KR101916572B1 - Compound and organic light electronic device comprising the same - Google Patents

Abstract

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

Description

BACKGROUND OF THE INVENTION 1. Field of the Invention [0001] The present invention relates to a compound and an organic electronic device including the compound,

This application claims the benefit of Korean Patent Application No. 10-2016-0045036 filed with the Korean Intellectual Property Office on April 12, 2016, the entire contents of which are incorporated herein by reference.

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

An organic electronic device is an electronic device using an organic semiconductor material, and requires holes and / or electrons to flow between the electrode and the organic semiconductor material. The organic electronic device can be roughly classified into two types according to the operating principle as described below. First, an exciton is formed in an organic material layer by a photon introduced into an element from an external light source. The exciton is separated into an electron and a hole, and the electrons and holes are transferred to different electrodes to be used as a current source Is an electronic device. The second type is an electronic device that injects holes and / or electrons into an organic semiconductor material layer that interfaces with the electrode by applying a voltage or current to two or more electrodes, and operates by injected electrons and holes.

Examples of the organic electronic device include an organic light emitting device, an organic solar cell, an organic photoconductor (OPC), an organic transistor, and the like. These devices may be used as a hole injecting or transporting material, an electron injecting or transporting material, need. Hereinafter, the organic light emitting device will be described in detail. However, in the organic electronic devices, hole injecting or transporting materials, electron injecting or transporting materials, or light emitting materials act on a similar principle.

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.

An embodiment of the present invention provides a compound represented by the following formula (1).

[Chemical Formula 1]

In Formula 1,

A is S, P (Ar) or SiRR '

B is O or S,

Provided that when A is S, then B is O,

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

L ₁ is a substituted or unsubstituted arylene group,

Ar, Ar ₁ and Ar ₂ are the same or different and each independently hydrogen; heavy hydrogen; A halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

R, R ', R ", R ₁ and R ₂ are the same or different from each other and each independently represents hydrogen, deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl 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 aryloxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, A substituted or unsubstituted aryloxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted aryloxy group, A substituted or unsubstituted arylamine group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,

p is an integer of 1 to 3,

q is an integer of 1 to 4,

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

When q is 2 or more, plural R ₂ are the same or different from each other.

In addition, one embodiment of the present disclosure includes 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 compound of the formula (1).

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. .

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.
FIG. 3 is a graph showing the MS DATA value of Compound 1. FIG.
4 shows the MS DATA value of compound 2. FIG.
FIG. 5 is a graph showing the MS DATA value of the compound 3. FIG.
6 shows the MS DATA value of compound 4. FIG.
7 is a graph showing the MS DATA value of Compound 5. FIG.

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

An embodiment of 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; A nitrile group; 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 two or more 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 number of carbon atoms in the imide 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 amide group may be substituted with nitrogen of the amide group by hydrogen, a straight chain, branched chain or cyclic alkyl group of 1 to 30 carbon atoms or an aryl group of 6 to 30 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 50. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec- N-pentyl, 3-dimethylbutyl, 2-ethylbutyl, heptyl, n-hexyl, Cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethyl Heptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl and 5-methylhexyl.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms. Specific examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, But are not limited to, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert- butylcyclohexyl, cycloheptyl and cyclooctyl 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 and p- 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, and styrenyl groups.

In the present specification, and include silyl group Si, and the substituents are directly connected, as the Si atom radical, R is represented by -SiR _{104 105} R _106, R ₁₀₄ to R _106, and is 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 trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group and phenylsilyl group. But is not limited thereto.

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 30 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 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, and a quarter phenyl group.

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, but are not limited to, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a klycenyl group and a fluorenyl group.

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

,

,

,

,

또는

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

,

,

,

,

or

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, a pyrazinyl group, a pyrazinyl group, a pyrazinyl group, a pyrazinyl group, a quinolinyl group, a quinazolinyl group, a quinoxalinyl group, a phthalazinyl group, a pyridopyrimidinyl group, , An indole group, a carbazole group, a benzoxazole group, a benzimidazole group, a benzothiazole group, a benzocarbazole group, a benzothiophene group, a dibenzothiophene group, a benzofuranyl group, a phenanthroline group, , An isoxazolyl group, an oxadiazolyl group, a thiadiazolyl group, a benzothiazolyl group, and a dibenzofuranyl group, but the present invention is not limited thereto.

As used herein, the term "adjacent group" means a group in which the substituent is substituted with an atom directly bonded to the atom to which the substituted atom is substituted, a substituent having the closest stereostructure to the substituent, It can mean. For example, two substituents substituted at the ortho position in the benzene ring and two substituents substituted at the same carbon in the aliphatic ring may be interpreted as "adjacent groups ".

