KR101850242B1 - Compound and organic electronic device using the same - Google Patents

Abstract

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

Description

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

This application claims the benefit of Korean Patent Application No. 10-2016-0033481 filed on March 21, 2016, filed with 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,

At least two of X ₁ to X ₃ are N and the others are N or CR,

X ₄ is a substituted or unsubstituted naphthylene group,

L ₁ and L ₂ are the same or different and are each independently a direct bond; Or a substituted or unsubstituted arylene group,

Y is O, or S,

Ar ₁ and Ar ₂ 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 cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

R, R ₁ , and R ₂ are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; Cyano; A hydroxy group; Carbonyl group; An ester group; Imide; Amide group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted amine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

a is an integer of 1 to 3,

b is an integer of 1 to 4,

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

When b is 2 or more, plural R ₂ 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).

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 alkoxy group; An aryloxy group; An alkyloxy group; Arylthioxy group; An alkylsulfoxy group; An amine group; An arylamine 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, and iodine.

In the present specification, the carbon number of the carbonyl group is not particularly limited, but it is preferably 1 to 40 carbon atoms. Specifically, it may be a compound having the following structure, 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 40 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.

In the present specification, the number of carbon atoms in the imide group is not particularly limited, but is preferably 1 to 40 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

In the present specification, the amide group may be substituted with nitrogen of the amide group, hydrogen, a straight chain, branched chain or cyclic alkyl group having 1 to 40 carbon atoms or an aryl group having 6 to 40 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 40 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 40 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, the alkenyl group may be straight-chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, Butenyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, (Diphenyl-1-yl) vinyl-1-yl, stilbenyl, stilenyl, and the like.

In the present specification, the boron group may be -BR ₁₀₀ R ₁₀₁ , wherein R ₁₀₀ and R ₁₀₁ are the same or different and each independently hydrogen; heavy hydrogen; halogen; A nitrile group; A substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 40 carbon atoms; A substituted or unsubstituted, straight or branched chain alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; And a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.

In this specification, the silyl group is a substituent including Si and a direct connection as the Si atom radical, R is represented by -SiR _{104 105} R _106, R ₁₀₄ to R ₁₀₆ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; An alkyl group; An alkenyl group; An alkoxy group; A cycloalkyl group; An aryl group; And a heterocyclic group. Specific examples of the silyl group include a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group and a phenylsilyl group. 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 40 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 40 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, and the number of carbon atoms is not particularly limited, but is preferably 6 to 40 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, , An indole group, a carbazole group, a benzoxazole group, a benzimidazole group, a benzothiazole group, a benzocarbazole group, A benzothiophene group, a benzothiophene group, a benzofuranyl group, a phenanthroline, a thiazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiadiazolyl group, a benzothiazolyl group, But are not limited to these.

In the present specification, the amine group means a monovalent amine in which at least one hydrogen atom of the amino group (-NH ₂ ) is substituted with another substituent, represented by -NR ₁₀₇ R ₁₀₈ , and R ₁₀₇ and R ₁₀₈ are the same or different Each independently selected from the group consisting of hydrogen; heavy hydrogen; A halogen group; An alkyl group; An alkenyl group; An alkoxy group; A cycloalkyl group; An aryl group; And a heterocyclic group (provided that at least one of R ₁₀₇ and R ₁₀₈ is not hydrogen). For example, -NH ₂ ; Monoalkylamine groups; A dialkylamine group; N-alkylarylamine groups; Monoarylamine groups; A diarylamine group; An N-arylheteroarylamine group; An N-alkylheteroarylamine group, a monoheteroarylamine group, and a diheteroarylamine group. The number of carbon atoms is not particularly limited, but is preferably 1 to 40. Specific examples of the amine group include methylamine, dimethylamine, ethylamine, diethylamine, phenylamine, naphthylamine, biphenylamine, anthracenylamine, 9-methyl- , Diphenylamine group, ditolylamine group, N-phenyltolylamine group, triphenylamine group, N-phenylbiphenylamine group; N-phenylnaphthylamine group; An N-biphenylnaphthylamine group; N-naphthylfluorenylamine group; N-phenylphenanthrenylamine group; An N-biphenyl phenanthrenyl amine group; N-phenylfluorenylamine group; An N-phenyltriphenylamine group; N-phenanthrenyl fluorenylamine group; And an N-biphenylfluorenylamine group, but are not limited thereto.

In the present specification, the phosphine oxide group specifically includes a diphenylphosphine oxide group, dinaphthylphosphine oxide, and the like, but is not limited thereto.

