JP6859587B2 - Compounds and organic electronic devices containing them - Google Patents

Description

This application claims the benefit of the filing date of Korean Patent Application No. 10-2016-0037222 filed with the Korean Intellectual Property Office on March 28, 2016, the entire contents of which are incorporated herein by reference.

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

A typical example of an organic electronic device is an organic light emitting device. Generally, the organic light emission phenomenon refers to a phenomenon in which electric energy is converted into light energy by using an organic substance. An organic light emitting device utilizing the organic light emitting phenomenon usually has a structure including an anode and a cathode, and an organic substance layer between them. Here, the organic substance layer often has a multi-layered structure composed of different substances in order to enhance the efficiency and stability of the organic light emitting device. For example, a hole injection layer, a hole transport layer, and a light emitting layer. , Electron transport layer, electron injection layer, etc. In such a structure of an organic light emitting element, when a voltage is applied between two electrodes, holes are injected from the anode and electrons are injected into the organic material layer from the cathode, and when the injected holes come into contact with electrons. , Excitons are formed and emit light when the excitons fall back to the basal state.

The development of new materials for organic light emitting devices as described above continues to be required.

International Patent Application Publication No. 2003-012890

The present specification provides a compound and an organic electronic component containing the compound.

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 chemical formula 1,
Q is a monocyclic aromatic group having 6 to 10 carbon atoms or a monocyclic heterocyclic group.
L ₁ and L ₂ are the same or different from each other and are independently bonded; substituted or unsubstituted arylene groups; or substituted or unsubstituted heteroarylene groups, respectively.
Ar ₁ is a 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.
Ar ₂ is hydrogen; heavy hydrogen; 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 It is a substituted or unsubstituted heteroaryl group and
R _{1 to} R ₃ are the same or different from each other, and independently of each other, hydrogen; heavy hydrogen; halogen group; cyano group; substituted or unsubstituted alkyl group; substituted or unsubstituted phosphine oxide group; 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 and
c is an integer of 1 to 4 and
when a is 2 or more, two or more _{R 1,} equal to or different from each other,
When b is 2 or more, R ₂ of 2 or more are the same or different from each other.
When c is 2 or more, R ₃ of 2 or more are the same or different from each other.

Further, in the present specification, the first electrode, the second electrode provided facing the first electrode, and one or more organic substances provided between the first electrode and the second electrode are described. Provided is an organic electronic device containing the above-mentioned compound, wherein one or more layers of the organic material layer contain the above-mentioned compound.

The compound according to one embodiment of the present specification is used for an organic electronic device including an organic light emitting device, lowers the driving voltage of the organic electronic device, improves the optical efficiency, and obtains the thermal stability of the compound. Life characteristics can be improved.

It shows the organic electronic device 10 which concerns on one Embodiment of this specification. It shows the organic electronic device 11 which concerns on another embodiment of this specification.

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

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

By introducing various substituents into the core structure, the compound of the chemical formula 1 can have properties suitable for use in an organic substance layer used in an organic light emitting device, and the core structure of the chemical formula 1 of the present application can be used. The characteristics and effects possessed play a role of improving the conductivity in the device, lowering the driving voltage, and improving the luminous efficiency. Specifically, it is as follows.

In the present specification, examples of substituents will be described below, but the present invention is not limited thereto.

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

Means the site to be connected.

The term "substituent" means that the hydrogen atom bonded to the carbon atom of the compound is changed to another substituent, and the position to be substituted is the position where the hydrogen atom is substituted, that is, the substituent can be substituted. When two or more substituents are substituted, the two or more substituents may be the same or different from each other.

As used herein, the term "substituted or unsubstituted" refers to dehydrogen; 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; and substituted with one or more substituents selected from the group consisting of substituted or unsubstituted heterocyclic groups, or 2 of the above exemplified substituents. It means that the above substituents are substituted with the linked substituents.

As used herein, the halogen group may be fluorine, chlorine, bromine, or iodine.

In the present specification, the alkyl group may be a straight chain or a branched chain, and the number of carbon atoms is not particularly limited, but those of 1 to 50 are preferable. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl. , Isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl- There are, but are not limited to, propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl and the like.

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

As used herein, the alkoxy group may be a straight chain, a branched chain or a ring chain. The number of carbon atoms 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, etc. may be used, but are limited thereto. It's not something.

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 a phenyl group, a biphenyl group, a terphenyl group, a quarter phenyl 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 those having 6 to 30 carbon atoms are preferable. Specifically, the polycyclic aryl group may be a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a peryleneyl group, a chrysenyl group, a fluorenyl group, or 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。 If the fluorenyl group is substituted

However, it is not limited to these.

In the present specification, the heteroaryl group is a heterocyclic group containing one or more of N, O, S, Si, and Se as heteroatoms, and the number of carbon atoms is not particularly limited, but the number of carbon atoms is 2 to 2. 50 is preferable. Examples of heteroaryl groups include thiophene group, furan group, pyrrol group, imidazole group, thiazole group, oxazole group, oxazole group, triazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group, triazole group, acridyl. Group, pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyridopyrimidinyl group, pyridopyrazinyl group, pyrazinopyrazinyl group, isoquinolin group, indole group, carbazole group, benzoxazole group, benzimidazole Groups, benzothiazole groups, benzocarbazole groups, benzothiophene groups, dibenzothiophene groups, benzofuranyl groups, phenanthroline groups, thiazolyl groups, isooxazolyl groups, oxadiazolyl groups, thiadiazolyl groups, benzothiazolyl groups, and dibenzofuranyl groups. However, it is not limited to these.