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

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 and is represented by -NR ₁₀₇ R ₁₀₈ , and R ₁₀₇ and R ₁₀₈ are the same or different from each other And at least one of R ₁₀₇ and R ₁₀₈ is not hydrogen, each of which may independently be hydrogen, deuterium, a halogen group, an alkyl group, an alkenyl group, an alkoxy group, a cycloalkyl group, an aryl group and a heterocyclic group ). Examples thereof include monoalkylamine groups, dialkylamine groups, N-alkylarylamine groups, monoarylamine groups, diarylamine groups, N-arylheteroarylamine groups, N-alkylheteroarylamine groups, monoheteroarylamine groups And a diheteroarylamine group. The number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, a phenylamine group, a naphthylamine group, a biphenylamine group, an anthracenylamine group, a 9- , Diphenylamine group, ditolylamine group, N-phenyltolylamine group, triphenylamine group, N-phenylbiphenylamine group, N-phenylnaphthylamine group, N-biphenylnaphthylamine group, N- Naphthylphenylenediamine amine group, N-phenylphenanthrenylamine group, N-biphenylphenanthrenylamine group, N-phenylfluorenylamine group, N-phenyltriphenylamine group, An oleylamine group, and an N-biphenylfluorenylamine group, but are not limited thereto.

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

In the present specification, the aryl group in the aryloxy group, the arylthioxy group and the arylsulfoxy 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, but are 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 containing two or more aryl groups may simultaneously contain a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group. 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 containing two or more heteroaryl groups may simultaneously contain a monocyclic heteroaryl group, a polycyclic heteroaryl group, or a monocyclic heteroaryl group and a polycyclic heteroaryl group. 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, the aromatic ring group may be monocyclic or polycyclic, and may be selected from the examples of the aryl group except that it is not monovalent.

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

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

In one embodiment of the present invention, the formula (1) may be represented by any one of the following formulas (2) to (4).

(2)

(3)

[Chemical Formula 4]

In the above formulas 2 to 4,

The definition of A, B, X ₁ to X ₃ , L ₁ , Ar ₁ , Ar ₂ , R ₁ and R ₂ , p, q is the same as defined in the above formula (1).

In one embodiment of the present invention, the formula (1) may be represented by any one of the following formulas (5) to (19).

[Chemical Formula 5]

[Chemical Formula 6]

(7)

[Chemical Formula 8]

[Chemical Formula 9]

[Chemical formula 10]

(11)

[Chemical Formula 12]

[Chemical Formula 13]

[Chemical Formula 14]

[Chemical Formula 15]

[Chemical Formula 16]

[Chemical Formula 17]

[Chemical Formula 18]

[Chemical Formula 19]

In the above formulas 5 to 19,

The definitions of X ₁ to X ₃ , L ₁ , Ar, Ar ₁ , Ar ₂ , R, R ', R ₁ , R ₂ , p and q are the same as those defined in Formula 1.

In one embodiment of the present disclosure, A is S, P (Ar) or SiRR '.

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

In one embodiment of the present disclosure, A is P (Ar).

In one embodiment of the present disclosure, A is P (Ph) and Ph is a phenyl group.

In one embodiment of the present disclosure, A is SiRR '.

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

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

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

In one embodiment of the present disclosure, if A is S then B is O.

In one embodiment of the present specification, at least two of X ₁ to X ₃ are N and the remaining are N or CR ".

In one embodiment of the present disclosure, X1 to X3 are N.

In one embodiment of the present specification, L 1 is a substituted or unsubstituted arylene group.

In one embodiment of the present invention, L 1 is a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, or a substituted or unsubstituted naphthylene group.

In one embodiment of the present disclosure, L1 is a naphthylene group substituted with an aryl group.

In one embodiment of the present disclosure, L1 is a naphthylene group substituted with a phenyl group.

In one embodiment of the present disclosure, L1 is a naphthylene group.

In one embodiment of the present disclosure, L1 is a phenylene group.

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; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted phosphine oxide 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 30 carbon atoms.

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

In one embodiment of the present specification, Ar ₁ and Ar ₂ are the same or different from each other, and each is a terphenyl group substituted with pyridine.

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, a biphenyl group, a terphenyl group or a naphthyl group.

In one embodiment of the present specification, Ar ₁ and Ar ₂ are phenyl groups.

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 heteroaryl group having 6 to 50 carbon atoms.

