CN111448184B

CN111448184B - Compound and organic electronic device comprising same

Info

Publication number: CN111448184B
Application number: CN201980006249.4A
Authority: CN
Inventors: 车龙范; 徐尚德; 洪性佶; 金性昭; 千民承
Original assignee: LG Chem Ltd
Current assignee: LG Chem Ltd
Priority date: 2018-04-05
Filing date: 2019-04-04
Publication date: 2023-12-19
Anticipated expiration: 2039-04-04
Also published as: KR102262687B1; KR20190116686A; WO2019194594A1; CN111448184A

Abstract

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

Description

Compound and organic electronic device comprising same

Technical Field

The present application claims priority from korean patent application No. 10-2018-0039633, filed to the korean patent office on the 05 th month of 2018, the entire contents of which are incorporated herein.

The present specification relates to compounds and organic electronic devices comprising the same.

Background

As a representative example of the organic electronic device, there is an organic light emitting device. In general, the organic light emitting phenomenon refers to a phenomenon of converting electric energy into light energy using an organic substance. An organic light emitting device using an organic light emitting phenomenon generally has a structure including an anode and a cathode and an organic layer therebetween. Here, in order to improve efficiency and stability of the organic light-emitting device, the organic layer is often formed of a multilayer structure composed of different substances, and may be formed of, for example, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, or the like. In such a structure of an organic light emitting device, if a voltage is applied between both electrodes, holes are injected from an anode to an organic layer, electrons are injected from a cathode to the organic layer, and when the injected holes and electrons meet, excitons (exiton) are formed, and light is emitted when the excitons re-transition to a ground state.

There is a continuing need to develop new materials for use in organic light emitting devices as described above.

Disclosure of Invention

Technical problem

The present specification provides compounds and organic electronic devices comprising the same.

Solution to the problem

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

[ chemical formula 1]

In the above-mentioned chemical formula 1,

x is O, S, CRaRb or SO ₂ ，

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

l is a direct bond, a substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene,

ar1 and Ar2 are the same or different from each other and are each independently a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group,

ra and Rb are the same or different from each other, each independently is a substituted or unsubstituted phenyl group, or may be combined with each other to form a ring,

r and R1 to R6 are the same or different from each other and are each independently hydrogen, deuterium, a 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 of 1 to 3,

r2 is an integer of 1 to 4,

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

In addition, the present specification provides an organic electronic device, including: a first electrode, a second electrode provided opposite to the first electrode, and an organic layer provided between the first electrode and the second electrode, wherein 1 or more of the organic layers contains the compound.

Effects of the invention

The compound according to an embodiment of the present specification is used in an organic electronic device typified by an organic light emitting device, and can reduce the driving voltage of the organic electronic device.

In addition, the compound according to an embodiment of the present specification is used in an organic electronic device typified by an organic light-emitting device, and can improve light efficiency.

In addition, the compound according to an embodiment of the present specification is used in an organic electronic device typified by an organic light emitting device, and life characteristics of the device can be improved based on thermal stability of the compound.

Drawings

Fig. 1 to 3 illustrate examples of an organic light emitting device according to an embodiment of the present specification, respectively.

101: substrate board

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 injection and transport layers

109: second electrode

Detailed Description

The present specification will be described in more detail below.

The present specification provides a compound represented by the above chemical formula 1.

In the present specification, examples of the substituents are described below, but are not limited thereto.

In the present description of the invention,indicating the location of the connection.

The term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the substituted position is not limited as long as it is a position where a hydrogen atom can be substituted, that is, a position where a substituent can be substituted, and when 2 or more substituents are substituted, 2 or more substituents may be the same or different from each other.

In the present specification, the term "substituted or unsubstituted" means that it is selected from deuterium; a halogen group; a nitrile group; an alkyl group; cycloalkyl; an amine group; a silyl group; a phosphine oxide group; an aryl group; and a substituent group containing 1 or 2 or more of the heteroaryl groups of 1 or more of N, O, S, se and Si atoms, or a substituent group formed by connecting 2 or more of the above-exemplified substituent groups, or no substituent group.

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

In the present specification, the alkyl group may be a straight chain or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 1 to 50, more preferably 1 to 30. Specific examples thereof 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-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2-dimethylheptyl, 1-ethyl-propyl, 1-dimethyl-propyl, isohexyl, 4-methylhexyl, 5-methylhexyl and the like, but are not limited thereto.

In the present specification, cycloalkyl is not particularly limited, but is preferably cycloalkyl having 3 to 60 carbon atoms, more preferably 3 to 30. Specifically, there are 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 the present invention is not limited thereto.

In the present specification, a silyl group is a substituent containing Si and directly bonded to the Si atom as a radical, and is represented by-SiR ₂₀₁ R ₂₀₂ R ₂₀₃ R represents ₂₀₁ To R ₂₀₃ Each of which may be the same or different from the other, independently may be a substituent composed of at least one of hydrogen, deuterium, a halogen group, an alkyl group, an alkenyl group, an alkoxy group, a cycloalkyl group, an aryl group, and a heterocyclic group. Specific examples of the silyl group include, but are not limited to, trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, and phenylsilyl group.

In this specification, when the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but the number of carbon atoms is preferably 6 to 50, more preferably 6 to 30. Specifically, the monocyclic aryl group may be phenyl, biphenyl, terphenyl, tetraphenyl, or 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, but is preferably 10 to 50, more preferably 10 to 30. Specifically, the polycyclic aryl group may be naphthyl, anthryl, phenanthryl, pyrenyl, perylenyl, triphenyl, A group, a fluorenyl group, etc., but is not limited thereto.

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

In the case where the fluorenyl group is substituted, it may be thatAnd the like, but is not limited thereto.