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

In the present specification, a monocyclic heterocyclic group means a ring containing one or more of N, O, or S atoms as a heteroatom, for example, pyridine, pyrimidine, pyridazine, triazine, pyran, and the like. Thiopyran, diazine, pyrazine, and the like may be selected from the examples of the heteroaryl group, but are not limited thereto.

As used herein, an arylene group means an aryl group having two bonding positions, that is, a divalent group. The above description of the aryl group is applicable, except that each of these is a divalent group.

As used herein, a heteroarylene group means a heteroaryl group having two bonding positions, that is, a divalent group. The above description of heteroaryl groups is applicable, except that they are each divalent groups.

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

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

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

In one embodiment of the specification, Q is benzene.

In one embodiment of the specification, Q is pyridine.

In one embodiment of the specification, L ₁ and L ₂ are the same or different from each other and are independently bonded; substituted or unsubstituted arylene groups; or substituted or unsubstituted heteroarylene groups, respectively.

In one embodiment of the present specification, L ₁ and L ₂ are the same or different from each other and are independently bonded; or substituted or unsubstituted arylene groups having 6 to 30 carbon atoms.

In one embodiment of the specification, L ₁ and L ₂ are the same or different from each other and are independent of each other, directly bonded; substituted or unsubstituted phenylene group; substituted or unsubstituted naphthylene group; or substituted or unsubstituted. It is an anthrasenilen group.

In one embodiment of the specification, L ₁ and L ₂ are the same or different from each other and are independently directly linked; 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 herein, Ar _1, equal to or different from each other, each independently, hydrogen, deuterium, 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 specification, Ar ₁ is a substituted or unsubstituted heteroaryl group.

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

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

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

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

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

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

In one embodiment of the specification, Ar ₁ is a triazine group in which one or more substituents selected from the group consisting of a substituted or unsubstituted aryl group; and a substituted or unsubstituted heteroaryl group are substituted or unsubstituted. Is.

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

In one embodiment of the 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 phenyl group. Turphenyl group; one or more substituents selected from the group consisting of a substituted or unsubstituted dibenzofuran group, a substituted or unsubstituted dibenzothiophene group, a substituted or unsubstituted carbazole group is a substituted or unsubstituted triazine group. ..

In one embodiment of the specification, Ar ₁ is an aryl group or a heteroaryl group substituted or unsubstituted phenyl group; an aryl group or a heteroaryl group substituted or an unsubstituted biphenyl group; an aryl group or a heteroaryl group. Substituted or unsubstituted naphthyl group; substituted or unsubstituted phenanthrene group with aryl group or heteroaryl group; substituted or unsubstituted terphenyl group with aryl group or heteroaryl group; and substituted or non-substituted with aryl group or heteroaryl group 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 one or more selected from the group consisting of a phenyl group substituted or unsubstituted with a heteroaryl group; a naphthyl group; a biphenyl group; a phenanthrene group; a terphenyl group; and a dibenzofuran group. Substituents are substituted or unsubstituted triazine groups.

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

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

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

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

In one embodiment of the present specification, Ar ₂ is a group consisting of hydrogen; dear hydrogen; or 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. The one or more substituents selected from the above are substituted or unsubstituted aryl groups having 6 to 16 carbon atoms.

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

In one embodiment of the specification, Ar ₂ is selected from the group consisting of hydrogen; heavy hydrogen; or a cyano group, fluorine, a fluorine-substituted or unsubstituted methyl group, and a fluorine-substituted or unsubstituted methoxy group. One or more substituents are substituted or unsubstituted aryl groups having 6 to 16 carbon atoms.

In one embodiment of the present specification, Ar ₂ is one or more substituents selected from the group consisting of a cyano group, a fluorine, a methyl group substituted or unsubstituted with fluorine, and a methoxy group substituted or unsubstituted with fluorine. Is a substituted or unsubstituted phenyl group; one or more substituents selected from the group consisting of a cyano group, a fluorine, a fluoride substituted or unsubstituted methyl group, and a fluorine substituted or unsubstituted methoxy group are substituted or unsubstituted. Substituent phenanthrene group; or one or more substituents selected from the group consisting of a cyano group, a fluorine, a methyl group substituted or unsubstituted with fluorine, and a methoxy group substituted or unsubstituted with fluorine is a substituted or unsubstituted fluorenyl. It is a group.

In one embodiment of the specification, Ar ₂ is one or more substituents selected from the group consisting of a cyano group, a 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 specification, Ar ₂ is substituted with one or more substituents selected from the group consisting of a cyano group, a fluorine, a fluorine-substituted methyl group, and a fluorine-substituted or unsubstituted methoxy group. Alternatively, an unsubstituted phenyl group; a phenanthrene group; or a methyl group or a cyano group is a substituted or unsubstituted fluorenyl group.

In one embodiment of the present specification, one or more substituents selected from the group consisting of a cyano group, a fluorine, a methyl group substituted with fluorine, and a methoxy group substituted with fluorine are substituted or unsubstituted phenyl groups. A phenanthrene group; or a 9,9-dimethylfluorenyl group substituted with a cyano group.