In the present specification, the aryl group in the aryloxy group, the arylthioxy group, the arylsulfoxy group, the N-arylalkylamine group, and the N-arylheteroarylamine group is the same as the aforementioned aryl group. Specific examples of the aryloxy group include a phenoxy group, a p-tolyloxy group, a m-tolyloxy group, a 3,5-dimethyl-phenoxy group, a 2,4,6- trimethylphenoxy group, a p- Naphthyloxy group, 4-methyl-1-naphthyloxy group, 5-methyl-2-naphthyloxy group, 1-anthryloxy group , 2-anthryloxy group, 9-anthryloxy group, 1-phenanthryloxy group, 3-phenanthryloxy group and 9-phenanthryloxy group and the arylthioxy group includes phenylthio group, 2- Methylphenylthio group, 4-tert-butylphenylthio group and the like, and examples of the arylsulfoxy group include a benzene sulfoxide group and a p-toluenesulfoxy group. However, the present invention is not limited thereto.

In the present specification, examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted triarylamine group. The aryl group in the arylamine group may be a monocyclic aryl group or a polycyclic aryl group. The arylamine group having at least two aryl groups may contain a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group at the same time. For example, the aryl group in the arylamine group may be selected from the examples of the aryl group described above. Specific examples of the arylamine group include phenylamine, naphthylamine, biphenylamine, anthracenylamine, 3-methylphenylamine, 4-methyl-naphthylamine, 2-methyl- But are not limited to, cenylamine, diphenylamine, phenylnaphthylamine, ditolylamine, phenyltolylamine, carbazole and triphenylamine groups.

In the present specification, examples of the heteroarylamine group include a substituted or unsubstituted monoheteroarylamine group, a substituted or unsubstituted diheteroarylamine group, or a substituted or unsubstituted triheteroarylamine group. The heteroarylamine group having two or more heteroaryl groups may include a monocyclic heteroaryl group, a polycyclic heteroaryl group, or a monocyclic heteroaryl group and a polycyclic heteroaryl group at the same time. For example, the heteroaryl group in the heteroarylamine group may be selected from the examples of the above-mentioned heteroaryl group.

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 one embodiment of the present invention, at least two of X ₁ to X ₃ are N and the others are the same or different, and each independently N or CR.

In one embodiment of the present specification, X ₄ is a substituted or unsubstituted naphthylene group.

In one embodiment of the present specification, X ₄ is a naphthylene group.

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; Or a substituted or unsubstituted arylene group.

In one embodiment of the present invention, L ₁ and L ₂ are the same or different and are each independently a direct bond or a substituted or unsubstituted phenylene group; Or a substituted or unsubstituted biphenylene group.

In one embodiment of the present invention, L ₁ and L ₂ are the same or different and each independently a direct bond or a phenylene group.

In one embodiment of the present invention, L ₁ and L ₂ are the same or different and are each independently a direct bond or a biphenylene group.

In one embodiment of the present disclosure, Y is O, or S.

In one embodiment of the present disclosure, Y is O.

In one embodiment of the present disclosure, Y is S.

In one embodiment of the present specification, Ar ₁ and Ar ₂ 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 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 represent a substituted or unsubstituted aryl group having 6 to 40 carbon atoms.

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

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

In one embodiment of the present disclosure, R, R ₁ , and R ₂ are the same or different and each independently hydrogen; heavy hydrogen; A halogen group; Cyano; A hydroxy group; Carbonyl group; An ester group; Imide; Amide group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted acyloxy group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted amine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

In one embodiment of the present specification, R, R ₁ , and R ₂ are the same or different and each independently represent a substituted or unsubstituted alkyl group having 1 to 40 carbon atoms.

In one embodiment of the present specification, R, R ₁ , and R ₂ are the same or different and each independently is a substituted or unsubstituted methyl group, or a substituted or unsubstituted ethyl group.

In one embodiment of the present specification, R, R ₁ , and R ₂ are the same or different from each other and are each independently a methyl group or an ethyl group.

In one embodiment of the present specification, R, R ₁ , and R ₂ are the same or different and each independently represent a substituted or unsubstituted aryl group having 6 to 40 carbon atoms.

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

In one embodiment of the present specification, R, R ₁ , and R ₂ are the same or different from each other and are each independently a phenyl group, a biphenyl group, or a naphthyl group.

In one embodiment of the present disclosure, R, R ₁ , and R ₂ are hydrogen.

In one embodiment of the present specification, a is an integer of 1 to 3, b is an integer of 1 to 4, and when a is 2 or more, plural R _{1 s} are the same or different from each other, and when b is 2 or more, The plurality of R < ₂ > s are the same or different from each other.

In one embodiment of the present invention, the formula (1) may be represented by any one of the following formulas (2) to (6).

(2)

(3)

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

In the above Formulas 2 to 6,

X ₁ to X ₃ , L ₁ and L ₂ , Y, Ar ₁ , Ar ₂ , R, R ₁ , and R ₂ are the same as defined in Formula 1,

R ₃ is hydrogen; heavy hydrogen; A halogen group; Cyano; A hydroxy group; Carbonyl group; An ester group; Imide; Amide group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted acyloxy group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted amine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

c is an integer of 1 to 6,

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

In one embodiment of the present specification, R ₃ is a substituted or unsubstituted alkyl group having 1 to 40 carbon atoms.

