KR20190116691A - 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 comprising the same. The compound according to an embodiment of the present specification can be used in the organic electronic device including an organic light emitting device to lower a driving voltage, and also improve light efficiency and lifespan characteristics of the organic electronic device.

Description

COMPOUND AND ORGANIC ELECTRONIC DEVICE COMPRISING THE SAME

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

Representative examples of the organic electronic device include an organic light emitting device. In general, organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material. An organic light emitting device using an organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer therebetween. In this case, the organic material layer is often formed of a multi-layered structure composed of different materials to increase the efficiency and stability of the organic light emitting device, for example, it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer. When the voltage is applied between the two electrodes in the structure of the organic light emitting device, holes are injected into the organic material layer at the anode and electrons are injected into the organic material layer, and excitons are formed when the injected holes and the electrons meet each other. When it falls back to the ground, it glows.

There is a continuing need for the development of new materials for such organic light emitting devices.

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 Chemical Formula 1,

X is O, S, CRaRb or SO ₂ ,

L is a direct bond; 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 each independently a substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or may combine with each other to form a ring,

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

r1 is an integer of 1 to 3,

r2 is an integer of 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.

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 the 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 one embodiment of the present specification may be used in an organic electronic device including an organic light emitting device, thereby improving light efficiency.

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

1 to 3 illustrate examples of the organic light emitting diode according to one embodiment of the present specification.

Hereinafter, this specification is demonstrated in detail.

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

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

는 연결되는 부위를 의미한다.In the present specification,

Means a site to be connected.

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

As used herein, the term "substituted or unsubstituted" is deuterium; Halogen group; Nitrile group; Alkyl groups; Cycloalkyl group; Amine group; Silyl groups; Phosphine oxide groups; Aryl group; And one or two or more substituents selected from the group consisting of heteroaryl groups including one or more of N, O, S, Se, and Si atoms, or two or more substituents among the substituents exemplified above are substituted with a substituent, 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, the carbon number 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, but is not limited thereto.

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 is a substituent including Si and the Si atom is directly connected as a radical, represented by -SiR ₂₀₁ R ₂₀₂ R ₂₀₃ , and R ₂₀₁ to R ₂₀₃ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Alkyl groups; Alkenyl groups; An 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, and the like. It is not limited.

In the present specification, when the aryl group is a monocyclic aryl group, carbon number is not particularly limited, but is 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 quarterphenyl group, etc., but is not limited thereto.

Carbon number is not particularly limited when the aryl group is a polycyclic aryl group. It is preferable that it is C10-C50, and 10-30 are more preferable. Specifically, the polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, peryllenyl group, triphenyl group, chrysenyl group, 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,

,

,

,

,

,

Etc., but is not limited thereto.

In the present specification, the heteroaryl group includes one or more of N, O, S, Si, and Se as hetero atoms, and the carbon number is not particularly limited, but is preferably 2 to 60 carbon atoms, 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 Dinyl groups, pyridazine groups, pyrazine groups, quinoline groups, quinazoline groups, quinoxaline groups, phthalazine groups, pteridine groups, pyrido pyrimidine groups, pyrido pyrazine groups pyrazine), pyrazino pyrazine, isoquinoline, indole, pyrido indole, innopyrimidine, 5b-indeno pyrimidine, carbazole group, benzoxazole group, benzimidazole group , Benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuran group, dibenzofuran group, phenanthroline group, thiazolyl group, isoxazolyl group, oxadiazolyl group and Thiadiazolyl groups and the like, but are not limited thereto.

In the present specification, phosphine oxide groups include, but are not limited to, diphenylphosphine oxide group, dinaphthylphosphine oxide, and the like.

In the present specification, the arylene group refers to a divalent group having two bonding positions in the aryl group. The description of the aforementioned aryl group can be applied except that they are each divalent.

In the present specification, the heteroarylene group means a divalent group having two bonding positions in the heteroaryl group. The description of the aforementioned heteroaryl group can be applied except that they are each divalent.

In one embodiment of the present specification, X is O, S, CRaRb or SO ₂ .

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

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

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

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

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

In one 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 group Ring fluorenylene group.

In one embodiment of the present specification, L is a phenylene group unsubstituted or substituted with an alkyl group.