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

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

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

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

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

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

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

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

In one embodiment herein, R ₁ to R _3, equal to or different from each other, each independently, hydrogen, deuterium, halogen, cyano groups, substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl Group; or a substituted or unsubstituted heteroaryl group.

In one embodiment _herein, R 1 to R ₃ is 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 chemical 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 N or CR, which are the same or different from each other and are independent of each other.
One or more of X _{4 to} X ₆ are N, and the rest are N or CR, which are the same or different from each other and are independent of each other.
The R is hydrogen,
Ar _{3 to} Ar ₆ are the same or different from each other, and independently of each other, hydrogen; deuterium; substituted or unsubstituted alkyl group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted aryl group; substituted or unsubstituted. Heteroaryl group.

In one embodiment _herein, X 1 to X ₃ is N.

In one embodiment herein, _{X 4} is CR, _{X 5} and _{X 6} are N.

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

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

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

In one embodiment of the specification, Ar ₃ and Ar ₄ are the same or different from each other and are independently substituted or unsubstituted aryl groups having 6 to 20 carbon atoms; or substituted or unsubstituted having 12 to 20 carbon atoms. Heteroaryl group.

In one embodiment of the specification, Ar ₃ and Ar ₄ are the same or different from each other and are independent of each other, substituted or unsubstituted phenyl group; substituted or unsubstituted biphenyl group; substituted or unsubstituted naphthyl group; substituted. Alternatively, it is an unsubstituted phenanthrene group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted dibenzofuran group; a substituted or unsubstituted dibenzothiophene group; or a substituted or unsubstituted carbazole group.

In one embodiment of the specification, Ar ₃ and Ar ₄ are identical or different from each other and independently substituted or unsubstituted with an aryl group or a heteroaryl group; substituted or non-substituted with an aryl group or a heteroaryl group. Substituted biphenyl group; aryl group or heteroaryl group substituted or unsubstituted naphthyl group; aryl group or heteroaryl group substituted or unsubstituted phenanthrene group; aryl group or heteroaryl group substituted or unsubstituted terphenyl group Alternatively, it is a dibenzofuran group substituted or unsubstituted with an aryl group or a heteroaryl group.

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

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

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

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

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

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

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

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

［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 chemical 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 N or CR, which are the same or different from each other and are independent of each other.
The R is hydrogen,
One or more of X _{4 to} X ₆ are N, and the rest are N or CR, which are the same or different from each other and are independent of each other.
Ar _{3 to} Ar ₆ are the same or different from each other, and independently of each other, hydrogen; deuterium; substituted or unsubstituted alkyl group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted aryl group; substituted or unsubstituted. Heteroaryl group.

In one embodiment _herein, X 1 to X ₃ is N.

In one embodiment herein, _{X 4} is CR, _{X 5} and _{X 6} are N.

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

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

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

In one embodiment of the specification, Ar ₃ and Ar ₄ are the same or different from each other and are independently substituted or unsubstituted aryl groups having 6 to 20 carbon atoms; or substituted or unsubstituted having 12 to 20 carbon atoms. Heteroaryl group.

In one embodiment of the specification, Ar ₃ and Ar ₄ are the same or different from each other and are independent of each other, substituted or unsubstituted phenyl group; substituted or unsubstituted biphenyl group; substituted or unsubstituted naphthyl group; substituted. Alternatively, it is an unsubstituted phenanthrene group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted dibenzofuran group; a substituted or unsubstituted dibenzothiophene group; or a substituted or unsubstituted carbazole group.

In one embodiment of the specification, Ar ₃ and Ar ₄ are identical or different from each other and independently substituted or unsubstituted with an aryl group or a heteroaryl group; substituted or non-substituted with an aryl group or a heteroaryl group. Substituted biphenyl group; aryl group or heteroaryl group substituted or unsubstituted naphthyl group; aryl group or heteroaryl group substituted or unsubstituted phenanthrene group; aryl group or heteroaryl group substituted or unsubstituted terphenyl group Alternatively, it is a dibenzofuran group substituted or unsubstituted with an aryl group or a heteroaryl group.

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

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

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

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

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

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

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

［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 chemical 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 N or CR, which are the same or different from each other and are independent of each other.
One or more of X _{4 to} X ₆ are N, and the rest are N or CR, which are the same or different from each other and are independent of each other.
The R is hydrogen,
Ar _{3 to} Ar ₆ are the same or different from each other, and independently of each other, hydrogen; deuterium; substituted or unsubstituted alkyl group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted aryl group; substituted or unsubstituted. Heteroaryl group.

In one embodiment _herein, X 1 to X ₃ is N.

In one embodiment herein, _{X 4} is CR, _{X 5} and _{X 6} are N.

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

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

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

In one embodiment of the specification, Ar ₃ and Ar ₄ are the same or different from each other and are independently substituted or unsubstituted aryl groups having 6 to 20 carbon atoms; and substituted or unsubstituted having 12 to 20 carbon atoms, respectively. Heteroaryl group.

