KR102235993B1 - Compound and organic electronic device comprising the same - Google Patents

Abstract

The present specification relates to a compound represented by Chemical Formula 1 and an organic electronic device including the same.

Description

A compound and an organic electronic device comprising the same TECHNICAL FIELD

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

A typical example of an organic electronic device is an organic light emitting device. In general, the organic light emission phenomenon refers to a phenomenon in which electrical energy is converted into light energy by using an organic material. An organic light-emitting device using the organic light-emitting phenomenon has a structure including an anode, a cathode, and an organic material layer therebetween. Here, the organic material layer is often made of a multilayer structure made of different materials in order to increase the efficiency and stability of the organic light-emitting device.For example, the organic material layer may be formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. In the structure of such an organic light emitting device, when a voltage is applied between the two electrodes, holes are injected from the anode and electrons from the cathode are injected into the organic material layer, and excitons are formed when the injected holes and electrons meet. When it falls back to the ground, it glows.

Development of a new material for the organic light emitting device as described above is continuously required.

International Patent Application Publication No. 2003-012890

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

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

[Formula 1]

In Formula 1,

At least one of X1 to X3 is N, and the others are each independently N or CR,

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

Ar1 to Ar3 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

R and R1 to R6 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

r1 is an integer from 1 to 3,

r2 is an integer from 1 to 4,

When r1 and r2 are each 2 or more, two or more R1 and R2 are each the same as or different from each other.

In addition, the present specification is a first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound.

The compound according to the exemplary embodiment of the present specification is used in an organic electronic device including an organic light emitting device, so that a driving voltage of the organic electric device may be reduced.

In addition, the compound according to the exemplary embodiment of the present specification may be used in organic electronic devices including organic light emitting devices, thereby improving light efficiency.

In addition, the compound according to the exemplary embodiment of the present specification is used in an organic electronic device including an organic light emitting device, and the lifespan characteristics of the device may be improved by thermal stability of the compound.

1 to 4 illustrate examples of an organic light-emitting device according to an exemplary embodiment of the present specification.

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

The present specification provides a compound represented by Chemical Formula 1.

Examples of the substituent in the present specification are described below, but are not limited thereto.

는 연결되는 부위를 의미한다.In this specification,

Means the connected part.

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

In the present specification, the term "substituted or unsubstituted" refers to deuterium; Halogen group; Nitrile group; Alkyl group; Cycloalkyl group; Silyl group; Phosphine oxide group; Aryl group; And substituted with one or two or more substituents selected from the group consisting of a heteroaryl group containing one or more of N, O, and S atoms, or substituted with a substituent to which two or more of the substituents are connected, or not having any substituents. Means that.

According to an exemplary embodiment of the present application, the term "substituted or unsubstituted" deuterium; Nitrile group; Alkyl group; Cycloalkyl group; Aryl group; And it is unsubstituted or substituted with one or two or more substituents selected from the group consisting of a heteroaryl group containing one or more of N, O, and S atoms.

According to an exemplary embodiment of the present application, the term "substituted or unsubstituted" deuterium; Nitrile group; Aryl group having 6 to 15 carbon atoms; And one or more substituents selected from the group consisting of 2 to 15 heteroaryl groups and including at least one of N, O, and S atoms.

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

In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but it is preferably 1 to 50, and more preferably 1 to 30. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methylbutyl, 1-ethylbutyl, pentyl, n-pentyl, iso Pentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentyl Methyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethylpropyl, 1,1 -Dimethylpropyl, isohexyl, 4-methylhexyl, 5-methylhexyl, and the like, but are not limited thereto.

In the present specification, the cycloalkyl group is not particularly limited, but it is preferably 3 to 60 carbon atoms, and more preferably 3 to 30 carbon atoms. Specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3 ,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but are not limited thereto.

In the present specification, the silyl group is a substituent including Si and the Si atom is directly connected as a radical, represented by _{-SiR 201} R ₂₀₂ R _{203 , R 201} to R ₂₀₃ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Alkyl group; Alkenyl group; Alkoxy group; Cycloalkyl group; Aryl group; And it may be a substituent consisting of at least one of 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, phenylsilyl group, etc. It is not limited.

In the present specification, when the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but it is preferably 6 to 50 carbon atoms, and more preferably 6 to 30 carbon atoms. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, or a quarterphenyl group, but is not limited thereto.

When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited. It is preferably 10 to 50 carbon atoms, and more preferably 10 to 30 carbon atoms. Specifically, the polycyclic aryl group may be a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a triphenyl group, a chrysenyl group, a fluorenyl group, and the like, but is not limited thereto.

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 is not limited thereto.

In the present specification, the heteroaryl group is one containing one or more of N, O, S, Si and Se as a heteroatom, and the number of carbons is not particularly limited, but is preferably 2 to 60 carbon atoms, and more preferably 2 to 30 carbon atoms. Do. Examples of the heteroaryl group include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridine group, bipyridine group, pyrimidine group, triazine group, acri Dine group, pyridazine group, pyrazine group, quinoline group, quinazoline group, quinoxaline group, phthalazine group (phthalazine), pteridine group (pteridine), pyridopyrimidine group (pyridopyrimidine), pyridopyrazine group (pyridopyrazine), Pyrazinopyrazine, isoquinoline, indole, pyridoindole, indenopyrimidine (5H-indenopyrimidine), carbazole group, benzoxazole group, benzimidazole group, benzothiazole group, benzocarba There are sol group, benzothiophene group, dibenzothiophene group, benzofuran group, dibenzofuran group, phenanthroline group, thiazolyl group, isoxazolyl group, oxadiazolyl group and thiadiazolyl group, etc. , It is not limited to these.

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

In the present specification, an arylene group means that the aryl group has two bonding positions, that is, a divalent group. Except that each of these is a divalent group, the description of the aryl group described above may be applied.

In the present specification, the heteroarylene group means that the heteroaryl group has two bonding positions, that is, a divalent group. Except that each of these is a divalent group, the description of the aforementioned heteroaryl group may be applied.

