CN109071465B

CN109071465B - Compound and organic electronic element comprising same

Info

Publication number: CN109071465B
Application number: CN201780021064.1A
Authority: CN
Inventors: 郑珉祐; 李东勋; 许瀞午; 张焚在; 姜敏英; 许东旭; 韩美莲
Original assignee: LG Chem Ltd
Current assignee: LG Chem Ltd
Priority date: 2016-03-28
Filing date: 2017-03-28
Publication date: 2022-02-11
Anticipated expiration: 2037-03-28
Also published as: WO2017171376A1; JP2019515877A; CN109071465A; JP6859587B2; KR101850243B1; KR20170113342A

Abstract

The present specification relates to a compound of chemical formula 1 and an organic electronic device comprising the same.

Description

Compound and organic electronic element comprising same

Technical Field

The present application claims priority to korean patent application No. 10-2016-.

The present description relates to a compound and an organic electronic element 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 element utilizing an organic light emitting phenomenon generally has a structure including an anode and a cathode with an organic layer interposed therebetween. In order to improve the efficiency and stability of the organic light-emitting device, the organic layer is often composed of a multilayer structure composed of different materials, and the multilayer structure 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. With the structure of such an organic electroluminescent element, if a voltage is applied between both electrodes, holes are injected from the anode into the organic layer, electrons are injected from the cathode into the organic layer, excitons (exiton) are formed when the injected holes and electrons meet, and light is emitted when the excitons are transitioned again to the ground state.

There is a continuing demand for the development of new materials for organic light emitting elements as described above.

Documents of the prior art

Patent document

International patent application publication No. 2003-012890

Disclosure of Invention

The present specification provides a compound and an organic electronic element comprising the same.

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

[ chemical formula 1]

In the chemical formula 1 described above,

q is a monocyclic aromatic group or a monocyclic heterocyclic group having 6 to 10 carbon atoms,

L₁and L₂The same or different from each other, each independently is a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,

Ar₁is hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,

Ar₂hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted phosphinoxide group, a substituted or unsubstituted aryl group having 6 to 16 carbon atoms, or a substituted or unsubstituted heteroaryl group,

R₁to R₃The same or different from each other, each independently is hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted phosphinoxide group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,

a is an integer of 1 to 4,

b is an integer of 1 to 4,

c is an integer of 1 to 4,

when a is 2 or more, 2 or more R₁Are the same as or different from each other,

when b is 2 or more, 2 or more R₂Are the same as or different from each other,

when c is 2 or more, 2 or more R₃The same or different from each other.

In addition, the present specification provides an organic electronic element comprising: the organic light-emitting device includes a first electrode, a second electrode provided so as to face the first electrode, and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers include the compound.

The compound according to one embodiment of the present specification is used for an organic electronic device typified by an organic light-emitting device, and can reduce a driving voltage of the organic electronic device, improve light efficiency, and improve life characteristics of the device by thermal stability of the compound.

Drawings

Fig. 1 illustrates an organic electronic component 10 according to an embodiment of the present description.

Fig. 2 illustrates an organic electronic component 11 according to another embodiment of the present description.

Description of the symbols

10. 11: organic light emitting element

20: substrate

30: a first electrode

40: luminescent layer

50: second electrode

60: hole injection layer

70: hole transport layer

80: electron blocking layer

90: electron transport layer

100: electron injection layer

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.

The compound of chemical formula 1 can have characteristics suitable for use as an organic layer for an organic light-emitting element by introducing various substituents into the core structure, and the core structure of chemical formula 1 of the present application has characteristics and effects that serve to reduce driving voltage and improve light-emitting efficiency by improving electrical conductivity in the element. The concrete description is as follows.

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

In the context of the present specification,

refers to the site of attachment.

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

In the present specification, the term "substituted or unsubstituted" means that the substituent is substituted with 1 or 2 or more substituents selected from deuterium, a halogen group, a cyano group, a hydroxyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group, or a substituent in which 2 or more substituents among the above-exemplified substituents are bonded.

In the present specification, the halogen group may be fluorine, chlorine, bromine, or iodine.

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

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

In the present specification, the alkoxy group may be linear, branched or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but the number of carbon atoms is preferably 1 to 20. Specifically, it may be methoxy, ethoxy, n-propoxy, isopropoxy, isopropyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexoxy, 3-dimethylbutoxy, 2-ethylbutoxy, n-octoxy, n-nonoxy, n-decoxy, benzyloxy, p-methylbenzyloxy and the like, but is not limited thereto.

In the present specification, when the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 6 to 30. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, a quaterphenyl group, 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 6 to 30. Specifically, the polycyclic aryl group may be a naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a perylene group,

And a fluorenyl group, 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.

When the above-mentioned fluorenyl group is substituted, it may be

And the like, but is not limited thereto.

In the present specification, a heteroaryl group is a heterocyclic group containing at least 1 of N, O, S, Si and Se as a heteroatom, and the number of carbon atoms is not particularly limited, but is preferably 2 to 50. Examples of heteroaryl groups include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, thienyl,

Azolyl group,

Oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, triazolyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzopyrazinyl, pyrazinyl, triazinyl, pyrazinyl, carbazolyl, benzoxazolyl, and benzoxazolyl

Azolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, benzofuranyl, phenanthrolinyl, thiazolyl, isoquinoyl

Azolyl group,

Examples of the organic solvent include, but are not limited to, an organic solvent such as ethanol, and the like.

In the present specification, a monocyclic aromatic group means a monocyclic aromatic hydrocarbon ring, and includes, for example, benzene.

In the present specification, a monocyclic heterocyclic group means a ring containing N, O or 1 or more of S atoms as a hetero atom, and examples thereof include pyridine, pyrimidine, pyridazine, triazine, pyran, thiopyran, diazine, pyrazine and the like, and may be selected from the above-mentioned heteroaryl groups, but the present invention is not limited thereto.

In the present specification, arylene means a 2-valent group having 2 binding sites on an aryl group. The above description of aryl groups applies in addition to the 2-valent groups.

In the present specification, heteroarylene means a 2-valent group having 2 binding sites on a heteroaryl group. The above description of heteroaryl groups applies in addition to the respective 2-valent groups.

In one embodiment of the present specification, Q is a monocyclic aromatic group or a monocyclic heterocyclic group having 6 to 10 carbon atoms.

In one embodiment of the present specification, Q is substituted or unsubstituted benzene.

In one embodiment of the present specification, Q is a substituted or unsubstituted pyridine.

In one embodiment of the present specification, Q is benzene.

In one embodiment of the present specification, Q is pyridine.

In one embodiment of the present specification, L₁And L₂The same or different from each other, each independently is a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group.

In one embodiment of the present specification, L₁And L₂The same or different from each other, and each independently is a direct bond, or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

In one embodiment of the present specification, L₁And L₂The same or different from each other, each independently is a direct bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, or a substituted or unsubstituted anthracenylene group.