In one embodiment of the present specification, R ₃ is a substituted or unsubstituted methyl group, or a substituted or unsubstituted ethyl group.

In one embodiment of the present disclosure, R ₃ is a methyl group or an ethyl group.

In one embodiment of the present specification, R ₃ is a substituted or unsubstituted aryl group having 6 to 40 carbon atoms.

In one embodiment of the present specification, R ₃ is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted naphthyl group.

In one embodiment of the present specification, R ₃ is a phenyl group, a biphenyl group, or a naphthyl group.

In one embodiment of the present disclosure, R ₃ is hydrogen.

In one embodiment of the present specification, the compound may be any one selected from the following structural formulas.

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

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

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

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

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

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

Hereinafter, the organic light emitting device will be described.

In one embodiment of the present invention, the organic layer includes a 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 compound 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 layer is a layer for injecting holes from an electrode. The hole injecting material has a hole injecting effect, and has a hole injecting effect on the light emitting layer or a light emitting material. A compound which prevents the migration of excitons to the electron injecting layer or the electron injecting 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 dibenzofuran derivatives, ladder furan compounds, And derivatives thereof, 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 with a low work function followed by an aluminum layer or silver layer. Specifically cesium, barium, calcium, ytterbium and samarium, in each case followed by an aluminum layer or a silver layer.

The electron injection layer is a layer for injecting electrons from the electrode. The electron injection layer has the ability to transport electrons, has an electron injection effect from the cathode, and has an excellent electron injection effect with respect to the light emitting layer or the light emitting material. A compound which prevents migration to a layer and is excellent in a thin film forming ability is preferable. Specific examples thereof include fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, A complex compound and a nitrogen-containing five-membered ring derivative, but are not limited thereto.

Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, bis (8- Tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8- hydroxyquinolinato) gallium, bis (10- Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8- quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) (2-naphtholato) gallium, and the like, But is not limited thereto.

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

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

In one embodiment of the present invention, the compound 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.

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.

[ Manufacturing example ]

Manufacturing example  1: Intermediate 1- 1 of  Produce

 Reagent 1-1 Reagent 1-2 Intermediate 1-1

1) Preparation of intermediate 1-1

2- (4-bromophenyl) -4,6-diphenyl-1,3,5-triazine (2- (Reagent 1-1, 50 g, 129 mmol) and (4-chloronaphthalen-1-yl) boronic acid (reagent 1-2, 29.2 g, 142 mmol ) Were added to 600 ml of tetrahydrofuran, and the mixture was stirred and refluxed. After that, potassium carbonate (53 g, 386 mmol) was dissolved in 60 ml of water and stirred. Tetraquistriphenylphosphinopalladium (4.5 g, 4 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 Intermediate 1-1 (49 g, 81%).

Manufacturing example  2: Synthetic example 1 of  Produce

Intermediate 1-1 Reagent 2-1 Synthesis Example 1

One) Synthetic example  1

(10 g, 21 mmol) and dibenzo [b, d] thiophen-4-ylboronic acid (reagents 2-1, 5.3 g, 23 mmol) were added to 150 ml of dioxane, which was stirred and refluxed. After dissolving potassium phosphate (14 g, 64 mmol) in 50 ml of water and stirring well, bis (dibenzylidineacetone) palladium (0.4 g, 0.6 mmol) and tricyclohexylphosphine (0.4 g, 0.6 mmol ). After 24 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 then recrystallized from ethyl acetate and purified by column chromatography (chloroform: hexane). The purified product was dried to give Synthesis Example 1 (10 g, 74%).

MS: [M + H] < + > = 617

Manufacturing example  3: Synthetic example 2 of  Produce

Intermediate 1-1 Reagent 3-1 Synthesis Example 2

One) Synthetic example  Preparation of 2

(10 g, 21 mmol) and dibenzo [b, d] furan-4-ylboronic acid (reagent 3-1, 5.0 g , 23 mmol) were added to 150 ml of dioxane, which was stirred and refluxed. After dissolving potassium phosphate (14 g, 64 mmol) in 50 ml of water and stirring well, bis (dibenzylidineacetone) palladium (0.4 g, 0.6 mmol) and tricyclohexylphosphine (0.4 g, 0.6 mmol ). After 24 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 then recrystallized from ethyl acetate and purified by column chromatography (chloroform: hexane). The purified product was dried to give Synthesis Example 2 (7 g, 54%).

MS: [M + H] < + > = 601

Manufacturing example  4: Synthetic example 3 of  Produce

Intermediate 1-1 Reagent 4-1 Synthesis Example 3

One) Synthetic example  3 Preparation of

Dibenzo [b, d] furan-4-ylboronic acid (reagent 3-1) was used in place of dibenzo [b, d] furan- (13 g, 64%) was synthesized in the same manner as in Preparation Example 3 except that dibenzo [b, d] furan-3-ylboronic acid (Reagent 4-1) Respectively.