In one embodiment of the present specification, Ar ₁ and Ar ₂ are the same or different and each independently represents a substituted or unsubstituted carbazole group, a substituted or unsubstituted dibenzofurane group, or a substituted or unsubstituted dibenzothi Lt; / RTI >

In one embodiment of the present specification, Ar ₁ and Ar ₂ are the same or different and each independently is a carbazole group, a dibenzofurane group or a dibenzothiophene group.

In one embodiment of the present specification, R, R ', R ", R ₁ and R ₂ are the same or different from each other and each independently represents hydrogen, deuterium, halogen, nitrile, nitro, A substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted alkylthio group, or a substituted or unsubstituted alkylthio group; A substituted or unsubstituted aryloxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylthioxy 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 amino 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 disclosure, R ", R ₁ and R ₂ , equal to or different from each other, are each independently hydrogen.

According to one embodiment of the present disclosure, the compound 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 and reaction conditions and the like can be changed.

One embodiment of the present invention provides an organic electronic device comprising the above-mentioned compound.

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 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 and / .

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.

According to one embodiment of the present invention, the organic electronic device is an organic light emitting device.

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 electronic device includes one or more layers selected from the group consisting of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, a hole blocking layer, .

In one embodiment of the present invention, the organic electronic 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; And two or more organic layers provided between the light emitting layer and the first electrode or between the light emitting layer and the second electrode, and at least one of the two or more organic layers includes the compound. 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 the 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 electronic device may be a normal type organic electronic device in which an anode, at least one organic layer, and a cathode are sequentially stacked on a substrate.

In one embodiment of the present invention, when the organic compound layer containing the compound is an electron transport layer, the electron transport 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 one example, the electron transport layer containing the compound may further include LiQ.

In one embodiment of the present specification, when the electron transport layer further contains an n-type dopant in addition to the compound, the weight ratio of the compound and the n-type dopant may be 1: 100 to 100: 1. Specifically 1:10 to 10: 1. More specifically, it may be 1: 1.

In one embodiment of the present specification, when the organic compound layer containing the compound is a light emitting layer, the compound includes the light emitting dopant as a host of the light emitting layer.

In another embodiment of the present invention, the luminescent dopant includes a fluorescent dopant or a phosphorescent dopant, and the phosphorescent dopant includes an iridium (Ir) phosphorescent dopant.

In another embodiment, the phosphorescent dopant material comprises Ir (ppy) ₃ or (piq) ₂ Ir (acac).

In another embodiment, the concentration of the dopant may be between 1 wt% and 90 wt%. Specifically, it may be 1 wt% to 10 wt%.

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

For example, the structure of the organic electronic device in this specification may have a structure as shown in Figs. 1 and 2, but is not limited thereto.

1 illustrates a structure of an organic electronic device 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 electronic device 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 stacked on a substrate. 2 is an exemplary structure according to an embodiment of the present invention, and may further include another organic layer.

When the organic electronic device includes a plurality of organic layers, the organic layers may be formed of the same material or another material.

 The organic electronic device in this specification can be produced by materials and methods known in the art, except that at least one of the organic layers includes the compound, that is, 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 injection 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 the present invention is 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; And rubrene, but are not limited thereto.

The light emitting layer may include a host material and a dopant material. The host material includes a condensed aromatic ring derivative and a hetero ring-containing 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 And pyrimidine derivatives, 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 A substituted or unsubstituted compound in which at least one aryl vinyl group is substituted with an arylamine, and wherein one or more substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group are substituted or unsubstituted. Specific examples thereof include, but are not limited to, styrylamine, styryldiamine, styryltriamine, and styryltetraamine. Examples of the metal complexes include iridium complexes and platinum complexes, but are not limited thereto.

The electron transporting layer is a layer that receives electrons from the electron injecting layer and transports electrons to the light emitting layer. The electron transporting material is a material capable of transferring electrons from the cathode well to the light emitting layer. Do. Specific examples include an Al complex of 8-hydroxyquinoline; Complexes containing Alq ₃ ; Organic radical compounds; And hydroxyflavone-metal complexes, 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, there are cesium, barium, calcium, ytterbium, and samarium, which are in each case followed by an aluminum layer or a silver layer.

The electron injection layer is a layer for injecting electrons from an electrode and has an ability to transport electrons and has an electron injection effect from the cathode and 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-hydroxyquinolinato) manganese , Tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8-hydroxyquinolinato) gallium, bis (10-hydroxybenzo [h ] Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8- quinolinato) (2-methyl-8-quinolinato) (1-naphtholato) aluminum and bis (2-methyl-8-quinolinato) , 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 include oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP (bathocuproine), and aluminum complexes, but are not limited thereto.