In one embodiment of the specification, Ar ₃ and Ar ₄ are the same or different from each other and are independent of each other, substituted or unsubstituted phenyl group; substituted or unsubstituted biphenyl group; substituted or unsubstituted naphthyl group; substituted. Alternatively, it is an unsubstituted phenanthrene group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted dibenzofuran group, a substituted or unsubstituted dibenzothiophene group, or a substituted or unsubstituted carbazole group.

In one embodiment of the specification, Ar ₃ and Ar ₄ are identical or different from each other and independently substituted or unsubstituted with an aryl group or a heteroaryl group; substituted or non-substituted with an aryl group or a heteroaryl group. Substituted biphenyl group; aryl group or heteroaryl group substituted or unsubstituted naphthyl group; aryl group or heteroaryl group substituted or unsubstituted phenanthrene group; aryl group or heteroaryl group substituted or unsubstituted terphenyl group ; And an aryl group or a heteroaryl group substituted or unsubstituted dibenzofuran group.

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

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

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

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

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

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

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

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

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

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

According to one embodiment of the present specification, the compound of the chemical 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 a production method described later. In the production examples described later, typical examples will be described, but if necessary, substituents can be added or excluded, and the positions of the substituents can be changed. In addition, starting materials, reactants, reaction conditions and the like can be changed based on the techniques known in the art.

The present specification also provides an organic electronic component containing the above-mentioned compound.

In one embodiment of the present specification, one or more layers of a first electrode, a second electrode provided facing the first electrode, and between the first electrode and the second electrode. An organic electronic element including an organic material layer, wherein one or more layers of the organic material layer provide an organic electronic element containing the compound.

As used herein, when one member is located "above" another member, this is not only when one member is in contact with another member, but also between other members. Including the case where is present.

In the present specification, when a component is referred to as "contains" a component, this means that the other component can be further included rather than excluding the other component unless otherwise specified. To do.

The organic material layer of the organic electronic device described in the present specification may have a single-layer structure, but may also have a multi-layer structure in which two or more organic material layers are laminated. For example, as a typical example of the organic electronic device of the present invention, the organic light emitting device may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer and the like as an organic substance layer. it can. However, the structure of the organic electronic device is not limited to this, 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 element, an organic solar cell, an organic photoconductor (OPC), and an organic transistor.

Hereinafter, an organic light emitting device will be illustrated.

In one embodiment of the specification, the organic layer comprises a light emitting layer and the light emitting layer comprises the compound.

In one embodiment of the specification, the organic layer comprises a hole injecting layer or a hole transporting layer, and the hole injecting layer or the hole transporting layer comprises the compound.

In one embodiment of the specification, the organic layer comprises an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer comprises the compound.

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

In one embodiment of the present specification, 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. Further includes one layer or two or more layers to be formed.

In one embodiment of the present specification, the organic light emitting element is provided between a first electrode, a second electrode provided facing the first electrode, and between the first electrode and the second electrode. The two or more organic substances include the light emitting layer 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. At least one of the layers comprises said compound. In one embodiment of the present specification, two or more organic layers are selected from the group consisting of an electron transport layer, an electron injection layer, a layer that simultaneously performs electron transport and electron injection, and a hole blocking layer. You may.

In one embodiment of the specification, the organic layer comprises two or more electron transport layers, and at least one of the two or more electron transport layers comprises 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. It may be.

Further, in one embodiment of the present specification, when the compound is contained in each of the two or more electron transport layers, the other materials excluding the compound may be the same 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. Including further.

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

When the organic substance layer containing the compound of Chemical Formula 1 is an electron transporting layer, the electron transporting layer may further contain an n-type dopant. As the n-type dopant, those known in the art can be used, and for example, a metal or a metal complex can be used. According to one example, the electron transport layer containing the compound of Chemical Formula 1 may further contain LiQ.

In one embodiment of the present specification, the weight ratio of the compound of the chemical 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 organic light emitting device having an inverted type in which a cathode, one or more organic layers, and an anode are sequentially laminated 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 an organic light emitting element 10 in which a first electrode 30, a light emitting layer 40, and a second electrode 50 are sequentially laminated on a substrate 20. FIG. 1 is an exemplary structure of an organic light emitting device according to an embodiment of the present specification, and may further include another organic substance layer.

In FIG. 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 are shown on the substrate 20. The structure of an organic light emitting device in which 50s are sequentially laminated is illustrated. FIG. 2 is an exemplary structure according to an embodiment of the present specification, which may further include other organic layers.

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

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

The organic light emitting element of the present specification is a material and method known in the art except that one or more layers of the organic material layer contain the compound, that is, the compound represented by the chemical formula 1. Can be manufactured.

For example, the organic light emitting device of the present specification can be manufactured by sequentially laminating a first electrode, an organic substance layer, and a second electrode on a substrate. At this time, using a PVD (Physical Vapor Deposition) method such as a sputtering method or an electron beam evaporation method, a metal or a conductive metal oxide or an alloy thereof is used on the substrate. 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 on the anode, and then a substance that can be used as a cathode is vapor-deposited on the organic layer. It can be manufactured by. In addition to this method, an organic light emitting device can be produced by depositing an organic substance layer and an anode substance in this order on a substrate.

Further, the compound of the chemical formula 1 is formed in the organic substance layer not only by the vacuum vapor deposition method but also by the solution coating method at the time of manufacturing the organic light emitting device. Here, the solution coating method means, but is not limited to, spin coating, dip coating, doctor braiding, inkjet printing, screen printing, spraying method, roll coating and the like.