MS: [M + H] < + > = 601

Manufacturing example  5: Synthetic example 4 of  Produce

Intermediate 1-1 Reagent 5-1 Synthesis Example 4

One) Synthetic example  4

Dibenzo [b, d] furan-4-ylboronic acid (reagent 3-1) was used in place of dibenzo [b, d] furan- (6 g, 48%) was synthesized in the same manner as in Preparation Example 3 except that dibenzo [b, d] furan-2-ylboronic acid (Reagent 5-1) Respectively.

MS: [M + H] < + > = 601

Manufacturing example  6: Synthetic example 5 of  Produce

Intermediate 1-1 Reagent 6-1 Synthesis Example 5

One) Synthetic example  Preparation of 5

Dibenzo [b, d] furan-4-ylboronic acid (reagent 3-1) was used in place of dibenzo [b, d] furan- Synthesis Example 5 (6 g, 44%) was synthesized in the same manner as in Preparation Example 3 except that dibenzo [b, d] furan-1-ylboronic acid (Reagent 6-1) .

MS: [M + H] < + > = 601

Manufacturing example  7: Intermediate 2 of  Produce

   Reagent 7-1 Reagent 7-2 Intermediate 7-1

1) Preparation of intermediate 7-1

Diphenyl-6- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) 1,3,5- (2,4-diphenyl-6- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) -1,3,5-triazine 1-bromonaphthalen-2-ol (Reagent 7-2, 15 g, 69 mmol) was added to 300 ml of tetrahydrofuran, followed by stirring And refluxed. Then, potassium carbonate (29 g, 206 mmol) was dissolved in 90 ml of water and stirred. After the addition, bis (tri-tert butylphosphine) palladium (0.4 g, 0.7 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 7-1 (24 g, 77%).

     Intermediate 7-1 Reagent 7-3 Intermediate 2

2) Preparation of intermediate 2

Intermediate 7-1 (30 g, 69 mmol) and 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonyl fluoride (1,1, (Reagent 7-3, 18 g, 80 mmol) was added to 400 ml of acetonitrile and stirred. After that, potassium carbonate (15 g, 147 mmol) was dissolved in 50 ml of water and the mixture was reacted for 1 hour and filtered. The filtrate was dried to give Intermediate 2 (33 g, 84%).

Manufacturing example  8: Synthetic example 6 of  Produce

Intermediate 2 Reagent 8-1 Synthesis Example 6

One) Synthetic example  Preparation of 6

(20 g, 21 mmol) and dibenzo [b, d] thiophen-4-ylboronic acid (reagent 8-1, 5.0 g, 27 mmol) were added to dioxane (200 ml), and the mixture was stirred and refluxed. Then, potassium phosphate (17 g, 82 mmol) was dissolved in 50 ml of water. After stirring well, bis (dibenzylidineacetone) palladium (0.5 g, 0.8 mmol) and tricyclohexylphosphine (0.5 g, 1.6 mmol ). 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 then recrystallized from ethyl acetate and purified by column chromatography (chloroform: hexane). The purified product was distilled and dried to give Synthesis Example 6 (7 g, 54%).

MS: [M + H] < + > = 617

Manufacturing example  9: Synthetic example 7's  Produce

Intermediate 2 Reagent 9-1 Synthesis Example 7

One) Synthetic example  Preparation of 7

Dibenzo [b, d] thiophen-4-ylboronic acid (Reagent 8-1) in place of dibenzo [b, d] thiophen- (12 g, 71%) was synthesized in the same manner as in Preparation Example 8, except that dibenzo [b, d] furan-4-ylboronic acid (Reagent 9-1) .

MS: [M + H] < + > = 601

Manufacturing example  10: Intermediate 3 of  Produce

Reagent 10-1 Reagent 10-2 Intermediate 10-1

1) Preparation of intermediate 10-1

Diphenyl-6- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) 1,3,5- (2,4-diphenyl-6- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) -1,3,5-triazine 4-bromonaphthalen-2-ol (Reagent 10-2, 15 g, 69 mmol) was added to 300 ml of tetrahydrofuran, followed by stirring And refluxed. Then, potassium carbonate (29 g, 206 mmol) was dissolved in 90 ml of water and stirred. After the addition, bis (tri-tert butylphosphine) palladium (0.4 g, 0.7 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 10-1 (12 g, 71%).

Intermediate 10-1 Reagent 10-3 Intermediate 3

2) Preparation of intermediate 3

Intermediate 10-1 (30 g, 69 mmol) and 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonyl fluoride (1,1, 2,30,3,4,4,4-nonafluorobutane-1-sulfonyl fluoride) (reagent 10-3, 18 g, 80 mmol) was added to 400 ml of acetonitrile and stirred. After that, potassium carbonate (15 g, 147 mmol) was dissolved in 50 ml of water and the mixture was reacted for 1 hour and filtered. The filtrate was dried to give Intermediate 3 (44 g, 88%).

