KR102262687B1 - Compound and organic electronic device comprising the same - Google Patents

Abstract

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

Description

COMPOUND AND ORGANIC ELECTRONIC DEVICE COMPRISING THE SAME

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

A typical example of the organic electronic device is an organic light emitting device. In general, the organic light emitting phenomenon refers to a phenomenon in which electric energy is converted into light energy using an organic material. An organic light emitting device using an organic light emitting phenomenon has a structure including an anode and a cathode and an organic material layer therebetween. Here, the organic material layer is often formed of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device, and may include, for example, 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 the organic light emitting device, when a voltage is applied between the two electrodes, holes are injected into the organic material layer from the anode and electrons from the cathode are injected into the organic material layer. When the injected holes and electrons meet, excitons are formed, and the excitons When it falls back to the ground state, it lights up.

The development of new materials for the organic light emitting device as described above is continuously required.

International Patent Application Publication No. 2003-012890

An object of 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,

X is O, S, CRaRb or SO ₂ ,

At least one of X1 to X3 is N, the rest 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; Or a substituted or unsubstituted heteroaryl group,

Ra and Rb are the same as or different from each other, and are each independently a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, may be bonded to each other to form a ring,

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 the same as or different from each other, respectively.

In addition, the present specification is a first electrode; a second electrode provided to face 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.

The compound according to an exemplary embodiment of the present specification may be used in an organic electronic device including an organic light emitting device to lower the driving voltage of the organic electric device.

In addition, the compound according to an exemplary embodiment of the present specification may be used in an organic electronic device including an organic light emitting device to improve light efficiency.

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

1 to 3 each show an example 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 Formula 1 above.

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

는 연결되는 부위를 의미한다.In this specification,

means the part to be connected.

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

As used herein, the term "substituted or unsubstituted" refers to deuterium; halogen group; nitrile group; an alkyl group; cycloalkyl group; amine group; silyl group; phosphine oxide group; aryl group; and one or more substituents selected from the group consisting of a heteroaryl group containing at least one of N, O, S, Se and Si atoms, or is substituted with a substituent to which two or more of the above exemplified substituents are linked, or any It means that it does not have a substituent.

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 is preferably 1 to 50, more preferably 1 to 30. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl , isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n -Heptyl, 1-methylhexyl, cyclopentylmethyl, 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, 4-methylhexyl, 5-methylhexyl, and the like.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, 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 is not limited thereto.

In the present specification, the silyl group includes Si and is a substituent directly connected to the Si atom as a radical, and is 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; an 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 a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group, and the like. 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 preferably 6 to 50 carbon atoms, more preferably 6 to 30 carbon atoms. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, a quaterphenyl group, and the like, 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 preferable that it is C10-50, and 10-30 are more preferable. 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 combine with 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 includes at least one of N, O, S, Si and Se as a heteroatom, and the number of carbon atoms is not particularly limited, but preferably has 2 to 60 carbon atoms, more preferably 2 to 30 carbon atoms. Do. Examples of the heteroaryl group include a thiophene group, a furan group, a pyrrole group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridine group, a bipyridine group, a pyrimidine group, a triazine group, acri Din group, pyridazine group, pyrazine group, quinoline group, quinazoline group, quinoxaline group, phthalazine group, pteridine group, pyrido pyrimidine group, pyrido group pyrazine), pyrazino pyrazine, isoquinoline, indole, pyrido indole, indeno pyrimidine, carbazole, benzoxazole, benzimidazole , benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuran group, dibenzofuran group, phenanthroline group, thiazolyl group, isoxazolyl group, oxadiazolyl group and and a thiadiazolyl group, but is not limited thereto.

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

In the present specification, the 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 heteroaryl group described above may be applied.

In an exemplary embodiment of the present specification, X is O, S, CRaRb or SO _{2 Is} .

In one embodiment of the present specification, X is O.

In one embodiment of the present specification, X is S.

In an exemplary embodiment of the present specification, X is CRaRb.

In an exemplary embodiment of the present specification, X is SO ₂ .

In the exemplary embodiment of the present specification, at least one of X1 to X3 is N, and the others are each independently N or CR.