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

In one embodiment of the 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, a material having a large work function is usually preferable so that holes can be smoothly injected into the organic substance layer. Specific examples of the anode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc and gold, or alloys thereof; zinc oxide, indium oxide, indium tin oxide (ITO), indium. Metal oxides such as zinc oxide (IZO); _{Combinations of metals and oxides such as ZnO: Al or SNO 2} : Sb; poly (3-methylthiophene), poly [3,4- (ethylene-1) , 2-Dioxy) thiophene] (PEDOT), conductive polymers such as polypyrrole and polyaniline, but are not limited to these.

The cathode substance is usually preferably a substance having a small work function so that electrons can be easily injected into the organic substance layer. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, ittrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; LiF / Al or LiO ₂ /. There are substances having a multi-layer structure such as Al, but the present invention is not limited to these.

The hole injecting substance is a layer for injecting holes from an electrode, and the hole injecting substance has an ability to transport holes, and has a hole injecting effect from an anode, a light emitting layer or a light emitting material. On the other hand, a compound having an excellent hole injection effect, preventing the transfer of excitators generated in the light emitting layer to the electron injection layer or the electron injection material, and having an excellent thin film forming ability is preferable. It is preferable that the hole injecting substance HOMO (highest expanded molecular orbital) is between the work function of the anode material and the HOMO of the peripheral organic matter layer. Specific examples of the hole injecting substance include metal porphyrin, oligothiophene, arylamine-based organic substances, hexanitrile hexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based organic substances. There are, but are not limited to, anthraquinone and polyaniline-polythiophene-based conductive polymers.

The hole transport layer is a layer that receives holes from the hole injection layer and transports holes to the light emitting layer, and as a hole transport substance, receives hole transport from the anode or the hole injection layer and emits light. A substance that can be transferred to a layer and has a high mobility to holes is preferable. Specific examples include, but are not limited to, arylamine-based organic substances, conductive polymers, and block copolymers having both conjugated and non-conjugated moieties.

The electron blocking layer is a layer capable of preventing holes injected from the hole injection layer from entering the electron injection layer via the light emitting layer to improve the life and efficiency of the device, and if necessary. In addition, it is formed in an appropriate portion between the light emitting layer and the electron injection layer using a known material.

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

The light emitting layer can include a host material and a dopant material. Host materials include condensed aromatic ring derivatives, heterocyclic ring-containing compounds, and the like. Specifically, the condensed aromatic ring derivative includes anthracene derivative, pyrene derivative, naphthalene derivative, pentacene derivative, phenanthrene compound, fluoranthene compound and the like, and the heterocycle-containing compound includes a compound, a dibenzofuran derivative and a ladder-type furan compound. , Pyrimidine derivatives, etc., but are not limited to these.

Examples of the dopant material include an aromatic amine derivative, a styrylamine compound, a boron complex, a fluorantene compound, and a metal complex. Specifically, the aromatic amine derivative includes a fused aromatic ring derivative having a substituted or unsubstituted arylamino group, such as pyrene, anthracene, chrysen, and perifrantene having an arylamino group, and a styrylamine compound. Is a compound in which at least one arylvinyl group is substituted with a substituted or unsubstituted arylamine, and 1 or 2 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. Specifically, there are, but are not limited to, styrylamine, styryldiamine, styryltriamine, styryltetraamine and the like. Further, examples of the metal complex include, but are not limited to, an iridium complex and a platinum complex.

The electron-transporting substance of the electron-transporting layer is a layer that receives electrons from the electron-injecting layer and transports electrons to the light-emitting layer, and the electron-transporting substance is a substance that can be well received by electron injection from the cathode and transferred to the light-emitting layer. Therefore, a substance having a high mobility to electrons is preferable. Specific examples include, but are not limited to, an Al complex of 8-hydroxyquinoline _{; a complex containing Alq 3} ; an organic radical compound; and a hydroxyflavon-metal complex. The electron transport layer can be used with any desired cathode material, such as that used in the prior art. In particular, an example of a suitable cathode material is a normal material that has a low work function and is followed by an aluminum or silver layer. Specifically, they are cesium, barium, calcium, ytterbium, and samarium, each of which is followed by an aluminum layer or a silver layer.

The electron injection layer is a layer for injecting electrons from an electrode, has an ability to transport electrons, has an electron injection effect from a cathode, and has an excellent electron injection effect on a light emitting layer or a light emitting material, and emits light. A compound that prevents excitons generated in the layer from moving to the hole injection layer and has an excellent thin film forming ability is preferable. Specifically, fluorenone, anthracinodimethane, diphenoquinone, thiopyrandioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylidenemethane, anthrone and their derivatives, metal complex compounds, etc. And, but not limited to, nitrogen-containing 5-membered ring derivatives.

Examples of the metal complex compound include 8-hydroxyquinolinat lithium, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, bis (8-hydroxyquinolinato) manganese, and tris (8-hydroxyquino). Linato) Aluminum, Tris (2-Methyl-8-Hydroxyquinolinato) Aluminum, Tris (8-Hydroxyquinolinato) gallium, Bis (10-Hydroxybenzo [h] Kinolinato) Berylium, Bis (10-Hydroxybenzo [h] Kinolinato) Zinc, bis (2-methyl-8-quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) (o-cresolate) gallium, bis (2-methyl-8-quinolinato) (1-naphtholate) aluminum , Bis (2-methyl-8-quinolinato) (2-naphtholate) gallium, and the like, but are not limited thereto.

