JP2019515877A - Compound and organic electronic device containing the same - Google Patents

Abstract

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

Description

  This application claims the benefit of the filing date of Korean Patent Application No. 10-2016-0037222, filed on March 28, 2016, to the Korean Patent Office, the entire content of which is incorporated herein.

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

  As a representative example of the organic electronic device, there is an organic light emitting device. In general, the organic light emission phenomenon refers to a phenomenon in which electric energy is converted into light energy using an organic substance. An organic light emitting device utilizing an organic light emitting phenomenon usually has a structure including an anode and a cathode, and an organic layer between them. Here, in order to increase the efficiency and stability of the organic light emitting device, the organic material layer often has a multilayer structure made of different materials, for example, a hole injection layer, a hole transport layer, and a light emitting layer. , Electron transport layer, electron injection layer and the like. In the structure of such an organic light emitting device, when a voltage is applied between the two electrodes, holes are injected from the anode and electrons from the cathode into the organic layer, and the injected holes and the electrons come into contact with each other. , An exciton is formed and emits light when the exciton falls back to the ground state again.

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

International Patent Application Publication No. 2003-012890

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

前記化学式１において、
Ｑは、炭素数６〜１０の単環の芳香族基または単環のヘテロ環基であり、
Ｌ_１およびＬ_２は、互いに同一または異なり、それぞれ独立に、直接結合；置換もしくは非置換のアリーレン基；または置換もしくは非置換のヘテロアリーレン基であり、
Ａｒ_１は、水素；重水素；置換もしくは非置換のアルキル基；置換もしくは非置換のシクロアルキル基；置換もしくは非置換のアリール基；または置換もしくは非置換のヘテロアリール基であり、
Ａｒ_２は、水素；重水素；置換もしくは非置換のアルキル基；置換もしくは非置換のシクロアルキル基；置換もしくは非置換のホスフィンオキシド基；置換もしくは非置換の炭素数６〜１６のアリール基；または置換もしくは非置換のヘテロアリール基であり、
Ｒ_１〜Ｒ_３は、互いに同一または異なり、それぞれ独立に、水素；重水素；ハロゲン基；シアノ基；置換もしくは非置換のアルキル基；置換もしくは非置換のホスフィンオキシド基；置換もしくは非置換のアリール基；または置換もしくは非置換のヘテロアリール基であり、
ａは、１〜４の整数であり、
ｂは、１〜４の整数であり、
ｃは、１〜４の整数であり、
ａが２以上の場合、２以上のＲ_１は、互いに同一または異なり、
ｂが２以上の場合、２以上のＲ_２は、互いに同一または異なり、
ｃが２以上の場合、２以上のＲ_３は、互いに同一または異なる。 The present specification provides a compound represented by the following chemical formula 1.
[Chemical formula 1]

In the above Chemical Formula 1,
Q is a C6-C10 monocyclic aromatic group or a monocyclic heterocyclic group,
L ₁ and L ₂ are the same or different from each other, each independently being a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group,
Ar ₁ is hydrogen; deuterium; substituted or unsubstituted alkyl group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted aryl group; or substituted or unsubstituted heteroaryl group,
Ar ₂ represents hydrogen, deuterium, substituted or unsubstituted alkyl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted phosphine oxide group, substituted or unsubstituted aryl group having 6 to 16 carbon atoms, or A substituted or unsubstituted heteroaryl group,
R _{1 to} R ₃ are the same or different from each other and each independently hydrogen; deuterium; halogen group; cyano group; substituted or unsubstituted alkyl group; substituted or unsubstituted phosphine oxide group; substituted or unsubstituted aryl A substituted or unsubstituted heteroaryl group;
a is an integer of 1 to 4 and
b is an integer of 1 to 4 and
c is an integer of 1 to 4 and
When a is 2 or more, two or more R _{1 's} are the same or different from each other,
When b is 2 or more, two or more R _{2 's} are the same or different from each other,
When c is 2 or more, 2 or more of R ₃ are the same or different from each other.

  In the present specification, a first electrode, a second electrode provided opposite to the first electrode, and one or more organic layers provided between the first electrode and the second electrode And at least one layer of the organic layer contains the above-mentioned compound.

  The compound according to one embodiment of the present invention is used in an organic electronic device including an organic light emitting device, reduces the driving voltage of the organic electronic device, improves the light efficiency, and improves the light stability of the device. Lifetime characteristics can be improved.

1 shows an organic electronic device 10 according to an embodiment of the present specification. 5 shows an organic electronic device 11 according to another embodiment of the present specification.

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

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

  The compound of Formula 1 may have various properties suitable for use in an organic layer used in an organic light emitting device by introducing various substituents into the core structure, and the core structure of Formula 1 of the present invention is The characteristics and effects possessed play a role of improving the conductivity in the device to lower the driving voltage and improving the light emission efficiency. It will be as follows if it explains concretely.

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

は、連結される部位を意味する。 In the present specification,

Represents a site to be linked.

  The term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is changed to another substituent, and the position to be substituted is the position at which the hydrogen atom is substituted, that is, the substituent can be substituted There is no limitation as long as it is a position, and when two or more substituents are substituted, two or more substituents may be the same or different from each other.

  In the present specification, the term "substituted or unsubstituted" is deuterium; halogen group; cyano group; hydroxy group; substituted or unsubstituted alkyl group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted Alkoxy group; substituted or unsubstituted aryl group selected from the group consisting of substituted or unsubstituted aryl group; and substituted or unsubstituted heterocyclic group, or two of the substituents exemplified above It means that the above substituents are substituted by the connected substituent.

  As used herein, a 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 include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl and n-pentyl , Isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3, 3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl- Propyl, 1,1-dimethyl-propyl, iso Hexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl there are such as, but not limited to.

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

  In the present specification, the alkoxy group may be linear, branched or cyclic. The carbon number of the alkoxy group is not particularly limited, but those having 1 to 20 carbon atoms are preferable. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n- Hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy and the like, but is limited thereto It is not a thing.

  In the present specification, when the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but those having 6 to 30 carbon atoms are preferable. Specifically, the monocyclic aryl group may be, for example, a phenyl group, a biphenyl group, a terphenyl group, or a quaternary phenyl group, but is not limited thereto.

  When the said aryl group is a polycyclic aryl group, carbon number is not specifically limited, However, A C6-C30 thing is preferable. Specifically, the polycyclic aryl group may be, for example, naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, perylenyl group, chrysenyl group, fluorenyl group and the like, but is not limited thereto.

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

などになってもよいが、これらに限定されるものではない。 When the fluorenyl group is substituted,

Or the like, but is not limited thereto.

  In the present specification, a heteroaryl group is a heterocyclic group containing one or more of N, O, S, Si and Se as hetero atoms, and the number of carbon atoms is not particularly limited, 50 are preferred. Examples of the heteroaryl group include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group, triazole group, acridyl group Group, pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyridopyrimidinyl group, pyridopyrazinyl group, pyrazinopyrazinyl group, isoquinoline group, indole group, carbazole group, benzoxazole group, benzimidazole Group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, phenanthroline group, thiazolyl group, isoxazolyl group, Sajiazoriru group, thiadiazolyl group, benzothiazolyl group, and the like dibenzofuranyl group, but is not limited to only these.

  In the present specification, a monocyclic aromatic group means a monocyclic aromatic hydrocarbon ring, and examples thereof include benzene.

  In the present specification, a monocyclic heterocyclic group means a ring containing one or more of N, O or S atoms as a hetero atom, and examples thereof include pyridine, pyrimidine, pyridazine, triazine, pyran, There are thiopyran, diazine, pyrazine and the like, which may be selected among the examples of the heteroaryl group, but not limited thereto.

  In the present specification, an arylene group means an aryl group having two bonding sites, ie, a divalent group. Except for the fact that each of these is a divalent group, the description of the above-mentioned aryl group is applicable.

  In the present specification, a heteroarylene group means a heteroaryl group having two bonding sites, ie, a divalent group. The descriptions of the above-mentioned heteroaryl groups are applicable except that they are each a divalent group.

  In one embodiment of the present specification, Q is a C6-C10 monocyclic aromatic group or a monocyclic heterocyclic group.

  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, L ₁ and L ₂ are the same or different from each other, and are each independently a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group.

In one embodiment of the present specification, L ₁ and L ₂ are the same as or different from one another, and each is independently a direct bond; or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

In one embodiment of the present specification, L ₁ and L ₂ are the same or different from each other, each independently being a direct bond; substituted or unsubstituted phenylene group; substituted or unsubstituted naphthylene group; or substituted or unsubstituted It is an anthracenylene group.

In one embodiment of the present specification, L ₁ and L ₂ are the same or different from each other, and are each independently a direct bond; a phenylene group; a naphthylene group; or an anthracenylene group.

In one embodiment of the present specification, L ₁ is a direct bond.

In one embodiment of the present specification, Ar _{1 's} are the same as or different from each other, and each independently hydrogen; deuterium; substituted or unsubstituted alkyl group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted aryl Or a substituted or unsubstituted heteroaryl group.

In one embodiment of the present specification, Ar ₁ is a substituted or unsubstituted heteroaryl group.

In one embodiment of the present specification, Ar ₁ is a substituted or unsubstituted single ring heteroaryl group.

In one embodiment of the present specification, Ar ₁ is a monocyclic heteroaryl group containing one or more substituted or unsubstituted nitrogen atoms.