In this specification, the heteroaryl group contains 1 or more of N, O, S, si and Se as hetero atoms, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60, more preferably 2 to 30. Examples of heteroaryl groups include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, and the like,Azolyl, (-) -and (II) radicals>Diazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl (phtalazine), pteridinyl (pteridinyl), pyridopyrimidinyl (pyrido pyrimidine), pyridopyrazinyl (pyrido pyrazine), pyrazinopyrazinyl (pyrazino pyrazine), isoquinolinyl, indolyl, pyridoindolyl (pyrido indole), indenopyrimidinyl (5H-indenopyridinyl), carbazolyl, benzo->Oxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothiophenyl, benzofuranyl Dibenzofuranyl, phenanthroline (phenanthrinyl), thiazolyl, iso +.>Azolyl, (-) -and (II) radicals>Diazolyl, thiadiazolyl, and the like, but is not limited thereto.

In the present specification, the phosphine oxide group specifically includes, but is not limited to, diphenyl phosphine oxide group, dinaphthyl phosphine oxide group, and the like.

In the present specification, arylene means a group having two bonding positions on an aryl group, i.e., a 2-valent group. They are each a 2-valent group, and the above description of aryl groups can be applied.

In the present specification, heteroarylene refers to a group having two binding sites on the heteroaryl group, i.e., a 2-valent group. They may be suitable for the description of heteroaryl groups described above, except that each is a 2-valent group.

In one embodiment of the present disclosure, X is O, S, CRaRb or SO ₂ 。

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

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

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

In one embodiment of the present disclosure, X is SO ₂ 。

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

In one embodiment of the present disclosure, X1 is N.

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

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

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

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

In one embodiment of the present description, X2 and X3 are each N.

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

In one embodiment of the present description, L is a direct bond, a substituted or unsubstituted arylene, or a substituted or unsubstituted heteroarylene.

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

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

In one embodiment of the present disclosure, L is a substituted or unsubstituted arylene group having 6 to 15 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 fluorenylene group.

In one embodiment of the present description, L is a direct bond, or a substituted or unsubstituted phenylene group.

In one embodiment of the present disclosure, L is phenylene.

In one embodiment of the present specification, ar1 and Ar2 are the same or different from each other and are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzothienyl group, or a substituted or unsubstituted dibenzofuranyl group.

In one embodiment of the present specification, ar1 and Ar2 are the same or different from each other, and are each independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

In one embodiment of the present disclosure, ar1 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In one embodiment of the present disclosure, ar1 is a substituted or unsubstituted aryl group having 6 to 15 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 naphthyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted phenanthryl group, or a substituted or unsubstituted fluorenyl group.

In one embodiment of the present disclosure, ar1 is phenyl substituted or unsubstituted with an alkyl group.

In one embodiment of the present disclosure, ar1 is phenyl substituted or unsubstituted with methyl, ethyl, propyl, isopropyl, or tert-butyl.

In one embodiment of the present disclosure, arl is phenyl.

In one embodiment of the present disclosure, ar1 is biphenyl substituted or unsubstituted with an alkyl group.

In one embodiment of the present disclosure, ar1 is biphenyl substituted or unsubstituted with methyl, ethyl, propyl, isopropyl, or tert-butyl.

In one embodiment of the present disclosure, ar1 is biphenyl.

In one embodiment of the present disclosure, ar1 is naphthyl substituted or unsubstituted with an alkyl group.

In one embodiment of the present disclosure, ar1 is naphthyl substituted or unsubstituted with methyl, ethyl, propyl, isopropyl, or tert-butyl.

In one embodiment of the present disclosure, ar1 is naphthyl.

In one embodiment of the present description, ar1 is a phenanthryl group that is substituted or unsubstituted with an alkyl group.

In one embodiment of the present description, ar1 is a phenanthryl group that is substituted or unsubstituted with methyl, ethyl, propyl, isopropyl, or tert-butyl.

In one embodiment of the present disclosure, ar1 is a phenanthryl group.

In one embodiment of the present disclosure, ar1 is fluorenyl substituted or unsubstituted with an alkyl group.

In one embodiment of the present disclosure, ar1 is fluorenyl substituted or unsubstituted with methyl, ethyl, propyl, isopropyl, or tert-butyl.

In one embodiment of the present disclosure, ar1 is fluorenyl substituted or unsubstituted with methyl.

In one embodiment of the present disclosure, ar1 is a dimethylfluorenyl group.

In one embodiment of the present disclosure, ar1 is a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

In one embodiment of the present disclosure, ar1 is a substituted or unsubstituted heteroaryl group having 2 to 15 carbon atoms.

In one embodiment of the present description, ar1 is a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, or a substituted or unsubstituted triazinyl group.

In one embodiment of the present description, ar1 is a dibenzofuranyl group substituted or unsubstituted with an aryl group.

In one embodiment of the present description, ar1 is a dibenzofuranyl group substituted or unsubstituted with phenyl, biphenyl, or naphthyl.

In one embodiment of the present description, ar1 is a dibenzofuranyl group.

In one embodiment of the present disclosure, ar1 is dibenzothienyl substituted with aryl or unsubstituted.

In one embodiment of the present description, ar1 is dibenzothienyl substituted or unsubstituted with phenyl, biphenyl, or naphthyl.

In one embodiment of the present disclosure, ar1 is dibenzothienyl.

In one embodiment of the present disclosure, ar1 is a carbazolyl group substituted or unsubstituted with an aryl group.

In one embodiment of the present disclosure, ar1 is a carbazolyl group substituted or unsubstituted with a phenyl, biphenyl, or naphthyl group.