In an exemplary embodiment of the present specification, X1 is N.

In an exemplary embodiment of the present specification, X2 is N.

In an exemplary embodiment of the present specification, X3 is N.

In an exemplary embodiment of the present specification, X1 and X2 are each N.

In an exemplary embodiment of the present specification, X1 and X3 are each N.

In an exemplary embodiment of the present specification, X1 to X3 are each N.

In an exemplary embodiment of the present specification, L is a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group.

In an exemplary embodiment of the present specification, L is a direct bond.

In the exemplary embodiment of the present specification, L is a direct bond or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

In the exemplary embodiment of the present specification, L is a direct bond or a substituted or unsubstituted arylene group having 6 to 13 carbon atoms.

In the exemplary embodiment of the present specification, L is a direct bond or an arylene group within a substituted or unsubstituted bicyclic ring.

In an exemplary embodiment of the present specification, L is a direct bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted naphthylene group, or a substituted or unsubstituted fluorenylene group. to be.

In an exemplary embodiment of the present specification, L is a direct bond, a phenylene group, a biphenylene group, or a naphthylene group.

In the exemplary embodiment of the present specification, Ar1 to Ar3 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

In the exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently has 6 to 20 carbon atoms substituted or unsubstituted with a nitrile group, an alkyl group having 1 to 3 carbon atoms, or a heteroaryl group having 2 to 12 carbon atoms. Aryl group; Or it is a C2-C12 heteroaryl group substituted or unsubstituted with a C1-C3 alkyl group or a C6-C15 aryl group.

In the exemplary embodiment of the present specification, Ar1 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In the exemplary embodiment of the present specification, Ar1 is a substituted or unsubstituted aryl group having 6 to 15 carbon atoms.

In the exemplary embodiment of the present specification, Ar1 is a substituted or unsubstituted bicyclic aryl group.

In the exemplary embodiment of the present specification, Ar1 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group. , Or a substituted or unsubstituted fluorenyl group.

In the exemplary embodiment of the present specification, Ar1 is a phenyl group unsubstituted or substituted with an aryl group having 6 to 20 carbon atoms or a heteroaryl group having 2 to 12 carbon atoms, a biphenyl group unsubstituted or substituted with a nitrile group, an aryl having 6 to 20 carbon atoms A naphthyl group substituted or unsubstituted with a group, or a fluorenyl group unsubstituted or substituted with an alkyl group having 1 to 3 carbon atoms or an aryl group having 6 to 20 carbon atoms.

In the exemplary embodiment of the present specification, Ar1 is a phenyl group unsubstituted or substituted with a carbazole group or a quinoline group, a biphenyl group unsubstituted or substituted with a nitrile group, or a naphthyl group.

In an exemplary embodiment of the present specification, Ar1 is a phenyl group, a biphenyl group, or a naphthyl group.

In the exemplary embodiment of the present specification, Ar1 is a substituted or unsubstituted heteroaryl group having 6 to 30 carbon atoms.

In the exemplary embodiment of the present specification, Ar1 is a substituted or unsubstituted heteroaryl group having 6 to 18 carbon atoms.

In the exemplary embodiment of the present specification, Ar1 is a substituted or unsubstituted heteroaryl group within 3 rings.

In the exemplary embodiment of the present specification, Ar1 is a substituted or unsubstituted heteroaryl group within bicyclic rings.

In the exemplary embodiment of the present specification, Ar1 is a substituted or unsubstituted carbazole group, a substituted or unsubstituted pyridine group, a substituted or unsubstituted pyrimidine group, a substituted or unsubstituted triazine group, a substituted or unsubstituted quinoline. Group, a substituted or unsubstituted dibenzofuran group, or a substituted or unsubstituted dibenzothiophene group.

In an exemplary embodiment of the present specification, Ar1 is a carbazole group unsubstituted or substituted with a phenyl group, a pyridine group, a quinoline group unsubstituted or substituted with a phenyl group, a dibenzofuran group, or a dibenzothiophene group.

In an exemplary embodiment of the present specification, Ar1 is a carbazole group, a pyridine group, or a quinoline group.

In an exemplary embodiment of the present specification, Ar1 is a dibenzofuran group or a dibenzothiophene group.

In the exemplary embodiment of the present specification, Ar2 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In the exemplary embodiment of the present specification, Ar2 is a substituted or unsubstituted aryl group having 6 to 18 carbon atoms.

In the exemplary embodiment of the present specification, Ar2 is a substituted or unsubstituted bicyclic aryl group.

In the exemplary embodiment of the present specification, Ar2 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group , Or a substituted or unsubstituted fluorenyl group.

In the exemplary embodiment of the present specification, Ar2 is a phenyl group unsubstituted or substituted with an aryl group having 6 to 20 carbon atoms or a heteroaryl group having 2 to 12 carbon atoms, a biphenyl group unsubstituted or substituted with a nitrile group, an aryl having 6 to 20 carbon atoms A naphthyl group substituted or unsubstituted with a group, or a fluorenyl group unsubstituted or substituted with an alkyl group having 1 to 3 carbon atoms or an aryl group having 6 to 20 carbon atoms.

In the exemplary embodiment of the present specification, Ar2 is a phenyl group unsubstituted or substituted with a carbazole group or a quinoline group, a biphenyl group unsubstituted or substituted with a nitrile group, or a naphthyl group.

In an exemplary embodiment of the present specification, Ar2 is a phenyl group, a biphenyl group, or a naphthyl group.

In the exemplary embodiment of the present specification, Ar2 is a substituted or unsubstituted heteroaryl group having 6 to 30 carbon atoms.

In the exemplary embodiment of the present specification, Ar2 is a substituted or unsubstituted heteroaryl group having 6 to 18 carbon atoms.

In the exemplary embodiment of the present specification, Ar2 is a substituted or unsubstituted heteroaryl group within 3 rings.

In the exemplary embodiment of the present specification, Ar2 is a substituted or unsubstituted heteroaryl group within 2 rings.