Manufacturing example  11: Synthetic example 8 of  Produce

Intermediate 3 Reagent 11-1 Synthesis Example 8

One) Synthetic example  8 manufacture

(20 g, 21 mmol) and dibenzo [b, d] thiophen-4-ylboronic acid (reagent 11-1, 5.0 g, 27 mmol) were added to dioxane (200 ml), and the mixture was stirred and refluxed. Then, potassium phosphate (17 g, 82 mmol) was dissolved in 50 ml of water. After stirring well, bis (dibenzylidineacetone) palladium (0.5 g, 0.8 mmol) and tricyclohexylphosphine (0.5 g, 1.6 mmol ). 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 then recrystallized from ethyl acetate and purified by column chromatography (chloroform: hexane). The purified product was distilled and dried to give Synthesis Example 8 (11 g, 68%).

MS: [M + H] < + > = 617

Manufacturing example  12: Synthetic example 9 of  Produce

Intermediate 3 Reagent 12-1 Synthesis Example 9

One) Synthetic example  Preparation of 9:

Dibenzo [b, d] furan-4-ylboronic acid (reagent 11-1) was used in place of dibenzo [b, d] thiophen- (12 g, 71%) was synthesized in the same manner as in PREPARATION 11, except that dibenzo [b, d] furan-4-ylboronic acid (reagent 12-1) .

MS: [M + H] < + > = 601

Manufacturing example  13: Preparation of intermediate 4

Reagent 13-1 Reagent 13-2 Intermediate 13-1

1) Preparation of intermediate 13-1

Diphenyl-6- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) 1,3,5- (2,4-diphenyl-6- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) -1,3,5-triazine 13-1, 30 g, 69 mmol) and 7-bromonaphthalen-2-ol (reagent 13-2, 15 g, 69 mmol) were placed in 300 ml of tetrahydrofuran, And refluxed. Then, potassium carbonate (29 g, 206 mmol) was dissolved in 90 ml of water and stirred. After the addition, bis (tri-tert butylphosphine) palladium (0.4 g, 0.7 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 13-1 (17 g, 55%).

Intermediate 13-1 Reagent 13-3 Intermediate 4

2) Preparation of intermediate 4

Intermediate 13-1 (30 g, 69 mmol) and 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonyl fluoride (1,1, 2,3,3,4,4,4-nonafluorobutane-1-sulfonyl fluoride) (Reagent 13-3, 18 g, 80 mmol) was added to 400 ml of acetonitrile and stirred. After that, potassium carbonate (15 g, 147 mmol) was dissolved in 50 ml of water and the mixture was reacted for 1 hour and filtered. The filtrate was dried to give Intermediate 4 (47 g, 91%).

Manufacturing example  14: Synthetic example Ten  Produce

Intermediate 4 Reagent 14-1 Synthesis Example 10

One) Synthetic example  10 manufacture

(20 g, 21 mmol) and dibenzo [b, d] thiophen-4-ylboronic acid (reagent 14-1, 5.0 g, 27 mmol) were dissolved in 200 ml of dioxane and stirred and refluxed. Then, potassium phosphate (17 g, 82 mmol) was dissolved in 50 ml of water. After stirring well, bis (dibenzylidineacetone) palladium (0.5 g, 0.8 mmol) and tricyclohexylphosphine (0.5 g, 1.6 mmol ). 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 then recrystallized from ethyl acetate and purified by column chromatography (chloroform: hexane). The purified product was distilled and dried to give Synthesis Example 10 (7 g, 41%).

MS: [M + H] < + > = 617

Manufacturing example  15: Synthetic example Eleven  Produce

Intermediate 4 Reagent 15-1 Synthesis Example 11

One) Synthetic example  11 manufacture

Dibenzo [b, d] thiophen-4-ylboronic acid (Reagent 14-1) instead of dibenzo [b, d] thiophen- (10 g, 61%) was synthesized in the same manner as in Preparation Example 14, except that dibenzo [b, d] furan-4-ylboronic acid (Reagent 15-1) .

MS: [M + H] < + > = 601

Manufacturing example  16: Preparation of intermediate 5

Reagent 16-1 Reagent 16-2 Intermediate 16-1

1) Preparation of intermediate 16-1

Diphenyl-6- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) 1,3,5- (2,4-diphenyl-6- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) -1,3,5-triazine 6-bromonaphthalen-2-ol (Reagent 16-2, 15 g, 69 mmol) was added to 300 ml of tetrahydrofuran, followed by stirring And refluxed. Then, potassium carbonate (29 g, 206 mmol) was dissolved in 90 ml of water and stirred. After the addition, bis (tri-tert butylphosphine) palladium (0.4 g, 0.7 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 16-1 (13 g, 41%).