In one embodiment of the present specification, Ar ₁ is a substituted or unsubstituted pyridine group; a substituted or unsubstituted pyrimidine group; or a substituted or unsubstituted triazine group.

In one embodiment of the present specification, Ar ₁ is a pyrimidine group in which the aryl group is substituted or unsubstituted.

In one embodiment of the present specification, Ar ₁ is a pyrimidine group which is a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.

In one embodiment of the present specification, Ar ₁ is a pyrimidine group in which a phenyl group is substituted or unsubstituted.

In one embodiment of the present specification, Ar ₁ is a pyrimidine group substituted with a phenyl group.

In one embodiment of the present specification, Ar ₁ is a triazine group having one or more substituents selected from the group consisting of a substituted or unsubstituted aryl group; and a substituted or unsubstituted heteroaryl group. It is.

In one embodiment of the present specification, Ar ₁ is selected from the group consisting of substituted or unsubstituted aryl group having 6 to 20 carbon atoms; and substituted or unsubstituted heteroaryl group having 12 to 20 carbon atoms The above substituents are substituted or unsubstituted triazine groups.

In one embodiment of the present specification, Ar ₁ is a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted phenanthrene group; a substituted or unsubstituted Terphenyl group; at least one substituent selected from the group consisting of substituted or unsubstituted dibenzofuran group, substituted or unsubstituted dibenzothiophene group, substituted or unsubstituted carbazole group is a substituted or unsubstituted triazine group .

In one embodiment of the present specification, Ar ₁ 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; an aryl group or a heteroaryl group A substituted or unsubstituted naphthyl group; an aryl group or a heteroaryl group substituted or unsubstituted phenanthrene group; an aryl group or a heteroaryl group substituted or unsubstituted terphenyl group; and an aryl group or a heteroaryl group substituted or non-substituted One or more substituents selected from the group consisting of substituted dibenzofuran groups are substituted or unsubstituted triazine groups.

In one embodiment of the present specification, Ar ₁ is at least one selected from the group consisting of a heteroaryl group-substituted or unsubstituted phenyl group, a naphthyl group, a biphenyl group, a phenanthrene group, a terphenyl group, and a dibenzofuran group The substituent of is a substituted or unsubstituted triazine group.

In one embodiment of the present specification, Ar ₁ is a phenyl group substituted or unsubstituted with a heteroaryl group having 12 to 20 carbon atoms; naphthyl group; biphenyl group; phenanthrene group; terphenyl group; and dibenzofuran group One or more of the substituents selected is a substituted or unsubstituted triazine group.

In one embodiment of the present specification, Ar ₁ comprises a dibenzofuran group, a dibenzothiophene group, or a phenyl group substituted or unsubstituted with a carbazole group; a naphthyl group; a biphenyl group; a phenanthrene group; a terphenyl group; and a dibenzofuran group One or more substituents selected from the group are substituted or unsubstituted triazine groups.

In one embodiment of the present specification, Ar ₁ is at least one selected from the group consisting of a substituted or unsubstituted phenyl group, a naphthyl group, a biphenyl group, a phenanthrene group, a terphenyl group, and a dibenzofuran group with a dibenzofuran group. The substituent is a substituted or unsubstituted triazine group.

In one embodiment of the present specification, Ar ₁ is at least one selected from the group consisting of a substituted or unsubstituted phenyl group, a naphthyl group, a biphenyl group, a phenanthrene group, a terphenyl group, and a dibenzofuran group with a dibenzofuran group. It is a triazine group substituted by a substituent.

In one embodiment of the present specification, Ar ₂ is hydrogen; deuterium; or a substituted or unsubstituted aryl group having 6 to 16 carbon atoms.

In one embodiment of the present specification, Ar ₂ is hydrogen; deuterium; or a group consisting of a cyano group, a halogen group, an alkyl group substituted or unsubstituted with a halogen group, and an alkoxy group substituted or unsubstituted with a halogen group One or more substituents selected therefrom are substituted or unsubstituted aryl groups having 6 to 16 carbon atoms.

In one embodiment of the present specification, Ar ₂ is hydrogen; deuterium; or a cyano group, a halogen group, a halogen group-substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, and a halogen group substituted or unsubstituted And one or more substituents selected from the group consisting of an alkoxy group having 1 to 4 carbon atoms is a substituted or unsubstituted aryl group having 6 to 16 carbon atoms.

In one embodiment of the present specification, Ar ₂ is selected from the group consisting of hydrogen; deuterium; or cyano, fluorine, fluorine-substituted or unsubstituted methyl, and fluorine-substituted or unsubstituted methoxy. The at least one substituent is a substituted or unsubstituted aryl group having 6 to 16 carbon atoms.

In one embodiment of the present specification, Ar ₂ is at least one substituent selected from the group consisting of a cyano group, fluorine, a fluorine-substituted or unsubstituted methyl group, and a fluorine-substituted or unsubstituted methoxy group At least one substituent selected from the group consisting of a substituted or unsubstituted phenyl group; a cyano group, a fluorine, a fluorine-substituted or unsubstituted methyl group, and a fluorine-substituted or unsubstituted methoxy group is Or at least one substituent selected from the group consisting of a substituted phenanthrene group; or a cyano group, a fluorine, a fluorine, a fluorine-substituted or unsubstituted methyl group, and a fluorine-substituted or unsubstituted methoxy group, or a substituted or unsubstituted fluorenyl group It is a group.

In one embodiment of the present specification, Ar ₂ is at least one substituent selected from the group consisting of a cyano group, fluorine, a fluorine-substituted or unsubstituted methyl group, and a fluorine-substituted or unsubstituted methoxy group Is a substituted or unsubstituted phenyl group; a phenanthrene group; or a fluorine-substituted or unsubstituted methyl group or a cyano group is a substituted or unsubstituted fluorenyl group.

In one embodiment of the present specification, Ar ₂ is substituted with at least one substituent selected from the group consisting of a cyano group, fluorine, a fluorine-substituted methyl group, and a fluorine-substituted or unsubstituted methoxy group Or a non-substituted phenyl group; a phenanthrene group; or a methyl group or a cyano group is a substituted or non-substituted fluorenyl group.

  In one embodiment of the present specification, at least one substituent selected from the group consisting of a cyano group, fluorine, a fluorine-substituted methyl group, and a fluorine-substituted methoxy group is a substituted or unsubstituted phenyl group A phenanthrene group; or a 9,9-dimethylfluorenyl group substituted with a cyano group.

In one embodiment of the present specification, Ar ₂ is a substituted or unsubstituted heteroaryl group.

In one embodiment of the present specification, Ar ₂ is a substituted or unsubstituted C 4-20 heteroaryl group.

In one embodiment of the present specification, Ar ₂ is a heteroaryl group having 4 to 20 carbon atoms in which the aryl group is substituted or unsubstituted.

In one embodiment of the present specification, Ar ₂ is a heteroaryl group having 4 to 20 carbon atoms in which the aryl group having 6 to 12 carbon atoms is substituted or unsubstituted.

In one embodiment of the present specification, Ar ₂ is a heteroaryl group having 4 to 20 carbon atoms in which a phenyl group or a naphthyl group is substituted or unsubstituted.

In one embodiment of the present specification, Ar ₂ is a heteroaryl group having 4 to 20 carbon atoms in which the phenyl group is substituted or unsubstituted.

In one embodiment of the present specification, Ar ₂ is a pyridyl group substituted or unsubstituted with a phenyl group; a pyrimidyl group substituted or unsubstituted with a phenyl group; a phenanthroline group substituted or unsubstituted with a phenyl group; substituted with a phenyl group Or an unsubstituted dibenzothiophene group; a phenyl group is a substituted or unsubstituted dibenzofuran group; or a phenyl group is a substituted or unsubstituted carbazole group.

In one embodiment of the present specification, Ar ₂ is a pyridyl group substituted or unsubstituted with a phenyl group; a pyrimidyl group substituted with a phenyl group; a phenanthroline group; a dibenzothiophene group; a dibenzofuran group; or a carbazole group.

In one embodiment of the present specification, Ar ₂ is a substituted or unsubstituted phosphine oxide group.

In one embodiment of the present specification, Ar ₂ is a phosphine oxide group in which the aryl group is substituted or unsubstituted.

In one embodiment of the present specification, Ar ₂ is a phosphine oxide group in which an aryl group having 6 to 12 carbon atoms is substituted or unsubstituted.

In one embodiment of the present specification, Ar ₂ is a phosphine oxide group in which a phenyl group is substituted or unsubstituted.

In one embodiment of the present specification, Ar ₂ is a phosphine oxide group substituted with a phenyl group.

In one embodiment of the present specification, R _{1 to} R ₃ are the same or different from each other, and each independently hydrogen; deuterium; halogen group; cyano group; substituted or unsubstituted alkyl group; substituted or unsubstituted aryl Or a substituted or unsubstituted heteroaryl group.

In one embodiment of the present specification, R _{1 to} R ₃ are hydrogen.