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, BCPs, and aluminum complexes.

The organic light emitting device according to the present specification may be a front light emitting type, a rear light emitting type, or a double-sided light emitting type, depending on the material used.

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

The compound according to the present specification can act on an organic electronic device including an organic phosphorescent device, an organic solar cell, an organic photoconductor, an organic transistor, etc. on the same principle as that applied to an organic light emitting device.

Hereinafter, in order to specifically explain the present specification, examples will be given and described in detail. However, the examples according to the present specification can be transformed into various different forms, and the scope of the present specification is not construed as being limited to the examples described below. The examples herein are provided to provide a more complete description of the specification to those with average knowledge 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 the compound represented by Intermediate 1

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

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

(1) Production of Compound 1B Under a nitrogen atmosphere, 4 (4-chlorophenyl) (4-hydroxy) methanone (Compound 1A, 100.0 g, 429.81 mmol, manufactured by Alpha Chemistry) was added to 1000 ml of acetonitrile and stirred. , Potassium carbonate (118.8 g, 859.62 mmol) was added by mixing with 500 ml of water. Then, 1-butanesarotyl fluoride (194.8 g, 644.72 mmol) was slowly added while heating in a water bath. After that, the reaction was terminated after the reaction proceeded for about 1 hour. After completion of the reaction, the temperature was lowered to room temperature, the aqueous layer and the organic layer were separated, and then the organic layer was distilled under reduced pressure to produce Compound 1B (210 g, yield: 95%).

(2) Production of Compound 1C Under a nitrogen atmosphere, 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). ) Was mixed, added to 1000 ml of tetrahydrofuran (THF), and heated with stirring. In a refluxed state, [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. Water was poured into the filtrate and extracted with chloroform, and the organic layer was dried over anhydrous magnesium sulfate. After distillation under reduced pressure, it was recrystallized from ethanol to produce compound 1C (100.0 g, yield: 72%).

(3) Production of Intermediate 1 Under a nitrogen atmosphere, the compound 1C (39.0 g, 145.67 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (Compound 1D, 50.0 g, 145.67 mmol (manufactured by Alpha Chemistry) was placed in 300 ml of tetrahydrofuran, stirred and refluxed. Then, potassium carbonate (60.4 g, 437.02 mmol) was dissolved in 200 ml of water and added, and after sufficient stirring, tetrakistriphenyl-phosphinopalladium (5.0 g, 4.37 mmol) was added. After the reaction for 12 hours, the temperature was lowered to room temperature and the mixture was filtered. After extracting the filtrate 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 produced solid was filtered and 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 the 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 anhydrous tetrahydrofuran and cooled to −78 ° C. Then, n-butyllithium (50.9 mL, 127.13 mmol) was slowly added dropwise over 30 minutes with stirring, and then the reaction was carried out for 1 hour. After that, the intermediate 1 (28.5 g, 63.57) was added in a solid state, the temperature was slowly raised to room temperature, and the reaction was carried out for 4 hours. After the reaction, water was poured to separate the aqueous layer and the organic layer after the reaction was completed, and then the organic layer was distilled under reduced pressure to obtain Intermediate 2B. This was put into 500 ml of acetic acid again, sulfuric acid was added as a catalyst in 1 to 2 drops with stirring, and then reflux was performed. After reacting for 2 hours, the produced solid was filtered, the filtrate was dissolved again in chloroform, neutralized and extracted with water saturated with calcium carbonate, and the organic layer was dried over magnesium sulfate. .. Then, the organic layer was distilled under reduced pressure and then recrystallized using ethanol. The produced solid was filtered and 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 the compound represented by Compound 1

(Intermediate 2) (Compound 3A) (Compound 1)
Under a nitrogen atmosphere, intermediate 2 (10.0 g, 17 mmol) produced in <Synthesis Example 2>, carbazole (3.4 g, 21 mmol, manufactured by Daejung), and sodium t-butoxide (2.0 g, 21 mmol) were added. It was placed in 100 ml of xylene, stirred and refluxed. After this, bis (tritartbutylphosphine) palladium (0.3 g, 0.5 mmol) was added. After the reaction for 8 hours, the temperature was lowered to room temperature and the mixture was filtered. After extracting the filtrate with chloroform and water, the organic layer was dried over magnesium sulfate. Then, the organic layer was distilled under reduced pressure, purified by column chromatography (chloroform: hexane), and the concentrated solution was recrystallized from chloroform and ethyl acetate again. The produced solid was filtered and 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 the compound represented by Compound 2

(Intermediate 2) (Compound 4A) (Compound 2)
Under a nitrogen atmosphere, Intermediate 2 (10.0 g, 17 mmol) produced in <Synthesis Example 2> and Compound 4A (4.7 g, 21 mmol, manufactured by Alpha Chemistry) were added to 200 ml of 1,4-dioxane. Stirred and refluxed. After this, bis (tritartbutylphosphine) palladium (0.3 g, 0.5 mmol) was added. After the reaction for 8 hours, the temperature was lowered to room temperature and the mixture was filtered. After extracting the filtrate with chloroform and water, the organic layer was dried over magnesium sulfate. Then, the organic layer was distilled under reduced pressure, purified by column chromatography (chloroform: hexane), and the concentrated solution was recrystallized from chloroform and ethyl acetate again. The produced solid was filtered and 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 the compound represented by Compound 3