In one embodiment of the present specification, L is a phenylene group unsubstituted or substituted with a methyl group, an ethyl group, a propyl group, an isopropyl group, or a tert-butyl group.

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

In one embodiment of the present specification, L is a biphenylene group unsubstituted or substituted with an alkyl group.

In one embodiment of the present specification, L is a biphenylene group unsubstituted or substituted with a methyl group, an ethyl group, a propyl group, an isopropyl group, or a tert-butyl group.

In one embodiment of the present specification, L is a biphenylene group.

In one embodiment of the present specification, L is a fluorenylene group unsubstituted or substituted with an alkyl group.

In one embodiment of the present specification, L1 is a fluorenylene group unsubstituted or substituted with a methyl group, an ethyl group, a propyl group, an isopropyl group, or a tert-butyl group.

In one embodiment of the present specification, L is a fluorenylene group unsubstituted or substituted with a methyl group.

In one embodiment of the present specification, L is a dimethylfluorenylene group.

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

In one 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 triphenyl group, a substituted or unsubstituted phenanthryl group, Or a substituted or unsubstituted fluorenyl group.

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

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

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

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

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

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

In one embodiment of the present specification, Ar1 is a dimethylfluorenyl group.

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

In one 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 A substituted pyrimidine group or a substituted or unsubstituted triazine group.

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

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

In one 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 triphenyl group, a substituted or unsubstituted phenanthryl group, Or a substituted or unsubstituted fluorenyl group.

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

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

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

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

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

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

In one embodiment of the present specification, Ar2 is a dimethylfluorenyl group.

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

In one 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 A substituted pyrimidine group or a substituted or unsubstituted triazine group.

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

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

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

In one 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; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or may combine with each other to form a ring.

In one embodiment of the present specification, Ra is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

In one 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- Butyl group.

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

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

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

In one embodiment of the present specification, Rb is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

In one 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- Butyl group.

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

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

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

In one embodiment of the present specification, Ra and Rb may combine with each other to form a ring.

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

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

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

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

[Formula 2]

[Formula 3]

[Formula 4]

[Formula 5]

In Chemical Formulas 2 to 5,

Definitions for L, Ar1, Ar2, Ra, Rb, R1 to R6, r1 and r2 are the same as defined in Chemical Formula 1.

In one 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 Chemical Formulas 4-1 to 4-3,

Definitions for L, Ar1, Ar2, R1 to R6, r1 and r2 are the same as defined in Chemical Formula 1.

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

Compounds according to one embodiment of the present specification may be prepared by the production method described below. In the following production examples, 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, it is possible to change the starting materials, reactants, reaction conditions and the like.

For example, the compound represented by Formula 1 may be prepared in the core structure as shown in the general formulas 1 and 2. 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. Substituents may be bonded as in Formulas 1 and 2, but is not limited thereto.

[Formula 1]

[Formula 2]

In Formulas 1 and 2, the definitions for X, L, Ar1 and Ar2 are the same as defined in Chemical Formula 1.

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

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

In the present specification, when a part "contains" a certain component, this means that the component may further include other components, except for the case where there is no contrary description.

The organic material layer of the organic electronic device of the present specification may have a single layer structure, but may have a multi-layered 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 one embodiment of the present specification, the organic material layer includes a light emitting layer, and the light emitting layer includes a compound represented by Chemical Formula 1.

In one embodiment of the present specification, the organic material layer includes a light emitting layer, and the light emitting layer includes a compound represented by Chemical Formula 1 as a host of the light emitting layer.

In one embodiment of the present specification, the organic material layer includes a hole injection layer or a hole transport layer, the hole injection layer or a hole transport layer comprises a compound represented by the formula (1).

In one 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 a compound represented by Chemical Formula 1.

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

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

In one embodiment of the present specification, the organic light emitting device is a hole injection layer, a hole transport layer. It further comprises 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 one 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, the organic light emitting device will be described.

In one 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 Chemical Formula 1.

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 transporting layer, a hole injection layer, a layer for simultaneously transporting holes and injecting holes, and an electron blocking layer.

In one 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 Chemical Formula 1. Specifically, in one embodiment of the present specification, the compound represented by Formula 1 may be included in one layer 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 two or more electron transport layers, other materials except for 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 Chemical Formula 1 is an electron transport layer, the electron transport layer may further include an n-type dopant. The n-type dopant may be those known in the art, for example, may be a metal or metal complex. For example, the electron transport layer including the compound represented by Chemical Formula 1 may further include LiQ (Lithium Quinolate).