［化学式３］

前記化学式２および３において、
Ｑ、Ｌ_１、Ｌ_２、Ａｒ_２、Ｒ_１〜Ｒ_３、およびａ〜ｃに関する定義は、前記化学式１で定義したものと同じであり、
Ｘ_１〜Ｘ_３のうちの２以上は、Ｎであり、残りは、互いに同一または異なり、それぞれ独立に、ＮまたはＣＲであり、
Ｘ_４〜Ｘ_６のうちの１以上は、Ｎであり、残りは、互いに同一または異なり、それぞれ独立に、ＮまたはＣＲであり、
前記Ｒは、水素であり、
Ａｒ_３〜Ａｒ_６は、互いに同一または異なり、それぞれ独立に、水素；重水素；置換もしくは非置換のアルキル基；置換もしくは非置換のシクロアルキル基；置換もしくは非置換のアリール基；置換もしくは非置換のヘテロアリール基である。 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 formulas 2 and 3,
The definitions for Q, L ₁ , L ₂ , Ar ₂ , R _{1 to} R ₃ , and a to c are the same as those defined in Chemical Formula 1 above,
Two or more of X _{1 to} X ₃ are N, and the rest are the same or different from one another, and each independently N or CR,
One or more of X _{4 to} X ₆ are N, and the rest are the same or different from one another, and each independently N or CR,
R is hydrogen,
Ar _{3 to} Ar ₆ are the same or different from each other, each independently hydrogen; deuterium; substituted or unsubstituted alkyl group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted aryl group; substituted or unsubstituted Is a heteroaryl group of

In one embodiment of the present specification, X _{1 to} X ₃ are N.

In one embodiment of the present specification, X ₄ is CR and X ₅ and X ₆ are N.

In one embodiment of the present specification, X ₄ and X ₆ are CR and X ₅ is N.

In one embodiment of the present specification, X ₄ and X ₅ are N and X ₆ is CR.

In one embodiment of the present specification, Ar ₃ and Ar ₄ are the same or different from each other, and each independently is a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group.

In one embodiment of the present specification, Ar ₃ and Ar ₄ are the same as or different from each other, and each independently represent a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted carbon having 12 to 20 carbon atoms Is a heteroaryl group of

In one embodiment of the present specification, Ar ₃ and Ar ₄ are the same as or different from each other, and each independently represent a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; Or substituted phenanthrene group; substituted or unsubstituted terphenyl group; substituted or unsubstituted dibenzofuran group; substituted or unsubstituted dibenzothiophene group; or substituted or unsubstituted carbazole group.

In one embodiment of the present specification, Ar ₃ and Ar ₄ are the same as or different from each other, and each independently independently represent an aryl group or a substituted or unsubstituted phenyl group with an aryl group or a heteroaryl group; A substituted biphenyl group; an aryl group or a substituted or unsubstituted naphthyl group with an heteroaryl group; an aryl group or a substituted or unsubstituted phenanthrene group with a heteroaryl group; an aryl group or a substituted or unsubstituted terphenyl group Or a dibenzofuran group substituted or unsubstituted with an aryl group or a heteroaryl group.

In one embodiment of the present specification, Ar ₃ and Ar ₄ are the same or different from each other, and each independently a phenyl group substituted or unsubstituted with a heteroaryl group; a biphenyl group; a naphthyl group; a phenanthrene group; a terphenyl group; And a dibenzofuran group.

In one embodiment of the present specification, Ar ₃ and Ar ₄ are the same as or different from each other, and each independently represent a phenyl group substituted or unsubstituted with a heteroaryl group having 12 to 20 carbon atoms; biphenyl group; naphthyl group; phenanthrene A terphenyl group; or a dibenzofuran group.

In one embodiment of the present specification, Ar ₃ and Ar ₄ are the same as or different from each other, and each independently represent a dibenzofuran group, a dibenzothiophene group, or a phenyl group substituted or unsubstituted with a carbazole group; biphenyl group; naphthyl group; Phenanthrene group; terphenyl group; or dibenzofuran group.

In one embodiment of the present specification, Ar ₃ and Ar ₄ are the same or different from each other, and each independently a phenyl group substituted or unsubstituted with a dibenzofuran group; a biphenyl group; a naphthyl group; a phenanthrene group; a terphenyl group or a dibenzofuran It is a group.

In one embodiment of the present specification, Ar ₅ and Ar ₆ are the same or different from each other, and each independently hydrogen; or a substituted or unsubstituted aryl group.

In one embodiment of the present specification, Ar ₅ and Ar ₆ are the same as or different from each other, each independently hydrogen; or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.

In one embodiment of the present specification, Ar ₅ and Ar ₆ are the same or different from each other, and each independently is hydrogen; or a substituted or unsubstituted phenyl group.

In one embodiment of the present specification, Ar ₅ and Ar ₆ are the same or different from each other, and each independently hydrogen; or a phenyl group.

［化学式５］

前記化学式４および５において、
Ｑ、Ｌ_１、Ｌ_２、Ａｒ_２、Ｒ_１〜Ｒ_３、およびａ〜ｃに関する定義は、前記化学式１で定義したものと同じであり、
Ｘ_１〜Ｘ_３のうちの２以上は、Ｎであり、残りは、互いに同一または異なり、それぞれ独立に、ＮまたはＣＲであり、
前記Ｒは、水素であり、
Ｘ_４〜Ｘ_６のうちの１以上は、Ｎであり、残りは、互いに同一または異なり、それぞれ独立に、ＮまたはＣＲであり、
Ａｒ_３〜Ａｒ_６は、互いに同一または異なり、それぞれ独立に、水素；重水素；置換もしくは非置換のアルキル基；置換もしくは非置換のシクロアルキル基；置換もしくは非置換のアリール基；置換もしくは非置換のヘテロアリール基である。 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 formulas 4 and 5,
The definitions for Q, L ₁ , L ₂ , Ar ₂ , R _{1 to} R ₃ , and a to c are the same as those defined in Chemical Formula 1 above,
Two or more of X _{1 to} X ₃ are N, and the rest are the same or different from one another, and each independently N or CR,
R is hydrogen,
One or more of X _{4 to} X ₆ are N, and the rest are the same or different from one another, and each independently N or CR,
Ar _{3 to} Ar ₆ are the same or different from each other, each independently hydrogen; deuterium; substituted or unsubstituted alkyl group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted aryl group; substituted or unsubstituted Is a heteroaryl group of

In one embodiment of the present specification, X _{1 to} X ₃ are N.

In one embodiment of the present specification, X ₄ is CR and X ₅ and X ₆ are N.

In one embodiment of the present specification, X ₄ and X ₆ are CR and X ₅ is N.

In one embodiment of the present specification, X ₄ and X ₅ are N and X ₆ is CR.

In one embodiment of the present specification, Ar ₃ and Ar ₄ are the same or different from each other, and each independently is a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group.

In one embodiment of the present specification, Ar ₃ and Ar ₄ are the same as or different from each other, and each independently represent a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted carbon having 12 to 20 carbon atoms Is a heteroaryl group of

In one embodiment of the present specification, Ar ₃ and Ar ₄ are the same as or different from each other, and each independently represent a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; Or substituted phenanthrene group; substituted or unsubstituted terphenyl group; substituted or unsubstituted dibenzofuran group; substituted or unsubstituted dibenzothiophene group; or substituted or unsubstituted carbazole group.

In one embodiment of the present specification, Ar ₃ and Ar ₄ are the same as or different from each other, and each independently independently represent an aryl group or a substituted or unsubstituted phenyl group with an aryl group or a heteroaryl group; A substituted biphenyl group; an aryl group or a substituted or unsubstituted naphthyl group with an heteroaryl group; an aryl group or a substituted or unsubstituted phenanthrene group with a heteroaryl group; an aryl group or a substituted or unsubstituted terphenyl group Or a dibenzofuran group substituted or unsubstituted with an aryl group or a heteroaryl group.

In one embodiment of the present specification, Ar ₃ and Ar ₄ are the same or different from each other, and each independently a phenyl group substituted or unsubstituted with a heteroaryl group; a biphenyl group; a naphthyl group; a phenanthrene group; a terphenyl group; And a dibenzofuran group.

In one embodiment of the present specification, Ar ₃ and Ar ₄ are the same as or different from each other, and each independently represent a phenyl group substituted or unsubstituted with a heteroaryl group having 12 to 20 carbon atoms; biphenyl group; naphthyl group; phenanthrene A terphenyl group; or a dibenzofuran group.

In one embodiment of the present specification, Ar ₃ and Ar ₄ are the same as or different from each other, and each independently represent a dibenzofuran group, a dibenzothiophene group, or a phenyl group substituted or unsubstituted with a carbazole group; biphenyl group; naphthyl group; Phenanthrene group; terphenyl group; or dibenzofuran group.

In one embodiment of the present specification, Ar ₃ and Ar ₄ are the same or different from each other, and each independently a phenyl group substituted or unsubstituted with a dibenzofuran group; a biphenyl group; a naphthyl group; a phenanthrene group; a terphenyl group or a dibenzofuran It is a group.

In one embodiment of the present specification, Ar ₅ and Ar ₆ are the same as or different from each other, each independently hydrogen; or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.

In one embodiment of the present specification, Ar ₅ and Ar ₆ are the same or different from each other, and each independently is hydrogen; or a substituted or unsubstituted phenyl group.

In one embodiment of the present specification, Ar ₅ and Ar ₆ are the same or different from each other, and each independently hydrogen; or a phenyl group.