In one embodiment of the present specification, L₁And L₂The same or different from each other, each independently is a direct bond, a phenylene group, a naphthylene group, or an anthracenylene group.

In one embodiment of the present specification, L1 is a direct bond.

In one embodiment of the present specification, Ar₁The same or different from each other, each independently is hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

In one embodiment of the present specification, Ar₁Is a substituted or unsubstituted heteroaryl.

In one embodiment of the present specification, Ar₁Is a substituted or unsubstituted monocyclic heteroaryl group.

In one embodiment of the present specification, Ar₁Is a substituted or unsubstituted monocyclic heteroaryl group containing more than 1 nitrogen atom.

In one embodiment of the present specification, Ar₁Is a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidyl group, or a substituted or unsubstituted triazinyl group.

In one embodiment of the present specification, Ar₁Is pyrimidinyl substituted or unsubstituted by aryl.

In one embodiment of the present specification, Ar₁Is a pyrimidinyl group substituted or unsubstituted with an aryl group having 6 to 12 carbon atoms.

In one embodiment of the present specification, Ar₁Is pyrimidinyl substituted or unsubstituted by phenyl.

In one embodiment of the present specification, Ar₁Is pyrimidinyl substituted by phenyl.

In one embodiment of the present specification, Ar₁Is a triazinyl group substituted or unsubstituted with 1 or more substituents selected from a substituted or unsubstituted aryl group and a substituted or unsubstituted heteroaryl group.

In one embodiment of the present specification, Ar₁Is a triazinyl group substituted or unsubstituted with 1 or more substituents selected from a substituted or unsubstituted aryl group having 6 to 20 carbon atoms and a substituted or unsubstituted heteroaryl group having 12 to 20 carbon atoms.

In one embodiment of the present specification, Ar₁Is a triazinyl group substituted or unsubstituted with 1 or more substituents selected from the group consisting of a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, and a substituted or unsubstituted carbazolyl group.

In one embodiment of the present specification, Ar₁Is selected from phenyl substituted or unsubstituted by aryl or heteroaryl, biphenyl substituted or unsubstituted by aryl or heteroaryl, naphthyl substituted or unsubstituted by aryl or heteroaryl, phenanthryl substituted or unsubstituted by aryl or heteroaryl, terphenyl substituted or unsubstituted by aryl or heteroaryl, and dibenzofuran substituted or unsubstituted by aryl or heteroarylAnd 1 or more substituents among the above groups are substituted or unsubstituted triazinyl groups.

In one embodiment of the present specification, Ar₁Is a triazinyl group substituted or unsubstituted with 1 or more substituents selected from the group consisting of a phenyl group, a naphthyl group, a biphenyl group, a phenanthryl group, a terphenyl group, and a dibenzofuranyl group, which are substituted or unsubstituted with a heteroaryl group.

In one embodiment of the present specification, Ar₁Is a triazinyl group substituted or unsubstituted with 1 or more substituents selected from phenyl, naphthyl, biphenyl, phenanthryl, terphenyl, and dibenzofuranyl groups substituted or unsubstituted with a heteroaryl group having 12 to 20 carbon atoms.

In one embodiment of the present specification, Ar₁Is a triazinyl group substituted or unsubstituted with 1 or more substituents selected from the group consisting of a phenyl group, a naphthyl group, a biphenyl group, a phenanthryl group, a terphenyl group, and a dibenzofuranyl group, which is substituted or unsubstituted.

In one embodiment of the present specification, Ar₁Is a triazinyl group substituted with 1 or more substituents selected from the group consisting of a phenyl group, a naphthyl group, a biphenyl group, a phenanthryl group, a terphenyl group, and a dibenzofuranyl group, which may be substituted or unsubstituted.

In one embodiment of the present specification, Ar₂Hydrogen, deuterium, or a substituted or unsubstituted aryl group having 6 to 16 carbon atoms.

In one embodiment of the present specification, Ar₂Is hydrogen; deuterium; or an aryl group having 6 to 16 carbon atoms which is substituted or unsubstituted with 1 or more substituents selected from the group consisting of a cyano group, a halogen group, an alkyl group which is substituted or unsubstituted with a halogen group, and an alkoxy group which is substituted or unsubstituted with a halogen group.

In one embodiment of the present specification, Ar₂Is hydrogen(ii) a Deuterium; or an aryl group having 6 to 16 carbon atoms which is substituted or unsubstituted with 1 or more substituents selected from the group consisting of a cyano group, a halogen group, an alkyl group having 1 to 4 carbon atoms which is substituted or unsubstituted with a halogen group, and an alkoxy group having 1 to 4 carbon atoms which is substituted or unsubstituted with a halogen group.

In one embodiment of the present specification, Ar₂Is hydrogen; deuterium; or an aryl group having 6 to 16 carbon atoms which is substituted or unsubstituted with 1 or more substituents selected from the group consisting of a cyano group, fluorine, a methyl group substituted or substituted by fluorine, and a methoxy group substituted or unsubstituted by fluorine.

In one embodiment of the present specification, Ar₂Is a phenyl group which is substituted or unsubstituted with 1 or more substituents selected from the group consisting of cyano, fluorine, a methyl group which is substituted or unsubstituted with fluorine, and a methoxy group which is substituted or unsubstituted with fluorine; phenanthryl substituted or unsubstituted with 1 or more substituents selected from cyano, fluoro, methyl substituted or unsubstituted with fluoro, and methoxy substituted or unsubstituted with fluoro; or a fluorenyl group which is substituted or unsubstituted with 1 or more substituents selected from the group consisting of a cyano group, fluorine, a methyl group which is substituted or unsubstituted with fluorine, and a methoxy group which is substituted or unsubstituted with fluorine.

In one embodiment of the present specification, Ar₂Is a phenyl group which is substituted or unsubstituted with 1 or more substituents selected from the group consisting of cyano, fluorine, a methyl group which is substituted or unsubstituted with fluorine, and a methoxy group which is substituted or unsubstituted with fluorine; phenanthryl; or fluorenyl which is substituted or unsubstituted by methyl or cyano which are substituted or unsubstituted by fluorine.

In one embodiment of the present specification, Ar₂Is a phenyl group which is substituted or unsubstituted with 1 or more substituents selected from the group consisting of cyano, fluorine, a methyl group substituted with fluorine, and a methoxy group substituted or unsubstituted with fluorine; phenanthryl; or fluorenyl substituted or unsubstituted by methyl or cyano.

In one embodiment of the present specification, Ar₂Phenyl which is substituted or unsubstituted with 1 or more substituents selected from the group consisting of cyano, fluorine, methyl substituted with fluorine, and methoxy substituted with fluorine; phenanthryl; or 9, 9-dimethylfluorenyl substituted with cyano.