In one embodiment of the present disclosure, ar1 is a carbazolyl group substituted with a phenyl group.

In one embodiment of the present disclosure, ar2 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In one embodiment of the present disclosure, ar2 is a substituted or unsubstituted aryl group having 6 to 15 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 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 one embodiment of the present disclosure, ar2 is phenyl substituted or unsubstituted with an alkyl group.

In one embodiment of the present disclosure, ar2 is phenyl substituted or unsubstituted with methyl, ethyl, propyl, isopropyl, or tert-butyl.

In one embodiment of the present disclosure, ar2 is phenyl.

In one embodiment of the present disclosure, ar2 is biphenyl substituted or unsubstituted with an alkyl group.

In one embodiment of the present disclosure, ar2 is biphenyl substituted or unsubstituted with methyl, ethyl, propyl, isopropyl, or tert-butyl.

In one embodiment of the present disclosure, ar2 is biphenyl.

In one embodiment of the present disclosure, ar2 is naphthyl substituted or unsubstituted with an alkyl group.

In one embodiment of the present disclosure, ar2 is naphthyl substituted or unsubstituted with methyl, ethyl, propyl, isopropyl, or tert-butyl.

In one embodiment of the present disclosure, ar2 is naphthyl.

In one embodiment of the present disclosure, ar2 is a phenanthryl group that is substituted or unsubstituted with an alkyl group.

In one embodiment of the present description, ar2 is a phenanthryl group that is substituted or unsubstituted with methyl, ethyl, propyl, isopropyl, or tert-butyl.

In one embodiment of the present disclosure, ar2 is a phenanthryl group.

In one embodiment of the present disclosure, ar2 is fluorenyl substituted or unsubstituted with an alkyl group.

In one embodiment of the present disclosure, ar2 is fluorenyl substituted or unsubstituted with methyl, ethyl, propyl, isopropyl, or tert-butyl.

In one embodiment of the present disclosure, ar2 is fluorenyl substituted or unsubstituted with methyl.

In one embodiment of the present disclosure, ar2 is a dimethylfluorenyl group.

In one embodiment of the present disclosure, ar2 is a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

In one embodiment of the present disclosure, ar2 is a substituted or unsubstituted heteroaryl group having 2 to 15 carbon atoms.

In one embodiment of the present description, ar2 is a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, or a substituted or unsubstituted triazinyl group.

In one embodiment of the present description, ar2 is a dibenzofuranyl group substituted or unsubstituted with an aryl group.

In one embodiment of the present description, ar2 is a dibenzofuranyl group substituted or unsubstituted with phenyl, biphenyl, or naphthyl.

In one embodiment of the present description, ar2 is a dibenzofuranyl group.

In one embodiment of the present disclosure, ar2 is dibenzothienyl substituted with aryl or unsubstituted.

In one embodiment of the present description, ar2 is dibenzothienyl substituted or unsubstituted with phenyl, biphenyl, or naphthyl.

In one embodiment of the present disclosure, ar2 is dibenzothienyl.

In one embodiment of the present disclosure, ar2 is a carbazolyl group substituted or unsubstituted with an aryl group.

In one embodiment of the present disclosure, ar2 is a carbazolyl group substituted or unsubstituted with a phenyl, biphenyl, or naphthyl group.

In one embodiment of the present disclosure, ar2 is a carbazolyl group substituted with a phenyl group.

In one embodiment of the present specification, ar1 or Ar2 may have any one of the following structures.

In one embodiment of the present specification, the Arl or Ar2 may have any one of the following structures.

In one embodiment of the present description, ra and Rb are the same or different from each other, each independently is a substituted or unsubstituted phenyl group, or may be combined with each other to form a ring.

In one embodiment of the present description, ra and Rb are the same or different from each other and are each independently a substituted or unsubstituted phenyl group.

In one embodiment of the present disclosure, ra is phenyl.

In one embodiment of the present description, rb is phenyl.

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

In one embodiment of the present specification, R and R1 to R6 are the same or different from each other, and are each independently hydrogen, deuterium, a 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 one embodiment of the present description, R and R1 to R6 are each hydrogen.

In one 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 2 or more, 2 or more R1 and R2 are the same or different from each other.

In one embodiment of the present specification, r1 is an integer of 1 to 3.

In one embodiment of the present description, r2 is an integer from 1 to 4.

In one embodiment of the present specification, the above chemical formula 1 may be represented by any one of the following chemical formulas 2 to 5.

[ chemical formula 2]

[ chemical formula 3]

[ chemical formula 4]

[ chemical formula 5]

In the above-mentioned chemical formulas 2 to 5,

the definitions for X1 to X3, L, ar1, ar2, ra, rb, R1 to R6, R1 and R2 are the same as those in the above chemical formula 1.

In one embodiment of the present specification, the above chemical formula 4 may be represented by any one of the following chemical formulas 4-2 and 4-3.

[ chemical formula 4-2]

[ chemical formula 4-3]

In the above chemical formulas 4-2 and 4-3,

the definitions for X1 to X3, L, ar1, ar2, R1 to R6, R1 and R2 are the same as those in the above chemical formula 1.

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

/>

The compound according to an embodiment of the present specification can be produced by a production method described below. Although a representative example is described in the production example described below, substituents may be added or removed as necessary, and the positions of the substituents may be changed. The starting materials, the reaction conditions, and the like may be changed based on techniques known in the art.

For example, the compound represented by the above chemical formula 1 can produce a core structure represented by the following general formulas 1 and 2. The substituents may be bonded by methods known in the art, and the kinds, positions or numbers of the substituents may be changed according to techniques known in the art. The substituents shown in the following general formulae 1 and 2 may be bonded, but are not limited thereto.