Intermediate 16-1 Reagent 16-3 Intermediate 5

2) Preparation of intermediate 5

Intermediate 16-1 (30 g, 69 mmol) and 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonyl fluoride (1,1, 2,2,3,3,4,4,4-nonafluorobutane-1-sulfonyl fluoride) (reagent 16-3, 18 g, 80 mmol) was added to 400 ml of acetonitrile and stirred. After that, potassium carbonate (15 g, 147 mmol) was dissolved in 50 ml of water and the mixture was reacted for 1 hour and filtered. The filtrate was dried to afford Intermediate 5 (43 g, 87%).

Manufacturing example  17: Synthetic example  12 manufacture

Intermediate 5 Reagent 17-1 Synthesis Example 12

One) Synthetic example  12 manufacture

(20 g, 21 mmol) and dibenzo [b, d] thiophen-4-ylboronic acid (reagent 17-1, 5.0 g, 27 mmol) were added to dioxane (200 ml), and the mixture was stirred and refluxed. Then, potassium phosphate (17 g, 82 mmol) was dissolved in 50 ml of water. After stirring well, bis (dibenzylidineacetone) palladium (0.5 g, 0.8 mmol) and tricyclohexylphosphine (0.5 g, 1.6 mmol ). 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 then recrystallized from ethyl acetate and purified by column chromatography (chloroform: hexane). The purified product was distilled and dried to give Synthesis Example 12 (9 g, 54%).

MS: [M + H] < + > = 617

Manufacturing example  18: Synthetic example  13 manufacture

Intermediate 5 Reagent 18-1 Synthesis Example 13

One) Synthetic example  13 manufacture

Dibenzo [b, d] furan-4-ylboronic acid (reagent 17-1) was used in place of dibenzo [b, d] thiophen- (7 g, 44%) was synthesized in the same manner as in PREPARATION 17, except that dibenzo [b, d] furan-4-ylboronic acid (reagent 18-1) .

MS: [M + H] < + > = 601

Manufacturing example  19: Synthetic example  14 manufacture

Reagent 19-1 Reagent 19-2 Intermediate 19-1

1) Preparation of intermediate 19-1

2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine) was obtained in a nitrogen atmosphere. (Reagent 19-1, 50 g, 129 mmol) and (4-chloronaphthalen-1-yl) boronic acid (reagent 19-2, 29.2 g, 142 mmol) (53 g, 386 mmol) was dissolved in 60 ml of water. After sufficiently stirring, tetrakistriphenylphosphinopalladium (4.5 g, 4 mmol) was added to the solution, and the mixture was stirred at room temperature for 2 hours. After the reaction was completed for 8 hours, the reaction mixture was cooled to room temperature and filtered, and the organic layer was dried over magnesium sulfate using chloroform and water, and the organic layer was distilled under reduced pressure and recrystallized using ethyl acetate. Followed by drying to obtain Intermediate 19-1 (43 g, 71%).

Intermediate 19-1 Reagent 19-3 Synthesis Example 14

2) Synthetic example  14 manufacture

(10 g, 21 mmol) and dibenzo [b, d] thiophen-4-ylboronic acid (reagent 19-3, 5.3 g, 23 mmol) were added to 150 ml of dioxane, which was stirred and refluxed. After dissolving potassium phosphate (14 g, 64 mmol) in 50 ml of water and stirring well, bis (dibenzylidineacetone) palladium (0.4 g, 0.6 mmol) and tricyclohexylphosphine (0.4 g, 0.6 mmol ). After 24 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 then recrystallized from ethyl acetate and purified by column chromatography (chloroform: hexane). The purified product was dried to give Synthesis Example 14 (7 g, 54%).

MS: [M + H] < + > = 617

Manufacturing example  20: Synthetic example  15 manufacture

Intermediate 19-1 Reagent 20-1 Synthesis Example 15

One) Synthetic example  15 manufacture

Dibenzo [b, d] thiophen-4-ylboronic acid (reagent 19-3) was used in place of dibenzo [b, d] thiophen- (8 g, 61%) was synthesized in the same manner as in PREPARATION 19, except that dibenzo [b, d] furan-4-ylboronic acid (reagent 20-1) .

MS: [M + H] < + > = 601

Manufacturing example  21: Synthetic example  16 manufacture

Intermediate 1-1 Reagent 21-1 Synthesis Example 16

One) Synthetic example  16 manufacture

Intermediate 1-1 (10 g, 21 mmol) and reagent 21-1 (5.3 g, 23 mmol) were added to 150 ml of dioxane in a nitrogen atmosphere, and the mixture was stirred and refluxed. After dissolving potassium phosphate (14 g, 64 mmol) in 50 ml of water and stirring well, bis (dibenzylidineacetone) palladium (0.4 g, 0.6 mmol) and tricyclohexylphosphine (0.4 g, 0.6 mmol ). After 24 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 then recrystallized from ethyl acetate and purified by column chromatography (chloroform: hexane). The purified product was dried to give Synthesis Example 16 (10 g, 61%).