(Intermediate 2) (Compound 5A) (Compound 3)
Under a nitrogen atmosphere, Intermediate 2 (10.0 g, 17 mmol) produced in <Synthesis Example 2> and Compound 5A (4.4 g, 21 mmol, manufactured by Alpha Chemistry) were added to 200 ml of 1,4-dioxane. Stirred and refluxed. After that, potassium phosphate (10.0 g, 47.31 mmol) was dissolved in 50 ml of water and added, and after thorough stirring, bis (dibenzylideneacetone) palladium (0.3 g, 0.47 mmol) and tricyclohexylphosphine (0.3 g, 0.47 mmol) were added. 0.3 mg, 0.95 mmol) was added. After the reaction for 18 hours, the temperature was lowered to room temperature and the mixture was filtered. After extracting the filtrate 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 produced solid was filtered and 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 the compound represented by Compound 4

(Intermediate 2) (Compound 6A) (Compound 4)
Under a nitrogen atmosphere, Intermediate 2 (10.0 g, 15.77 mmol) produced in <Synthesis Example 2> and Compound 6A (4.1 g, 21 mmol, manufactured by Alfa Chemistry) were placed in 200 ml of 1,4-dioxane. The mixture was stirred and refluxed. After this, bis (tritartbutylphosphine) palladium (0.3 g, 0.5 mmol) was added. After the reaction for 8 hours, the temperature was lowered to room temperature and the mixture was filtered. After extracting the filtrate with chloroform and water, the organic layer was dried over magnesium sulfate. Then, the organic layer was distilled under reduced pressure, purified by column chromatography (chloroform: hexane), and the concentrated solution was recrystallized from chloroform and ethyl acetate again. The produced solid was filtered and 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 the compound represented by Compound 5

(Intermediate 2) (Compound 7A) (Compound 5)
Under a nitrogen atmosphere, Intermediate 2 (10.0 g, 15.77 mmol) produced in <Synthesis Example 2> and Compound 7A (3.0 g, 21 mmol, manufactured by Alpha Chemistry) were placed in 200 ml of 1,4-dioxane. The mixture was stirred and refluxed. After this, bis (tritartbutylphosphine) palladium (0.3 g, 0.5 mmol) was added. After the reaction for 8 hours, the temperature was lowered to room temperature and the mixture was filtered. After extracting the filtrate with chloroform and water, the organic layer was dried over magnesium sulfate. Then, the organic layer was distilled under reduced pressure, purified by column chromatography (chloroform: hexane), and the concentrated solution was recrystallized from chloroform and ethyl acetate again. The produced solid was filtered and 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 the 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) produced in <Synthesis Example 2> above under a nitrogen atmosphere. ) Was mixed, added to 300 ml of Dioxane, and heated with stirring. In a refluxed state, 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. Water was poured into the filtrate and extracted with chloroform, and the organic layer was dried over anhydrous magnesium sulfate. After distillation under reduced pressure, it was recrystallized from ethanol to produce 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 the compound represented by Compound 6

(Intermediate 3) (Compound 9A) (Compound 6)
Under a nitrogen atmosphere, Intermediate 3 (15.0 g, 22 mmol) produced in <Synthesis Example 8> and Compound 9A (5.9 g, 18.75 mmol, manufactured by TCI) were placed in 150 ml of tetrahydrofuran, and the mixture was stirred and refluxed. did. Then, potassium carbonate (9.2 g, 67 mmol) was dissolved in water (40 ml) and added, and after sufficient stirring, tetrakistriphenyl-phosphinopalladium (0.9 g, 1.5 mmol) was added. After the reaction for 6 hours, the temperature was lowered to room temperature and the mixture was filtered. After extracting the filtrate with chloroform and water, the organic layer was dried over magnesium sulfate. Then, the organic layer was distilled under reduced pressure, purified by column chromatography (chloroform: hexane), and the concentrated solution was recrystallized from chloroform and ethyl acetate again. The produced solid was filtered and 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 the compound represented by Compound 7.

(Intermediate 3) (Compound 10A) (Compound 7)
Under a nitrogen atmosphere, Intermediate 3 (15.0 g, 22 mmol) produced in <Synthesis Example 8> and Compound 10A (5.9 g, 18.75 mmol, manufactured by TCI) were placed in 150 ml of tetrahydrofuran, and the mixture was stirred and refluxed. did. Then, potassium carbonate (9.2 g, 67 mmol) was dissolved in 40 ml of water and added, and after sufficient stirring, tetrakistriphenyl-phosphinopalladium (0.9 g, 1.5 mmol) was added. After the reaction for 6 hours, the temperature was lowered to room temperature and the mixture was filtered. After extracting the filtrate with chloroform and water, the organic layer was dried over magnesium sulfate. Then, the organic layer was distilled under reduced pressure, purified by column chromatography (chloroform: hexane), and the concentrated solution was recrystallized from chloroform and ethyl acetate again. The produced solid was filtered and 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 the compound represented by Compound 8