［化学式７］

［化学式８］

［化学式９］

前記化学式６〜９において、
Ｑ、Ｌ_１、Ｌ_２、Ａｒ_２、Ｒ_１〜Ｒ_３、およびａ〜ｃに関する定義は、前記化学式１で定義したものと同じであり、
Ｘ_１〜Ｘ_３のうちの２以上は、Ｎであり、残りは、互いに同一または異なり、それぞれ独立に、ＮまたはＣＲであり、
Ｘ_４〜Ｘ_６のうちの１以上は、Ｎであり、残りは、互いに同一または異なり、それぞれ独立に、ＮまたはＣＲであり、
前記Ｒは、水素であり、
Ａｒ_３〜Ａｒ_６は、互いに同一または異なり、それぞれ独立に、水素；重水素；置換もしくは非置換のアルキル基；置換もしくは非置換のシクロアルキル基；置換もしくは非置換のアリール基；置換もしくは非置換のヘテロアリール基である。 In one embodiment of the present specification, the chemical formula 1 may be represented by the following chemical formulas 6 to 9.
[Chemical formula 6]

[Chemical formula 7]

[Chemical formula 8]

[Chemical formula 9]

In the above formulas 6 to 9,
The definitions for Q, L ₁ , L ₂ , Ar ₂ , R _{1 to} R ₃ , and a to c are the same as those defined in Chemical Formula 1 above,
Two or more of X _{1 to} X ₃ are N, and the rest are the same or different from one another, and each independently N or CR,
One or more of X _{4 to} X ₆ are N, and the rest are the same or different from one another, and each independently N or CR,
R is hydrogen,
Ar _{3 to} Ar ₆ are the same or different from each other, each independently hydrogen; deuterium; substituted or unsubstituted alkyl group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted aryl group; substituted or unsubstituted Is a heteroaryl group of

In one embodiment of the present specification, X _{1 to} X ₃ are N.

In one embodiment of the present specification, X ₄ is CR and X ₅ and X ₆ are N.

In one embodiment of the present specification, X ₄ and X ₆ are CR and X ₅ is N.

In one embodiment of the present specification, X ₄ and X ₅ are N and X ₆ is CR.

In one embodiment of the present specification, Ar ₃ and Ar ₄ are the same or different from each other, and each independently is a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group.

In one embodiment of the present specification, Ar ₃ and Ar ₄ are the same as or different from one another, and each independently represent a substituted or unsubstituted C 6-20 aryl group; and a C 12-20 substituted or unsubstituted Is a heteroaryl group of

In one embodiment of the present specification, Ar ₃ and Ar ₄ are the same as or different from each other, and each independently represent a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; Or unsubstituted phenanthrene group; substituted or unsubstituted terphenyl group; substituted or unsubstituted dibenzofuran group, substituted or unsubstituted dibenzothiophene group, substituted or unsubstituted carbazole group.

In one embodiment of the present specification, Ar ₃ and Ar ₄ are the same as or different from each other, and each independently independently represent an aryl group or a substituted or unsubstituted phenyl group with an aryl group or a heteroaryl group; A substituted biphenyl group; an aryl group or a substituted or unsubstituted naphthyl group with an heteroaryl group; an aryl group or a substituted or unsubstituted phenanthrene group with a heteroaryl group; an aryl group or a substituted or unsubstituted terphenyl group And a dibenzofuran group substituted or unsubstituted with an aryl group or a heteroaryl group.

In one embodiment of the present specification, Ar ₃ and Ar ₄ are the same or different from each other, each independently a phenyl group substituted or unsubstituted with a heteroaryl group; a biphenyl group substituted or unsubstituted with an aryl group; A phenanthrene group; a terphenyl group; and a dibenzofuran group.

In one embodiment of the present specification, Ar ₃ and Ar ₄ are the same or different, and each independently a phenyl group substituted or unsubstituted with a heteroaryl group having 12 to 20 carbon atoms; biphenyl group; phenanthrene group; Phenyl group; or dibenzofuran group.

In one embodiment of the present specification, Ar ₃ and Ar ₄ are the same as or different from each other, and each independently a dibenzofuran group, a dibenzothiophene group, or a phenyl group substituted or unsubstituted with a carbazole group; biphenyl group; phenanthrene group; A terphenyl group; or a dibenzofuran group.

In one embodiment of the present specification, Ar ₃ and Ar ₄ are the same or different from each other, and each independently a phenyl group substituted or unsubstituted with a dibenzofuran group; a biphenyl group; a phenanthrene group; a terphenyl group or a dibenzofuran group .

In one embodiment of the present specification, Ar ₅ and Ar ₆ are the same or different from each other, and each independently hydrogen; or a substituted or unsubstituted aryl group.

In one embodiment of the present specification, Ar ₅ and Ar ₆ are the same as or different from each other, each independently hydrogen; or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.

In one embodiment of the present specification, Ar ₅ and Ar ₆ are the same or different from each other, and each independently is hydrogen; or a substituted or unsubstituted phenyl group.

In one embodiment of the present specification, Ar ₅ and Ar ₆ are the same or different from each other, and each independently hydrogen; or a phenyl group.

In one embodiment of the present specification, Ar ₅ and Ar ₆ are the same or different from each other, and each independently is hydrogen; or a substituted or unsubstituted phenyl group.

In one embodiment of the present specification, Ar ₅ and Ar ₆ are the same or different from each other, and each independently hydrogen; or a phenyl group.

According to one embodiment of the present specification, the compound of Formula 1 may be any one selected from the following structural formulas.

  The compound according to one embodiment of the present specification can be produced by the production method described later. Although representative examples will be described in the preparation examples described below, if necessary, substituents can be added or excluded, and the positions of substituents can be changed. Also, starting materials, reactants, reaction conditions, etc. can be varied based on techniques known in the art.

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

  In one embodiment of the present specification, a first electrode, a second electrode provided opposite to the first electrode, and one or more layers provided between the first electrode and the second electrode. An organic electronic device comprising an organic layer, wherein one or more of the organic layers comprise the compound.

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

  In the present specification, when a part is referred to as “including” a component, this means that the other component can be further included without excluding the other component unless specifically stated otherwise. Do.

  The organic layer of the organic electronic device of 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 device of the present invention, the organic light emitting device has a structure including a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, an electron injecting layer and the like as the organic layer it can. However, the structure of the organic electronic device is not limited thereto, and may include a smaller number of organic layers.

  According to one embodiment of the present specification, the organic electronic device may be selected from the group consisting of an organic light emitting device, an organic phosphorescent device, an organic solar cell, an organic photoreceptor (OPC), and an organic transistor.

  Hereinafter, the organic light emitting element is illustrated.

  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 specification, 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 comprises an electron blocking layer, and the electron blocking layer comprises the compound.

  In one embodiment of the present invention, the organic light emitting device is selected from the group consisting of 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. And one or more layers.

  In one embodiment of the present specification, the organic light emitting element is provided between a first electrode, a second electrode provided opposite to the first electrode, and the first electrode and the second electrode. And two or more organic layers provided between the light emitting layer and the first electrode or between the light emitting layer and the second electrode, and the organic substance of the two or more layers At least one of the layers comprises the compound. In one embodiment of the present specification, two or more of the two or more organic layers are selected from the group consisting of an electron transport layer, an electron injection layer, a layer simultaneously performing electron transport and electron injection, and a hole blocking layer May be

  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 included in one of the two or more electron transport layers, or included in each of the two or more electron transport layers. It may be

  Moreover, in one embodiment of the present specification, when the compound is contained in the respective two or more electron transport layers, other materials excluding the compound may be the same as or different from each other.

  In one embodiment of the present specification, the organic layer is a hole injection layer or a hole transport layer containing a compound containing an arylamino group, a carbazolyl group, or a benzocarbazolyl group in addition to the organic layer containing the compound. Further includes

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

  When the organic layer containing the compound of Formula 1 is an electron transport layer, the electron transport layer may further include an n-type dopant. As the n-type dopant, those known in the art can be used, and for example, metals or metal complexes can be used. According to one example, the electron transport layer including the compound of Formula 1 may further include LiQ.

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

  In another embodiment, the organic light emitting device may be an inverted type organic light emitting device 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 device of the present specification can have a structure as shown in FIGS. 1 and 2, but is not limited thereto.

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

  2, the first electrode 30, the hole injection layer 60, the hole transport layer 70, the electron blocking layer 80, the light emitting layer 40, the electron transport layer 90, the electron injection layer 100, and the second electrode on the substrate 20. The structure of the organic light emitting device in which 50 are sequentially stacked is illustrated. FIG. 2 is an exemplary structure according to embodiments herein, and may further include other organic layers.

  The organic light emitting devices herein can be made with materials and methods known in the art except that one or more of the organic layers comprises the compound herein, ie, the compound.

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

  In the organic light emitting device of the present invention, materials and methods known in the art are used except that one or more of the organic layers contain the compound, ie, the compound represented by Formula 1 above. It can be manufactured.

  For example, the organic light emitting device 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, a metal or a conductive metal oxide or an alloy thereof on the substrate using a PVD (Physical Vapor Deposition) method such as sputtering or e-beam evaporation. Is formed to form an anode, and an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer is formed thereon, and then a substance usable as a cathode is vapor deposited thereon Can be manufactured by In addition to this method, an organic light emitting element can be formed by depositing a cathode material, an organic material layer, and an anode material in this order on a substrate.

