KR20170113334A - Compound and organic electronic device comprising the same - Google Patents

Abstract

The present disclosure relates to compounds and organic electronic devices comprising them.

Description

BACKGROUND OF THE INVENTION 1. Field of the Invention [0001] The present invention relates to a compound and an organic electronic device including the compound.

The present invention claims the benefit of Korean Patent Application No. 10-2016-0037219, filed on March 28, 2016, to the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference.

The present disclosure relates to compounds and organic electronic devices comprising them.

A representative example of the organic electronic device is an organic light emitting device. In general, organic light emission phenomenon refers to a phenomenon in which an organic material is used to convert electric energy into light energy. An organic light emitting device using an organic light emitting phenomenon generally has a structure including an anode, a cathode, and an organic material layer therebetween. Here, in order to increase the efficiency and stability of the organic light emitting device, the organic material layer may have a multi-layer structure composed of different materials and may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. When a voltage is applied between the two electrodes in the structure of such an organic light emitting device, holes are injected in the anode, electrons are injected into the organic layer in the cathode, excitons are formed when injected holes and electrons meet, When it falls back to the ground state, the light comes out.

Development of new materials for such organic light emitting devices has been continuously required.

International Patent Application Publication No. 2003-012890

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

The present invention provides a compound represented by the following formula (1).

[Chemical Formula 1]

In Formula 1,

L is a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,

n is an integer of 0 to 2,

When n is 2 or more, the plural Ls are the same or different from each other,

Ar and R ₁ to R ₃ are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; Cyano; A nitro group; A hydroxy group; A carbonyl group; An ester group; Imide; An amino group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

a is an integer of 1 to 4,

b is an integer of 1 to 4,

c is an integer of 1 to 6,

When a is 2 or more, a plurality of R < ₁ > s are the same or different from each other,

When b is 2 or more, a plurality of R < ₂ &_gt; s are the same or different from each other,

When c is 2 or more, a plurality of R ₃ are the same or different from each other.

Also, the present specification discloses a plasma display panel comprising a first electrode; A second electrode facing the first electrode; And at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the above-described compound.

The compound according to one embodiment of the present invention is used in an organic electronic device including an organic light emitting device to lower the driving voltage of the organic electronic device, improve the light efficiency, and improve the lifetime characteristics of the device by the thermal stability of the compound. have.

1 shows an organic electronic device 10 according to an embodiment of the present invention.
2 shows an organic electronic device 11 according to another embodiment of the present invention.
Fig. 3 is LC / MS synthesis confirmation data of the formula 2-1-A.
FIG. 4 is LC / MS synthesis confirmation data of the formula (2-1-B).
FIG. 5 is an LC / MS synthesis confirmation data of the formula 3-1-A.
Fig. 6 is LC / MS synthesis confirmation data of the formula 4-1-B.

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

The present invention provides a compound represented by the above formula (1).

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

는 연결되는 부위를 의미한다.In the present specification,

Refers to the connected area.

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

As used herein, the term " substituted or unsubstituted " A halogen group; Cyano; A nitro group; A hydroxy group; A carbonyl group; An ester group; Imide; An amino group; An alkyl group; A cycloalkyl group; An alkenyl group; An alkoxy group; An aryloxy group; An alkyloxy group; Arylthioxy group; An alkylsulfoxy group; An amine group; An arylamine group; Phosphine oxide groups; An aryl group; Silyl group; And a heterocyclic group containing at least one of N, O, S, Se and Si atoms, or wherein at least two of the substituents exemplified above are substituted with a substituent to which they are connected, Quot; means < / RTI >

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

In the present specification, the carbon number of the carbonyl group is not particularly limited, but it is preferably 1 to 40 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

In the present specification, the number of carbon atoms of the ester group is not particularly limited, but is preferably 1 to 40 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.

In the present specification, the number of carbon atoms in the imide group is not particularly limited, but is preferably 1 to 40 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

In the present specification, the amide group may be substituted with nitrogen of the amide group by hydrogen, a straight chain, branched chain or cyclic alkyl group of 1 to 50 carbon atoms or an aryl group of 6 to 50 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.