[ general formula 1]

In the above general formulae 1 and 2, the definitions for X, X1 to X3, L, ar1 and Ar2 are the same as those in the above chemical formula 1.

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

In an embodiment of the present specification, there is provided an organic light emitting device including: a first electrode, a second electrode provided opposite to the first electrode, and an organic layer provided between the first electrode and the second electrode, wherein 1 or more of the organic layers contains the compound.

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

In the present specification, when a certain component is referred to as "including" or "comprising" a certain component, unless otherwise specified, it means that the component may be further included, and that the component is not excluded.

The organic layer of the organic electronic device of the present specification may be formed of a single layer structure, or may be formed of a multilayer structure in which 2 or more organic layers are stacked. For example, as a representative example of the organic electronic device of the present specification, the organic electronic 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, and the like as an organic layer. 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 layer includes a light emitting layer including a compound represented by chemical formula 1.

In one embodiment of the present specification, the organic layer includes a light emitting layer including the compound represented by chemical formula 1 as a host of the light emitting layer.

In one embodiment of the present disclosure, the organic layer includes a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer includes a compound represented by chemical formula 1.

In one embodiment of the present specification, the organic layer includes an electron injection layer, an electron transport layer, or a layer that performs electron injection and transport at the same time, and the electron injection layer, the electron transport layer, or the layer that performs electron injection and transport at the same time includes the compound represented by chemical formula 1.

In one embodiment of the present specification, the organic layer includes an electron blocking layer including a compound represented by chemical formula 1.

In one embodiment of the present specification, the organic 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 disclosure, the organic light emitting device further includes 1 layer or 2 layers or more selected from a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, a hole blocking layer, and an electron blocking layer.

In an 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.

The organic light emitting device is exemplified below.

In one embodiment of the present specification, the organic light emitting device includes: a first electrode; a second electrode provided opposite to the first electrode; a light-emitting layer provided between the first electrode and the second electrode; and an organic layer having 2 or more layers between the light-emitting layer and the first electrode or between the light-emitting layer and the second electrode, wherein at least one layer of the 2 or more organic layers contains a compound represented by the chemical formula 1.

In one embodiment of the present invention, the 2 or more organic layers may be 2 or more layers selected from a light-emitting layer, a hole-transporting layer, a hole-injecting layer, a layer that performs hole transport and hole injection simultaneously, and an electron blocking layer.

In one embodiment of the present specification, the organic layer includes 2 or more electron transport layers, and at least one of the 2 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 chemical formula 1 may be contained in 1 of the 2 or more electron transport layers, or may be contained in 2 or more electron transport layers.

In addition, in an embodiment of the present specification, when the compound represented by the above chemical formula 1 is included in each of the 2 or more electron transport layers, materials other than the compound represented by the above chemical formula 1 may be the same as or different from each other.

When the organic 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 a material known in the art, for example, a metal or a metal complex may be used. For example, the electron transport layer including the compound represented by the above chemical formula 1 may further include LiQ (Lithium Quinolate, 8-lithium hydroxyquinoline).

In one embodiment of the present specification, the organic layer includes 2 or more hole transport layers, and at least one of the 2 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 chemical formula 1 may be contained in 1 layer of the 2 or more hole transport layers, or may be contained in each of the 2 or more hole transport layers.

In addition, in one embodiment of the present specification, when the compound represented by the above chemical formula 1 is contained in each of the hole transport layers of 2 or more layers, materials other than the compound represented by the above chemical formula 1 may be the same or different from each other.

In one embodiment of the present specification, the organic layer may further include a hole injection layer or a hole transport layer including a compound including an arylamine group, a carbazole group, or a benzocarbazole group, in addition to the organic layer including the compound represented by the chemical formula 1.

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

In one embodiment of the present disclosure, the second electrode is a cathode or an anode.

In one embodiment of the present specification, the organic light-emitting device may have a structure (standard type) in which an anode, one or more organic layers, and a cathode are sequentially stacked on a substrate.

In one embodiment of the present disclosure, the organic light emitting device may have a reverse structure (inverted type) in which a cathode, one or more organic layers, and an anode are sequentially stacked on a substrate.

For example, a structure of an organic light emitting device according to an embodiment of the present specification is illustrated in fig. 1 to 3. The above-described fig. 1 to 3 illustrate an organic light emitting device, and are not limited thereto.

Fig. 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 109 are sequentially stacked on a substrate 101.

Fig. 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 109 are sequentially stacked on a substrate 101.

Fig. 3 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, an electron blocking layer 105, a light emitting layer 106, a hole blocking layer 107, an electron injection and transport layer 108, and a second electrode 109 are sequentially stacked on a substrate 101.

The organic light emitting device of the present specification may be manufactured using materials and methods known in the art, except that 1 or more of the organic layers include the above-described compound, that is, the compound represented by the above chemical formula 1.

When the organic light emitting device includes a plurality of organic layers, the organic 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 layer, and a second electrode on a substrate. At this time, it can be manufactured as follows: PVD (physical Vapor Deposition) process such as sputtering (sputtering) or electron beam evaporation (physical vapor deposition) is used to vapor-deposit a metal or a metal oxide having conductivity or an alloy thereof on a substrate to form an anode, then an organic layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer is formed on the anode, and then a substance that can be used as a cathode is vapor-deposited on the organic layer. In addition to this method, an organic light-emitting device may be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate.

In addition, in the case of manufacturing an organic light-emitting device, the compound represented by the above chemical formula 1 may be used to form an organic layer not only by a vacuum vapor deposition method but also by a solution coating method. Here, the solution coating method refers to spin coating, dip coating, blade coating, inkjet printing, screen printing, spray coating, roll coating, and the like, but is not limited thereto.