In one 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 Chemical Formula 1. Specifically, in one embodiment of the present specification, the compound represented by Formula 1 may be included in one layer 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, other materials except for the compound represented by Formula 1 may be the same or different from each other. have.

In one 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, carbazolyl group, or benzocarbazolyl group in addition to the organic material layer including the compound represented by Chemical Formula 1 It 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 one embodiment of the present specification, the organic light emitting device may be an organic light emitting device having a structure in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.

In one embodiment of the present specification, the organic light emitting diode may be an organic light emitting diode having an inverted type 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 one embodiment of the present specification is illustrated in FIGS. 1 to 3. 1 to 3 illustrate an organic light emitting device and are not limited thereto.

1 illustrates a structure of an organic light emitting diode in which a first electrode 102, a light emitting layer 106, and a second electrode 110 are sequentially stacked on a substrate 101.

2 illustrates 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 illustrated.

3, the first electrode 102, the hole injection layer 103, the hole transport layer 104, the electron blocking layer 105, the light emitting layer 106, the hole blocking layer 107, and the electron transporting layer ( 108, the structure of the organic light emitting device in which the electron injection layer 109 and the second electrode 110 are sequentially stacked is illustrated.

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 layer of the organic material layer includes the compound, that is, the compound represented by Chemical 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 stacking a first electrode, an organic material layer, and a second electrode on a substrate. In this case, by using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation, a metal or conductive metal oxide or an alloy thereof is deposited on the substrate to form an anode. It can be prepared by forming and 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 such a 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 Chemical Formula 1 may be formed as an organic material layer by a solution coating method as well as a vacuum deposition method in the manufacture of the organic light emitting device. Here, the solution coating method means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spray method, roll coating, but is not limited thereto.

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

In one 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 first electrode material, a material having a large work function is generally preferred to facilitate hole injection 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), indium zinc oxide (IZO); ZnO: Al or SnO ₂ : Combination of metals and oxides such as Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole and polyaniline, and the like, but are not limited thereto.

It is preferable that the second electrode material is a material having a small work function to facilitate electron injection into the organic material layer. Metals such as, for example, magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof; Multilayer structure materials such as LiF / Al or LiO ₂ / Al, and the like, but are not limited thereto.

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

Examples of the dopant material include aromatic amine derivatives, styrylamine 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 periplanthene 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, selected from the group consisting of aryl group, silyl group, alkyl group, cycloalkyl group and arylamine group. The substituent is substituted or unsubstituted. Specifically, 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 Chemical Formula 1 is included in an organic material layer other than the light emitting layer, or when an additional light emitting layer is provided, the light emitting material of the light emitting layer is transported and bonded with holes and electrons from the hole transporting layer and the electron transporting layer, respectively. As a material capable of emitting light in the visible ray region, a material having good quantum efficiency with respect to fluorescence or phosphorescence is preferable. For example, 8-hydroxy-quinoline aluminum complex (Alq 3); Carbazole series compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compound; Benzoxazole, benzthiazole and benzimidazole series compounds; Poly (p-phenylenevinylene) (PPV) -based polymers; Spiro compounds; Polyfluorene; And rubrene, but are not limited thereto.

The hole injection layer is a layer for injecting holes from the electrode. The hole injection material preferably has the ability to transport holes, and thus has a hole injection effect in the first electrode and an excellent hole injection effect for the light emitting layer or the light emitting material. In addition, a material having excellent ability to prevent the excitons generated in the light emitting layer from moving to the electron injection layer or the electron injection material is preferable. In addition, a material excellent in thin film formation ability 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 may include metal porphyrin, oligothiophene, and arylamine-based organic material; Hexanitrile hexaazatriphenylene-based organic material; Quinacridone series organics; Perylene-based organic material; 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 light emitting layer. As the hole transporting material, a material capable of receiving holes from the first electrode or the hole injection layer and transferring the holes to the light emitting layer 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 the electrons to the light emitting layer. As the electron transporting material, a material capable of injecting electrons well from the second electrode to be transferred to the light emitting layer, and a material having high mobility to electrons is preferable. Specific examples include Al complexes of 8-hydroxyquinoline; Complexes including Alq3; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but is not limited thereto. The electron transport layer can be used with any desired first electrode material, as used in accordance with the prior art. In particular, suitable first electrode materials have a low work function and are conventional materials followed by aluminum layers or silver layers. Specifically, there are cesium, barium, calcium, ytterbium, samarium, and the like, each followed by an aluminum layer or a silver layer.