In the exemplary embodiment of the present specification, Ar2 is a substituted or unsubstituted carbazole group, a substituted or unsubstituted pyridine group, a substituted or unsubstituted pyrimidine group, a substituted or unsubstituted triazine group, a substituted or unsubstituted quinoline. Group, a substituted or unsubstituted dibenzofuran group, or a substituted or unsubstituted dibenzothiophene group.

In the exemplary embodiment of the present specification, Ar2 is a carbazole group unsubstituted or substituted with a phenyl group, a pyridine group, a quinoline group unsubstituted or substituted with a phenyl group, a dibenzofuran group, or a dibenzothiophene group.

In an exemplary embodiment of the present specification, Ar2 is a carbazole group, a pyridine group, or a quinoline group.

In an exemplary embodiment of the present specification, Ar2 is a dibenzofuran group or a dibenzothiophene group.

In the exemplary embodiment of the present specification, Ar3 is an aryl group having 6 to 20 carbon atoms unsubstituted or substituted with an alkyl group having 1 to 3 carbon atoms or a heteroaryl group having 2 to 12 carbon atoms; Or it is a C2-C12 heteroaryl group substituted or unsubstituted with a C1-C3 alkyl group or a C6-C15 aryl group.

In the exemplary embodiment of the present specification, Ar3 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In the exemplary embodiment of the present specification, Ar3 is a substituted or unsubstituted aryl group having 6 to 18 carbon atoms.

In the exemplary embodiment of the present specification, Ar3 is a substituted or unsubstituted bicyclic aryl group.

In an exemplary embodiment of the present specification, Ar3 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group. , Or a substituted or unsubstituted fluorenyl group.

In an exemplary embodiment of the present specification, Ar3 is a phenyl group or a naphthyl group.

In an exemplary embodiment of the present specification, Ar3 is a phenyl group.

In the exemplary embodiment of the present specification, Ar3 is a substituted or unsubstituted heteroaryl group having 6 to 30 carbon atoms.

In the exemplary embodiment of the present specification, Ar3 is a substituted or unsubstituted heteroaryl group within 3 rings.

In the exemplary embodiment of the present specification, Ar3 is a substituted or unsubstituted carbazole group, a substituted or unsubstituted dibenzofuran group, a substituted or unsubstituted dibenzothiophene group, a substituted or unsubstituted pyridine group, a substituted or It is an unsubstituted pyrimidine group, or a substituted or unsubstituted triazine group.

In an exemplary embodiment of the present specification, Ar3 is a dibenzofuran group.

In an exemplary embodiment of the present specification, Ar3 is a dibenzothiophene group.

In the exemplary embodiment of the present specification, Ar1 to Ar3 may be any one selected from the following structures.

In the exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently is any one selected from the above structure.

In the exemplary embodiment of the present specification, Ar3 is any one selected from the above structures.

In the exemplary embodiment of the present specification, Ar1 to Ar3 may be any one selected from the following structures.

In the exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently is any one selected from the above structure.

In the exemplary embodiment of the present specification, Ar3 is any one selected from the above structures.

In an exemplary embodiment of the present specification, R and R1 to R6 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

In the exemplary embodiment of the present specification, r1 is an integer of 1 to 3, r2 is an integer of 1 to 4, and when r1 and r2 are each 2 or more, 2 or more R1 and R2 are each the same or different from each other.

In an exemplary embodiment of the present specification, R is hydrogen.

In an exemplary embodiment of the present specification, R1 to R6 are each hydrogen.

In the exemplary embodiment of the present specification, the compound represented by Formula 1 is any one selected from the following compounds.

The compound according to an exemplary embodiment of the present specification may be prepared by a manufacturing method described below. In the preparation examples described below, representative examples are described, but if necessary, a substituent may be added or excluded, and the position of the substituent may be changed. In addition, starting materials, reactants, reaction conditions, and the like can be changed based on techniques known in the art.

For example, the compound represented by Formula 1 may have a core structure as shown in Formulas 1 and 2 below. Substituents may be bonded by methods known in the art, and the type, position, or number of substituents may be changed according to techniques known in the art. Substituents may be combined as shown in Formulas 1 and 2 below, but are not limited thereto.

[General Formula 1]

[General Formula 2]

In the general formulas 1 and 2, the definitions for X1 to X3, L, Ar1, and Ar2 are the same as those defined in Chemical Formula 1. Although R1 to R6 are not indicated in the general formula, R1 to R6 may be substituted by using a reactant in which R1 to R6 is substituted, or for the product produced by the general formula 1 or 2 by a method known in the art. have.

In addition, the present specification provides an organic electronic device including the above compound.

In an exemplary embodiment of the present specification, the first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound.

In this specification, when a member is positioned "on" another member, this includes not only the case where the member is in contact with the other member, but also the case where another member exists between the two members.

In the present specification, when a part "includes" a certain component, it means that other components may be further included rather than excluding other components unless specifically stated to the contrary.

The organic material layer of the organic electronic device of the present specification may have a single-layer structure, but may have a multilayer 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 specification, the organic light emitting device may have 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, a hole blocking layer, etc. as an organic material layer. have. However, the structure of the organic electronic device is not limited thereto and may include a smaller number of organic layers.

In the exemplary embodiment of the present specification, the organic material layer includes an emission layer, and the emission layer includes the compound represented by Formula 1 above. The light emitting layer including the compound represented by Formula 1 has a green color.

In the exemplary embodiment of the present specification, the organic material layer includes an emission layer, and the emission layer includes the compound represented by Formula 1 as a host of the emission layer.

In the exemplary embodiment of the present specification, the organic material layer includes a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer includes the compound represented by Formula 1 above.

In the exemplary embodiment of the present specification, the organic material layer includes an electron injection layer or an electron transport layer, and the electron injection layer or the electron transport layer includes the compound represented by Formula 1 above.

In the exemplary embodiment of the present specification, the organic material layer includes an electron blocking layer, and the electron blocking layer includes the compound represented by Formula 1 above.