In addition to these methods, an organic light-emitting device can be manufactured by sequentially depositing a cathode material, an organic 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 disclosure, the first electrode is an anode, and the second electrode is a cathode.

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

As the first electrode material, a material having a large work function is generally preferable in order to allow holes to be smoothly injected into the organic layer. For example, there are metals such as vanadium, chromium, copper, zinc, gold, etc., or alloys thereof; metal oxides such as zinc 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; poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene ]Conductive polymers such as (PEDOT), polypyrrole and polyanilineAnd the like, but is not limited thereto.

As the second electrode material, a material having a small work function is generally preferable in order to facilitate injection of electrons into the organic layer. For example, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; liF/Al or LiO ₂ And/or Al, but is not limited thereto.

The light emitting layer may include a host material and a dopant material. The host material includes aromatic condensed ring derivatives, heterocyclic compounds, and the like. Specifically, examples of the aromatic condensed ring derivative include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene derivatives, fluoranthene compounds, and the like, and examples of the heterocyclic compound include dibenzofuran derivatives and ladder-type furan compounds ) Pyrimidine derivatives, and the like, but are 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 an aromatic condensed ring derivative having a substituted or unsubstituted arylamine group, and includes pyrene, anthracene having an arylamine group, Bisindenopyrene, and the like. Further, the styrylamine compound is a compound in which at least one arylvinyl group is substituted on a substituted or unsubstituted arylamine, and is substituted or unsubstituted with 1 or 2 or more substituents selected from the group consisting of aryl, silyl, alkyl, cycloalkyl, and arylamine groups. Specifically, there are styrylamine, styrylenediamine, styrylenetriamine, styrylenetetramine, and the like, but the present invention is not limited thereto. The metal complex includes, but is not limited to, iridium complex, platinum complex, and the like.

In the present specification, the chemical is defined asIn the case where the compound represented by formula 1 is contained in an organic layer other than the light-emitting layer or an additional light-emitting layer is provided, the light-emitting substance of the light-emitting layer is a substance capable of receiving holes and electrons from the hole-transporting layer and the electron-transporting layer, respectively, and combining them to emit light in the visible light region, and preferably a substance having high quantum efficiency for fluorescence or phosphorescence. For example, there are 8-hydroxyquinoline aluminum complex (Alq ₃ ) The method comprises the steps of carrying out a first treatment on the surface of the Carbazole-based compounds; dimeric styryl (dimerized styryl) compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo (E) benzo (E Azole, benzothiazole, and benzimidazole compounds; poly (p-phenylene vinylene) (PPV) based polymers; spiro (spiro) compounds; polyfluorene; rubrene, etc., but is not limited thereto.

The hole injection layer is a layer that injects holes from the electrode. The hole-injecting substance preferably has a hole-transporting ability and has a hole-injecting effect from the first electrode and an excellent hole-injecting effect for the light-emitting layer or the light-emitting material. Further, a substance excellent in the ability to prevent migration of excitons generated in the light-emitting layer to the electron injection layer or the electron injection material is preferable. Further, a substance excellent in film forming ability is preferable. In addition, it is preferable that the HOMO (highest occupied molecular orbital) of the hole injecting substance is interposed between the work function of the first electrode substance and the HOMO of the surrounding organic layer. Specific examples of the hole injection substance include metalloporphyrin (porphyrin), oligothiophene, and arylamine-based organic substances; carbazole-based organic material; nitrile organic matter; hexanitrile hexaazatriphenylene organic compounds; organic compounds of quinacridone (quinacridone) system; perylene (perylene) based organic compounds; polythiophene-based conductive polymers such as anthraquinone and polyaniline; or a mixture of 2 or more of the above examples, 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-transporting substance is a substance that can receive holes from the first electrode or the hole-injecting layer and transfer the holes to the light-emitting layer, and preferably has a high mobility to holes. Specific examples thereof include, but are not limited to, arylamine-based organic substances, carbazole-based organic substances, conductive polymers, and block copolymers having both conjugated and unconjugated portions.

The electron transport layer is a layer that receives electrons from the electron injection layer and transports the electrons to the light emitting layer. The electron mediator is a substance that can well inject electrons from the second electrode and transfer the electrons to the light-emitting layer, and preferably has high mobility to electrons. Specifically, there is an Al complex of 8-hydroxyquinoline containing Alq ₃ But not limited to, complexes of (a) and (b), organic radical compounds, hydroxyflavone-metal complexes, triazine derivatives, liQ, and the like. The electron transport layer may be used with any desired first electrode material as used in the art. In particular, suitable first electrode materials are the usual materials having a low work function accompanied by an aluminum layer or a silver layer. Specifically, cesium, barium, calcium, ytterbium, samarium, and the like are included, and an aluminum layer or a silver layer is included in each case.

The electron injection layer is a layer that injects electrons from the electrode. The electron-injecting substance preferably has an excellent electron-transporting ability, an excellent electron-injecting effect from the second electrode, and an excellent electron-injecting effect for the light-emitting layer or the light-emitting material. Further, a substance which prevents migration of excitons generated in the light-emitting layer to the hole injection layer and is excellent in thin film forming ability is preferable. Specifically, fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, and the like,Azole,/->Examples of the compound include, but are not limited to, diazoles, triazoles, triazines, imidazoles, perylenetetracarboxylic acids, fluorenylenemethanes, anthrones, and the like, derivatives thereof, metal complexes, and nitrogen-containing five-membered ring derivatives, and mixtures of 2 or more of the foregoing examples.