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

In one embodiment of the present specification, X2 is N.

In one embodiment of the present specification, X3 is N.

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

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

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

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

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

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

In an exemplary embodiment of the present specification, L is a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted naphthylene group, or a substituted or unsubstituted It is a cyclic fluorenylene group.

In an exemplary embodiment of the present specification, L is a phenylene group.

In an exemplary embodiment of the present specification, Ar1 and Ar2 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 an exemplary embodiment of the present specification, Ar1 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

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

In an exemplary embodiment of the present specification, Ar1 is a phenyl group unsubstituted or substituted with an alkyl group.

In an exemplary embodiment of the present specification, Ar1 is a phenyl group unsubstituted or substituted with a methyl group, an ethyl group, a propyl group, an isopropyl group, or a tert-butyl group.

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

In an exemplary embodiment of the present specification, Ar1 is a biphenyl group unsubstituted or substituted with an alkyl group.

In an exemplary embodiment of the present specification, Ar1 is a biphenyl group unsubstituted or substituted with a methyl group, an ethyl group, a propyl group, an isopropyl group, or a tert-butyl group.

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

In an exemplary embodiment of the present specification, Ar1 is a naphthyl group unsubstituted or substituted with an alkyl group.

In an exemplary embodiment of the present specification, Ar1 is a naphthyl group unsubstituted or substituted with a methyl group, an ethyl group, a propyl group, an isopropyl group, or a tert-butyl group.

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

In an exemplary embodiment of the present specification, Ar1 is a fluorenyl group unsubstituted or substituted with an alkyl group.

In an exemplary embodiment of the present specification, Ar1 is a fluorenyl group unsubstituted or substituted with a methyl group, an ethyl group, a propyl group, an isopropyl group, or a tert-butyl group.

In an exemplary embodiment of the present specification, Ar1 is a fluorenyl group unsubstituted or substituted with a methyl group.

In an exemplary embodiment of the present specification, Ar1 is a dimethyl fluorenyl group.

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

In an exemplary embodiment of the present specification, Ar1 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 unsubstituted It is a cyclic pyrimidine group, or a substituted or unsubstituted triazine group.

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

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

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

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

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

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

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

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

In an exemplary embodiment of the present specification, Ar1 is a carbazole group substituted with a phenyl group.

In an exemplary embodiment of the present specification, Ar2 is a substituted or unsubstituted C6-C30 aryl group.

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

In an exemplary embodiment of the present specification, Ar2 is a phenyl group unsubstituted or substituted with an alkyl group.

In an exemplary embodiment of the present specification, Ar2 is a phenyl group unsubstituted or substituted with a methyl group, an ethyl group, a propyl group, an isopropyl group, or a tert-butyl group.

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

In an exemplary embodiment of the present specification, Ar2 is a biphenyl group unsubstituted or substituted with an alkyl group.

In an exemplary embodiment of the present specification, Ar2 is a biphenyl group unsubstituted or substituted with a methyl group, an ethyl group, a propyl group, an isopropyl group, or a tert-butyl group.

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

In an exemplary embodiment of the present specification, Ar2 is a naphthyl group unsubstituted or substituted with an alkyl group.

In an exemplary embodiment of the present specification, Ar2 is a naphthyl group unsubstituted or substituted with a methyl group, an ethyl group, a propyl group, an isopropyl group, or a tert-butyl group.

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

In an exemplary embodiment of the present specification, Ar2 is a fluorenyl group unsubstituted or substituted with an alkyl group.

In an exemplary embodiment of the present specification, Ar2 is a fluorenyl group unsubstituted or substituted with a methyl group, an ethyl group, a propyl group, an isopropyl group, or a tert-butyl group.

In an exemplary embodiment of the present specification, Ar2 is a fluorenyl group unsubstituted or substituted with a methyl group.

In an exemplary embodiment of the present specification, Ar2 is a dimethyl fluorenyl group.

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

In an exemplary embodiment of the present specification, Ar2 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 unsubstituted It is a cyclic pyrimidine group, or a substituted or unsubstituted triazine group.