In one embodiment of the present specification, Ar₂Is a substituted or unsubstituted heteroaryl.

In one embodiment of the present specification, Ar₂Is a substituted or unsubstituted heteroaryl group having 4 to 20 carbon atoms.

In one embodiment of the present specification, Ar₂Is a heteroaryl group having 4 to 20 carbon atoms which is substituted or unsubstituted with an aryl group.

In one embodiment of the present specification, Ar₂Is a heteroaryl group having 4 to 20 carbon atoms which is substituted or unsubstituted with an aryl group having 6 to 12 carbon atoms.

In one embodiment of the present specification, Ar₂Is a heteroaryl group having 4 to 20 carbon atoms which is substituted or unsubstituted with a phenyl group or a naphthyl group.

In one embodiment of the present specification, Ar₂Is a heteroaryl group having 4 to 20 carbon atoms which is substituted or unsubstituted with a phenyl group.

In one embodiment of the present specification, Ar₂Is pyridyl substituted or unsubstituted by phenyl, pyrimidinyl substituted or unsubstituted by phenyl, phenanthrolinyl substituted or unsubstituted by phenyl, dibenzothienyl substituted or unsubstituted by phenyl, dibenzofuranyl substituted or unsubstituted by phenyl, or carbazolyl substituted or unsubstituted by phenyl.

In one embodiment of the present specification, Ar₂Is pyridyl substituted or unsubstituted by phenyl, pyrimidinyl substituted by phenyl, phenanthrolinyl, dibenzothienyl, dibenzofuranyl, or carbazolyl.

In one embodiment of the present specification, Ar₂Is a substituted or unsubstituted phosphine oxide group.

In one embodiment of the present specification, Ar₂Is a phosphine oxide group substituted or unsubstituted by an aryl group.

In one embodiment of the present specification, Ar₂Is a phosphine oxide group which is unsubstituted or substituted with an aryl group having 6 to 12 carbon atoms.

In one embodiment of the present specification, Ar₂Is a phosphinoxide group substituted or unsubstituted with a phenyl group.

In one embodiment of the present specification, Ar₂Is a phosphinoxide group substituted by a phenyl group.

In one embodiment of the present specification, R₁To R₃The same or different from each other, each independently is hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

In one embodiment of the present specification, R₁To R₃Is hydrogen.

In one embodiment of the present specification, the chemical formula 1 may be represented by the following chemical formula 2 or 3.

[ chemical formula 2]

[ chemical formula 3]

In the above-described chemical formulas 2 and 3,

for Q, L₁、L₂、Ar₂、R₁To R₃And a to c are the same as defined in the above chemical formula 1,

X₁to X₃2 or more of them are N, and the others are the same or different from each other, and each independently is N or CR,

X₄to X₆1 or more of them are N, and the others are the same or different from each other, and each independently is N or CR,

the above-mentioned R is a hydrogen atom,

Ar₃to Ar₆The same or different from each other, each independently is hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl.

In one embodiment of the present specification, X₁To X₃Is N.

In one embodiment of the present specification, X₄Is CR, X₅And X₆Is N.

In one embodiment of the present specification, X₄And X₆Is CR, X₅Is N.

In one embodiment of the present specification, X₄And X₅Is N, X₆Is CR.

In one embodiment of the present specification, Ar₃And Ar₄The same or different from each other, each independently is a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

In one embodiment of the present specification, Ar₃And Ar₄The same or different from each other, each independently is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms or a substituted or unsubstituted heteroaryl group having 12 to 20 carbon atoms.

In one embodiment of the present specification, Ar₃And Ar₄The same or different from each other, each independently is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted carbazolyl group.

In one embodiment of the present specification, Ar₃And Ar₄The same or different from each other, each independently is a phenyl group substituted or unsubstituted with an aryl group or a heteroaryl group, a biphenyl group substituted or unsubstituted with an aryl group or a heteroaryl group, a naphthyl group substituted or unsubstituted with an aryl group or a heteroaryl group, a phenanthryl group substituted or unsubstituted with an aryl group or a heteroaryl group, a terphenyl group substituted or unsubstituted with an aryl group or a heteroaryl group, or a dibenzofuranyl group substituted or unsubstituted with an aryl group or a heteroaryl group.

In one embodiment of the present specification, Ar₃And Ar₄The same or different from each other, and each independently is phenyl, biphenyl, naphthyl, phenanthryl, terphenyl, and dibenzofuranyl, substituted or unsubstituted with heteroaryl.

In one embodiment of the present specification, Ar₃And Ar₄The same or different from each other, and each independently is a phenyl group, a biphenyl group, a naphthyl group, a phenanthryl group, a terphenyl group, or a dibenzofuranyl group, which is substituted or unsubstituted with a heteroaryl group having 12 to 20 carbon atoms.

In one embodiment of the present specification, Ar₃And Ar₄The same or different from each other, each independently is a phenyl group substituted or unsubstituted with a dibenzofuranyl group, a dibenzothiophenyl group, or a carbazolyl group; a biphenyl group; a naphthyl group; phenanthryl; a terphenyl group; or a dibenzofuranyl group.

In one embodiment of the present specification, Ar₃And Ar₄The same or different from each other, each independently is a phenyl group, a biphenyl group, a naphthyl group, a phenanthryl group, a terphenyl group or a dibenzofuranyl group, which is substituted or unsubstituted with a dibenzofuranyl group.

In one embodiment of the present specification, Ar₅And Ar₆The same or different from each other, each independently is hydrogen, or a substituted or unsubstituted aryl group.

In one embodiment of the present specification, Ar₅And Ar₆The same or different from each other, each independently is hydrogen or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.

In one embodiment of the present specification, Ar₅And Ar₆The same or different from each other, each independently is hydrogen, or a substituted or unsubstituted phenyl group.

In one embodiment of the present specification, Ar₅And Ar₆The same or different from each other, each independently is hydrogen or phenyl.

In one embodiment of the present specification, the chemical formula 1 may be represented by the following chemical formula 4 or 5.

[ chemical formula 4]

[ chemical formula 5]

In the above-described chemical formulas 4 and 5,

for Q, L1, L2, Ar₂R1 to R3, and a to c are as defined in the above chemical formula 1,

2 or more of X1 to X3 are N, and the others are the same or different from each other, and each independently is N or CR,

the above-mentioned R is a hydrogen atom,

1 or more of X4 to X6 are N, the remainder are the same or different from each other, and each is independently N or CR,

ar3 to Ar6, which are the same or different from each other, are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

In one embodiment of the present specification, X₁To X₃Is N.

In one embodiment of the present specification, X₄Is CR, X₅And X₆Is N.

In one embodiment of the present specification, X₄And X₆Is CR, X₅Is N.

In one embodiment of the present specification, X₄And X₅Is N, X₆Is CR.