Examples of the metal complex include, but are not limited to, lithium 8-hydroxyquinoline, zinc bis (8-hydroxyquinoline), copper bis (8-hydroxyquinoline), manganese bis (8-hydroxyquinoline), aluminum tris (2-methyl-8-hydroxyquinoline), gallium tris (8-hydroxyquinoline), beryllium bis (10-hydroxybenzo [ h ] quinoline), zinc bis (10-hydroxybenzo [ h ] quinoline), gallium chloride bis (2-methyl-8-quinoline) (o-cresol) gallium, aluminum bis (2-methyl-8-quinoline) (1-naphthol), gallium bis (2-methyl-8-quinoline) (2-naphthol).

The electron blocking layer is a layer that prevents holes injected from the hole injection layer from entering the electron injection layer through the light emitting layer, and thus can improve the lifetime and efficiency of the device. The known material may 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 a layer that performs hole injection and hole transport at the same time.

The hole blocking layer is a layer that blocks holes from reaching the second electrode, and can be formed under the same conditions as the hole injection layer. Specifically, there areThe diazole derivative or triazole derivative, phenanthroline derivative, aluminum complex (aluminum complex), pyridine, pyrimidine, triazine derivative, or the like, but is not limited thereto.

The organic light emitting device according to the present specification may be of a top emission type, a bottom emission type, or a bi-directional emission type, depending on the materials used.

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

The compounds according to the present specification can also function on a principle similar to that applied to an organic light emitting device in an organic electronic device typified by an organic phosphorescent device, an organic solar cell, an organic photoreceptor, an organic transistor, or the like. For example, the organic solar cell may include a cathode, an anode, and a photoactive layer disposed between the cathode and the anode, and the photoactive layer may include the compound.

Modes for carrying out the invention

Hereinafter, examples, comparative examples, and the like will be described in detail for the purpose of specifically describing the present specification. However, the examples and comparative examples according to the present specification may be modified into various forms, and the scope of the present specification should not be construed as being limited to the examples and comparative examples described in detail below. Examples and comparative examples of the present description are provided to more fully illustrate the present description to those skilled in the art.

< production example >

PREPARATION EXAMPLE 1-intermediate Synthesis

The following intermediates a to E and intermediates a-1 to E-1 were produced by the production methods of the above general formulae 1 and 2.

PREPARATION EXAMPLE 2

After intermediate A-1 (5.12 g,10.71 mmol) and compound a-1 (4.35 g,12.32 mmol) were completely dissolved in 280ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate (140 ml) was added. After adding tetrakis (triphenylphosphine) palladium (0.37 g,0.32 mmol), the mixture was stirred with heating for 5 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, the mixture was concentrated under reduced pressure and recrystallized from 160ml of tetrahydrofuran to give compound 1 (5.23 g, 69%). MS [ M+H ]] ⁺ ＝576

PREPARATION EXAMPLE 3

After intermediate A-1 (4.67 g,9.77 mmol) and compound a-2 (3.97 g,11.24 mmol) were completely dissolved in 200ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, 2M carbonic acid was added Aqueous potassium solution (100 ml). After adding tetrakis (triphenylphosphine) palladium (0.34 g,0.29 mmol), the mixture was stirred with heating for 3 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, the mixture was concentrated under reduced pressure and recrystallized from 220ml of ethyl acetate to give compound 2 (4.19 g, 61%). MS [ M+H ]] ⁺ ＝576

PREPARATION EXAMPLE 4

After intermediate A-1 (5.36 g,13.14 mmol) and compound a-3 (4.55 g,12.90 mmol) were completely dissolved in 220ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate (110 ml) was added. After adding tetrakis (triphenylphosphine) palladium (0.39 g,0.34 mmol), the mixture was stirred with heating for 4 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, concentration was performed under reduced pressure, and recrystallization was performed with 280ml of acetone, whereby compound 3 (4.64 g, 58%) was produced. MS [ M+H ]] ⁺ ＝575

PREPARATION EXAMPLE 5

After intermediate A-1 (5.29 g,11.07 mmol) and compound a-4 (4.49 g,12.73 mmol) were completely dissolved in 240ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate (120 ml) was added. After adding tetrakis (triphenylphosphine) palladium (0.38 g,0.33 mmol), the mixture was stirred with heating for 5 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, the mixture was concentrated under reduced pressure and recrystallized from 220ml of acetone to give compound 4 (3.97 g, 51%). MS [ M+H ] ] ⁺ ＝574

PREPARATION 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 260ml of tetrahydrofuran, and a 2M aqueous potassium carbonate solution (130 ml) was added. After adding tetrakis (triphenylphosphine) palladium (0.44 g,0.38 mmol), the mixture was stirred with heating for 4 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, concentration was performed under reduced pressure, and recrystallization was performed with 210ml of ethyl acetate, whereby compound 5 (6.85 g, 75%) was produced. MS [ M+H ]] ⁺ ＝592

PREPARATION EXAMPLE 7

After intermediate C-1 (5.36 g,11.21 mmol) and compound a-2 (4.55 g,12.90 mmol) were completely dissolved in 240ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate (120 ml) was added. After adding tetrakis (triphenylphosphine) palladium (0.39 g,0.34 mmol), the mixture was stirred with heating for 4 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, the mixture was concentrated under reduced pressure and recrystallized from 220ml of ethyl acetate to give compound 6 (4.56 g, 57%). MS [ M+H ]] ⁺ ＝624

PREPARATION EXAMPLE 8

After intermediate D (7.19 g,13.66 mmol) and compound a-5 (4.26 g,12.42 mmol) were completely dissolved in 200ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate (100 ml) was added. After adding tetrakis (triphenylphosphine) palladium (0.43 g,3755 mmol), the mixture was stirred with heating for 4 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, concentration was performed under reduced pressure, and recrystallization was performed with 220ml of acetonitrile, whereby compound 7 (6.37 g, 72%) was produced. MS [ M+H ] ] ⁺ ＝650