MS: [M + H] < + > = 678

Manufacturing example  22: Synthetic example  Preparation of 17

Intermediate 19-1 Reagent 22-1 Synthesis Example 17

One) Synthetic example  Preparation of 17

Synthesis Example 17 (7 g, 50%) was synthesized in the same manner as in PREPARATION 19, except that the reagent 22-1 was used instead of the reagent 19-3 in PREPARATION 19.

MS: [M + H] < + > = 678

[ Experimental Example ] Preparation of Organic Light Emitting Device

Experimental Example  One

A glass substrate (corning 7059 glass) coated with ITO (indium tin oxide) with a thickness of 1,000 Å was immersed in distilled water containing a dispersant and washed with ultrasonic waves. The detergent was a product of Fischer Co. The distilled water was supplied by Millipore Co. Distilled water, which was secondly filtered with a filter of the product, was used. After the ITO was washed for 30 minutes, 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.

The following HI-1 compound was thermally vacuum deposited on the prepared ITO transparent electrode to a thickness of 500 Å to form a hole injection layer. On the hole injection layer, the following HT-1 compound was vacuum deposited to a thickness of 400 Å to form a hole transport layer, and a host H1 and a dopant D1 compound (2.5 wt%) were vacuum deposited as a light emitting layer to a thickness of 300 Å. The following compound ET-A was vacuum deposited on the light emitting layer to a thickness of 50 Å to form an a-electron transporting layer. The compound of Synthesis Example 1 and LiQ (Lithium Quinolate) were vacuum deposited on the a-electron transport 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 the deposition rate was 0.4 ~ 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 < ^-6 > 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 the compound of Synthesis Example 2 was used instead of the compound of Synthesis Example 1 in Experimental Example 1 above.

Experimental Example  3

An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that the compound of Synthesis Example 3 was used instead of the compound of Synthesis Example 1 in Experimental Example 1.

Experimental Example  4

An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that the compound of Synthesis Example 4 was used instead of the compound of Synthesis Example 1 in Experimental Example 1.

Experimental Example  5

An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that the compound of Synthesis Example 5 was used instead of the compound of Synthesis Example 1 in Experimental Example 1.

Experimental Example  6

An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that the compound of Synthesis Example 6 was used instead of the compound of Synthesis Example 1 in Experimental Example 1.

Experimental Example  7

An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that the compound of Synthesis Example 7 was used instead of the compound of Synthesis Example 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 the compound of Synthesis Example 8 was used instead of the compound of Synthesis Example 1 in Experimental Example 1 above.

Experimental Example  9

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

Experimental Example  10

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

Experimental Example  11

An organic light emitting device was fabricated in the same manner as in Experimental Example 1 except that the compound of Synthesis Example 11 was used instead of the compound of Synthesis Example 1 in Experimental Example 1. [

Experimental Example  12

An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that the compound of Synthesis Example 12 was used in place of the compound of Synthesis Example 1 in Experimental Example 1 above.

Experimental Example  13

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

Experimental Example  14

An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that the compound of Synthesis Example 14 was used instead of the compound of Synthesis Example 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 the compound of Synthesis Example 15 was used instead of the compound of Synthesis Example 1 in Experimental Example 1 above.

Experimental Example  16

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

Experimental Example  17

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that the compound of Synthesis Example 17 was used instead of the compound of Synthesis Example 1 in Experimental Example 1 above.

Comparative Example 1 Comparative Example 2 Comparative Example 3

Comparative Example  One

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

Comparative Example  2

An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that the compound of Comparative Example 2 was used instead of the compound of Synthesis Example 1 in Experimental Example 1.

Comparative Example  3

An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that the compound of Comparative Example 3 was used instead of the compound of Synthesis Example 1 in Experimental Example 1.

Experimental Example 1 to 17 and Comparative Experiment 1 The organic light-emitting device manufactured to 3 at a current density of 10 mA / cm ² was measured drive voltage and luminous efficiency, the initial luminance at a current density of 50 mA / cm ² Contrast The time (LT95), which is 95%, was measured. The results are shown in Tables 1 and 2 below.