In one embodiment of the present specification, Ar₃And Ar₄The same or different from each other, each independently is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl groupA naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted carbazolyl group.

In one embodiment of the present specification, Ar₃And Ar₄The same or different from each other, each independently is a phenyl group substituted or unsubstituted with a dibenzofuranyl group, a dibenzothienyl group or a carbazolyl group; a biphenyl group; a naphthyl group; phenanthryl; a terphenyl group; or a dibenzofuranyl group.

In one embodiment of the present specification，Ar₅And Ar₆The same or different from each other, each independently is hydrogen, or a substituted or unsubstituted phenyl group.

In one embodiment of the present specification, the chemical formula 1 may be represented by the following chemical formulae 6 to 9.

[ chemical formula 6]

[ chemical formula 7]

[ chemical formula 8]

[ chemical formula 9]

In the above-mentioned chemical formulas 6 to 9,

the above-mentioned R is a hydrogen atom,

Ar₃to Ar₆Are the same or different from each other, eachIndependently hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl.

In one embodiment of the present specification, X₁To X₃Is N.

In one embodiment of the present specification, X₄Is CR, X₅And X₆Is N.

In one embodiment of the present specification, X₄And X₆Is CR, X₅Is N.

In one embodiment of the present specification, X₄And X₅Is N, X₆Is CR.

In one embodiment of the present specification, Ar₃And Ar₄The same or different from each other, each independently is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, and a substituted or unsubstituted heteroaryl group having 12 to 20 carbon atoms.

In one embodiment of the present specification, Ar₃And Ar₄The same or different from each other, each independently is a phenyl group substituted or unsubstituted with an aryl group or a heteroaryl group, a biphenyl group substituted or unsubstituted with an aryl group or a heteroaryl group, a naphthyl group substituted or unsubstituted with an aryl group or a heteroaryl group, a phenanthryl group substituted or unsubstituted with an aryl group or a heteroaryl group, a terphenyl group substituted or unsubstituted with an aryl group or a heteroaryl group, and a dibenzofuranyl group substituted or unsubstituted with an aryl group or a heteroaryl group.

In one embodiment of the present specification, Ar₃And Ar₄The same or different from each other, each independently is a phenyl group substituted or unsubstituted with a heteroaryl group, a biphenyl group substituted or unsubstituted with an aryl group, a naphthyl group, a phenanthryl group, a terphenyl group, and a dibenzofuranyl group.

In one embodiment of the present specification, Ar₃And Ar₄The same or different from each other, each independently is a phenyl group, a biphenyl group, a phenanthryl group, a terphenyl group, or a dibenzofuranyl group, which is substituted or unsubstituted with a heteroaryl group having 12 to 20 carbon atoms.

In one embodiment of the present specification, Ar₃And Ar₄The same or different from each other, each independently is a phenyl group, a biphenyl group, a phenanthryl group, a terphenyl group, or a dibenzofuranyl group, which is substituted or unsubstituted with a dibenzofuranyl group, a dibenzothiophenyl group, or a carbazolyl group.

In one embodiment of the present specification, Ar₃And Ar₄The same or different from each other, each independently is a phenyl group, a biphenyl group, a phenanthryl group, a terphenyl group or a dibenzofuranyl group, which is substituted or unsubstituted with a dibenzofuranyl group.

One of the specificationIn the embodiment, Ar₅And Ar₆The same or different from each other, each independently is hydrogen or phenyl.

According to an embodiment of the present specification, the compound of the chemical formula 1 may be any one selected from the following structural formulae.

The compound according to one embodiment of the present specification can be produced by a production method described later. Typical examples are described in the production examples described later, but substituents may be added or excluded as needed, and the positions of the substituents may be changed. Further, starting materials, reaction conditions, and the like may be changed based on techniques well known in the art.

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

One embodiment of the present specification provides an organic electronic device, including: the organic light-emitting device includes a first electrode, a second electrode provided so as to face the first electrode, and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers contain the compound.

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

In the present specification, when a part is referred to as "including" a certain component, unless specifically stated to the contrary, it means that the other component may be further included, and the other component is not excluded.

The organic layer of the organic electronic device in the present specification may have a single-layer structure, or may have a multilayer structure in which two or more organic layers are stacked. For example, as a representative example of the organic electronic element of the present invention, the organic light emitting element 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, and the like as an organic layer. However, the structure of the organic electronic element is not limited thereto, and a smaller number of organic layers may be included.

According to an embodiment of the present specification, the organic electronic element may be selected from an organic light emitting element, an organic phosphorescent element, an organic solar cell, an Organic Photoconductor (OPC), and an organic transistor.

Next, an organic light-emitting element will be exemplified.

In one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer includes the compound.

In one embodiment of the present specification, the organic layer includes a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer includes the compound.

In one embodiment of the present disclosure, the organic layer includes an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer includes the compound.

In one embodiment of the present specification, the organic layer includes an electron blocking layer, and the electron blocking layer includes the compound.

In one embodiment of the present specification, the organic light-emitting element further includes one or more layers 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 one embodiment of the present disclosure, the organic light emitting device includes: the organic light emitting device includes a first electrode, a second electrode provided so as to face the first electrode, a light emitting layer provided between the first electrode and the second electrode, and 2 or more organic 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 2 or more organic layers contains the compound. In one embodiment of the present specification, the 2 or more organic layers may be 2 or more selected from an electron transport layer, an electron injection layer, a layer which simultaneously performs electron transport and electron injection, and a hole blocking layer.

In one embodiment of the present specification, the organic layer includes two or more electron transport layers, and at least one of the two or more electron transport layers includes the compound. Specifically, in one embodiment of the present specification, the compound may be contained in one of the two or more electron transport layers, or may be contained in each of the two or more electron transport layers.

In one embodiment of the present specification, when the compounds are contained in the electron transport layers of two or more layers, the materials other than the compounds may be the same or different from each other.

In one embodiment of the present specification, the organic layer includes an organic layer containing the compound, and in addition, a hole injection layer or a hole transport layer containing a compound containing an aromatic amino group, a carbazolyl group, or a benzocarbazolyl group.

In another embodiment, the organic light-emitting element may be a normal type organic light-emitting element having a structure in which an anode, one or more organic layers, and a cathode are sequentially stacked on a substrate.

When the organic layer including the compound of 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 one known in the art, and may be, for example, a metal or a metal complex. According to one example, the electron transport layer including the compound of chemical formula 1 may further include LiQ.

In one embodiment of the present specification, a weight ratio of the compound of chemical formula 1 to the LiQ included in the electron transport layer may be 1:9 to 9: 1.

In another embodiment, the organic light emitting element may be an inverted type organic light emitting element in which a cathode, one or more organic layers, and an anode are sequentially stacked on a substrate.

For example, the structure of the organic light-emitting element in the present specification may have the structure shown in fig. 1 and 2, but is not limited thereto.

