. 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 6. The organic electronic device according to claim 1, Electronic device. The organic electronic device according to claim 7, wherein the organic layer includes a light emitting layer, and the light emitting layer comprises the compound. The organic electronic device according to claim 7, 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 7, wherein the organic material layer includes an electron injection layer or an electron transport layer, and the electron transport layer or the electron injection layer comprises the compound. The organic electronic device according to claim 7, 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. The organic electronic device according to claim 7, 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 7, 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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