In the exemplary embodiment of the present specification, the organic material layer includes a hole blocking layer, and the hole blocking layer includes a compound represented by Formula 1 above.

In the exemplary embodiment of the present specification, the organic electronic device is a hole injection layer and a hole transport layer. It further includes one or two or more layers selected from the group consisting of a light-emitting layer, an electron transport layer, an electron injection layer, a hole blocking layer, and an electron blocking layer.

In the exemplary embodiment of the present specification, the organic electronic device is a hole injection layer and a hole transport layer. It further includes one or two or more layers selected from the group consisting of a light-emitting layer, an electron transport layer, an electron injection layer, a hole blocking layer, an electron blocking layer, and an electron injection and transport layer.

In the exemplary embodiment of the present specification, the organic electronic device may be selected from the group consisting of an organic light emitting device, an organic phosphorescent device, an organic solar cell, an organic photoconductor (OPC), and an organic transistor.

Hereinafter, an organic light-emitting device is illustrated.

In the exemplary embodiment of the present specification, the organic light emitting device includes a first electrode; A second electrode provided to face the first electrode; A light emitting layer provided between the first electrode and the second electrode; And two or more organic material 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 material layers includes a compound represented by Formula 1 above.

In the exemplary embodiment of the present specification, two or more organic material layers may be selected from the group consisting of a light emitting layer, a hole transport layer, a hole injection layer, a layer for simultaneously transporting and injecting holes, and an electron blocking layer.

In the exemplary embodiment of the present specification, the organic material layer includes two or more electron transport layers, and at least one of the two or more electron transport layers includes a compound represented by Formula 1 above. Specifically, in the exemplary embodiment of the present specification, the compound represented by Formula 1 may be included in one of the two or more electron transport layers, and may be included in each of two or more electron transport layers.

In addition, in the exemplary embodiment of the present specification, when the compound represented by Formula 1 is included in each of the two or more electron transport layers, materials other than the compound represented by Formula 1 may be the same or different from each other. have.

When the organic material layer including the compound represented by Formula 1 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 may be used, for example, a metal or a metal complex. For example, the electron transport layer including the compound represented by Formula 1 may further include LiQ (Lithium Quinolate).

In the exemplary embodiment of the present specification, the organic material layer includes two or more hole transport layers, and at least one of the two or more hole transport layers includes a compound represented by Formula 1 above. Specifically, in the exemplary embodiment of the present specification, the compound represented by Formula 1 may be included in one of the two or more hole transport layers, and may be included in each of two or more hole transport layers.

In addition, in the exemplary embodiment of the present specification, when the compound represented by Formula 1 is included in each of the two or more hole transport layers, materials other than the compound represented by Formula 1 may be the same or different from each other. have.

In the exemplary embodiment of the present specification, the organic material layer further includes a hole injection layer or a hole transport layer including a compound including an arylamine group, a carbazole group, or a benzocarbazole group in addition to the organic material layer including the compound represented by Formula 1 can do.

In the exemplary embodiment of the present specification, the first electrode is an anode or a cathode.

In the exemplary embodiment of the present specification, the second electrode is a cathode or an anode.

In the exemplary embodiment of the present specification, the organic light-emitting device may be a normal type organic light-emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.

In the exemplary embodiment of the present specification, the organic light emitting device may be an inverted type organic light emitting device in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate.

For example, the structure of an organic light-emitting device according to an exemplary embodiment of the present specification is illustrated in FIGS. 1 to 4. 1 to 4 illustrate an organic light emitting device, but are not limited thereto.

1 illustrates a structure of an organic light-emitting device in which a first electrode 102, a light emitting layer 106, and a second electrode 110 are sequentially stacked on a substrate 101. The compound represented by Formula 1 is included in the emission layer.

2 shows a structure of an organic light emitting diode in which a first electrode 102, a hole injection layer 103, a hole transport layer 104, a light emitting layer 106, and a second electrode 110 are sequentially stacked on a substrate 101. It is illustrated. According to an exemplary embodiment of the present invention, the compound represented by Formula 1 is included in one or more of the organic material layers. According to another exemplary embodiment, the compound represented by Formula 1 is included in at least one of a hole injection layer, a hole transport layer, and a light emitting layer.

3, a first electrode 102, a hole injection layer 103, a hole transport layer 104, an electron blocking layer 105, a light emitting layer 106, a hole blocking layer 107, an electron transport layer ( 108), the electron injection layer 109, and the second electrode 110 are sequentially stacked in an organic light-emitting device. According to an exemplary embodiment of the present invention, the compound represented by Formula 1 is included in one or more of the organic material layers. According to another exemplary embodiment, the compound represented by Formula 1 is included in at least one of a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer. According to another exemplary embodiment, the compound represented by Formula 1 is included in the hole blocking layer or the electron transport layer.

4, a first electrode 102, a hole injection layer 103, a hole transport layer 104, an electron blocking layer 105, a light emitting layer 106, a hole blocking layer 107, an electron injection layer on the substrate 101, and Transport layer 111. The structure of an organic light-emitting device in which the second electrodes 110 are sequentially stacked is illustrated. According to an exemplary embodiment of the present invention, the compound represented by Formula 1 is included in one or more of the organic material layers. According to another exemplary embodiment, the compound represented by Formula 1 is included in at least one of a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron injection and an electron transport layer. According to another exemplary embodiment, the compound represented by Formula 1 is included in a hole blocking layer or an electron injection and electron transport layer.

The organic light-emitting device of the present specification may be manufactured by materials and methods known in the art, except that at least one of the organic material layers includes the compound, that is, the compound represented by Formula 1.

When the organic light-emitting device includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials.

For example, the organic light emitting device of the present specification may be manufactured by sequentially laminating an anode, an organic material layer, and a cathode on a substrate. At this time, using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation, the anode is deposited by depositing a metal or a conductive metal oxide or an alloy thereof on the substrate. It can be manufactured by forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer thereon, and then depositing a material that can be used as a cathode thereon. In addition to this method, an organic light-emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

In addition, the compound represented by Formula 1 may be formed as an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device. Here, the solution coating method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spray method, roll coating, and the like, but is not limited thereto.