The organic light emitting diode according to one embodiment of the present invention may be a front emission type, a back emission type, or a both-sided emission type, depending on the material used.

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

Hereinafter, the present invention will be described in detail by way of examples to illustrate the present invention. 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 above-described embodiments. Embodiments of the present disclosure are provided to more fully describe the present disclosure to those of ordinary skill in the art.

< Manufacturing example >

& Lt; Synthesis Example 1 > - Preparation of Intermediates 1 to 8

(1) Preparation of intermediate 1

 (Formula 1A) (Intermediate 1)

Sulfur (64g, 2.0mol) was added in a solid state while stirring the above-mentioned compound (1A) (340.0g, 2.0mol) with heating from 80 ° C to 90 ° C. Subsequently, aluminum chloride (AlCl ₃ ) (133.3 g, 1 mol) was added in three portions at 70 ° C slowly, and the mixture was reacted at 100 ° C for 4 hours. The diluted hydrochloric acid solution was then added to terminate the reaction, and the solution was extracted with 1 L of chloroform. The solution was then dried with magnesium sulfate. Subsequently, the organic layer was distilled under reduced pressure to remove the unchanged formula (IA), and a solid was formed using ethanol, followed by filtration and drying to prepare Intermediate 1 (115 g, 29%).

(2) Preparation of intermediate 2

 (Formula 1A) (Intermediate 2)

Was cooled to 78 ℃ - Formula 1A (100.0g, 587.51mmol) in tetrahydrofuran into 1000mL,. Then, n-butyllithium (n-BuLi) (470 mL, 1175.02 mmol) was slowly added dropwise over 1 hour while stirring, reacted for 1 hour, then heated to room temperature and reacted for 2 hours. Dichloro (phenyl) phosphazene (105 g, 587.51 mmol) was then added slowly after cooling to -78 ° C again. After the addition reaction for 2 hours, the temperature was slowly raised to room temperature and reacted for 4 hours. After the reaction, water was poured to terminate the reaction. The water layer and the organic layer were separated, and the organic layer was distilled off under reduced pressure and extracted with chloroform (1 L) / water (1 L). This solution was dried with magnesium sulfate. Subsequently, the organic layer was distilled under reduced pressure, and the unchanged formula (1A) was removed. A solid was formed using ethanol, followed by filtration and drying to prepare Intermediate 2 (71 g, 44%).

(3) Preparation of intermediate 3

  (Formula IA) (Intermediate 3)

It was cooled to 78 ℃ - Formula 1A (100.0g, 587.51mmol) into a tetrahydrofuran (THF) 1000mL,. Then, n-butyllithium (n-BuLi) (470 mL, 1175.02 mmol) was slowly added dropwise over 1 hour while stirring, reacted for 1 hour, heated to room temperature and reacted for 2 hours. After cooling to -78 ° C again, dichlorodimethylsilane (75.8 g, 587.51 mmol) was added slowly. After the addition, the temperature was slowly raised to room temperature and reacted for 4 hours. After the completion of the reaction, the water layer and the organic layer were separated. The organic layer was distilled under reduced pressure, and extracted with chloroform (1 L) / water (1 L). The solution was dried with magnesium sulfate. Subsequently, the organic layer was distilled under reduced pressure to remove the unchanged formula (1A), and a solid was formed using ethanol, followed by filtration and drying, to prepare Intermediate 3 (68 g, 51%).

 (4) Preparation of intermediate 4

    (Intermediate 1) (Intermediate 4)

Intermediate 1 (30 g, 145 mmol) was placed in 300 mL of tetrahydrofuran (THF) and cooled to -78 &lt; 0 &gt; C. Then, n-butyllithium (n-BuLi) (72 mL, 180 mmol) was slowly added dropwise over 1 hour while stirring, reacted for 1 hour, heated to room temperature and reacted for 2 hours. After cooling to -78 캜, triisopropylborate (33.8 g, 180 mmol) was slowly added thereto. After the addition reaction for 2 hours, the temperature was slowly raised to room temperature and reacted for 4 hours. After the reaction, diluted hydrochloric acid (HCl) was poured into the reaction mixture to separate the water layer and the organic layer. The organic layer was distilled under reduced pressure and extracted with chloroform (1 L) / water (1 L). This solution was dried using magnesium sulfate, and then the organic layer was distilled off under reduced pressure, and intermediate 4 (25 g, 68%) was prepared using hexane.