Fig. 1 illustrates a structure of an organic light emitting element 10 in which a first electrode 30, a light emitting layer 40, and a second electrode 50 are sequentially stacked on a substrate 20. Fig. 1 illustrates an exemplary structure of an organic light emitting device according to an embodiment of the present disclosure, and may further include another organic layer.

Fig. 2 illustrates a structure of an organic light emitting element in which a first electrode 30, a hole injection layer 60, a hole transport layer 70, an electron blocking layer 80, a light emitting layer 40, an electron transport layer 90, an electron injection layer 100, and a second electrode 50 are sequentially stacked on a substrate 20. Fig. 2 illustrates an exemplary structure according to an embodiment of the present disclosure, which may further include another organic layer.

In the organic light-emitting element of the present specification, one or more layers of the organic layer may contain the compound of the present specification, that is, the above compound, and may be produced by a material and a method known in the art.

When the organic light emitting element includes a plurality of organic layers, the organic layers may be formed of the same substance or different substances.

In the organic light-emitting device of the present specification, one or more layers of the organic layer include the compound represented by chemical formula 1, and in addition, the organic light-emitting device can be manufactured using a material and a method known in the art.

For example, the organic light-emitting element of the present specification can be manufactured by sequentially stacking a first electrode, an organic layer, and a second electrode on a substrate. At this time, the following can be made: a metal, a metal oxide having conductivity, or an alloy thereof is deposited on a substrate by a PVD (physical Vapor Deposition) method such as a sputtering method or an electron beam evaporation method (e-beam evaporation) to form an anode, 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 a substance which can be used as a cathode is deposited on the organic layer. In addition to the above method, an organic light-emitting element may be manufactured by depositing a cathode, an organic layer, and an anode material on a substrate in this order.

In addition, in the manufacture of the organic light emitting device, the compound of chemical formula 1 may be used to form an organic layer not only by vacuum evaporation but also by solution coating. Here, the solution coating method refers to spin coating, dip coating, blade coating, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited thereto.

In addition to these methods, an organic light-emitting element can be manufactured by depositing a cathode material, an organic layer, and an anode material on a substrate in this order (international patent application publication No. 2003/012890). However, the production 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.

The anode material is preferably a material having a large work function so that holes can be smoothly injected into the organic layer. Specific examples of the anode material which can be used in the present invention include metals such as vanadium, chromium, copper, zinc, gold, and alloys thereof; metal oxides such as zinc oxide, Indium Tin Oxide (ITO), Indium Zinc Oxide (IZO), and the like; such as ZnO, Al or SnO₂A combination of a metal such as Sb and an oxide; such as poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene]Conductive polymers such as (PEDOT), polypyrrole, and polyaniline, but the present invention is not limited thereto.

The cathode material is preferably a material having a small work function so that electrons can be easily injected into the organic layer. As cathode materialFor example, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; such as LiF/Al or LiO₂And a multilayer structure material such as Al, but not limited thereto.

The hole injection layer is a layer for injecting holes from the electrode, and the following compounds are preferable as the hole injection substance: has an ability to transport holes, has a hole injection effect from the anode, has an excellent hole injection effect with respect to the light-emitting layer or the light-emitting material, prevents excitons generated in the light-emitting layer from migrating to the electron injection layer or the electron injection material, and has excellent thin film-forming ability. Preferably, the HOMO (highest occupied molecular orbital) of the hole injecting substance is between the work function of the anode substance and the HOMO of the surrounding organic layer. Specific examples of the hole injecting substance include, but are not limited to, metalloporphyrin (porphyrin), oligothiophene, arylamine-based organic substances, hexanitrile-hexaazatriphenylene-based organic substances, quinacridone-based organic substances, perylene-based organic substances, anthraquinone, polyaniline, and polythiophene-based conductive polymers.

The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light-emitting layer, and the hole transport material is a material that can receive holes from the anode or the hole injection layer and transport the holes to the light-emitting layer. Specific examples thereof include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers in which a conjugated portion and a non-conjugated portion are present simultaneously.

The electron blocking layer is a layer which prevents holes injected from the hole injection layer from entering the electron injection layer through the light-emitting layer, and can improve the life and efficiency of the element.

The light-emitting substance of the light-emitting layer is a substance that can receive holes and electrons from the hole-transporting layer and the electron-transporting layer, respectively, and combine them to emit light in the visible light region, and is preferably excellent in quantum efficiency with respect to fluorescence or phosphorescenceThe substance of (1). As an example, there is an 8-hydroxyquinoline aluminum complex (Alq)₃) (ii) a A carbazole-based compound; dimeric styryl (dimerized styryl) compounds; BAlq; 10-hydroxybenzoquinoline metal compounds; benzo (b) is

Azole, benzothiazole and benzimidazole-based compounds; poly (p-phenylene vinylene) (PPV) polymers; spiro (spiroo) compounds; polyfluorene, rubrene, and the like, but are not limited thereto.

The light emitting layer may include a host material and a dopant material. The host material includes aromatic fused ring derivatives, heterocyclic compounds, and the like. Specifically, the aromatic condensed ring derivative includes an anthracene derivative, a pyrene derivative, a naphthalene derivative, a pentacene derivative, a phenanthrene compound, a fluoranthene compound, and the like, and the heterocyclic ring-containing compound includes a compound, a dibenzofuran derivative, a ladder-type furan compound

Pyrimidine derivatives, etc., but are not limited thereto.

As the dopant material, there are aromatic amine derivatives, styryl amine compounds, boron complexes, fluoranthene compounds, metal complexes, and the like. Specifically, the aromatic amine derivative is an aromatic fused ring derivative having a substituted or unsubstituted arylamine group, and includes pyrene, anthracene, or the like having an arylamine group,

Diindenoperene (Periflanthene) and the like, as the styrene amine compound, a compound in which at least one arylvinyl group is substituted on a substituted or unsubstituted arylamine, and which is substituted or unsubstituted with 1 or 2 or more substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group. Specific examples thereof include, but are not limited to, styrylamine, styryldiamine, styryltrimethylamine, and styryltretramine. The metal complex includes, but is not limited to, iridium complexes and platinum complexes.

The electron transport layer is a layer that receives electrons from the electron injection layer and transports the electrons to the light-emitting layer, and the electron transport layer is a substance that can favorably receive electrons from the cathode and transfer the electrons to the light-emitting layer, and a substance having a large electron mobility is suitable. Specific examples thereof include Al complexes of 8-hydroxyquinoline and Al complexes containing Alq₃The complex of (3), the organic radical compound, the hydroxyflavone-metal complex, etc., but are not limited thereto. The electron transport layer may be used with any desired cathode material as used in the art. In particular, examples of suitable cathode substances are the usual substances having a low work function and associated with an aluminum or silver layer. Specifically, cesium, barium, calcium, ytterbium and samarium are present, for each, along with an aluminum or silver layer.