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

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

In another exemplary embodiment, the first electrode is a cathode, and the second electrode is an anode.

As the anode material, a material having a large work function is preferable so that holes can be smoothly injected into the organic material layer. Metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); A combination of metal and oxide such as ZnO:Al or SnO _{2 :Sb;} Conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited thereto.

The cathode material is generally preferably a material having a small work function so that electrons can be easily injected into the organic material layer. Metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; There are a multi-layered material such as LiF/Al or LiO _{2 /Al, but are not limited thereto.}

The emission layer may include a host material and a dopant material. Host materials include condensed aromatic ring derivatives or heterocyclic-containing compounds. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and heterocycle-containing compounds include dibenzofuran derivatives, ladder furan compounds, And pyrimidine derivatives, but are not limited thereto.

Examples of the dopant material include aromatic amine derivatives, strylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamine group, and includes pyrene, anthracene, chrysene, and periflanthene having an arylamine group. In addition, the styrylamine compound is a compound in which at least one arylvinyl group is substituted with a substituted or unsubstituted arylamine, and is selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamine group. Substituents are substituted or unsubstituted. Specifically, there are styrylamine, styryldiamine, styryltriamine, and styryltetraamine, but are not limited thereto. In addition, examples of the metal complex include an iridium complex and a platinum complex, but are not limited thereto.

In the present specification, when the compound represented by Formula 1 is included in an organic material layer other than the emission layer or an additional emission layer is provided, the emission material of the emission layer is formed by transporting and bonding holes and electrons from the hole transport layer and the electron transport layer, respectively. As a material capable of emitting light in the visible region, a material having good quantum efficiency for fluorescence or phosphorescence is preferable. For example, 8-hydroxyquinoline aluminum complex (Alq3); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compound; Benzoxazole, benzthiazole, and benzimidazole-based compounds; Poly(p-phenylenevinylene) (PPV)-based polymer; Spiro compounds; Polyfluorene; And rubrene, but are not limited thereto.

The hole injection layer is a layer for injecting holes from an electrode. It is preferable that the hole injection material has an ability to transport holes and thus has an effect of receiving holes from the anode and an excellent hole injection effect to the light emitting layer or the light emitting material. In addition, a material having excellent ability to prevent the movement of excitons generated in the light emitting layer to the electron injection layer or the electron injection material is preferable. In addition, a material excellent in thin film formation ability is preferred. In addition, it is preferable that the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include metal porphyrin, oligothiophene, arylamine-based organic material; Hexanitrile hexaazatriphenylene-based organic material; Quinacridone series organic matter; Perylene-based organics; There are polythiophene-based conductive polymers such as anthraquinone and polyaniline, but are not limited thereto.

The hole transport layer is a layer that receives holes from the hole injection layer and transports holes to the emission layer. The hole transport material is a material capable of transporting holes from the anode or the hole injection layer and transferring them to the emission layer, and a material having high mobility for holes is preferable. Specific examples include, but are not limited to, an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together.

The electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer. The electron transport material is a material capable of receiving electrons from the cathode and transferring them to the light emitting layer, and a material having high mobility for electrons is preferable. Specific examples include Al complex of 8-hydroxyquinoline; Complexes containing Alq3; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited thereto. The electron transport layer can be used with any desired cathode material, as used according to the prior art. In particular, suitable cathode materials are conventional materials that have a low work function and are followed by an aluminum layer or a silver layer. Specifically, there are cesium, barium, calcium, ytterbium and samarium, and in each case, an aluminum layer or a silver layer follows. In an exemplary embodiment of the present invention, the compound represented by Formula 1 is included in the electron transport layer.

The electron injection layer is a layer that injects electrons from an electrode. The electron injection material preferably has an excellent ability to transport electrons, has an effect of receiving electrons from the cathode, and an excellent electron injection effect with respect to the light emitting layer or the light emitting material. In addition, a material that prevents excitons generated in the light emitting layer from moving to the hole injection layer and has excellent thin film formation ability is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, and their derivatives, Metal complex compounds and nitrogen-containing 5-membered ring derivatives, but are not limited thereto.

As the metal complex compound, 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)chlorogallium, bis(2-methyl-8-quinolinato) (o-cresolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtolato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtolato)gallium, etc. , But is not limited thereto.

The electron blocking layer is a layer capable of improving the lifespan and efficiency of a device by preventing holes injected from the hole injection layer from entering the electron injection layer through the emission layer. Known materials may be used without limitation, and may be formed between the light-emitting layer and the hole injection layer, between the light-emitting layer and the hole transport layer, or between the light-emitting layer and a layer for simultaneously injecting and transporting holes.

The hole blocking layer is a layer that prevents holes from reaching the cathode, and may be generally formed under the same conditions as the hole injection layer. Specifically, there are oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, aluminum complexes, and the like, but are not limited thereto. In an exemplary embodiment of the present invention, the compound represented by Formula 1 is included in the hole blocking layer.

The organic light emitting device according to the present specification may be a top emission type, a bottom emission type, or a double-sided emission type depending on the material used.

In the exemplary embodiment of the present specification, the compound represented by Formula 1 may be included in an organic solar cell or an organic transistor in addition to the organic light emitting device.

The compound according to the present specification may act on a principle similar to that applied to an organic light-emitting device in organic electronic devices, including an organic phosphorescent device, an organic solar cell, an organic photoreceptor, and an organic transistor. For example, the organic solar cell may have a structure including a first electrode, a second electrode, and a photoactive layer provided between the first electrode and the second electrode, and the photoactive layer may include the compound.

Hereinafter, examples and comparative examples will be described in detail to describe the present specification in detail. However, the Examples and Comparative Examples according to the present specification may be modified in various forms, and the scope of the present specification is not construed as being limited to the Examples and Comparative Examples described below. Examples and comparative examples of the present specification are provided to more completely describe the present specification to those of ordinary skill in the art.