(5) Preparation of intermediate 5

   (Intermediate 2) (Intermediate 5)

Intermediate 2 (30 g, 108 mmol) was placed in 300 mL of tetrahydrofuran (THF) and cooled to -78 &lt; 0 &gt; C. Then, n-butyllithium (n-BuLi) (52 mL, 130 mmol) was slowly added dropwise over 1 hour while stirring, reacted for 1 hour, and then heated to room temperature and reacted for 2 hours. After cooling to -78 캜, triisopropylborate (24.5 g, 130 mmol) was slowly added thereto. After the addition reaction for 2 hours, the temperature was slowly raised to room temperature and reacted for 4 hours. After the reaction, diluted hydrochloric acid (HCl) was poured into the reaction mixture to separate the water layer and the organic layer. The organic layer was distilled under reduced pressure and extracted with chloroform (1 L) / water (1 L). This solution was dried using magnesium sulfate, and then the organic layer was distilled off under reduced pressure, and intermediate 5 (25 g, 71%) was prepared using hexane.

(6) Preparation of intermediate 6

   (Intermediate 3) (Intermediate 6)

Intermediate 3 (30 g, 130 mmol) was added to 300 mL of tetrahydrofuran (THF) and cooled to -78 ° C. Then, n-butyllithium (n-BuLi) (63 mL, 156 mmol) was slowly added dropwise over 1 hour while stirring and reacted for 1 hour, then heated to room temperature and reacted for 2 hours. After cooling to -78 캜, triisopropylborate (29.4 g, 156 mmol) was slowly added thereto. Then, the reaction was continued for 2 hours, then slowly warmed to room temperature and reacted for 4 hours. After the reaction, diluted hydrochloric acid (HCl) was poured into the reaction mixture to separate the water layer and the organic layer. The organic layer was distilled under reduced pressure and extracted with chloroform (1 L) / water (1 L). This solution was dried using magnesium sulfate, and then the organic layer was distilled off under reduced pressure and hexane was used to prepare intermediate 6 (26 g, 74%).

(7) Preparation of intermediate 7

(Formula 7A) (Formula 7B) (Intermediate 7)

In a nitrogen atmosphere, the compound of Formula 7A (30.0 g, 135 mmol) and the compound of Formula 7B (59 g, 135 mmol) were added to 300 mL of tetrahydrofuran (THF) and stirred and refluxed. Potassium carbonate (K ₂ CO ₃ ) (37.2 g, 269 mmol) was dissolved in 100 mL of water, and the mixture was sufficiently stirred and tetrakistriphenylphosphinopalladium (4.7 g, 4.03 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 ethanol. The resulting solid was filtered and dried to give Intermediate 7 (28 g, 80%).

(8) Preparation of intermediate 8

  (Intermediate 7) (Intermediate 8)

Intermediate 7 (28 g, 62.01 mmol) was added to 300 mL of acetonitrile (AN) in a nitrogen atmosphere, and potassium carbonate (K ₂ CO ₃ ) (17.1 g, 124 mmol) was added to 50 mL of water while stirring. Then, 1-butanesulfonyl fluoride (28.1 g, 93 mmol) was slowly added while heating with a water bath. The reaction was then terminated after about 1 hour of reaction. After completion of the reaction, the temperature was lowered to room temperature, and the water layer and the organic layer were separated. The organic layer was distilled under reduced pressure to prepare Intermediate 8 (41.1 g, 91%).

<Synthesis Example 2> Preparation of Compound 1

(Intermediate 8) (Intermediate 4) (Compound 1)

Intermediate 8 (20.0 g, 27 mmol) and Intermediate 4 (6.7 g, 27 mmol) were dissolved in tetrahydrofuran (THF) (200 mL) under nitrogen atmosphere and stirred and refluxed. Potassium carbonate (K ₂ CO ₃ ) (7.5 g, 54.5 mmol) was dissolved in 30 mL of water and stirred sufficiently. Tetraquistriphenylphosphinopalladium (0.9 g, 0.8 mmol) was added thereto. After 6 hours of reaction, the temperature was lowered to room temperature and filtered. The filtrate was extracted with chloroform and water, and then the organic layer was dried with magnesium sulfate. The organic layer was then vacuum distilled and recrystallized using ethyl acetate. The resulting solid was filtered and dried to give Compound 1 (9.3 g, 54%). FIG. 3 is a diagram showing the MS DATA value of the compound 1. FIG.