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

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

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

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

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

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

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

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

In an exemplary embodiment of the present specification, Ar2 is a carbazole group substituted with a phenyl group.

In an exemplary embodiment of the present specification, Ar1 or Ar2 may be any one selected from the following structures.

In the exemplary embodiment of the present specification, Ar1 or Ar2 may be any one selected from the following structures.

In an exemplary embodiment of the present specification, Ra and Rb are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

In an exemplary embodiment of the present specification, Ra is a substituted or unsubstituted C 1 to C 10 alkyl group.

In an exemplary embodiment of the present specification, Ra is a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted propyl group, a substituted or unsubstituted isopropyl group, or a substituted or unsubstituted tert- It is a butyl group.

In an exemplary embodiment of the present specification, Ra is a methyl group.

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

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

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

In an exemplary embodiment of the present specification, Rb is a substituted or unsubstituted C 1 to C 10 alkyl group.

In an exemplary embodiment of the present specification, Rb is a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted propyl group, a substituted or unsubstituted isopropyl group, or a substituted or unsubstituted tert- It is a butyl group.

In an exemplary embodiment of the present specification, Rb is a methyl group.

In an exemplary embodiment of the present specification, Rb is a substituted or unsubstituted C6-C30 aryl group.

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

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

In an exemplary embodiment of the present specification, Ra and Rb may be bonded to each other to form a ring.

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 an 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, two or more R1 and R2 are the same as or different from each other.

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

In the exemplary embodiment of the present specification, Chemical Formula 1 may be represented by any one of Chemical Formulas 2 to 5 below.

[Formula 2]

[Formula 3]

[Formula 4]

[Formula 5]

In Formulas 2 to 5,

X1 to X3, L, Ar1, Ar2, Ra, Rb, R1 to R6, r1 and r2 are the same as defined in Formula 1 above.

In an exemplary embodiment of the present specification, Chemical Formula 4 may be represented by any one of the following Chemical Formulas 4-1 to 4-3.

[Formula 4-1]

[Formula 4-2]

[Formula 4-3]

In Formulas 4-1 to 4-3,

X1 to X3, L, Ar1, Ar2, R1 to R6, r1 and r2 are the same as defined in Formula 1 above.

In an 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 following preparations, 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, based on techniques known in the art, starting materials, reactants, reaction conditions, etc. can be changed.

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

[General formula 1]

[General Formula 2]

In Formulas 1 and 2, the definitions of X, X1 to X3, L, Ar1 and Ar2 are the same as defined in Formula 1 above.

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

In one embodiment of the present specification, the first electrode; a second electrode provided to face 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.

In the present specification, when a member is said to be located “on” another member, this includes not only a case in which a member is in contact with another member but also a case in which another member exists between the two members.

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

The organic material layer of the organic electronic device of the present specification may have a single-layer structure, but may have a multi-layer structure in which two or more organic material layers are stacked. For example, as a representative example of the organic electronic device of the present 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 a light emitting layer, and the light emitting layer includes a compound represented by Formula 1 above.

In an 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 an exemplary embodiment of the present specification, the organic material layer includes an electron injection layer, an electron transport layer, or a layer that simultaneously injects and transports electrons, and the electron injection layer, the electron transport layer, or a layer that simultaneously injects and transports electrons is the formula The compound represented by 1 is included.

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

In an 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 an exemplary embodiment of the present specification, the organic light emitting device includes a hole injection layer and a hole transport layer. It further includes one 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 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 exemplified.

In an 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, wherein at least one of the two or more organic material layers includes a compound represented by Formula 1 above.

In an exemplary embodiment of the present specification, the 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 the compound represented by Formula 1 above. Specifically, in an 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 the two or more electron transport layers.

In addition, in an 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 may be used. For example, the electron transport layer including the compound represented by Formula 1 may further include lithium quinolate (LiQ).

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 the compound represented by Formula 1 above. Specifically, in an 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 the two or more hole transport layers.