  In addition, the compound of Chemical Formula 1 is formed on the organic layer by the solution coating method as well as the vacuum deposition method when manufacturing the organic light emitting device. Here, the solution coating method means spin coating, dip coating, doctor blading, ink jet printing, screen printing, spray method, roll coating and the like, but is not limited thereto.

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

  In one embodiment of the present specification, 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 anode material, usually, a material having a large work function is preferable so as to facilitate the injection of holes into the organic layer. Specific examples of anode materials that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof; zinc oxide, indium oxide, indium tin oxide (ITO), indium Metal oxides such as zinc oxide (IZO); combinations of metals such as ZnO: Al or SNO ₂ : Sb with oxides; poly (3-methylthiophene), poly [3,4- (ethylene-1) And (2-dioxy) thiophene] (PEDOT), conductive polymers such as polypyrrole and polyaniline, etc., but not limited thereto.

The cathode material is preferably a material having a small work function to facilitate electron injection into the organic layer. Specific examples of the cathode material include magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, metals such as aluminum, silver, tin and lead, or alloys thereof; LiF / Al or LiO ₂ / There is a multilayer structure such as Al, but it is not limited thereto.

  The hole injection material is a layer for injecting holes from the electrode, and the hole injection material has the ability to transport holes, and the hole injection effect from the anode, the light emitting layer or the light emitting material On the other hand, a compound having an excellent hole injection effect, preventing migration of excitons generated in the light emitting layer to the electron injection layer or the electron injection material, and having an excellent ability to form a thin film is preferable. It is preferable that the hole injecting material HOMO (highest occupied molecular orbital) be between the work function of the anode material and the HOMO of the peripheral organic layer. Specific examples of the hole injecting material include metal porphyrin (porphyrin), oligothiophene, organic substance of arylamine type, organic substance of hexanitrile hexaazatriphenylene type, organic substance of quinacridone type, organic substance of perylene type, There are anthraquinone and conductive polymers of polyaniline and polythiophene, but 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, and as a hole transport material, it emits light by receiving hole transport from the anode or the hole injection layer Among the substances that can be transferred to the layer, substances having high mobility for holes are preferable. Specific examples thereof include, but are not limited to, arylamine-based organic substances, conductive polymers, and block copolymers having both conjugated and non-conjugated parts.

  The electron blocking layer is a layer capable of preventing the holes injected from the hole injection layer from entering the electron injection layer through the light emitting layer to improve the life and efficiency of the device, and the case may be necessary. The light emitting layer and the electron injection layer are formed at appropriate portions using known materials.

The light-emitting substance of the light-emitting layer is a substance capable of emitting light in the visible light region by receiving and combining holes and electron transport from the hole transport layer and the electron transport layer, and having quantum efficiency with respect to fluorescence and phosphorescence Good materials are preferred. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ); carbazole compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzoxazole, benzthiazole, and the like Benzimidazole compounds; poly (p-phenylene vinylene) (PPV) polymers; spiro compounds; polyfluorenes, rubrenes and the like, but not limited thereto.

  The light emitting layer can include a host material and a dopant material. Host materials include fused aromatic ring derivatives or heterocycle containing compounds. Specific examples of the fused aromatic ring derivative include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds and the like, and as the heterocycle-containing compounds, compounds, dibenzofuran derivatives, ladder type furan compounds And pyrimidine derivatives, but is not limited thereto.

  Examples of the dopant material include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes and the like. Specifically, the aromatic amine derivative is a fused aromatic ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene having an arylamino group, anthracene, chrysene, periflanthene, etc., and a styrylamine compound Is a compound in which at least one arylvinyl group is substituted by a substituted or unsubstituted arylamine, and one or two members selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamino group The substituent selected above is substituted or unsubstituted. Specific examples include, but are not limited to, styrylamine, styryl diamine, styryl triamine, styryl tetraamine and the like. In addition, metal complexes include, but are not limited to, iridium complexes and platinum complexes.

The electron transport material of the electron transport layer is a layer which receives electrons from the electron injection layer and transports the electrons to the light emitting layer, and as the electron transport material, a substance which can well receive electron injection from the cathode and transfer it to the light emitting layer A substance having high mobility to electrons is preferable. Specific examples thereof include Al complexes of 8-hydroxyquinoline; complexes containing Alq ₃ ; organic radical compounds; hydroxyflavone-metal complexes and the like, but are not limited thereto. The electron transport layer can be used with any desired cathode material, as used in the prior art. In particular, examples of suitable cathode materials are the usual materials which have a low work function and are followed by an aluminum or silver layer. Specifically, cesium, barium, calcium, ytterbium and samarium, in each case followed by an aluminum or silver layer.

  The electron injection layer is a layer for injecting electrons from the electrode, has an ability to transport electrons, has an electron injection effect from the cathode, and an excellent electron injection effect for the light emitting layer or the light emitting material, and emits light. It is preferable to prevent the transfer of excitons generated in the layer to the hole injection layer, and a compound excellent in thin film formation ability. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyrandioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylidene methane, anthrone and derivatives thereof, metal complex compounds, And nitrogen-containing 5-membered ring derivatives, but not limited thereto.

  As the metal complex compound, 8-hydroxyquinolinatolithium, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, bis (8-hydroxyquinolinato) manganese, tris (8-hydroxyquinato) Linato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8-hydroxyquinolinato) gallium, bis (10-hydroxybenzo [h] quinolinato) beryllium, bis (10-hydroxybenzo [h] Quinolinato) zinc, bis (2-methyl-8-quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) (o-cresolato) gallium, bis (2-methyl-8-quinolinato) (1-naphtholate) aluminum , Bis (2-methyl-8-quinolinato) (2-naphth) Acrylate), and the like gallium, but are not limited to these.

  The hole blocking layer is a layer that blocks holes from reaching the cathode, and is generally formed under the same conditions as the hole injection layer. Specific examples include, but are not limited to, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes, and the like.

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

  In one embodiment of the present specification, the compound represented by Chemical Formula 1 is included in an organic solar cell or an organic transistor other than the organic light emitting device.

  The compound according to the present specification can operate on the same principle as that applied to an organic light emitting device, also in an organic electronic device including an organic phosphorescent device, an organic solar cell, an organic photoreceptor, an organic transistor and the like.

  Hereinafter, in order to specifically describe the present specification, the present invention will be described in detail by way of examples. However, the embodiments according to the present specification can be transformed into various different forms, and the scope of the present specification is not interpreted as being limited to the embodiments described below. The examples herein are provided to more fully illustrate the present specification to those of average skill in the art.

  <Example>

（化合物１Ａ） （化合物１Ｂ） （化合物１Ｃ）

（化合物１Ｃ） （化合物１Ｄ） （中間体１） Synthesis Example 1 Production of Compound Represented by Intermediate 1

(Compound 1A) (Compound 1B) (Compound 1C)

(Compound 1C) (Compound 1D) (Intermediate 1)

(1) Preparation of Compound 1B Under nitrogen atmosphere, 4 (4-chlorophenyl) (4-hydroxy) methanone (Compound 1A, 100.0 g, 429.81 mmol, manufactured by Alfa chemistry) was added to 1000 ml of acetonitrile, and stirred while being stirred. , Potassium carbonate (118.8 g, 859.62 mmol) were added in admixture with 500 ml of water. After this, 1-butanesalotil fluoride (194.8 g, 644.72 mmol) was slowly added while heating in a water bath. After this, the reaction was terminated after progress of reaction for about 1 hour. After completion of the reaction, the temperature was lowered to normal temperature, the aqueous layer and the organic layer were separated, and the organic layer was distilled under reduced pressure to produce compound 1B (210 g, yield: 95%).

(2) Preparation of Compound 1C The compound 1B (210.2 g, 408.36 mmol), bis (pinacolato) diboron (103.7 g, 408.36 mmol), and potassium acetate (120.2 g, 1225.08 mmol) in a nitrogen atmosphere. ) Was added, added to 1000 ml of tetrahydrofuran (THF) and heated with stirring. At reflux, [1,1′-bis (diphenylphosphino) ferrocene] dichloropalladium (II) (1.8 g, 2.45 mmol) was added, and the mixture was heated and stirred for 24 hours. After completion of the reaction, the temperature was lowered to room temperature and then filtered. The filtrate was poured with water and extracted with chloroform, and the organic layer was dried over anhydrous magnesium sulfate. After distillation under reduced pressure, recrystallization from ethanol produced compound 1C (100.0 g, yield: 72%).

(3) Preparation of Intermediate 1 The compound 1C (39.0 g, 145.67 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (compound 1D, 50.0 g) under a nitrogen atmosphere 145.67 mmol (manufactured by Alfa chemistry) were placed in 300 ml of tetrahydrofuran, stirred and refluxed. After this, potassium carbonate (60.4 g, 437.02 mmol) was dissolved in 200 ml of water and charged, and after sufficient stirring, tetrakistriphenyl-phosphino palladium (5.0 g, 4.37 mmol) was charged. After reacting for 12 hours, the temperature was lowered to room temperature and filtered. The filtrate was extracted with chloroform and water, and the organic layer was dried using magnesium sulfate. After this, the organic layer was distilled under reduced pressure and recrystallized using ethyl acetate. The formed solid was filtered and then dried to produce Intermediate 1 (52.2 g, yield: 80%).