(Intermediate 2) (Compound 11A) (Compound 8)
Under a nitrogen atmosphere, Intermediate 2 (10.0 g, 17 mmol) produced in <Production Example 2> and Compound 11A (7.3 g, 21 mmol, manufactured by Acros) were placed in 200 ml of 1,4-dioxane and stirred. And refluxed. After this, bis (tritartbutylphosphine) palladium (0.3 g, 0.5 mmol) was added. After the reaction for 8 hours, the temperature was lowered to room temperature and the mixture was filtered. After extracting the filtrate with chloroform and water, the organic layer was dried over magnesium sulfate. Then, the organic layer was distilled under reduced pressure, purified by column chromatography (chloroform: hexane), and the concentrated solution was recrystallized from chloroform and ethyl acetate again. The produced solid was filtered and 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) thinly coated with ITO (indium tin oxide) to a thickness of 1000 Å was placed in distilled water in which a dispersant was dissolved and ultrasonically cleaned. The detergent is Fisher Co. Distilled water used from Millipore Co., Ltd. Distilled water secondarily filtered through the product filter was used. After washing ITO for 30 minutes, ultrasonic cleaning was repeated twice with distilled water for 10 minutes. After the distillation water washing was completed, the isopropyl alcohol, acetone, and methanol solvent were ultrasonically washed in this order and dried.

Hexanitrile hexazatriphenylene was hot-vacuum-deposited on the ITO transparent electrode prepared in this manner to a thickness of 500 Å to form a hole injection layer. On top of this, HT1 (400 Å), which is a substance that transports holes, was vacuum-deposited, and then a compound of host H1 and dopant D1 was vacuum-deposited to a thickness of 300 Å as a light emitting layer. On the light emitting layer, <Compound 1> produced in <Synthesis Example 3> and LiQ (Lithium Quinlate) were vacuum-deposited at a weight ratio of 1: 1 to form an electron injection and transport layer to a thickness of 350 Å. did. Lithium fluoride (LiF) to a thickness of 12 Å and aluminum were vapor-deposited to a thickness of 2,000 Å on the electron injection and transport layers in order to form a cathode to manufacture an organic light emitting device.

In the process, the deposition rate of organic matter was maintained at 0.4 to 0.7 Å / sec, the deposition rate of lithium fluoride at the cathode was 0.3 Å / sec, and the deposition rate of aluminum was 2 Å / sec. The degree was ^{maintained from 2 × 10 -7} torr to 5 × 10 ^-6 torr to produce an organic light emitting element.

<Experimental Example 1-2>
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 Example 1-3>
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 Example 1-4>
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 Example 1-5>
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 Example 1-6>
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 Example 1-7>
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 device was produced in the same manner as in Experimental Example 1-1, except that the following compound of ET1 was used instead of Compound 1 in Experimental Example 1-1.

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

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

<Comparative Example 1-4>
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.

An organic light emitting device manufactured by using each compound as an electron transport layer material as in Experimental Examples 1-1 to 1-7 and Comparative Examples 1-1 to 1-4 has a current density of ^{10 mA / cm 2.} The drive voltage and luminous efficiency were measured with, _{and the time (LT 98} ) at which ^{the current density was 20 mA / cm 2} and the initial luminance was 98% was measured. The results are shown in Table 1 below.

As can be seen from Table 1, it was confirmed that the compound represented by the chemical formula 1 according to the embodiment of the present specification can be used for the electron injection layer and the electron transport layer of the organic electronic device. ..

When compared with ET3, which has a structure similar to that of compounds 6 and 7, but not asymmetric, compounds 6 and 7 show excellent properties in terms of lifetime, and compounds 1 to 5 of the present specification are described. , It turned out that there is a big advantage in the life part.

10, 11: Organic light emitting element 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 (4)

Compounds represented by the following chemical formulas 2 or 3:
[Chemical formula 2]

[Chemical formula 3]

In the chemical formulas 2 and 3,
Q is an aromatic group of monocyclic 6 carbon atoms,
L ₁ and L ₂ are direct bonds and
Ar ₂ is a substituted or unsubstituted aryl group having a carbon number of 6 to 16 with a cyano group or a pyridyl group; a phenyl group is substituted or unsubstituted dibenzothiophenyl-phenyl group; a phenyl group is substituted or unsubstituted Jibenzofura sulfonyl group; or a carbazole re-group,
R ₁ to R ₃ is hydrogen; a or deuterium,
X _{1 to} X ₃ are N ,
1 or 2 of X ₄ to X ₆ is N, the rest is CR,
The R is hydrogen,
Ar ₃ and Ar _4, equal to or different from each other, each independently, an aryl group,
Ar ₅ and Ar _6, equal to or different from each other, each independently, an aryl group,
a is 4 ,
b is 4
c is, Ru 4 der. The compound according to claim 1, wherein the chemical formula 2 or 3 is any one selected from the following compounds:

.. An organic electronic element including a first electrode, a second electrode provided facing the first electrode, and one or more organic substances provided between the first electrode and the second electrode. An organic electronic element in which one or more layers of the organic material layer contain the compound according to claim 1 or 2. The organic electronic device according to claim 3, wherein the organic material layer includes an electron injecting layer or an electron transporting layer, and the electron transporting layer or the electron injecting layer contains the compound.

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