In addition, in an 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 an exemplary embodiment of the present specification, the organic material layer includes a hole injection layer or a hole transport layer containing a compound including an arylamine group, a carbazolyl group or a benzocarbazolyl group in addition to the organic material layer including the compound represented by Formula 1 may include

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

In one 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 an 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 the organic light emitting device according to an exemplary embodiment of the present specification is illustrated in FIGS. 1 to 3 . 1 to 3 illustrate an organic light emitting device, but is 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 .

2 shows a structure of an organic light emitting device 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. is exemplified.

3 shows 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, the structure of the organic light emitting device is exemplified.

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

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 stacking 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 sputtering or e-beam evaporation, a metal or conductive metal oxide or an alloy thereof is deposited on a substrate to form an anode. It can be prepared 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 into 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, spraying, 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 Laid-Open 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 material for the first electrode, a material having a large work function is generally preferred so that holes can be smoothly injected into the organic material layer. For example, 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); ZnO:Al or SnO ₂ : a combination of a metal such as Sb and an oxide; 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 second electrode material is preferably a material having a small work function to facilitate electron injection into the organic material layer. metals or alloys thereof such as, for example, magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead; A multi-layered material such as LiF/Al or LiO ₂ /Al, but is not limited thereto.

The emission layer may include a host material and a dopant material. The host material includes a condensed aromatic ring derivative or a compound containing a hetero ring. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and heterocyclic-containing compounds include dibenzofuran derivatives, ladder-type furan compounds, and pyrimidine derivatives, but is not limited thereto.

Examples of the dopant material include an aromatic amine derivative, a strylamine compound, a boron complex, a fluoranthene compound, and a metal complex. Specifically, the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamine group, and includes pyrene, anthracene, chrysene, periplanthene, and the like, 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 one or two or more selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamine group A substituent is substituted or unsubstituted. Specifically, there are styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like, but is not limited thereto. In addition, the metal complex includes an iridium complex, a platinum complex, and the like, but is not limited thereto.

In the present specification, when the compound represented by Formula 1 is included in an organic material layer other than the light emitting layer or an additional light emitting layer is provided, as a light emitting material of the light emitting layer, holes and electrons are transported from the hole transport layer and the electron transport layer, respectively. As a material capable of emitting light in the visible light region, a material having good quantum efficiency for fluorescence or phosphorescence is preferable. For example, 8-hydroxy-quinoline aluminum complex (Alq3); carbazole-based compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compounds; compounds of the benzoxazole, benzthiazole and benzimidazole series; Poly(p-phenylenevinylene) (PPV)-based polymers; spiro compounds; polyfluorene; and rubrene, but is not limited thereto.

The hole injection layer is a layer for injecting holes from the electrode. It is preferable that the hole injection material has the ability to transport holes and thus has a hole injection effect at the first electrode and an excellent hole injection effect on the light emitting layer or the light emitting material. Also, a material excellent in the ability to prevent 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 the ability to form a thin film is preferable. In addition, it is preferable that the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the first electrode 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 substances; quinacridone-based organic substances; perylene-based organic materials; There are polythiophene-based conductive polymers such as anthraquinone and polyaniline, but is not limited thereto.

The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light emitting layer. The hole transport material is a material capable of transporting holes from the first electrode or the hole injection layer to the light emitting layer, and a material having high hole mobility 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 well injecting electrons from the second electrode and transferring them to the light emitting layer, and a material having high electron mobility is preferable. Specific examples include an Al complex of 8-hydroxyquinoline; complexes comprising Alq3; organic radical compounds; hydroxyflavone-metal complexes, and the like, but are not limited thereto. The electron transport layer may be used with any desired first electrode material, as used in accordance with the prior art. In particular, suitable first electrode materials are conventional materials having a low work function, followed by a layer of aluminum or silver. Specifically, there are cesium, barium, calcium, ytterbium, samarium, and the like, followed by an aluminum layer or a silver layer in each case.

The electron injection layer is a layer that injects electrons from the electrode. It is preferable that the electron injection material has excellent electron transporting ability and has excellent electron injection effect from the second electrode and 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, perylene tetracarboxylic acid, preorenylidene methane, anthrone, etc. derivatives thereof; metal complex compounds and nitrogen-containing 5-membered ring derivatives, but are not limited thereto.

Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, and 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-crezolato)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 lifetime and efficiency of the device by preventing holes injected from the hole injection layer from entering the electron injection layer through the light emitting layer. A known material can be used without limitation, and may be formed between the light emitting layer and the hole injection layer, or between the light emitting layer and the layer that simultaneously injects and transports holes.

The hole blocking layer is a layer that blocks the holes from reaching the second electrode, 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 is not limited thereto.

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

In an 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 an organic electronic device 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 negative electrode, a positive electrode, and a photoactive layer provided between the negative electrode and the positive electrode, and the photoactive layer may include the compound.

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

< manufacturing example >

< manufacturing example 1> - Intermediate synthesis

The following intermediates A to E and intermediates A-1 to E-1 were prepared using the preparation methods of Formulas 1 and 2 above.

< manufacturing example 2>

Intermediate A-1 (5.12 g, 10.71 mmol) and compound a-1 (4.35 g, 12.32 mmol) were completely dissolved in 280 ml of tetrahydrofuran in a 500 ml round bottom flask in a nitrogen atmosphere, and 2M aqueous potassium carbonate solution (140 ml) was added. . Tetrakis-(triphenylphosphine)palladium (0.37g, 0.32mmol) was added, followed by heating and stirring 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 from 160 ml of tetrahydrofuran to prepare Compound 1 (5.23 g, 69%). MS[M+H] ⁺ = 576

< manufacturing example 3>

Intermediate A-1 (4.67 g, 9.77 mmol) and compound a-2 (3.97 g, 11.24 mmol) were completely dissolved in 200 ml of tetrahydrofuran in a 500 ml round bottom flask in a nitrogen atmosphere, and 2M aqueous potassium carbonate solution (100 ml) was added. . Tetrakis-(triphenylphosphine)palladium (0.34g, 0.29mmol) was added, followed by heating and stirring 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 from 220 ml of ethyl acetate to prepare Compound 2 (4.19 g, 61%). MS[M+H] ⁺ = 576

< manufacturing example 4>

Intermediate A-1 (5.36 g, 13.14 mmol) and compound a-3 (4.55 g, 12.90 mmol) were completely dissolved in 220 ml of tetrahydrofuran in a 500 ml round bottom flask in a nitrogen atmosphere, and 2M aqueous potassium carbonate solution (110 ml) was added. . Tetrakis-(triphenylphosphine)palladium (0.39g, 0.34mmol) was added, followed by heating and stirring 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 280 ml of acetone to prepare compound 3 (4.64 g, 58%). MS[M+H] ⁺ = 575

< manufacturing example 5>

Intermediate A-1 (5.29 g, 11.07 mmol) and compound a-4 (4.49 g, 12.73 mmol) were completely dissolved in 240 ml of tetrahydrofuran in a 500 ml round bottom flask in a nitrogen atmosphere, and 2M aqueous potassium carbonate solution (120 ml) was added. . Tetrakis-(triphenylphosphine)palladium (0.38g, 0.33mmol) was added, followed by heating and stirring 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 220 ml of acetone to prepare compound 4 (3.97 g, 51%). MS[M+H] ⁺ = 574

< manufacturing example 6>

Intermediate B-1 (6.13 g, 12.82 mmol) and compound a-1 (5.21 g, 14.75 mmol) were completely dissolved in 260 ml of tetrahydrofuran in a 500 ml round bottom flask in a nitrogen atmosphere, and 2M aqueous potassium carbonate solution (130 ml) was added. . Tetrakis-(triphenylphosphine)palladium (0.44g, 0.38mmol) was added, followed by heating and stirring 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 from 210 ml of ethyl acetate to prepare compound 5 (6.85 g, 75%). MS[M+H] ⁺ = 592

< manufacturing example 7>

Intermediate C-1 (5.36 g, 11.21 mmol) and compound a-2 (4.55 g, 12.90 mmol) were completely dissolved in 240 ml of tetrahydrofuran in a 500 ml round bottom flask in a nitrogen atmosphere, and 2M aqueous potassium carbonate solution (120 ml) was added. . Tetrakis-(triphenylphosphine)palladium (0.39g, 0.34mmol) was added, followed by heating and stirring 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 from 220 ml of ethyl acetate to prepare compound 6 (4.56 g, 57%). MS[M+H] ⁺ = 624