（化合物２Ａ） （中間体１） （化合物２Ｂ） （中間体２）
化合物２Ａ（２４．７ｇ、１０５．９４ｍｍｏｌ、Ａｌｄｒｉｃｈ社製造）を無水テトラヒドロフラン５００ｍｌに入れて、−７８℃に冷却した。この後、撹拌しながらｎ−ブチルリチウム（５０．９ｍＬ、１２７．１３ｍｍｏｌ）を３０分かけてゆっくり滴加した後、１時間反応した。この後、前記中間体１（２８．５ｇ、６３．５７）を固体状態で投入し、ゆっくり常温に昇温して４時間反応した。反応後、水を注いで反応終結後に水層と有機層とを分離した後、有機層は減圧蒸留して、中間体２Ｂを得た。これを再度酢酸５００ｍｌに入れて、撹拌しながら硫酸を１〜２滴触媒として投入した後、還流した。２時間反応した後、生成された固体を濾過し、濾過物を再度クロロホルムに溶かした後、カルシウムカーボネートで飽和した水を用いて中和および抽出した後、有機層を硫酸マグネシウムを用いて乾燥した。この後、有機層を減圧蒸留後、エタノールを用いて再結晶した。生成された固体を濾過後、乾燥して、中間体２（２４．１ｇ、収率：６５％）を製造した。 Synthesis Example 2 Production of Compound Represented by Intermediate 2

(Compound 2A) (Intermediate 1) (Compound 2B) (Intermediate 2)
Compound 2A (24.7 g, 105.94 mmol, manufactured by Aldrich) was placed in 500 ml of anhydrous tetrahydrofuran and cooled to -78.degree. After this, n-butyllithium (50.9 mL, 127.13 mmol) was slowly added dropwise over 30 minutes with stirring, and then reacted for 1 hour. Thereafter, Intermediate 1 (28.5 g, 63.57) was charged in a solid state, and the temperature was raised slowly to room temperature to react for 4 hours. After the reaction, water was poured and after completion of the reaction, the aqueous layer and the organic layer were separated, and then the organic layer was distilled under reduced pressure to obtain Intermediate 2B. This was again added to 500 ml of acetic acid, and 1 to 2 drops of sulfuric acid was added as a catalyst while stirring, and then it was refluxed. After reacting for 2 hours, the produced solid was filtered, the filtrate was redissolved in chloroform, neutralized and extracted with water saturated with calcium carbonate, and then the organic layer was dried using magnesium sulfate . After this, the organic layer was distilled under reduced pressure and then recrystallized using ethanol. The formed solid was filtered and then dried to produce Intermediate 2 (24.1 g, yield: 65%).

（中間体２） （化合物３Ａ） （化合物１）
窒素雰囲気下、前記＜合成例２＞で製造された中間体２（１０．０ｇ、１７ｍｍｏｌ）とカルバゾール（３．４ｇ、２１ｍｍｏｌ、Ｄａｅｊｕｎｇ社製造）、ソジウムｔ−ブトキシド（２．０ｇ、２１ｍｍｏｌ）をキシレン１００ｍｌに入れて、撹拌および還流した。この後、ビス（トリ−タートブチルホスフィン）パラジウム（０．３ｇ、０．５ｍｍｏｌ）を投入した。８時間反応後、常温に温度を下げて濾過した。濾過物をクロロホルムと水で抽出した後、有機層を硫酸マグネシウムを用いて乾燥した。この後、有機層を減圧蒸留後、カラムクロマトグラフィー（クロロホルム：ヘキサン）を用いて精製した後、濃縮液を再度クロロホルム、エチルアセテートを用いて再結晶した。生成された固体を濾過後、乾燥して、化合物１（９．４ｇ、収率：７７％）を製造した。 Synthesis Example 3 Production of Compound Represented by Compound 1

(Intermediate 2) (Compound 3A) (Compound 1)
Intermediate 2 (10.0 g, 17 mmol) prepared in the above <Synthesis example 2>, carbazole (3.4 g, 21 mmol, manufactured by Daejung Co., Ltd.), sodium t-butoxide (2.0 g, 21 mmol) in a nitrogen atmosphere Stir and reflux in 100 ml of xylene. After this, bis (tri-tert-butylphosphine) palladium (0.3 g, 0.5 mmol) was added. After reacting for 8 hours, the temperature was lowered to room temperature and filtered. The filtrate was extracted with chloroform and water, and the organic layer was dried using magnesium sulfate. After this, the organic layer was distilled under reduced pressure and then purified using column chromatography (chloroform: hexane), and then the concentrate was recrystallized again using chloroform and ethyl acetate. The produced solid was filtered and then dried to produce compound 1 (9.4 g, yield: 77%).

  MS: [M + H] + = 714

（中間体２） （化合物４Ａ） （化合物２）
窒素雰囲気下、前記＜合成例２＞で製造された中間体２（１０．０ｇ、１７ｍｍｏｌ）と化合物４Ａ（４．７ｇ、２１ｍｍｏｌ、Ａｌｆａ ｃｈｅｍｉｓｔｒｙ社製造）を１，４−ジオキサン２００ｍｌに入れて、撹拌および還流した。この後、ビス（トリ−タートブチルホスフィン）パラジウム（０．３ｇ、０．５ｍｍｏｌ）を投入した。８時間反応後、常温に温度を下げて濾過した。濾過物をクロロホルムと水で抽出した後、有機層を硫酸マグネシウムを用いて乾燥した。この後、有機層を減圧蒸留後、カラムクロマトグラフィー（クロロホルム：ヘキサン）を用いて精製した後、濃縮液を再度クロロホルム、エチルアセテートを用いて再結晶した。生成された固体を濾過後、乾燥して、化合物２（８．８ｇ、収率：７０％）を製造した。 Synthesis Example 4 Production of Compound Represented by Compound 2

(Intermediate 2) (Compound 4A) (Compound 2)
In a nitrogen atmosphere, the intermediate 2 (10.0 g, 17 mmol) prepared in the above <Synthesis example 2> and the compound 4A (4.7 g, 21 mmol, manufactured by Alfa chemistry) are placed in 200 ml of 1,4-dioxane, Stir and reflux. After this, bis (tri-tert-butylphosphine) palladium (0.3 g, 0.5 mmol) was added. After reacting for 8 hours, the temperature was lowered to room temperature and filtered. The filtrate was extracted with chloroform and water, and the organic layer was dried using magnesium sulfate. After this, the organic layer was distilled under reduced pressure and then purified using column chromatography (chloroform: hexane), and then the concentrate was recrystallized again using chloroform and ethyl acetate. The generated solid was filtered and then dried to produce compound 2 (8.8 g, yield: 70%).

  MS: [M + H] + = 731

（中間体２） （化合物５Ａ） （化合物３）
窒素雰囲気下、前記＜合成例２＞で製造された中間体２（１０．０ｇ、１７ｍｍｏｌ）と化合物５Ａ（４．４ｇ、２１ｍｍｏｌ、Ａｌｆａ ｃｈｅｍｉｓｔｒｙ社製造）を１，４−ジオキサン２００ｍｌに入れて、撹拌および還流した。この後、ポタシウムホスフェート（１０．０ｇ、４７．３１ｍｍｏｌ）を水５０ｍｌに溶かして投入した後、十分に撹拌後、ビス（ジベンジリデンアセトン）パラジウム（０．３ｇ、０．４７ｍｍｏｌ）とトリシクロヘキシルホスフィン（０．３ｍｇ、０．９５ｍｍｏｌ）を投入した。１８時間反応後、常温に温度を下げて濾過した。濾過物をクロロホルムと水で抽出した後、有機層を硫酸マグネシウムを用いて乾燥した。この後、有機層を減圧蒸留後、エチルアセテートを用いて再結晶した。生成された固体を濾過後、乾燥して、化合物３（７．５ｇ、収率：６１％）を製造した。 Synthesis Example 5 Production of Compound Represented by Compound 3

(Intermediate 2) (Compound 5A) (Compound 3)
In a nitrogen atmosphere, the intermediate 2 (10.0 g, 17 mmol) prepared in the above <Synthesis example 2> and the compound 5A (4.4 g, 21 mmol, manufactured by Alfa chemistry) are placed in 200 ml of 1,4-dioxane, Stir and reflux. After this, potassium phosphate (10.0 g, 47.31 mmol) was dissolved in 50 ml of water and charged, and after sufficient stirring, bis (dibenzylideneacetone) palladium (0.3 g, 0.47 mmol) and tricyclohexylphosphine ( 0.3 mg, 0.95 mmol) was added. After reaction for 18 hours, the temperature was lowered to room temperature and filtered. The filtrate was extracted with chloroform and water, and the organic layer was dried using magnesium sulfate. After this, the organic layer was distilled under reduced pressure and recrystallized using ethyl acetate. The generated solid was filtered and then dried to produce compound 3 (7.5 g, yield: 61%).