<Production Example>

<Production Example 1>-Intermediate synthesis

The following Intermediates A to D and Intermediates A-1 to D-1 were prepared using the preparation method of General Formulas 1 and 2.

<Production Example 2>

Intermediate A-1 (6.51g, 10.16mmol) and compound a-1 (3.94g, 11.17mmol) were completely dissolved in 280ml of tetrahydrofuran in a nitrogen atmosphere, and then 2M aqueous potassium carbonate solution (140ml) was added. . After tetrakis-(triphenylphosphine)palladium (0.35g, 0.30mmol) was added, the mixture was heated and stirred for 5 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 110 ml of tetrahydrofuran to prepare compound 1 (4.37g, 66%). MS[M+H] ⁺ = 651

<Production Example 3>

Intermediate A-1 (5.37 g, 8.38 mmol) and compound a-2 (3.25 g, 9.22 mmol) were completely dissolved in 200 ml of tetrahydrofuran in a 500 ml round bottom flask in a nitrogen atmosphere, and then 2M aqueous potassium carbonate solution (100 ml) was added. . After tetrakis-(triphenylphosphine)palladium (0.29g, 0.25mmol) was added, the mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 180 ml of ethyl acetate to prepare compound 2 (3.26 g, 60%). MS[M+H] ⁺ = 651

<Production Example 4>

Intermediate A-1 (7.23g, 11.28mmol) and compound a-3 (4.37g, 12.41mmol) were completely dissolved in 220 ml of tetrahydrofuran in a nitrogen atmosphere, and then 2M aqueous potassium carbonate solution (110ml) was added. . After tetrakis-(triphenylphosphine)palladium (0.39g, 0.34mmol) was added, the mixture was heated and stirred for 4 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 210 ml of acetone to prepare compound 3 (4.43 g, 60%). MS[M+H] ⁺ = 650

<Production Example 5>

Intermediate B-1 (8.12g, 11.75mmol) and compound a-4 (4.54g, 12.93mmol) were completely dissolved in 240ml of tetrahydrofuran in a 500ml round bottom flask in a nitrogen atmosphere, and then 2M aqueous potassium carbonate solution (120ml) was added. . After tetrakis-(triphenylphosphine)palladium (0.41g, 0.35mmol) was added, the mixture was heated and stirred for 5 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 170 ml of acetone to prepare compound 4 (5.76g, 70%). MS[M+H] ⁺ = 699

<Production Example 6>

Intermediate B-1 (7.56g, 10.94mmol) and compound a-1 (4.25g, 12.03mmol) were completely dissolved in 260ml of tetrahydrofuran in a nitrogen atmosphere, and then 2M aqueous potassium carbonate solution (130ml) was added. . After tetrakis-(triphenylphosphine)palladium (0.38g, 0.33mmol) was added, the mixture was heated and stirred for 4 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 190 ml of ethyl acetate to prepare compound 5 (4.92 g, 64%). MS[M+H] ⁺ = 701

<Production Example 7>

Intermediate C-1 (6.82g, 10.64mmol) and compound a-5 (4.72g, 11.70mmol) were completely dissolved in 240ml of tetrahydrofuran in a 500ml round bottom flask in a nitrogen atmosphere, and then 2M aqueous potassium carbonate solution (120ml) was added. . After tetrakis-(triphenylphosphine)palladium (0.37g, 0.32mmol) was added, the mixture was heated and stirred for 4 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 170 ml of ethyl acetate to prepare compound 6 (4.32 g, 58%). MS[M+H] ⁺ = 701

<Production Example 8>

Intermediate A (6.50 g, 16.80 mmol) and compound a-6 (5.62 g, 15.27 mmol) were completely dissolved in 200 ml of tetrahydrofuran in a 500 ml round bottom flask in a nitrogen atmosphere, and then 2M aqueous potassium carbonate solution (100 ml) was added. After tetrakis-(triphenylphosphine)palladium (0.53g, 0.46mmol) was added, the mixture was heated and stirred for 4 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 160 ml of acetonitrile to prepare compound 7 (7.16g, 69%). MS[M+H] ⁺ = 676

<Production Example 9>

Intermediate A (5.29g, 14.83mmol) and compound a-7 (4.96g, 13.48mmol) were completely dissolved in 200ml of tetrahydrofuran in a 500ml round bottom flask in a nitrogen atmosphere, and then 2M aqueous potassium carbonate solution (100ml) was added. After tetrakis-(triphenylphosphine)palladium (0.47g, 0.40mmol) was added, the mixture was heated and stirred for 5 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 190 ml of acetonitrile to prepare compound 8 (5.68 g, 57%). MS[M+H] ⁺ = 740

<Production Example 10>

Intermediate B (6.74 g, 15.42 mmol) and compound a-8 (5.23 g, 14.02 mmol) were completely dissolved in 260 ml of tetrahydrofuran in a 500 ml round bottom flask in a nitrogen atmosphere, and then 2M aqueous potassium carbonate solution (130 ml) was added. After tetrakis-(triphenylphosphine)palladium (0.49g, 0.42mmol) was added, the mixture was heated and stirred for 6 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 180 ml of acetonitrile to prepare compound 9 (6.65g, 65%). MS[M+H] ⁺ = 731

<Production Example 11>

Intermediate B (8.41 g, 19.25 mmol) and compound a-9 (7.56 g, 17.50 mmol) were completely dissolved in 280 ml of tetrahydrofuran in a 500 ml round bottom flask in a nitrogen atmosphere, and then 2M aqueous potassium carbonate solution (140 ml) was added. After tetrakis-(triphenylphosphine)palladium (0.61g, 0.53mmol) was added, the mixture was heated and stirred for 4 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 210 ml of acetonitrile to prepare compound 10 (7.16 g, 52%). MS[M+H] ⁺ = 790