The electron injection layer is a layer for injecting electrons from the electrode, and is preferably a compound of: has an ability to transport electrons, an electron injection effect from a cathode, an excellent electron injection effect for a light-emitting layer or a light-emitting material, prevents excitons generated in the light-emitting layer from migrating to a hole-injecting layer, and is excellent in thin film-forming ability. Specifically, there are fluorenone, anthraquinone dimethane (Anthraquinodimethane), diphenoquinone, thiopyran dioxide, and,

Azole,

Oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidene methane, anthrone, and the like, and derivatives thereof, metal complexes, nitrogen-containing five-membered ring derivatives, and the like, but are not limited thereto.

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

The hole blocking layer is a layer that prevents holes from reaching the cathode and can be formed under the same conditions as those of the hole injection layer. Specifically, there are

An oxadiazole derivative or a triazole derivative, a phenanthroline derivative, BCP, an aluminum complex (aluminum complex), and the like, but the present invention is not limited thereto.

The organic light emitting element of the present specification may be a top emission type, a bottom emission type, or a bidirectional emission type depending on a material used.

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

The compound according to the present specification can function similarly to the principle applied to an organic light-emitting element in an organic electronic element typified by an organic phosphorescent element, an organic solar cell, an organic photoconductor, an organic transistor, or the like.

Hereinafter, the present specification will be described in detail with reference to examples. However, the embodiments according to the present description may be modified into various other forms, and the scope of the present description should not be construed as being limited to the embodiments described in detail below. The embodiments of the present description are provided to more fully describe the present description to those skilled in the art.

< example >

< Synthesis example 1> -production of Compound represented by intermediate 1

(1) Production of chemical formula 1B

4 (4-chlorophenyl) (4-hydroxy) methanone (Compound 1A,100.0g,429.81mmol, manufactured by Alfa chemistry) was added to 1000ml of acetonitrile under a nitrogen atmosphere, and potassium carbonate (118.8g,859.62mmol) was mixed with 500ml of water under stirring. Then, while heating in a water bath, 1-butylsulfonyl fluoride was slowly added

(194.8g,644.72 mmol). Then, the reaction was terminated after about 1 hour. After the reaction was completed, the temperature was lowered to room temperature, and then the aqueous layer and the organic layer were separated, and then the organic layer was distilled under reduced pressure to produce compound 1B (210g, yield: 95%).

(2) Production of chemical formula 1C

Compound 1B (210.2g,408.36mmol) described above, bis (pinacolato) diboron (103.7g,408.36mmol) and potassium acetate (120.2g,1225.08mmol) were mixed under a nitrogen atmosphere, added to 1000ml of Tetrahydrofuran (THF), and heated with stirring. Under reflux, [1,1' -bis (diphenylphosphino) ferrocene ] dichloropalladium (II) (1.8g,2.45mmol) was added, and the mixture was stirred with heating for 24 hours. After the reaction is finished, the temperature is reduced to normal temperature and then the mixture is filtered. The filtrate was poured into water, extracted with chloroform, and the organic layer was dried over anhydrous magnesium sulfate. After distillation under reduced pressure, recrystallization from ethanol was performed to obtain Compound 1C (100.0g, yield: 72%).

(3) Production of intermediate 1

Compound 1C (39.0g,145.67mmol) and 2-chloro-4, 6-diphenyl-1, 3, 5-triazine (compound 1D,50.0g,145.67mmol, manufactured by Alfa chemistry) were added to 300ml of tetrahydrofuran under a nitrogen atmosphere, and refluxed with stirring. Then, potassium carbonate (60.4g,437.02 mmols) was dissolved in 200ml of water and charged, followed by stirring sufficiently, and tetrakis (triphenylphosphine) palladium (5.0g,4.37mmol) was charged. After 12 hours of reaction, the temperature was reduced to normal temperature and filtered. After the filtrate was extracted with chloroform and water, the organic layer was dried over magnesium sulfate. Then, the organic layer was distilled under reduced pressure, and then recrystallized from ethyl acetate. The resulting solid was filtered and dried to obtain intermediate 1(52.2g, yield: 80%).

< Synthesis example 2> -production of Compound represented by intermediate 2

Compound 2A (24.7g,105.94mmol, manufactured by Aldrich) was added to 500ml of anhydrous tetrahydrofuran and cooled to-78 ℃. Then, n-butyllithium (50.9mL,127.13mmol) was slowly dropped over 30 minutes while stirring, and the reaction was carried out for 1 hour. Then, the above intermediate 1(28.5g,63.57) was charged in a solid state, and the temperature was gradually raised to room temperature, followed by reaction for 4 hours. After the reaction, water was poured in to complete the reaction, and then an aqueous layer and an organic layer were separated, and the organic layer was distilled under reduced pressure to obtain intermediate 2B. This was added to 500ml of acetic acid, and 1 to 2 drops of sulfuric acid as a catalyst were added under stirring and then refluxed. After the reaction for 2 hours, the resultant solid was filtered, the filtrate was redissolved in chloroform, neutralized with water saturated with calcium carbonate and extracted, and the organic layer was dried with magnesium sulfate. Then, the organic layer was distilled under reduced pressure and recrystallized from ethanol. The resulting solid was filtered and dried to obtain intermediate 2(24.1g, yield: 65%).

< Synthesis example 3> -production of Compound represented by Compound 1

Under a nitrogen atmosphere, intermediate 2(10.0g,17mmol) produced in < synthesis example 2> above, carbazole (3.4g,21mmol, manufactured by daejung corporation), and sodium tert-butoxide (2.0g,21mmol) were added to 100ml of xylene, stirred and refluxed. Then, bis (tri-tert-butylphosphino) palladium (0.3g,0.5mmol) was charged. After 8 hours of reaction, the temperature was reduced to room temperature and filtered. The filtrate was extracted with chloroform and water, and the organic layer was dried over magnesium sulfate. Then, the organic layer was distilled under reduced pressure, and then purified by column chromatography (chloroform: hexane), and the concentrated solution was recrystallized again from chloroform and ethyl acetate. The resulting solid was filtered and dried to obtain Compound 1(9.4g, yield: 77%).

MS:[M+H]+＝714

< Synthesis example 4> -production of Compound represented by Compound 2

Under nitrogen atmosphere, will be in the above<Synthesis example 2>Intermediate 2(10.0g,17mmol) produced in (1) and Compound 4A (4.7g,21mmol, manufactured by Alfa chemistry) were added to 200ml of 1, 4-bis

In an alkane, stirred and refluxed. Then, bis (tri-tert-butylphosphino) palladium (0.3g,0.5mmol) was charged. After 8 hours of reaction, the temperature was reduced to room temperature and filtered. The filtrate was extracted with chloroform and water, and the organic layer was dried over magnesium sulfate. Then, the organic layer was distilled under reduced pressure, and then purified by column chromatography (chloroform: hexane), and the concentrated solution was recrystallized again from chloroform and ethyl acetate. The resulting solid was filtered and dried to obtain Compound 2(8.8g, yield: 70%).