< manufacturing example 8>

Intermediate A-1 (7.19 g, 13.66 mmol) and compound a-5 (4.26 g, 12.42 mmol) were completely dissolved in 200 ml of tetrahydrofuran in a 500 ml round bottom flask in a nitrogen atmosphere, and 2M aqueous potassium carbonate solution (100 ml) was added. . Tetrakis-(triphenylphosphine)palladium (0.43g, 3755mmol) was added, followed by heating and stirring 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 from 220 ml of acetonitrile to prepare compound 7 (6.37 g, 72%). MS[M+H] ⁺ = 650

< manufacturing example 9>

Intermediate D (7.88 g, 14.98 mmol) and compound a-6 (4.67 g, 13.62 mmol) were completely dissolved in 200 ml of tetrahydrofuran in a 500 ml round bottom flask in a nitrogen atmosphere, and 2M aqueous potassium carbonate solution (100 ml) was added. Tetrakis-(triphenylphosphine)palladium (0.47g, 0.41mmol) was added, followed by heating and stirring 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 from 230 ml of acetonitrile to prepare compound 8 (5.89 g, 61%). MS[M+H] ⁺ = 740

< manufacturing example 10>

Intermediate D (8.30 g, 15.78 mmol) and compound a-7 (4.92 g, 14.34 mmol) were completely dissolved in 260 ml of tetrahydrofuran in a 500 ml round bottom flask in a nitrogen atmosphere, and 2M aqueous potassium carbonate solution (130 ml) was added. Tetrakis-(triphenylphosphine)palladium (0.50g, 0.43mmol) was added, followed by heating and stirring 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 from 230 ml of acetonitrile to prepare compound 9 (6.23 g, 61%). MS[M+H] ⁺ = 756

< manufacturing example 11>

Intermediate E (7.73 g, 14.70 mmol) and compound a-8 (4.77 g, 13.36 mmol) were completely dissolved in 280 ml of tetrahydrofuran in a 500 ml round bottom flask in a nitrogen atmosphere, and 2M aqueous potassium carbonate solution (140 ml) was added. Tetrakis-(triphenylphosphine)palladium (0.64g, 0.55mmol) was added thereto, followed by heating and stirring 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 from 250 ml of acetonitrile to prepare compound 10 (5.14 g, 54%). MS[M+H] ⁺ = 813

< manufacturing example 12>

Intermediate A (9.70 g, 18.44 mmol) and compound a-9 (4.51 g, 16.77 mmol) were completely dissolved in 200 ml of tetrahydrofuran in a 500 ml round bottom flask in a nitrogen atmosphere, and 2M aqueous potassium carbonate solution (100 ml) was added. Tetrakis-(triphenylphosphine)palladium (0.58g, 0.50mmol) was added, followed by heating and stirring 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 from 180 ml of acetonitrile to prepare compound 11 (7.03 g, 66%). MS[M+H] ⁺ = 502

< manufacturing example 13>

Intermediate A-1 (6.47 g, 12.30 mmol) and compound a-10 (4.17 g, 11.18 mmol) were completely dissolved in 200 ml of tetrahydrofuran in a 500 ml round bottom flask in a nitrogen atmosphere, and 2M aqueous potassium carbonate solution (100 ml) was added. . Tetrakis-(triphenylphosphine)palladium (0.39g, 0.30mmol) was added, followed by heating and stirring 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 from 210 ml of acetonitrile to prepare compound 12 (5.19 g, 63%). MS[M+H] ⁺ = 652

< manufacturing example 14>

Intermediate B (7.29 g, 13.85 mmol) and compound a-11 (5.44 g, 12.59 mmol) were completely dissolved in 200 ml of tetrahydrofuran in a 500 ml round bottom flask in a nitrogen atmosphere, and 2M aqueous potassium carbonate solution (100 ml) was added. Tetrakis-(triphenylphosphine)palladium (0.44g, 0.38mmol) was added, followed by heating and stirring 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 from 230 ml of acetonitrile to prepare compound 13 (7.16 g, 71%). MS[M+H] ⁺ = 616