Experimental Example
number compound Voltage (V)
(@ 10 mA / cm ² ) Efficiency (Cd / A)
(@ 10 mA / cm ² ) Color coordinates
(x, y) Life span (h)
T ₉₅ at ₅₀ mA / cm ² One Synthesis Example 1 4.11 5.21 0.134, 0.133 120 2 Synthesis Example 2 4.14 5.11 0.133, 0.133 150 3 Synthesis Example 3 3.97 5.95 0.134, 0.132 90 4 Synthesis Example 4 3.80 7.14 0.134, 0.132 115 5 Synthesis Example 5 3.94 7.12 0.134, 0.132 110 6 Synthesis Example 6 3.91 6.95 0.134, 0.133 90 7 Synthesis Example 7 3.80 7.00 0.133, 0.133 150 8 Synthesis Example 8 3.91 7.00 0.134, 0.132 130 9 Synthesis Example 9 3.97 7.15 0.134, 0.132 99 10 Synthesis Example 10 3.91 7.10 0.134, 0.132 110 11 Synthesis Example 11 3.90 6.85 0.134, 0.133 121 12 Synthesis Example 12 3.90 7.00 0.132, 0.134 150 13 Synthesis Example 13 3.90 7.00 0.133, 0.135 63 14 Synthesis Example 14 3.99 7.10 0.134, 0.133 77 15 Synthesis Example 15 3.72 6.81 0.134, 0.133 90 16 Synthesis Example 16 3.72 7.12 0.134, 0.133 73 17 Synthesis Example 17 3.72 7.15 0.134, 0.133 69

Comparative Example
number compound Voltage (V)
(@ 10 mA / cm ² ) Efficiency (Cd / A)
(@ 10 mA / cm ² ) Color coordinates
(x, y) Life span (h)
T ₉₅ at ₅₀ mA / cm ² One Comparative Example 1 3.60 5.80 (0.133, 0.133) 60 2 Comparative Example 2 3.90 6.81 (0.134, 0.132) 50 3 Comparative Example 3 3.90 4.99 (0.134, 0.132) 55

As can be seen from Tables 1 and 2, when the compound of the present invention was used as an electron transport layer material, it was confirmed that the compound of the present invention exhibited excellent characteristics in terms of efficiency and stability as compared with the case of using the compounds of Comparative Examples 1 to 3 . In particular, in Examples 1 to 17, it was confirmed that life characteristics and efficiency were improved as compared with Comparative Example 3 in which a heteroarylene group was directly bonded to a monocyclic heteroaryl group containing two or more Ns. In addition, when Examples 1 to 17 were compared with Comparative Examples 1 to 3, it was confirmed that life characteristics were particularly improved.

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

Claims (9)

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

In Formula 1,
At least two of X ₁ to X ₃ are N and the others are N or CR,
X ₄ is a 1,2-naphthalene group; 1,3-naphthalene group; A 2,6-naphthalene group; Or a 2,7-naphthalene group,
L ₁ and L ₂ are the same or different and are each independently a direct bond; Or an arylene group,
Y is O or S,
Ar ₁ and Ar ₂ are the same or different and are each independently an aryl group,
R, R ₁ , and R ₂ are the same or different from each other, and each independently hydrogen; Or deuterium,
a is an integer of 1 to 3,
b is an integer of 1 to 4,
When a is 2 or more, a plurality of R < ₁ > s are the same or different from each other,
When b is 2 or more, plural R ₂ are the same or different from each other. The compound according to claim 1, wherein the compound represented by Formula 1 is represented by any one of Chemical Formulas 3 to 6:
(3)

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

In the above formulas 3 to 6,
X ₁ to X ₃ , L ₁ and L ₂ , Y, Ar ₁ , Ar ₂ , R, R ₁ , and R ₂ are the same as defined in Formula 1,
R ₃ is hydrogen; Or deuterium,
c is an integer of 1 to 6,
When c is 2 or more, a plurality of R ₃ 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 includes a compound according to any one of claims 1 to 3. 4. The organic electronic device according to claim 1, Electronic device. 5. The organic electronic device according to claim 4, wherein the organic layer includes a light emitting layer, and the light emitting layer comprises the compound. 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 the organic material layer comprises a hole injecting layer or a hole transporting layer and the hole injecting layer or the hole transporting layer comprises a compound represented by the following Formula 1:
[Chemical Formula 1]

In Formula 1,
At least two of X ₁ to X ₃ are N and the others are N or CR,
X ₄ is a naphthalene group,
L ₁ and L ₂ are the same or different and are each independently a direct bond; Or an arylene group,
Y is O or S,
Ar ₁ and Ar ₂ are the same or different and are each independently an aryl group,
R, R ₁ , and R ₂ are the same or different from each other, and each independently hydrogen; Or deuterium,
a is an integer of 1 to 3,
b is an integer of 1 to 4,
When a is 2 or more, a plurality of R < ₁ > s are the same or different from each other,
When b is 2 or more, plural R ₂ are the same or different from each other. 5. The organic electronic device according to claim 4, 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. 5. The organic electronic device according to claim 4, wherein the organic material layer includes an electron blocking layer or a hole blocking layer, and the electron blocking layer or the hole blocking layer comprises the compound. 5. The organic electroluminescent device according to claim 4, wherein the organic electronic device is a light emitting layer, a hole injecting layer, and a hole transporting layer. An electron injection layer, an electron transport layer, an electron blocking layer, and a hole blocking layer.

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