The electron injection layer is a layer for injecting electrons from the electrode. The electron injecting material is preferably excellent in the ability to transport electrons and has an electron injection effect from the second electrode, and an electron injection effect excellent with respect to the light emitting layer or the light emitting material. In addition, a material which prevents excitons generated in the light emitting layer from moving to the hole injection layer and is excellent in thin film formation ability is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and the like, and derivatives thereof, Metal complex compounds, nitrogen-containing five-membered ring derivatives, and the like, but is 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-cresolato) gallium, bis (2-methyl-8-quinolinato) (1-naphtholato) aluminum, bis (2-methyl-8-quinolinato) (2-naphtolato) gallium, It is not limited to this.

The electron blocking layer is a layer that prevents holes injected from the hole injection layer from passing through the light emitting layer to the electron injection layer, thereby improving lifetime and efficiency of the device. Known materials can be used without limitation, and can be formed between the light emitting layer and the hole injection layer, or between the light emitting layer and the layer simultaneously performing hole injection and hole transport.

The hole blocking layer is a layer that blocks reaching the second electrode of the hole, and may generally be 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.

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

In one embodiment of the present specification, the compound represented by Chemical 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 organic light emitting devices in organic electronic devices including organic phosphorescent devices, organic solar cells, organic photoconductors, organic transistors, and the like. For example, the organic solar cell may have a structure including a cathode, an anode, and a photoactive layer provided between the cathode and the anode, and the photoactive layer may include the compound.

Hereinafter, the present specification 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 many different forms, and the scope of the present specification is not interpreted to be limited to the examples and comparative examples described below. The examples and comparative examples herein are provided to more fully describe the present specification to those skilled in the art.

< Production Example >

< Production 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.

< Production Example  2>

In a 500 mL round bottom flask in nitrogen atmosphere, Intermediate A (6.47 g, 20.72 mmol) and Compound a1 (8.56 g, 18.02 mmol) were completely dissolved in 240 mL of tetrahydrofuran, followed by 2M aqueous potassium carbonate solution (120 mL). . Tetrakis- (triphenylphosphine) palladium (0.62 g, 0.54 mmol) 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 with 310 mL of ethyl acetate to obtain compound 1 (7.64 g, 64%). MS [M + H] ⁺ = 664

< Production Example  3>

In a 500 mL round bottom flask under nitrogen atmosphere, Intermediate C (6.37 g, 17.69 mmol) and Compound a2 (7.92 g, 15.38 mmol) were completely dissolved in 240 mL of tetrahydrofuran, followed by 2M aqueous potassium carbonate solution (120 mL). . Tetrakis- (triphenylphosphine) palladium (0.53 g, 0.46 mmol) was added thereto, followed by heating and stirring for 2 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 ethyl acetate to obtain compound 2 (6.83 g, 59%). MS [M + H] ⁺ = 752

< Production Example  4>

In a 500 mL round bottom flask in nitrogen atmosphere, intermediate B (12.82 g, 22.68 mmol) and Compound a3 (6.47 g, 19.73 mmol) were completely dissolved in 240 mL of tetrahydrofuran, followed by addition of 2M aqueous potassium carbonate solution (120 mL). Tetrakis- (triphenylphosphine) palladium (0.68 g, 0.59 mmol) was added thereto, followed by heating and stirring for 3 hours. After lowering the temperature to room temperature, removing the water layer and drying with anhydrous magnesium sulfate. Concentrated under reduced pressure and recrystallized with acetone 250 mL to give compound 3 (10.07 g, 63%). MS [M + H] ⁺ = 810

< Production Example  5>

In a 500 mL round bottom flask in nitrogen atmosphere, intermediate D (8.17 g, 17.69 mmol) and compound a4 (7.77 g, 15.39 mmol) were completely dissolved in 180 mL of tetrahydrofuran and 2M aqueous potassium carbonate solution (90 mL) was added. Tetrakis- (triphenylphosphine) palladium (0.53 g, 0.46 mmol) was added thereto, 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 210 mL of ethyl acetate to obtain compound 4 (6.78 g, 57%). MS [M + H] ⁺ = 768