MS: [M + H] &lt; ⁺ &gt; = 709

& Lt; Synthesis Example 3 > - Preparation of Compound 2

(Intermediate 8) (Intermediate 5) (Compound 2)

In a nitrogen atmosphere, Intermediate 8 (20.0 g, 27 mmol) and Intermediate 5 (8.7 g, 27 mmol) were added to 200 mL of tetrahydrofuran (THF) and stirred and refluxed. Potassium carbonate (K ₂ CO ₃ ) (7.5 g, 54.5 mmol) was dissolved in 30 mL of water and then stirred sufficiently. Tetraquistriphenylphosphinopalladium (0.9 g, 0.8 mmol) was added thereto. After 6 hours of reaction, the temperature was lowered to room temperature and filtered. The filtrate was extracted with chloroform and water, and then the organic layer was dried with magnesium sulfate. The organic layer was then distilled under reduced pressure and recrystallized using ethyl acetate. The resulting solid was filtered and dried to give Compound 2 (10.3 g, 53%). FIG. 4 is a diagram showing the MS DATA value of the compound 2. FIG.

MS: [M + H] &lt; ⁺ &gt; = 659

& Lt; Synthesis Example 4 > - Preparation of Compound 3

(Intermediate 8) (Intermediate 6) (Compound 3)

In a nitrogen atmosphere, Intermediate 8 (20.0 g, 27 mmol) and Intermediate 6 (8.7 g, 27 mmol) were added to 200 mL of tetrahydrofuran (THF) and stirred and refluxed. Potassium carbonate (K ₂ CO ₃ ) (7.5 g, 54.5 mmol) was dissolved in 30 mL of water and then stirred sufficiently. Tetraquistriphenylphosphinopalladium (0.9 g, 0.8 mmol) was added thereto. After 6 hours of reaction, the temperature was lowered to room temperature and filtered. The filtrate was extracted with chloroform and water, and then the organic layer was dried with magnesium sulfate. The organic layer was then distilled under reduced pressure and recrystallized using ethyl acetate. The resulting solid was filtered and dried to give Compound 3 (11 g, 61%). 5 is a graph showing the MS DATA value of the compound 3. FIG.

MS: [M + H] &lt; ⁺ &gt; = 633

& Lt; Synthesis Example 5 > - Preparation of Compound 4

  (Intermediate 8A) (Intermediate 4) (Compound 4)

Intermediate 8A (20.0 g, 27 mmol) and Intermediate 4 (6.7 g, 27 mmol) prepared in the same manner as in Synthesis Example of Intermediate 8 in a nitrogen atmosphere were placed in 200 mL of tetrahydrofuran (THF) and stirred and refluxed. Potassium carbonate (K ₂ CO ₃ ) (7.5 g, 54.5 mmol) was dissolved in 30 mL of water and then stirred sufficiently. Tetraquistriphenylphosphinopalladium (0.9 g, 0.8 mmol) was added thereto. After 6 hours of reaction, the temperature was lowered to room temperature and filtered. The filtrate was extracted with chloroform and water, and then the organic layer was dried with magnesium sulfate. The organic layer was then distilled under reduced pressure and recrystallized using ethyl acetate. The resulting solid was filtered and dried to give Compound 4 (12.3 g, 71%). FIG. 6 is a diagram showing the MS DATA value of the compound 4. FIG.

MS: [M + H] &lt; ⁺ &gt; = 633

& Lt; Synthesis Example 6 > - Preparation of Compound 5

 (Intermediate 8B) (Intermediate 4) (Compound 5)

Intermediate 8B (20.0 g, 27 mmol) and Intermediate 4 (6.7 g, 27 mmol) which were prepared in the same manner as in Synthesis Example of Intermediate 8 in a nitrogen atmosphere were placed in 200 mL of tetrahydrofuran and stirred and refluxed. Then, potassium carbonate (7.5 g, 54.5 mmol) was dissolved in 30 mL of water, and the mixture was sufficiently stirred. Tetraquistriphenylphosphinopalladium (0.9 g, 0.8 mmol) was added thereto. After 6 hours of reaction, the temperature was lowered to room temperature and filtered. The filtrate was extracted with chloroform and water, and then the organic layer was dried with magnesium sulfate. The organic layer was then distilled under reduced pressure and recrystallized using ethyl acetate. The resulting solid was filtered and dried to give Compound 5 (7.6 g, 44%). 7 is a graph showing the MS DATA value of Compound 5. FIG.