< manufacturing example 15>

Intermediate A (4.96 g, 10.38 mmol) and compound a-12 (5.12 g, 11.93 mmol) were completely dissolved in 240 ml of tetrahydrofuran in a 500 ml round bottom flask in a nitrogen atmosphere, and 2M aqueous potassium carbonate solution (120 ml) was added. Tetrakis-(triphenylphosphine)palladium (0.36g, 0.31mmol) was added, followed by heating and stirring 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 from 210 ml of tetrahydrofuran to prepare compound 14 (6.34 g, 78%). MS[M+H] ⁺ = 628

< Example >

< Example 1-1>

A glass substrate coated with indium tin oxide (ITO) to a thickness of 1,000 Å was placed in distilled water in which detergent was dissolved and washed with ultrasonic waves. At this time, a product manufactured by Fischer Co. was used as the detergent, and distilled water that was secondarily filtered with a filter manufactured by Millipore Co. was used as the distilled water. After washing ITO for 30 minutes, ultrasonic cleaning was performed for 10 minutes by repeating twice with distilled water. 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, the compound of the compound HI1 and the compound HI2 below was thermally vacuum deposited to a thickness of 100 Å in a ratio of 98:2 (molar ratio) to form a hole injection layer. On the hole injection layer, the following compound HT1 was vacuum-deposited to a thickness of 1,150 Å to form a hole transport layer. Then, the following compound EB1 was vacuum-deposited to a thickness of 50 Å on the hole transport layer to form an electron blocking layer. Then, the following compound BH and the following compound BD were vacuum-deposited in a weight ratio of 50:1 to a film thickness of 200 Å on the electron blocking layer to form an emission layer. A hole blocking layer was formed by vacuum-depositing the compound 1 prepared above to a film thickness of 50 Å on the light emitting layer. Then, on the hole blocking layer, the following compound ET1 and the following compound LiQ were vacuum-deposited in a weight ratio of 1:1 to form an electron injection and transport layer to 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.

In the above process, the deposition rate of organic material was maintained at 0.4 to 0.7 Å/sec, the deposition rate of lithium fluoride of the negative electrode was maintained at 0.3 Å/sec, and the deposition rate of aluminum was maintained at 2 Å/sec, and the vacuum degree during deposition was 2 X 10 ^{- By maintaining 7} to 5 X 10 ^-6 torr, an organic light emitting device was manufactured.

< Example 1-2 to 1-5>

An organic light emitting diode 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 example 1-1 and comparative example 1-2>

An organic light emitting diode 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.

Driving voltage, efficiency, and color coordinates were measured for the organic light emitting devices manufactured in Examples 1-1 to 1-5, Comparative Examples 1-1 and 1-2 at ^{a current density of 20 mA/cm 2 , and 20 mA} At a current density of /cm ² , the time (T95) to 95% of the initial luminance 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 Examples 1-3 compound 5 4.34 6.66 (0.143, 0.047) 270 Examples 1-4 compound 6 4.36 6.77 (0.143, 0.046) 255 Examples 1-5 compound 12 4.17 6.68 (0.144, 0.045) 280 Comparative Example 1-1 HB 2 4.79 5.53 (0.145, 0.047) 135 Comparative Example 1-2 HB 3 4.65 5.81 (0.148, 0.051) 110

As shown in Table 1, in the case of an organic light emitting device manufactured by using the compound represented by Formula 1 of the present specification as a hole blocking layer, compared to Comparative Examples 1-1 and 1-2, the 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 Formula 1 of the present specification have superior lifespan characteristics compared to Comparative Examples 1-1 and 1-2.

< Example 2-1 to 2-11>

An organic light emitting diode 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 example 2-1 and comparative example 2-2>

An organic light emitting diode was manufactured in the same manner as in Example 1-1, except that Compound HB1 was used instead of Compound 1 in Example 1-1, and the following compounds ET2 and ET3 were used instead of Compound ET1.