PREPARATION EXAMPLE 9

After intermediate D (7.88 g,14.98 mmol) and compound a-6 (4.67 g,13.62 mmol) were completely dissolved in 200ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate (100 ml) was added. After adding tetrakis (triphenylphosphine) palladium (0.47 g,0.41 mmol), the mixture was stirred with heating for 5 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, the mixture was concentrated under reduced pressure and recrystallized from 230ml of acetonitrile to yield compound 8 (5.89 g, 61%). MS [ M+H ]] ⁺ ＝740

Production example 10 ]

After intermediate D (8.30 g,15.78 mmol) and compound a-7 (4.92 g,14.34 mmol) were completely dissolved in 260ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate (130 ml) was added. After adding tetrakis (triphenylphosphine) palladium (0.50 g,0.43 mmol), the mixture was stirred with heating for 6 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, the mixture was concentrated under reduced pressure and recrystallized from 230ml of acetonitrile to yield compound 9 (6.23 g, 61%). MS [ M+H ]] ⁺ ＝756

PREPARATION EXAMPLE 11

After intermediate E (7.73 g,14.70 mmol) and compound a-8 (4.77 g,13.36 mmol) were completely dissolved in 280ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate (140 ml) was added. After adding tetrakis (triphenylphosphine) palladium (0.64 g,0.55 mmol), the mixture was stirred with heating for 4 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, concentration was performed under reduced pressure, and recrystallization was performed with 250ml of acetonitrile, whereby compound 10 (5.14 g, 54%) was produced. MS [ M+H ] ] ⁺ ＝813

PREPARATION EXAMPLE 12

After intermediate A (9.70 g,18.44 mmol) and compound a-9 (4.51 g,16.77 mmol) were completely dissolved in 200ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate (100 ml) was added. After adding tetrakis (triphenylphosphine) palladium (0.58 g,0.50 mmol), the mixture was stirred with heating for 3 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, the mixture was concentrated under reduced pressure and recrystallized from 180ml of acetonitrile to yield compound 11 (7.03 g, 66%). MS [ M+H ]] ⁺ ＝502

PREPARATION 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 200ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, and then 2M aqueous potassium carbonate (100 ml) was added. After adding tetrakis (triphenylphosphine) palladium (0.39 g,0.30 mmol), the mixture was stirred with heating for 3 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, the mixture was concentrated under reduced pressure and recrystallized from 210ml of acetonitrile to yield compound 12 (5.19 g, 63%). MS [ M+H ]] ⁺ ＝652

PREPARATION EXAMPLE 14

After intermediate B (7.29 g,13.85 mmol) and compound a-11 (5.44 g,12.59 mmol) were completely dissolved in 200ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate (100 ml) was added. After adding tetrakis (triphenylphosphine) palladium (0.44 g,0.38 mmol), the mixture was stirred with heating for 4 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, the mixture was concentrated under reduced pressure and recrystallized from 230ml of acetonitrile to yield compound 13 (7.16 g, 71%). MS [ M+H ] ] ⁺ ＝616

PREPARATION EXAMPLE 15

After intermediate A (4.96 g,10.38 mmol) and compound a-12 (5.12 g,11.93 mmol) were completely dissolved in 240ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate (120 ml) was added. After adding tetrakis (triphenylphosphine) palladium (0.36 g,0.31 mmol), the mixture was stirred with heating for 3 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, concentration was performed under reduced pressure, and recrystallization was performed with 210ml of tetrahydrofuran, whereby compound 14 (6.34 g, 78%) was produced. MS [ M+H ]] ⁺ ＝628

< example >

< examples 1 to 1>

To ITO (indium tin oxide)The glass substrate coated to have a thin film thickness is put into distilled water in which a detergent is dissolved, and washed with ultrasonic waves. In this case, a product of fei he er (Fischer co.) was used as the detergent, and distilled water was filtered twice using a Filter (Filter) manufactured by millbore co. After washing the ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After the distilled water washing is completed, ultrasonic washing is performed by using solvents of isopropanol, acetone and methanol, and the obtained product is dried and then conveyed to a plasma cleaning machine. After the substrate was cleaned with oxygen plasma for 5 minutes, the substrate was transferred to a vacuum vapor deposition machine.

On the ITO transparent electrode prepared as described above, the following compound HI1 and the following compound HI2 were combined to be 98:2 (molar ratio) in a manner ofAnd performing thermal vacuum evaporation to form a hole injection layer. On the hole injection layer, the following compound HT1 was used as +.>Vacuum deposition is performed to form a hole transport layer. Next, on the hole transport layer, the film thickness is +.>The following compound EB1 was vacuum-deposited to form an electron blocking layer. Next, on the above electron blocking layer, the film thickness is +.>The following compound BH and the following compound BD were mixed at 50: the light-emitting layer was formed by vacuum deposition at a weight ratio of 1. On the above-mentioned light-emitting layer, the film thickness is +.>The compound 1 produced as described above was vacuum-evaporated to form a hole blocking layer. Next, on the hole blocking layer, the following compound ET1 and the following compound LiQ were vacuum-evaporated at a weight ratio of 1:1 to give +.>Form an electron injection and transport layer. On the electron injection and transport layer, lithium fluoride (LiF) is sequentially added +.>Is made of aluminum +.>And the thickness of the metal layer is evaporated to form a cathode.

In the above process, the vapor deposition rate of the organic matter is maintained To->Lithium fluoride maintenance of cathode>Is kept at>Is to maintain a vacuum degree of 2X 10 during vapor deposition ^-7 Up to 5X 10 ^-6 The support is thus fabricated into an organic light emitting device. />

< examples 1-2 to 1-9>

An organic light-emitting device was fabricated in the same manner as in example 1-1, except that the compound described in table 1 below was used instead of the compound 1 in example 1-1.