MS: [M + H] &lt; ⁺ &gt; = 633

< Example >

< Experimental Example  1-1>

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

Hexanitrile hexaazatriphenylene was thermally vacuum deposited on the prepared ITO transparent electrode to a thickness of 500 Å to form a hole injection layer. HT1 (400 Å), which is a hole transporting material, was vacuum-deposited thereon, and a host H1 and a dopant D1 compound were vacuum deposited as a light emitting layer to a thickness of 300 Å. Compound 1 prepared in Synthesis Example 2 and LiQ (Lithium Quinolate) were vacuum deposited on the light emitting layer at a weight ratio of 1: 1 to form an electron injection and transport layer having a thickness of 350 Å. Aluminum was sequentially deposited on the electron injecting and transporting layer to a thickness of 12 Å and lithium foil (LiF) to a thickness of 2,000 Å to form a cathode, thereby preparing an organic light emitting device.

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 torr to 5 x 10 &lt; ^-6 &gt; torr.

[LINE]

[LiQ]

[HT 1]

[H1]

[D1]

< Experimental Example  1-2>

The same experiment was conducted except that Compound 2 was used instead of Compound 1 as the electron transporting layer in Experimental Example 1-1.

< Experimental Example  1-3>

The same experiment was conducted except that Compound 3 was used instead of Compound 1 as the electron transporting layer in Experimental Example 1-1.

< Experimental Example  1-4>

The same experiment was conducted except that Compound 4 was used instead of Compound 1 as the electron transporting layer in Experimental Example 1-1.

< Experimental Example  1-5>

The same experiment was conducted except that Compound 5 was used instead of Compound 1 as the electron transporting layer in Experimental Example 1-1.

< Experimental Example  2-1> - Light Emitting Layer (EML)

A glass substrate coated with ITO (indium tin oxide) film having a thickness of 1,500 Å was immersed in distilled water containing detergent and washed with ultrasonic waves. At this time, a Fischer Co. product was used as a detergent, and distilled water, which was filtered with a filter of Millipore Co., was used as distilled water. The ITO was washed for 30 minutes and then washed twice with distilled water and ultrasonically cleaned for 10 minutes. After the distilled water was washed, it was ultrasonically washed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. Further, the substrate was cleaned using oxygen plasma for 5 minutes, and then the substrate was transported by a vacuum evaporator.

Hexanitrile hexaazatriphenylene (HAT) of the following chemical formula was thermally vacuum deposited on the prepared ITO transparent electrode to a thickness of 500 Å to form a hole injection layer.

[LINE]

(1, 1-biphenyl) -4,4-diamine (N, N-bis (1-naphthalenyl) -N, N-bis - (1-naphthalenyl) -N, N-bis-phenyl- (1,1-biphenyl) -4,4-diamine and NPB were thermally vacuum deposited to a thickness of 400 Å to form a hole transport layer.

[NPB]

Subsequently, Compound (1) prepared in Synthesis Example 2 was used as a host (90 wt%) and a 10 wt% Ir (ppy) ₃ was vapor-deposited as a dopant in a film thickness of 300 ANGSTROM on the hole transport layer to form a light emitting layer. The following electron transport material was vacuum deposited on the light emitting layer to a thickness of 200 Å to form an electron injection and transport layer.

[Electron transport material]

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

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

< Experimental Example  2-2>

The same experiment was conducted except that Compound 2 was used instead of Compound 1 as the light emitting layer in Experimental Example 2-1.

< Experimental Example  2-3>

The same experiment was conducted except that Compound 3 was used instead of Compound 1 as the light emitting layer in Experimental Example 2-1.

< Experimental Example  2-4>

The same experiment was conducted except that Compound 4 was used instead of Compound 1 as the light emitting layer in Experimental Example 2-1.

< Experimental Example  2-5>

The same experiment was conducted except that Compound 5 was used instead of Compound 1 as the light emitting layer in Experimental Example 2-1.

< Comparative Example  1-1>

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

[ET 1]

< Comparative Example  1-2>

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

[ET 2]

< Comparative Example  2-1>

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

[EM 1]

Experimental Example 1-1 to 1-5 were measured for each compound of the organic light-emitting device manufactured using the electron transport material in the driving voltage at a current density of 10mA / cm ² and the luminous efficiency, the current density of 20mA / cm ² (LT95), which is 95% of the initial luminance, was measured. The results are shown in Table 1 below.