< Production Example  6>

To a 500 mL round bottom flask in nitrogen atmosphere, intermediate E (6.77 g, 14.73 mmol) and compound a5 (6.39 g, 12.81 mmol) were completely dissolved in 240 mL of tetrahydrofuran and 2M aqueous potassium carbonate solution (120 mL) was added. Tetrakis- (triphenylphosphine) palladium (0.44 g, 0.38 mmol) was added thereto, 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 with 280 mL of ethyl acetate to obtain compound 5 (5.59 g, 52%). MS [M + H] ⁺ = 836

< Production Example  7>

Intermediate A-1 (6.13 g, 10.83 mmol) and Compound a6 (5.02 g, 11.91 mmol) were completely dissolved in 200 mL of xylene in a 500 mL round bottom flask in a nitrogen atmosphere. NaOtBu (2.12 g, 22.06 mmol) was added, Bis (tri-tert-butylphosphine) palladium (0) (0.11 g, 0.22 mmol) was added thereto, and the mixture was heated and stirred for 2 hours. After cooling to room temperature to remove salt by filtration, xylene (Xylene) was concentrated under reduced pressure and recrystallized with 250 mL of ethyl acetate to give compound 6 (4.98 g, yield: 67%). MS [M + H] ⁺ = 688

< Production Example  8>

Intermediate B-1 (5.88 g, 10.10 mmol) and Compound a7 (4.56 g, 11.11 mmol) were completely dissolved in 160 mL Xylene in a 500 mL round bottom flask in a nitrogen atmosphere. NaOtBu (1.26 g, 13.13 mmol) was added, Bis (tri-tert-butylphosphine) palladium (0) (0.10g, 0.20 mmol) was added thereto, and the mixture was heated and stirred for 4 hours. After cooling to room temperature to remove the salt by filtration, Xylene was concentrated under reduced pressure and recrystallized with 210 mL of ethyl acetate to give compound 7 (4.07 g, yield: 58%). MS [M + H] ⁺ = 693

< Production Example  9>

Intermediate D-1 (9.16 g, 12.79 mmol) and Compound a8 (5.64 g, 14.07 mmol) were completely dissolved in 200 mL of Xylene in a 500 mL round bottom flask in a nitrogen atmosphere. NaOtBu (1.60 g, 16.63 mmol) was added, Bis (tri-tert-butylphosphine) palladium (0) (0.13 g, 0.26 mmol) was added thereto, and the mixture was heated and stirred for 2 hours. After cooling to room temperature to remove the salt by filtration, Xylene was concentrated under reduced pressure and recrystallized with 150 mL of ethyl acetate to give compound 8 (5.24 g, yield: 54%). MS [M + H] ⁺ = 764

< Example >

< Example  1-1>

A glass substrate coated with a thin film of ITO (indium tin oxide) at a thickness of 1,000 Å was placed in distilled water in which detergent was dissolved and ultrasonically cleaned. In this case, Fischer Co. was used as a detergent, and distilled water was filtered secondly as a filter of Millipore Co. as a distilled water. After ITO was washed for 30 minutes, ultrasonic washing was performed twice with distilled water for 10 minutes. After washing the distilled water, ultrasonic washing with a solvent of isopropyl alcohol, acetone, methanol, dried and transported to a plasma cleaner. In addition, the substrate was cleaned for 5 minutes using an oxygen plasma, and then the substrate was transferred to a vacuum evaporator.

On the ITO transparent electrode prepared as above, the compound of the following compound HI1 and the following compound HI2 was thermally vacuum deposited to a thickness of 100 kPa so that the ratio of 98: 2 (molar ratio) was formed to form a hole injection layer. The following compound HT1 was vacuum deposited to a thickness of 1,150 위에 on the hole injection layer to form a hole transport layer. Subsequently, Compound 1 prepared above was vacuum deposited on the hole transport layer with a film thickness of 50 GPa to form an electron blocking layer. Subsequently, the following Compound BH and the following Compound BD were vacuum-deposited at a weight ratio of 25: 1 to form a light emitting layer on the electron blocking layer at a film thickness of 200 GPa. Compound HB1 was vacuum deposited on the light emitting layer with a film thickness of 50 GPa to form a hole blocking layer. Subsequently, the following compound ET1 and the following compound LiQ were vacuum-deposited on the hole blocking layer in a weight ratio of 1: 1 to form an electron injection and transport layer at a thickness of 310 Å. The cathode was formed by sequentially depositing lithium fluoride (LiF) and aluminum at a thickness of 1,000 Å on the electron injection and transport layer sequentially.