Comparative examples 1-1 to 1-5 ]

An organic light-emitting device was fabricated in the same manner as in example 1-1, except that the following compounds HB2 to HB6 were used instead of the compound 1 in the above-described example 1-1.

For the organic light emitting devices fabricated according to the above examples 1-1 to 1-9 and comparative examples 1-1 to 1-5, the light emitting device was fabricated at 20mA/cm ² The driving voltage, efficiency and color coordinates were measured at a current density of 20mA/cm ² The time (T95) at which the initial luminance was 95% was measured at the current density of (a). The results are shown in table 1 below.

TABLE 1

As shown in table 1 above, it is understood that the organic light emitting device manufactured using the compound represented by chemical formula 1 of the present specification as a hole blocking layer shows excellent characteristics in terms of efficiency, driving voltage and/or stability as compared with comparative examples 1-1 to 1-5. In particular, it is understood that examples 1-1 to 1-9 using the compound represented by chemical formula 1 in the present specification are superior in life characteristics to comparative examples 1-1 to 1-5. The T95 of examples 1-6 to 1-9 using the compound of the present application having a phenyl group or a ring structure in the core structure was increased by 264% at the maximum, as compared with comparative examples 1-3 and 1-4 using HB4 and HB5 having a methyl group or an ethyl group in the core structure.

Examples 1-1 to 1-9 using the compound of the present application having an N-containing heterocycle with a single ring in the core structure, T95 was increased by 160% at the maximum, as compared with comparative examples 1-5 using HB6 having an N-containing polycyclic heterocycle in the core structure.

< examples 2-1 to 2-11>

An organic light-emitting device was produced in the same manner as in example 1-1 except that in example 1-1, the compound HB1 was used in place of compound 1 and the compound ET1 was used in place of the compound ET1 described in Table 2 below.

Comparative examples 2-1 and 2-2 ]

An organic light-emitting device was fabricated in the same manner as in example 1-1 above, except that in example 1-1 above, compound HB1 was used in place of compound 1, and the following compounds ET2 and ET3 were used in place of compound ET 1.

For the organic light emitting devices fabricated according to the above examples 2-1 to 2-11, comparative examples 2-1 and 2-2, the light emitting device was fabricated at 20mA/cm ² The driving voltage, efficiency and color coordinates were measured at a current density of 20mA/cm ² The time (T95) at which the initial luminance was 95% was measured at the current density of (a). The results are shown in table 2 below.

TABLE 2

As shown in table 2 above, it is understood that the organic light emitting device manufactured using the compound represented by chemical formula 1 of the present specification as an electron injection and transport layer shows excellent characteristics in terms of efficiency, driving voltage and/or stability as compared to comparative example 2-1 and comparative example 2-2. In particular, it is understood that examples 2-1 to 2-11 using the compound represented by chemical formula 1 in the present specification are superior in life characteristics to comparative examples 2-1 and 2-2.

While the preferred embodiments of the present invention have been described above, the present invention is not limited to the above, and can be modified and implemented in various forms within the scope of the invention as claimed and the detailed description of the invention, and the present invention is also within the scope of the invention.

Claims

1. A compound represented by the following chemical formula 1:

chemical formula 1

In the chemical formula 1 described above, a compound having the formula,

x is O, S, CRaRb or SO ₂ ，

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

l is a direct bond, unsubstituted phenylene, or unsubstituted biphenylene,

ar1 and Ar2 are the same or different from each other and are each independently an unsubstituted or quinolinyl-substituted phenyl group, an unsubstituted biphenyl group, an unsubstituted terphenyl group, an unsubstituted naphthyl group, an unsubstituted phenanthryl group, an unsubstituted dibenzofuranyl group, an unsubstituted dibenzothienyl group, an unsubstituted or phenyl-substituted carbazolyl group, or an unsubstituted pyridyl group,

ra and Rb are each an unsubstituted phenyl group or combine with each other to form a fluorene ring,

r and R1 to R6 are each hydrogen,

the r1 is 3, and the number of the components is 3,

r2 is 4.

2. The compound of claim 1, wherein L is a direct bond, or an unsubstituted phenylene group.

3. The compound of claim 1, wherein Ar1 and Ar2 are the same or different from each other, each independently being phenyl, unsubstituted biphenyl, unsubstituted naphthyl, unsubstituted carbazolyl, unsubstituted dibenzothienyl, or unsubstituted dibenzofuranyl, which are unsubstituted or substituted with quinolinyl.

4. The compound according to claim 1, wherein the compound represented by chemical formula 1 is any one selected from the group consisting of:

/>

5. an organic electronic device, comprising: a first electrode, a second electrode provided opposite to the first electrode, and an organic layer provided between the first electrode and the second electrode, wherein 1 or more of the organic layers contains the compound according to any one of claims 1 to 4.

6. The organic electronic device of claim 5, wherein the organic layer comprises a light-emitting layer comprising the compound.

7. The organic electronic device of claim 5, wherein the organic layer comprises a hole injection layer or a hole transport layer, the hole injection layer or the hole transport layer comprising the compound.

8. The organic electronic device of claim 5, wherein the organic layer comprises an electron injection layer, an electron transport layer, or a layer that performs electron injection and transport simultaneously, the electron injection layer, the electron transport layer, or the layer that performs electron injection and transport simultaneously comprising the compound.

9. The organic electronic device of claim 5, wherein the organic layer comprises a hole blocking layer comprising the compound.

10. The organic electronic device of claim 5, wherein the organic electronic device further comprises 1 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.