MS:[M+H]+＝731

< Synthesis example 5> -production of Compound represented by Compound 3

Under nitrogen atmosphere, will be in the above<Synthesis example 2>Intermediate 2(10.0g,17mmol) produced in (1) and Compound 5A (4.4g,21mmol, manufactured by Alfa chemistry) were added to 200ml of 1, 4-bis

In an alkane, stirred and refluxed. Then, potassium phosphate (10.0g,47.31mmol) was dissolved in 50ml of water and charged, followed by sufficient stirring,bis (dibenzylideneacetone) palladium (0.3g,0.47mmol) and tricyclohexylphosphine (0.3mg,0.95mmol) were charged. After 18 hours of reaction, the temperature was lowered to room temperature and filtered. The filtrate was extracted with chloroform and water, and the organic layer was dried over magnesium sulfate. Then, the organic layer was distilled under reduced pressure and recrystallized from ethyl acetate. The resulting solid was filtered and dried to obtain Compound 3(7.5g, yield: 61%).

MS:[M+H]+＝715

< Synthesis example 6> -production of Compound represented by Compound 4

Under nitrogen atmosphere, will be in the above<Synthesis example 2>Intermediate 2(10.0g,15.77mmol) produced in (1) and Compound 6A (4.1g,21mmol, manufactured by Alfa chemistry) were added to 200ml of 1, 4-bis

In an alkane, stirred and refluxed. Then, bis (tri-tert-butylphosphine) palladium (0.3g,0.5m mol) was charged. After 8 hours of reaction, the temperature was reduced to room temperature and filtered. The filtrate was extracted with chloroform and water, and the organic layer was dried over magnesium sulfate. Then, the organic layer was distilled under reduced pressure, and then purified by column chromatography (chloroform: hexane), and the concentrated solution was recrystallized again from chloroform and ethyl acetate. The resulting solid was filtered and dried to obtain Compound 4(5.3g, yield: 44%).

MS:[M+H]+＝702

< Synthesis example 7> -production of Compound represented by Compound 5

Under nitrogen atmosphere, will be in the above<Synthesis example 2>Intermediate 2(10.0g,15.77mmol) produced in (1) and Compound 7A (3.0g,21mmol, manufactured by Alfa chemistry) were added to 200ml of 1, 4-bis

In an alkane, stirred and refluxed. Then, bis (tri-tert-butylphosphino) palladium (0.3g,0.5mmol) was charged. After 8 hours of reaction, the temperature was reduced to room temperature and filtered. The filtrate was extracted with chloroform and water, and the organic layer was dried over magnesium sulfate. Then, the organic layer was distilled under reduced pressure, and then purified by column chromatography (chloroform: hexane), and the concentrated solution was recrystallized again from chloroform and ethyl acetate. The resulting solid was filtered and dried to obtain Compound 5(5.7g, yield: 51%).

MS:[M+H]+＝650

< Synthesis example 8> -production of Compound represented by intermediate 3

Under nitrogen atmosphere, will be in the above<Synthesis example 2>Intermediate 2(30.0g,51mmol) produced in (1), bis (pinacolato) diboron (14.3g,57mmol, Compound 8A) and potassium acetate (15.1g,154mmol) were mixed and added to 300ml of di

In an alkane (Dioxane), the mixture was heated with stirring. Under reflux, add [1,1' -bis (diphenylphosphino) ferrocene]Palladium (II) dichloride (0.9g,1.5mmol) and tris (cyclohexyl) phosphine (0.9g,3.1 mmol) were heated and stirred for 24 hours. After the reaction is finished, the temperature is reduced to normal temperature and then the mixture is filtered. The filtrate was poured into water, extracted with chloroform, and the organic layer was dried over anhydrous magnesium sulfate. After distillation under reduced pressure, recrystallization from ethanol was performed to produce intermediate 3(28.1g. yield: 81%).

< Synthesis example 9> -production of Compound represented by Compound 6

Intermediate 3(15.0g,22mmol) produced in < Synthesis example 8> above and compound 9A (5.9g,18.75mmol, produced by TCI Co.) were added to 150ml of tetrahydrofuran under nitrogen atmosphere, stirred and refluxed. Then, potassium carbonate (9.2g,67mmol) was dissolved in water (40ml) and charged, followed by charging tetrakis (triphenylphosphine) palladium (0.9g,1.5mmol) after sufficiently stirring. After 6 hours of reaction, the temperature was reduced to room temperature and filtered. The filtrate was extracted with chloroform and water, and the organic layer was dried over magnesium sulfate. Then, the organic layer was distilled under reduced pressure, and then purified by column chromatography (chloroform: hexane), and the concentrated solution was recrystallized again from chloroform and ethyl acetate. The resulting solid was filtered and dried to obtain Compound 6(11.4g, yield: 66%).

MS:[M+H]+＝779

< Synthesis example 10> -production of Compound represented by Compound 7

Intermediate 3(15.0g,22mmol) produced in < Synthesis example 8> above and compound 10A (5.9g,18.75mmol, produced by TCI Co.) were added to 150ml of tetrahydrofuran under nitrogen atmosphere, stirred and refluxed. Then, potassium carbonate (9.2g,67mmol) was dissolved in 40ml of water and charged, followed by charging tetrakis (triphenylphosphine) palladium (0.9g,1.5mmol) with sufficient stirring. After 6 hours of reaction, the temperature was reduced to room temperature and filtered. The filtrate was extracted with chloroform and water, and the organic layer was dried over magnesium sulfate. Then, the organic layer was distilled under reduced pressure, and then purified by column chromatography (chloroform: hexane), and the concentrated solution was recrystallized again from chloroform and ethyl acetate. The resulting solid was filtered and dried to obtain Compound 7(12.3g, yield: 71%).

MS:[M+H]+＝778

< Synthesis example 11> -production of Compound represented by Compound 8

Under nitrogenUnder the atmosphere, the above-mentioned<Production example 2>Intermediate 2(10.0g,17mmol) produced in (1) and Compound 11A (7.3g,21mmol, produced by acros) were added to 200ml of 1, 4-bis

In an alkane, stirred and refluxed. Then bis (tri-tert-butylphosphine) palladium (0.3g,0.5mmol) was charged. After 8 hours of reaction, the temperature was reduced to room temperature and filtered. The filtrate was extracted with chloroform and water, and the organic layer was dried over magnesium sulfate. Then, the organic layer was distilled under reduced pressure, and then purified by column chromatography (chloroform: hexane), and the concentrated solution was recrystallized again from chloroform and ethyl acetate. The resulting solid was filtered and dried to obtain Compound 8(6.8g, yield: 51%).