<Production Example 12>

Intermediate C (9.50g, 19.91mmol) and compound a-10 (4.87g, 18.10mmol) were completely dissolved in 200ml of tetrahydrofuran in a nitrogen atmosphere, and then 2M aqueous potassium carbonate solution (100ml) was added. After tetrakis-(triphenylphosphine)palladium (0.63g, 0.54mmol) was added, the mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 180 ml of acetonitrile to prepare compound 11 (6.11 g, 51%). MS[M+H] ⁺ = 667

<Production Example 13>

Intermediate A-1 (5.98 g, 13.93 mmol) and compound a-11 (8.12 g, 12.67 mmol) were completely dissolved in 200 ml of tetrahydrofuran in a 500 ml round bottom flask in a nitrogen atmosphere, and then 2M aqueous potassium carbonate solution (100 ml) was added. . After tetrakis-(triphenylphosphine)palladium (0.44g, 0.38mmol) was added, the mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 210 ml of acetonitrile to prepare compound 12 (5.56g, 60%). MS[M+H] ⁺ = 727

<Production Example 14>

Intermediate B (8.28g, 18.94mmol) and compound a-12 (6.32g, 17.22mmol) were completely dissolved in 200ml of tetrahydrofuran in a 500ml round bottom flask in a nitrogen atmosphere, and then 2M aqueous potassium carbonate solution (100ml) was added. After tetrakis-(triphenylphosphine)palladium (0.60g, 0.52mmol) was added, the mixture was heated and stirred for 4 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 230 ml of acetonitrile to prepare compound 13 (6.82g, 55%). MS[M+H] ⁺ = 725

<Production Example 15>

Intermediate D (7.78g, 15.79mmol) and compound a-13 (5.67g, 14.35mmol) were completely dissolved in 240ml of tetrahydrofuran in a 500ml round bottom flask in a nitrogen atmosphere, and then 2M aqueous potassium carbonate solution (120ml) was added. After tetrakis-(triphenylphosphine)palladium (0.50g, 0.43mmol) was added, the mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 210 ml of tetrahydrofuran to prepare compound 14 (5.55 g, 48%). MS[M+H] ⁺ = 809

<Example>

<Example 1-1>

A glass substrate coated with a thin film of ITO (indium tin oxide) having a thickness of 1,000Å was put in distilled water dissolved in a detergent and washed with ultrasonic waves. At this time, a product made by Fischer Co. was used as a detergent, and distilled water secondarily filtered with a filter manufactured by Millipore Co. was used as distilled water. After washing the ITO for 30 minutes, it was repeated twice with distilled water to perform ultrasonic cleaning for 10 minutes. After washing with distilled water, ultrasonic washing was performed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. In addition, after cleaning the substrate for 5 minutes using oxygen plasma, the substrate was transported to a vacuum evaporator.

On the ITO transparent electrode prepared as described above, a compound of the following compound HI1 and the following compound HI2 was thermally vacuum deposited to a thickness of 100 Å in a ratio of 98:2 (molar ratio) to form a hole injection layer. The following compound HT1 was vacuum deposited on the hole injection layer to a thickness of 1,150 Å to form a hole transport layer. Subsequently, the following compound EB1 was vacuum deposited on the hole transport layer with a film thickness of 50 Å to form an electron blocking layer. Subsequently, the following compound BH and the following compound BD were vacuum-deposited at a weight ratio of 50:1 with a film thickness of 200 Å on the electron blocking layer to form a light emitting layer. A hole blocking layer was formed by vacuum depositing Compound 1 prepared above with a film thickness of 50 Å on the emission layer. Subsequently, the following compound ET1 and the following compound LiQ were vacuum-deposited at a weight ratio of 1:1 on the hole blocking layer to form an electron injection and transport layer with a thickness of 30 Å. A cathode was formed by sequentially depositing lithium fluoride (LiF) to a thickness of 12 Å and aluminum to a thickness of 1,000 Å on the electron injection and transport layer.

Was the deposition rate of the organic material in the above process, maintaining the range of 0.4 to 0.7Å / sec, the lithium fluoride of the cathode 0.3Å / sec, the deposition rate of aluminum was maintained 2Å / sec, During the deposition, a vacuum 10 2 X ^{- Maintaining 7} to 5 X 10 ^-6 torr, an organic light emitting device was manufactured.

<Examples 1-2 to 1-7>

An organic light-emitting device was manufactured in the same manner as in Example 1-1, except that the compound shown in Table 1 was used instead of Compound 1 in Example 1-1.

<Comparative Examples 1-1 to 1-3>

An organic light-emitting device was manufactured in the same manner as in Example 1-1, except that the following compounds HB2 and HB3 were used instead of compound 1 in Example 1-1.

The driving voltage, efficiency, and color coordinates were measured for the organic light-emitting devices fabricated in Examples 1-1 to 1-5 and Comparative Examples 1-1 to 1-3 at ^{a current density of 20 mA/cm 2, and 20 mA} The time (T95) to be 95% of the initial luminance at a current density of /cm ^{2 was measured.} The results are shown in Table 1 below.

compound
(Hole blocking layer) Voltage
(V@20mA
/cm ² ) efficiency
(cd/A@20mA
/cm ² ) Color coordinates
(x,y) T95
(hr) Example 1-1 Compound 1 4.25 6.53 (0.144, 0.046) 240 Example 1-2 Compound 2 4.23 6.46 (0.142, 0.048) 265 Example 1-3 Compound 5 4.34 6.66 (0.143, 0.047) 270 Example 1-4 Compound 6 4.36 6.77 (0.143, 0.046) 255 Example 1-5 Compound 10 4.17 6.68 (0.144, 0.044) 280 Example 1-6 Compound 11 4.45 6.56 (0.143, 0.045) 245 Example 1-7 Compound 12 4.42 6.51 (0.145, 0.044) 230 Comparative Example 1-1 HB 2 4.89 5.54 (0.141, 0.047) 135 Comparative Example 1-2 HB 3 4.75 5.72 (0.143, 0.047) 110 Comparative Example 1-3 HB 4 4.62 5.95 (0.142, 0.048) 180

As shown in Table 1, in the case of an organic light-emitting device manufactured using the compound represented by Formula 1 of the present specification as a hole blocking layer, compared to Comparative Examples 1-1 to 1-3, efficiency and driving voltage And/or it can be seen that exhibit excellent properties in terms of stability. In particular, it can be seen that Examples 1-1 to 1-5 using the compound represented by Chemical Formula 1 of the present specification have superior lifetime characteristics compared to Comparative Examples 1-1 to 1-3.