Experimental Example
(at 10 mA / cm ² ) compound Driving voltage
(V) Current efficiency
(cd / A) Color coordinates LT95
(at 20 mA / cm ² ) Experimental Example 1-1 Compound 1 3.7 6.3 (0.134, 0.133) 100 Experimental Example 1-2 Compound 2 3.8 6.0 (0.134, 0.133) 70 Experimental Example 1-3 Compound 3 3.9 5.9 (0.134, 0.133) 110 Experimental Examples 1-4 Compound 4 3.6 6.5 (0.134, 0.133) 79 Experimental Examples 1-5 Compound 5 3.6 6.6 (0.134, 0.133) 91

Also, the Experimental Examples 2-1 to 2-5 were measured for each compound of the organic light-emitting device manufactured using a light-emitting layer material at a current density of 10mA / cm ² Drive voltage and light emission efficiency, a current of 20mA / cm ² (LT95) was measured at a density of 95% of the initial luminance. The results are shown in Table 2 below.

Experimental Example
(at 10 mA / cm ² ) compound Driving voltage
(V) Current efficiency
(cd / A) Color coordinates LT95
(at 20 mA / cm ² ) Experimental Example 2-1 Compound 1 (10 wt% doping) 4.10 60.3 (0.445, 0.543) 111 EXPERIMENTAL EXAMPLE 2-2 Compound 2 (10 wt% doping) 4.20 58.4 (0.450, 0.539) 99 Experimental Example 2-3 Compound 3 (10 wt% doping) 4.22 55.6 (0.448, 0.544) 79 Experimental Example 2-4 Compound 4 (10 wt% doping) 4.14 63.2 (0.455, 0.535) 94 Experimental Example 2-5 Compound 5 (10 wt% doping) 4.24 64.1 (0.455, 0.535) 97

The organic light emitting device manufactured by using the compound of Comparative Examples 1-1 and 1-2 as an electron transport layer material and the organic light emitting device prepared by using the compound of Comparative Example 2-1 as a light emitting layer material were mixed at a current density of 10 mA / cm &lt; ^{2 &} gt ;. In addition, the time (LT95) at which the initial luminance was 95% at a current density of 20 mA / cm ² was measured. The results are shown in Table 3 below.

Experimental Example
(at 10 mA / cm ² ) compound Driving voltage
(V) Current efficiency
(cd / A) Color coordinates LT95
(at 20 mA / cm ² ) Comparative Example 1-1 ET 1 3.9 5.0 (0.134, 0.133) 51 Comparative Example 1-2 ET 2 4.3 4.4 (0.134, 0.133) 48 Comparative Example 2-1 EM 1 (doping 10 wt%) 4.0 50.5 (0.452, 0.549) 65

When the compounds 1 to 5 of the present invention were used as an electron transport layer material, the results of the Experimental Examples and the Comparative Examples were compared with those of Comparative Examples 1-1 and 1-2, It can be seen that the device can be manufactured. In addition, when used as a light emitting layer material, it also shows superior characteristics in terms of efficiency and lifetime as compared with the material of Comparative Example 2-1.

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

10, 11: organic electronic 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 (11)

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

In Formula 1,
A is S, P (Ar) or SiRR '
B is O or S,
Provided that when A is S, then B is O,
X ₁ to X ₃ are N,
L ₁ is an arylene group having 6 to 20 carbon atoms,
Ar, Ar ₁ and Ar ₂ are the same or different and each independently an aryl group having 6 to 20 carbon atoms,
R, R ', R ₁ and R ₂ are the same or different and each independently hydrogen; An alkyl group having 1 to 10 carbon atoms; Or an aryl group having 6 to 20 carbon atoms,
p is an integer of 1 to 3,
q is an integer of 1 to 4,
When p is 2 or more, a plurality of R &lt; ₁ &gt; s are the same or different from each other,
When q 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 the following Formulas 2 to 4:
(2)

(3)

[Chemical Formula 4]

In the above formulas 2 to 4,
The definition of A, B, X ₁ to X ₃ , L ₁ , Ar ₁ , Ar ₂ , R ₁ and R ₂ , p, q is the same as defined in the above formula (1). The compound according to claim 1, wherein the compound represented by Formula 1 is represented by any one of Chemical Formulas 5 to 19:
[Chemical Formula 5]

[Chemical Formula 6]

(7)

[Chemical Formula 8]

[Chemical Formula 9]

[Chemical formula 10]

(11)

[Chemical Formula 12]

[Chemical Formula 13]

[Chemical Formula 14]

[Chemical Formula 15]

[Chemical Formula 16]

[Chemical Formula 17]

[Chemical Formula 18]

[Chemical Formula 19]

In the above formulas 5 to 19,
The definitions of X ₁ to X ₃ , L ₁ , Ar, Ar ₁ , Ar ₂ , R, R ', R ₁ , R ₂ , p and q are the same as those defined in Formula 1. The compound according to claim 1, wherein the compound of formula (1) is any one selected from the following compounds:

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

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