The organic light emitting devices manufactured by Examples 2-1 to 2-11, Comparative Examples 2-1 and 2-2 were measured for driving voltage, efficiency and color coordinates at a current density of ^{20 mA/cm 2 , and 20 mA} At a current density of /cm ² , the time (T95) to 95% of the initial luminance was measured. The results are shown in Table 2 below.

compound
(electron injection and transport layer) Voltage
(V@20mA
/cm ² ) efficiency
(cd/A@20mA
/cm ² ) color coordinates
(x,y)
T95
(hr) Example 2-1 compound 1 4.31 6.30 (0.144, 0.046) 285 Example 2-2 compound 2 4.36 6.80 (0.144, 0.044) 295 Example 2-3 compound 3 4.37 6.53 (0.145, 0.048) 305 Example 2-4 compound 4 4.38 6.74 (0.144, 0.044) 300 Example 2-5 compound 7 4.29 6.65 (0.144, 0.04) 280 Example 2-6 compound 8 4.26 6.58 (0.145, 0.047) 280 Example 2-7 compound 9 4.31 6.79 (0.145, 0.046) 285 Examples 2-8 compound 10 4.35 6.67 (0.144, 0.048) 285 Examples 2-9 compound 11 4.34 6.53 (0.146, 0.045) 290 Example 2-10 compound 13 4.25 6.44 (0.147, 0.047) 295 Example 2-11 compound 14 4.25 6.61 (0.144, 0.046) 290 Comparative Example 2-1 ET2 4.81 5.72 (0.142, 0.047) 180 Comparative Example 2-2 ET3 5.42 4.85 (0.143, 0.050) 165

As shown in Table 2, in the case of an organic light emitting device manufactured by using the compound represented by Formula 1 of the present specification as an electron injection and transport layer, compared to Comparative Examples 2-1 and 2-2, efficiency, driving It can be seen that excellent characteristics in terms of voltage and/or stability are exhibited. In particular, it can be seen that Examples 2-1 to 2-11 using the compound represented by Formula 1 of the present specification have superior lifespan characteristics compared to Comparative Examples 2-1 and 2-2.

Through the above, the preferred embodiments of the present specification have been described, but the present invention is not limited thereto, and various modifications can be made within the scope of the claims and 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

Claims (11)

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

In Formula 1,
X is O, S, CRaRb or SO ₂ ,
At least one of X1 to X3 is N, the rest are each independently N or CR,
L is a direct bond; or an arylene group having 6 to 30 carbon atoms,
Ar1 and Ar2 are the same as or different from each other, and are each independently an aryl group having 6 to 30 carbon atoms substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms or a quinoline group; dibenzofuran group; dibenzothiophene group; a carbazole group unsubstituted or substituted with an aryl group having 6 to 30 carbon atoms; or a pyridyl group,
Ra and Rb are the same as or different from each other, and each independently an alkyl group having 1 to 10 carbon atoms; or an aryl group having 6 to 30 carbon atoms, or may combine with each other to form a fluorene ring,
R and R1 to R6 are hydrogen,
r1 is an integer from 1 to 3,
r2 is an integer from 1 to 4. The compound according to claim 1, wherein Formula 1 is represented by any one of Formulas 2 to 5:
[Formula 2]

[Formula 3]

[Formula 4]

[Formula 5]

In Formulas 2 to 5,
X1 to X3, L, Ar1, Ar2, Ra, Rb, R1 to R6, r1 and r2 are the same as defined in Formula 1 above. The method according to claim 1, wherein L is a direct bond; phenylene group; Or a compound that is a biphenylene group. The method according to claim 1, wherein Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with a quinoline group; biphenyl group; terphenyl group; naphthyl group; phenanthrenyl group; dimethyl fluorenyl group; a carbazole group unsubstituted or substituted with a phenyl group; dibenzothiophene group; dibenzofuran group; Or a compound that is a pyridyl group. The compound according to 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 at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers comprises 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 method according to claim 6, wherein the organic layer comprises an electron injection layer, an electron transport layer, or a layer that simultaneously injects and transports electrons, and the electron injection layer, the electron transport layer, or the layer that simultaneously injects and transports electrons contains the compound. Phosphorus organic electronic device. 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 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.

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