Was maintained at a vapor deposition rate of 0.4 to 0.7Å / sec for organic material in the above process, the lithium fluoride of the cathode was 0.3Å / sec, aluminum is deposited at a rate of 2Å / sec, During the deposition, a vacuum 10 2 X ^{- The} organic light emitting device was manufactured by maintaining ⁷ to 5 × 10 ⁻⁶ torr.

< Example  1-2 to 1-8>

An organic light-emitting device was manufactured in the same manner as in Example 1-1, except that Compound 2 to Compound 8 were used instead of Compound 1 in Example 1-1.

< Comparative example  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 EB1 to EB3 were used instead of Compound 1 in Example 1-1.

The organic light emitting diodes manufactured according to Examples 1-1 to 1-8 and Comparative Examples 1-1 to 1-3 measured driving voltage, efficiency, and color coordinate at a current density of 20 mA / cm ² , and 20 mA / cm ^The time T95 of 95% of the initial luminance at the current density of ² was measured. The results are shown in Table 1 below.

compound
(Electron blocking layer) Voltage
(V @ 20mA
/ cm ² ) efficiency
(cd / A @ 20mA
/ cm ² ) Color coordinates
(x, y) T95
(hr) Example 1-1 Compound 1 3.53 6.35 (0.140, 0.048) 275 Example 1-2 Compound 2 3.51 6.23 (0.141, 0.047) 280 Example 1-3 Compound 3 3.52 6.34 (0.143, 0.046) 285 Example 1-4 Compound 4 3.54 6.22 (0.139, 0.048) 280 Example 1-5 Compound 5 3.66 6.31 (0.140, 0.047) 285 Example 1-6 Compound 6 3.67 6.16 (0.141, 0.048) 275 Example 1-7 Compound 7 3.68 6.27 (0.140, 0.047) 280 Example 1-8 Compound 8 3.79 6.49 (0.139, 0.047) 290 Comparative Example 1-1 EB1 4.17 5.78 (0.139, 0.045) 160 Comparative Example 1-2 EB2 4.31 5.32 (0.142, 0.042) 25 Comparative Example 1-3 EB3 3.95 6.01 (0.142, 0.042) 230

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 an electron blocking layer, compared to Comparative Examples 1-1 to 1-3, efficiency, driving voltage and / Or it can be seen that the excellent properties in terms of stability. In particular, it can be seen that Examples 1-1 to 1-8 using the compound represented by the formula (1) of the present specification have superior life characteristics as compared to Comparative Examples 1-1 to 1-3.

Although the preferred embodiments of the present specification have been described above, the present invention is not limited thereto, and various modifications and changes can be made within the scope of the claims and the detailed description 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 (10)

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

In Chemical Formula 1,
X is O, S, CRaRb or SO ₂ ,
L is a direct bond; 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 each independently a substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or may combine with each other to form a ring,
R1 to R6 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
r1 is an integer of 1 to 3,
r2 is an integer of 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. The compound of claim 1, wherein Formula 1 is represented by any one of Formulas 2 to 5.
[Formula 2]

[Formula 3]

[Formula 4]

[Formula 5]

In Chemical Formulas 2 to 5,
The definitions for L, Ar1, Ar2, Ra, Rb, R1 to R6, r1 and r2 are the same as defined in Chemical Formula 1. The compound according to claim 1, wherein L is a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylylene group, or a substituted or unsubstituted fluorenylene group. The method of claim 1, wherein 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 fluorenyl group, or a substituted or unsubstituted di Compound which is a benzofuran group. The compound of claim 1, wherein the compound represented by Chemical Formula 1 is any one selected from the following compounds:

A first electrode; A second electrode provided to face the first electrode; And an organic electronic device comprising 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 a compound according to any one of claims 1 to 5. Electronic devices. The organic electronic device of claim 6, wherein the organic material layer includes a light emitting layer, and the light emitting 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 an electron blocking layer, and the electron blocking layer includes the compound. The method of 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.

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