MS:[M+H]+＝775

< example >

< Experimental examples 1-1>

Will be provided with

The glass substrate (corning 7059 glass) coated with ITO (indium tin oxide) was put in distilled water in which a dispersant was dissolved, and washed with ultrasonic waves. The detergent used was a product of fisher (Fischer Co.) and the distilled water was filtered twice using a Filter (Filter) manufactured by Millipore Co. The ITO was washed for 30 minutes and then twice with distilled water to perform ultrasonic washing for 10 minutes. After the completion of the distilled water washing, ultrasonic washing was performed with a solvent of isopropyl alcohol, acetone and methanol, and drying was performed.

On the ITO transparent electrode thus prepared

The thickness of (a) was measured, and a hole injection layer was formed by thermally vacuum-evaporating hexanitrile hexaazatriphenylene (hexaazatriphenylene). HT1 as a hole transporting substance was vacuum-evaporated on the hole injection layer

Then, as a light-emitting layer, a host material H1 and a dopant material D1 are mixed with each other

Vacuum evaporation to the thickness of (1). Vacuum evaporating the luminescent layer at a weight ratio of 1:1<Synthesis example 3>Of<Compound 1>And LiQ (8-quinolinolatium), to produce

The thickness of (a) forms an electron injection and transport layer. Sequentially adding lithium fluoride (LiF) on the electron injection and transport layer to

Thickness of aluminum and

the organic light-emitting element is manufactured by forming a cathode by vapor deposition in a thickness.

In the above process, the evaporation rate of the organic material is maintained at 0.4-0.4

Lithium fluoride maintenance of cathode

Deposition rate of (3), aluminum maintenance

The vapor deposition rate of (2) is maintained at a vacuum degree of 2X 10 during vapor deposition^-7To 5X 10^-6torr to thereby fabricate an organic light emitting element.

[ Hexanitrile hexaazatriphenylene ] [ LiQ ]

[HT1]

[H1]

[D1]

< Experimental examples 1 and 2>

An organic light-emitting device was produced in the same manner as in experimental example 1-1, except that compound 2 was used instead of compound 1 as the electron transport layer in experimental example 1-1.

< Experimental examples 1 to 3>

An organic light-emitting device was produced in the same manner as in experimental example 1-1, except that compound 3 was used instead of compound 1 in experimental example 1-1.

< Experimental examples 1 to 4>

An organic light-emitting device was produced in the same manner as in experimental example 1-1, except that compound 4 was used instead of compound 1 in experimental example 1-1.

< Experimental examples 1 to 5>

An organic light-emitting device was produced in the same manner as in experimental example 1-1, except that compound 5 was used instead of compound 1 in experimental example 1-1.

< Experimental examples 1 to 6>

An organic light-emitting device was produced in the same manner as in experimental example 1-1, except that compound 6 was used instead of compound 1 in experimental example 1-1.

< Experimental examples 1 to 7>

An organic light-emitting device was produced in the same manner as in experimental example 1-1, except that compound 7 was used instead of compound 1 in experimental example 1-1.

< comparative example 1-1>

An organic light-emitting element was produced in the same manner as in experimental example 1-1, except that in experimental example 1-1, the compound of ET1 described below was used instead of compound 1.

[ET1]

< comparative examples 1 and 2>

An organic light-emitting element was produced in the same manner as in experimental example 1-1, except that in experimental example 1-1, a compound of ET2 described below was used instead of compound 1 of chemical formula.

[ET2]

< comparative examples 1 to 3>

An organic light-emitting element was produced in the same manner as in experimental example 1-1, except that in experimental example 1-1, a compound of ET3 described below was used instead of compound 1 of chemical formula.

[ET3]

< comparative examples 1 to 4>

An organic light-emitting device was produced in the same manner as in experimental example 1-1, except that compound 8 was used instead of compound 1 in experimental example 1-1.

Organic light-emitting devices produced by using the respective compounds as electron transport layer materials as in the above-described experimental examples 1-1 to 1-7 and comparative examples 1-1 to 1-4 were controlled at 10mA/cm²The driving voltage and the luminous efficiency were measured at a current density of 20mA/cm²The time (LT) to reach 98% with respect to the initial luminance was measured at the current density of (1)₉₈). It is prepared byThe results are shown in Table 1 below.

[ Table 1]

As can be seen from table 1, the compound represented by chemical formula 1 according to one embodiment of the present specification can be used for an electron injection layer and an electron transport layer of an organic electronic device.

ET3 shows excellent characteristics in terms of lifetime when compared with ET3, which is similar to the structure of compounds 6 and 7 described above but is not asymmetric, and it is understood that compounds 1 to 5 of the present specification have great advantages in terms of lifetime.

Claims

1. A compound represented by the following chemical formula 2 or 3:

chemical formula 2

Chemical formula 3

In the chemical formula 2, the first and second organic solvents,

q is benzene, and Q is benzene,

L₁in order to realize the direct bonding,

L₂in order to realize the direct bonding,

Ar₂is phenyl, dibenzothienyl, dibenzofuranyl, or carbazolyl, substituted or unsubstituted with cyano,

X₁to X₃The content of the N is N,

Ar₃and Ar₄The same or different from each other, each independently is phenyl, biphenyl, naphthyl, phenanthryl, terphenyl or dibenzofuranyl substituted or unsubstituted with dibenzofuranyl，

R₁To R₃Is a hydrogen atom, and is,

a is the number of 4, and a is the number of 4,

b is the number 4 of the hydroxyl groups,

c is the number of 4, and c is,

in the chemical formula 3, the first and second organic solvents,

q is benzene, and Q is benzene,

L₁in order to realize the direct bonding,

L₂is a direct bond or a phenylene group,

X₁to X₃The content of the N is N,

X₄is CR, X₅And X₆Is N; x₄And X₆Is CR, X₅Is N; or X₄And X₅Is N, X₆In the presence of a catalyst having a chemical formula of CR,

the R is hydrogen, and the compound has the structure of,

Ar₃and Ar₄Identical to or different from each other, each independently a phenyl, biphenyl, naphthyl, phenanthryl, terphenyl or dibenzofuranyl group, substituted or unsubstituted with a dibenzofuranyl group,

Ar₅and Ar₆Identical to or different from each other, are each independently hydrogen or phenyl,

R₁to R₃Is a hydrogen atom, and is,

a is the number of 4, and a is the number of 4,

b is the number 4 of the hydroxyl groups,

c is 4.

2. The compound of claim 1, wherein the chemical formula 2 or 3 is any one selected from the following compounds:

3. an organic electronic component, comprising: a first electrode, a second electrode provided so as to face the first electrode, and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers contain the compound according to claim 1 or 2.

4. The organic electronic element according to claim 3, wherein the organic layer comprises an electron injection layer or an electron transport layer, and the electron transport layer or the electron injection layer comprises the compound.