  MS: [M + H] + = 715

（中間体２） （化合物６Ａ） （化合物４）
窒素雰囲気下、前記＜合成例２＞で製造された中間体２（１０．０ｇ、１５．７７ｍｍｏｌ）と化合物６Ａ（４．１ｇ、２１ｍｍｏｌ、Ａｌｆａ ｃｈｅｍｉｓｔｒｙ社製造）を１，４−ジオキサン２００ｍｌに入れて、撹拌および還流した。この後、ビス（トリ−タートブチルホスフィン）パラジウム（０．３ｇ、０．５ｍｍｏｌ）を投入した。８時間反応後、常温に温度を下げて濾過した。濾過物をクロロホルムと水で抽出した後、有機層を硫酸マグネシウムを用いて乾燥した。この後、有機層を減圧蒸留した後、カラムクロマトグラフィー（クロロホルム：ヘキサン）を用いて精製した後、濃縮液を再度クロロホルム、エチルアセテートを用いて再結晶した。生成された固体を濾過後、乾燥して、化合物４（５．３ｇ、収率：４４％）を製造した。 Synthesis Example 6 Production of Compound Represented by Compound 4

(Intermediate 2) (Compound 6A) (Compound 4)
In a nitrogen atmosphere, the intermediate 2 (10.0 g, 15.77 mmol) prepared in the above <Synthesis example 2> and the compound 6A (4.1 g, 21 mmol, manufactured by Alfa chemistry) are placed in 200 ml of 1,4-dioxane Stir and reflux. After this, bis (tri-tert-butylphosphine) palladium (0.3 g, 0.5 mmol) was added. After reacting for 8 hours, the temperature was lowered to room temperature and filtered. The filtrate was extracted with chloroform and water, and the organic layer was dried using magnesium sulfate. After this, the organic layer was distilled under reduced pressure, and after purification using column chromatography (chloroform: hexane), the concentrate was recrystallized again using chloroform and ethyl acetate. The generated solid was filtered and then dried to produce compound 4 (5.3 g, yield: 44%).

  MS: [M + H] + = 702

（中間体２） （化合物７Ａ） （化合物５）
窒素雰囲気下、前記＜合成例２＞で製造された中間体２（１０．０ｇ、１５．７７ｍｍｏｌ）と化合物７Ａ（３．０ｇ、２１ｍｍｏｌ、Ａｌｆａ ｃｈｅｍｉｓｔｒｙ社製造）を１，４−ジオキサン２００ｍｌに入れて、撹拌および還流した。この後、ビス（トリ−タートブチルホスフィン）パラジウム（０．３ｇ、０．５ｍｍｏｌ）を投入した。８時間反応後、常温に温度を下げて濾過した。濾過物をクロロホルムと水で抽出した後、有機層を硫酸マグネシウムを用いて乾燥した。この後、有機層を減圧蒸留した後、カラムクロマトグラフィー（クロロホルム：ヘキサン）を用いて精製した後、濃縮液を再度クロロホルム、エチルアセテートを用いて再結晶した。生成された固体を濾過後、乾燥して、化合物５（５．７ｇ、収率：５１％）を製造した。 Synthesis Example 7 Production of Compound Represented by Compound 5

(Intermediate 2) (Compound 7A) (Compound 5)
In a nitrogen atmosphere, the intermediate 2 (10.0 g, 15.77 mmol) prepared in the above <Synthesis example 2> and the compound 7A (3.0 g, 21 mmol, manufactured by Alfa chemistry) are placed in 200 ml of 1,4-dioxane Stir and reflux. After this, bis (tri-tert-butylphosphine) palladium (0.3 g, 0.5 mmol) was added. After reacting for 8 hours, the temperature was lowered to room temperature and filtered. The filtrate was extracted with chloroform and water, and the organic layer was dried using magnesium sulfate. After this, the organic layer was distilled under reduced pressure, and after purification using column chromatography (chloroform: hexane), the concentrate was recrystallized again using chloroform and ethyl acetate. The generated solid was filtered and then dried to produce compound 5 (5.7 g, yield: 51%).

  MS: [M + H] + = 650

（中間体２） （化合物８Ａ） （中間体３）
窒素雰囲気下、前記＜合成例２＞で製造された中間体２（３０．０ｇ、５１ｍｍｏｌ）、ビス（ピナコラト）ジボロン（１４．３ｇ、５７ｍｍｏｌ、化合物８Ａ）、および酢酸カリウム（１５．１ｇ、１５４ｍｍｏｌ）を混合し、ジオキサン（Ｄｉｏｘａｎｅ）３００ｍｌに添加し、撹拌しながら加熱した。還流する状態で、［１，１'−ビス（ジフェニルホスフィノ）フェロセン］ジクロロパラジウム（ＩＩ）（０．９ｇ、１．５ｍｍｏｌ）とトリ（シクロヘキシル）ホスフィン（０．９ｇ、３．１ｍｍｌ）を入れて、２４時間加熱、撹拌した。反応終了後、常温に温度を下げた後、濾過した。濾過液に水を注いでクロロホルムで抽出し、有機層を無水硫酸マグネシウムで乾燥した。減圧蒸留後、エタノールで再結晶して、中間体３（２８．１ｇ、収率：８１％）を製造した。 Synthesis Example 8 Production of Compound Represented by Intermediate 3

(Intermediate 2) (Compound 8A) (Intermediate 3)
Intermediate 2 (30.0 g, 51 mmol), bis (pinacolato) diboron (14.3 g, 57 mmol, compound 8A), and potassium acetate (15.1 g, 154 mmol) prepared in <Synthesis Example 2> under a nitrogen atmosphere. ) Was added, added to 300 ml of dioxane (Dioxane) and heated with stirring. At reflux, add [1,1′-bis (diphenylphosphino) ferrocene] dichloropalladium (II) (0.9 g, 1.5 mmol) and tri (cyclohexyl) phosphine (0.9 g, 3.1 mml). The mixture was heated and stirred for 24 hours. After completion of the reaction, the temperature was lowered to room temperature and then filtered. The filtrate was poured with water and extracted with chloroform, and the organic layer was dried over anhydrous magnesium sulfate. After distillation under reduced pressure, recrystallization from ethanol produced Intermediate 3 (28.1 g, yield: 81%).

（中間体３） （化合物９Ａ） （化合物６）
窒素雰囲気下、前記＜合成例８＞で製造された中間体３（１５．０ｇ、２２ｍｍｏｌ）と化合物９Ａ（５．９ｇ、１８．７５ｍｍｏｌ、ＴＣＩ社製造）をテトラヒドロフラン１５０ｍｌに入れて、撹拌および還流した。この後、ポタシウムカーボネート（９．２ｇ、６７ｍｍｏｌ）を水（４０ｍｌ）に溶かして投入した後、十分に撹拌後、テトラキストリフェニル−ホスフィノパラジウム（０．９ｇ、１．５ｍｍｏｌ）を投入した。６時間反応後、常温に温度を下げて濾過した。濾過物をクロロホルムと水で抽出した後、有機層を硫酸マグネシウムを用いて乾燥した。この後、有機層を減圧蒸留した後、カラムクロマトグラフィー（クロロホルム：ヘキサン）を用いて精製した後、濃縮液を再度クロロホルム、エチルアセテートを用いて再結晶した。生成された固体を濾過後、乾燥して、化合物６（１１．４ｇ、収率：６６％）を製造した。 Synthesis Example 9 Production of Compound Represented by Compound 6

(Intermediate 3) (Compound 9A) (Compound 6)
In a nitrogen atmosphere, the intermediate 3 (15.0 g, 22 mmol) prepared in the above <Synthesis example 8> and the compound 9A (5.9 g, 18.75 mmol, manufactured by TCI) are put into 150 ml of tetrahydrofuran, and stirred and refluxed. did. After this, potassium carbonate (9.2 g, 67 mmol) was dissolved in water (40 ml) and charged, and then after sufficient stirring, tetrakistriphenyl-phosphino palladium (0.9 g, 1.5 mmol) was charged. After reacting for 6 hours, the temperature was lowered to room temperature and filtered. The filtrate was extracted with chloroform and water, and the organic layer was dried using magnesium sulfate. After this, the organic layer was distilled under reduced pressure, and after purification using column chromatography (chloroform: hexane), the concentrate was recrystallized again using chloroform and ethyl acetate. The generated solid was filtered and then dried to produce compound 6 (11.4 g, yield: 66%).

  MS: [M + H] + = 779

（中間体３） （化合物１０Ａ） （化合物７）
窒素雰囲気下、前記＜合成例８＞で製造された中間体３（１５．０ｇ、２２ｍｍｏｌ）と化合物１０Ａ（５．９ｇ、１８．７５ｍｍｏｌ、ＴＣＩ社製造）をテトラヒドロフラン１５０ｍｌに入れて、撹拌および還流した。この後、ポタシウムカーボネート（９．２ｇ、６７ｍｍｏｌ）を４０ｍｌの水に溶かして投入した後、十分に撹拌後、テトラキストリフェニル−ホスフィノパラジウム（０．９ｇ、１．５ｍｍｏｌ）を投入した。６時間反応後、常温に温度を下げて濾過した。濾過物をクロロホルムと水で抽出した後、有機層を硫酸マグネシウムを用いて乾燥した。この後、有機層を減圧蒸留後、カラムクロマトグラフィー（クロロホルム：ヘキサン）を用いて精製した後、濃縮液を再度クロロホルム、エチルアセテートを用いて再結晶した。生成された固体を濾過後、乾燥して、化合物７（１２．３ｇ、収率：７１％）を製造した。 Synthesis Example 10 Production of Compound Represented by Compound 7

(Intermediate 3) (Compound 10A) (Compound 7)
In a nitrogen atmosphere, the intermediate 3 (15.0 g, 22 mmol) prepared in the above <Synthesis example 8> and the compound 10A (5.9 g, 18.75 mmol, manufactured by TCI) are put into 150 ml of tetrahydrofuran, and stirred and refluxed. did. Then, potassium carbonate (9.2 g, 67 mmol) was dissolved in 40 ml of water and charged, and then after sufficient stirring, tetrakistriphenyl-phosphino palladium (0.9 g, 1.5 mmol) was charged. After reacting for 6 hours, the temperature was lowered to room temperature and filtered. The filtrate was extracted with chloroform and water, and the organic layer was dried using magnesium sulfate. After this, the organic layer was distilled under reduced pressure and then purified using column chromatography (chloroform: hexane), and then the concentrate was recrystallized again using chloroform and ethyl acetate. The generated solid was filtered and then dried to produce compound 7 (12.3 g, yield: 71%).