<Examples 2-1 to 2-10>

An organic light-emitting device was manufactured in the same manner as in Example 1-1, except that the following compound HB1 was used instead of the compound 1 in Example 1-1, and the compound shown in Table 2 was used instead of the compound ET1.

<Comparative Examples 2-1 and 2-2>

An organic light-emitting device was manufactured in the same manner as in Example 1-1, except that the compound HB1 was used instead of the compound 1 in Example 1-1, and the compound shown in Table 2 below was used instead of the compound ET1.

The driving voltage, efficiency, and color coordinates were measured for the organic light-emitting devices fabricated in Examples 2-1 to 2-10, Comparative Example 2-1, and Comparative Example 2-2 at ^{a current density of 20 mA/cm 2, and 20 mA} The time (T95) to be 95% of the initial luminance at a current density of /cm ^{2 was measured.} The results are shown in Table 2 below.

compound
(Electron transport layer) Voltage
(V@20mA
/cm ² ) efficiency
(cd/A@20mA
/cm ² ) Color coordinates
(x,y) TT95
(hr) Example 2-1 Compound 1 4.32 6.31 (0.144, 0.046) 275 Example 2-2 Compound 2 4.33 6.82 (0.144, 0.044) 280 Example 2-3 Compound 3 4.35 6.53 (0.145, 0.048) 290 Example 2-4 Compound 4 4.34 6.74 (0.144, 0.044) 285 Example 2-5 Compound 5 4.26 6.66 (0.144, 0.04) 270 Example 2-6 Compound 6 4.28 6.58 (0.145, 0.047) 275 Example 2-7 Compound 7 4.37 6.77 (0.145, 0.046) 270 Example 2-8 Compound 8 4.39 6.65 (0.144, 0.048) 265 Example 2-9 Compound 13 4.45 6.42 (0.146, 0.045) 270 Example 2-10 Compound 14 4.43 6.41 (0.147, 0.047) 275 Comparative Example 2-1 ET2 4.92 5.43 (0.143, 0.047) 160 Comparative Example 2-2 ET3 5.36 4.85 (0.144, 0.049) 125

As shown in Table 2, in the case of an organic light-emitting device manufactured using the compound represented by Formula 1 of the present specification as an electron transport layer, compared to Comparative Examples 2-1 and 2-2, efficiency, driving voltage, and/or It can be seen that it shows excellent properties in terms of stability. In particular, it can be seen that Examples 2-1 to 2-10 using the compound represented by Chemical Formula 1 of the present specification have superior lifespan characteristics compared to Comparative Examples 2-1 and 2-2.

Through the above, although the preferred embodiment of the present specification has been described, the present invention is not limited thereto, and it is possible to implement various modifications within the scope of the claims and the detailed description of the invention, and this is also the scope of the invention. Belongs to.

101: substrate
102: first electrode
103: hole injection layer
104: hole transport layer
105: electron blocking layer
106: light-emitting layer
107: hole blocking layer
108: electron transport layer
109: electron injection layer
110: second electrode
111: electron injection and transport layer

Claims (10)

Compound represented by the following formula (1):
[Formula 1]

In Formula 1,
At least one of X1 to X3 is N, and the others are each independently N or CR,
L is a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; A substituted or unsubstituted carbazole group; A substituted or unsubstituted pyridine group; A substituted or unsubstituted pyrimidine group; A substituted or unsubstituted triazine group; A substituted or unsubstituted quinoline group; A substituted or unsubstituted dibenzofuran group; Or a substituted or unsubstituted dibenzothiophene group,
Ar3 is a substituted or unsubstituted aryl group; A substituted or unsubstituted dibenzofuran group; Or a substituted or unsubstituted dibenzothiophene group,
When Ar3 is a substituted or unsubstituted aryl group, Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; A substituted or unsubstituted carbazole group; A substituted or unsubstituted dibenzofuran group; Or a substituted or unsubstituted dibenzothiophene group,
Ar3 is a substituted or unsubstituted dibenzofuran group; Or in the case of a substituted or unsubstituted dibenzothiophene group, Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; A substituted or unsubstituted pyridine group; A substituted or unsubstituted pyrimidine group; A substituted or unsubstituted triazine group; Or a substituted or unsubstituted quinoline group,
R and R1 to R6 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
r1 is an integer from 1 to 3,
r2 is an integer from 1 to 4,
When r1 and r2 are each 2 or more, two or more R1 and R2 are each the same as or different from each other. The method according to claim 1, L is a direct bond; A substituted or unsubstituted phenylene group; Or a substituted or unsubstituted biphenylene group. The method according to claim 1, Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted carbazole group; A substituted or unsubstituted pyridine group; A substituted or unsubstituted dibenzofuran group; Or a substituted or unsubstituted dibenzothiophene group. The method according to claim 1, Ar3 is a substituted or unsubstituted phenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted dibenzofuran group; Or a substituted or unsubstituted dibenzothiophene group. The compound of claim 1, wherein the compound represented by Formula 1 is any one selected from the following compounds:

A first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers contains the compound according to any one of claims 1 to 5 Electronic device. The organic electronic device of claim 6, wherein the organic material layer includes an emission layer, and the emission layer includes the compound. The organic electronic device of claim 6, wherein the organic material layer includes a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer includes the compound. The organic electronic device of claim 6, wherein the organic material layer includes a hole blocking layer, and the hole blocking layer includes the compound. The method according to claim 6, wherein the organic electronic device further comprises one or two or more layers selected from the group consisting of a light emitting layer, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, an electron blocking layer and a hole blocking layer. Phosphorus organic electronic device.

Images