  MS: [M + H] + = 778

（中間体２） （化合物１１Ａ） （化合物８）
窒素雰囲気下、前記＜製造例２＞で製造された中間体２（１０．０ｇ、１７ｍｍｏｌ）と化合物１１Ａ（７．３ｇ、２１ｍｍｏｌ、Ａｃｒｏｓ社製造）を１，４−ジオキサン２００ｍｌに入れて、撹拌および還流した。この後、ビス（トリ−タートブチルホスフィン）パラジウム（０．３ｇ、０．５ｍｍｏｌ）を投入した。８時間反応後、常温に温度を下げて濾過した。濾過物をクロロホルムと水で抽出した後、有機層を硫酸マグネシウムを用いて乾燥した。この後、有機層を減圧蒸留した後、カラムクロマトグラフィー（クロロホルム：ヘキサン）を用いて精製した後、濃縮液を再度クロロホルム、エチルアセテートを用いて再結晶した。生成された固体を濾過後、乾燥して、化合物８（６．８ｇ、収率：５１％）を製造した。 Synthesis Example 11 Production of Compound Represented by Compound 8

(Intermediate 2) (Compound 11A) (Compound 8)
In a nitrogen atmosphere, the intermediate 2 (10.0 g, 17 mmol) produced in the above <Production Example 2> and the compound 11A (7.3 g, 21 mmol, manufactured by Acros) are placed in 200 ml of 1,4-dioxane and stirred And reflux. After this, bis (tri-tert-butylphosphine) palladium (0.3 g, 0.5 mmol) was added. After reacting for 8 hours, the temperature was lowered to room temperature and filtered. The filtrate was extracted with chloroform and water, and the organic layer was dried using magnesium sulfate. After this, the organic layer was distilled under reduced pressure, and after purification using column chromatography (chloroform: hexane), the concentrate was recrystallized again using chloroform and ethyl acetate. The generated solid was filtered and then dried to produce compound 8 (6.8 g, yield: 51%).

  MS: [M + H] + = 775

  <Example>

<Experimental Example 1-1>
A glass substrate (corning 7059 glass) thin film coated with ITO (indium tin oxide) to a thickness of 1000 Å was placed in distilled water in which a dispersing agent was dissolved, and ultrasonically cleaned. The detergent is Fischer Co. Using distilled water from Millipore Co. Distilled water secondary filtered with a product filter (Filter) was used. After the ITO was washed for 30 minutes, ultrasonic cleaning was allowed to proceed for 10 minutes twice with distilled water. After distilled water washing was completed, ultrasonic washing was carried out in the order of isopropyl alcohol, acetone and methanol solvent and dried.

  On the ITO transparent electrode thus prepared, hexanitrile hexaazatriphenylene was thermally vacuum deposited to a thickness of 500 Å to form a hole injection layer. On top of that, HT1 (400 Å), a substance that transports holes, was vacuum deposited, and then a compound of host H1 and dopant D1 was vacuum deposited as a light emitting layer to a thickness of 300 Å. The <Compound 1> and LiQ (Lithium Quinolate) prepared in <Synthesis Example 3> were vacuum deposited on the light emitting layer at a weight ratio of 1: 1 to form an electron injecting and transporting layer to a thickness of 350 Å. did. Lithium fluoride (LiF) and aluminum having a thickness of 2,000 Å were sequentially deposited on the electron injecting and transporting layer to a thickness of 12 Å to form a cathode, thereby manufacturing an organic light emitting device.

In the above process, the deposition rate of the organic substance is maintained at 0.4 to 0.7 Å / sec, the lithium fluoride of the cathode is maintained at 0.3 Å / sec, and the deposition rate of aluminum is maintained at 2 Å / sec. The organic light emitting device was manufactured maintaining the degree of 2 × 10 ⁻⁷ torr to 5 × 10 ⁻⁶ torr.

<Experimental Example 1-2>
An organic light emitting device was manufactured in the same manner as in Experimental Example 1-1 except that Compound 2 was used instead of Compound 1 as the electron transporting layer in Experimental Example 1-1.

<Experimental Example 1-3>
An organic light emitting device was manufactured 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 Example 1-4
An organic light emitting diode was manufactured 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 Example 1-5
An organic light emitting device was manufactured 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 Example 1-6
An organic light-emitting device was manufactured 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 Example 1-7
An organic light-emitting device was manufactured 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 device was manufactured in the same manner as in Experimental Example 1-1 except that the following compound ET1 was used instead of compound 1 in Experimental Example 1-1.

Comparative Example 1-2
An organic light-emitting device was manufactured in the same manner as in Experimental Example 1-1 except that the following ET2 compound was used instead of Compound 1 in Experimental Example 1-1.
[ET2]

Comparative Example 1-3
An organic light emitting device was manufactured in the same manner as in Experimental Example 1-1 except that the following compound ET3 was used instead of Compound 1 in Experimental Example 1-1.
[ET3]

Comparative Example 1-4
An organic light emitting device was manufactured 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.

The current density of 10 mA / cm ² is the organic light emitting device manufactured using the respective compounds as the electron transport layer material as in the above-mentioned Experimental Examples 1-1 to 1-7 and Comparative Examples 1-1 to 1-4. in measuring the driving voltage and light emission efficiency was measured 20 mA / cm initial luminance compared to 98% become time ² of current density _{(LT 98).} The results are shown in Table 1 below.

  As can be seen from Table 1 above, it was possible to confirm that the compound represented by Chemical Formula 1 according to one embodiment of the present specification can be used for the electron injection layer and the electron transport layer of the organic electronic device. .

  Compounds 6 and 7 exhibit excellent properties in terms of life when compared with ET3 which is similar to the structures of Compounds 6 and 7 but not the asymmetry, and Compounds 1 to 5 of the present specification It has been found that there is a great advantage in the lifetime part.

10, 11: Organic light emitting device 20: Substrate 30: First electrode 40: Light emitting layer 50: Second electrode 60: Hole injection layer 70: Hole transport layer 80: Electron blocking layer 90: Electron transport layer 100: Electron injection layer

Claims (5)

The compound represented by the following chemical formula 1:
[Chemical formula 1]

In the above Chemical Formula 1,
Q is a C6-C10 monocyclic aromatic group or a monocyclic heterocyclic group,
L ₁ and L ₂ are the same or different from each other, each independently being a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group,
Ar ₁ is hydrogen; deuterium; substituted or unsubstituted alkyl group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted aryl group; or substituted or unsubstituted heteroaryl group,
Ar ₂ represents hydrogen, deuterium, substituted or unsubstituted alkyl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted phosphine oxide group, substituted or unsubstituted aryl group having 6 to 16 carbon atoms, or A substituted or unsubstituted heteroaryl group,
R _{1 to} R ₃ are the same or different from each other and each independently hydrogen; deuterium; halogen group; cyano group; substituted or unsubstituted alkyl group; substituted or unsubstituted aryl group; or substituted or unsubstituted hetero An aryl group,
a is an integer of 1 to 4 and
b is an integer of 1 to 4 and
c is an integer of 1 to 4 and
When a is 2 or more, two or more R _{1 's} are the same or different from each other,
When b is 2 or more, two or more R _{2 's} are the same or different from each other,
When c is 2 or more, 2 or more of R ₃ are the same or different from each other. The compound according to claim 1, wherein the chemical formula 1 is represented by the following chemical formula 2 or 3.
[Chemical formula 2]

[Chemical formula 3]

In the above formulas 2 and 3,
The definitions for Q, L ₁ , L ₂ , Ar ₂ , R _{1 to} R ₃ , and a to c are the same as those defined in Chemical Formula 1 above,
Two or more of X _{1 to} X ₃ are N, and the rest are the same or different from one another, and each independently N or CR,
One or more of X _{4 to} X ₆ are N, and the rest are the same or different from one another, and each independently N or CR,
R is hydrogen,
Ar _{3 to} Ar ₆ are the same or different from each other, each independently hydrogen; deuterium; substituted or unsubstituted alkyl group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted aryl group; substituted or unsubstituted Is a heteroaryl group of The compound according to claim 1, wherein the chemical formula 1 is any one selected from the following compounds:

.   An organic electronic device comprising: a first electrode; a second electrode provided opposite to the first electrode; and one or more organic layers provided between the first electrode and the second electrode An organic electronic device, wherein one or more of the organic layers contain the compound according to any one of claims 1 to 3.   The organic electronic device according to claim 4, wherein the organic layer includes an electron injection layer or an electron transport layer, and the electron transport layer or the electron injection layer includes the compound.

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