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- N-pentyl, 3-dimethylbutyl, 2-ethylbutyl, heptyl, n-hexyl, Cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethyl Heptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl and the like.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 40 carbon atoms, and specifically includes cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, But are not limited to, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert- butylcyclohexyl, cycloheptyl, Do not.

In the present specification, the alkoxy group may be linear, branched or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 40 carbon atoms. Specific examples include methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n Butyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy and the like. But is not limited thereto.

In the present specification, the alkenyl group may be straight-chain or branched, and the number of carbon atoms is not particularly limited, but is preferably from 2 to 30. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, Butenyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, (Diphenyl-1-yl) vinyl-1-yl, stilbenyl, stilenyl, and the like.

In the present specification, the boron group may be -BR ₁₀₀ R ₁₀₁ , wherein R ₁₀₀ and R ₁₀₁ are the same or different and each independently hydrogen; heavy hydrogen; halogen; A nitrile group; A substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 40 carbon atoms; A substituted or unsubstituted, straight or branched chain alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; And a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.

In this specification, the silyl group is a substituent including Si and a direct connection as the Si atom radical, R is represented by -SiR _{104 105} R _106, R ₁₀₄ to R ₁₀₆ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; An alkyl group; An alkenyl group; An alkoxy group; A cycloalkyl group; An aryl group; And a heterocyclic group. Specific examples of the silyl group include a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylenesilyl group, a diphenylsilyl group, But is not limited thereto.

In the present specification, when the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 6 to 50 carbon atoms. Specific examples of the monocyclic aryl group include, but are not limited to, a phenyl group, a biphenyl group, a terphenyl group, a quaterphenyl group, and the like.

When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited. And preferably has 10 to 40 carbon atoms. Specific examples of the polycyclic aryl group include naphthyl, anthracenyl, phenanthryl, pyrenyl, perylenyl, klychenyl, fluorenyl, and the like.

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

,

,

,

,

,

등이 될 수 있으나, 이에 한정되는 것은 아니다.When the fluorenyl group is substituted,

,

,

,

,

,

And the like, but the present invention is not limited thereto.

In the present specification, the heteroaryl group is a heterocyclic group and is a heterocyclic group containing at least one of N, O, S, Si and Se. The number of carbon atoms is not particularly limited, but is preferably 6 to 50 carbon atoms. Examples of the heteroaryl group include a thiophene group, a furane group, a furyl group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, a bipyridyl group, a pyrimidyl group, A pyridazinyl group, a pyrazinopyrazinyl group, an isoquinoline group, an isoquinolinyl group, an isoquinolinyl group, an isoquinolinyl group, an isoquinolinyl group, an isoquinolyl group, , An indole group, a carbazole group, a benzoxazole group, a benzoimidazole group, a benzothiazole group, a benzocarbazole group, But are not limited to, a benzothiophene group, a dibenzothiophene group, a benzofuranyl group, a phenanthroline, an isoxazolyl group, a thiadiazolyl group, and a dibenzofuranyl group.

In the present specification, the amine group means a monovalent amine in which at least one hydrogen atom of the amino group (-NH ₂ ) is substituted with another substituent, represented by -NR ₁₀₇ R ₁₀₈ , and R ₁₀₇ and R ₁₀₈ are the same or different Each independently selected from the group consisting of hydrogen; heavy hydrogen; A halogen group; An alkyl group; An alkenyl group; An alkoxy group; A cycloalkyl group; An aryl group; And a heterocyclic group (provided that at least one of R ₁₀₇ and R ₁₀₈ is not hydrogen). For example, a monoalkylamine group; A dialkylamine group; N-alkylarylamine groups; Monoarylamine groups; A diarylamine group; An N-arylheteroarylamine group; An N-alkylheteroarylamine group, a monoheteroarylamine group, and a diheteroarylamine group. The number of carbon atoms is not particularly limited, but is preferably 1 to 40. Specific examples of the amine group include methylamine, dimethylamine, ethylamine, diethylamine, phenylamine, naphthylamine, biphenylamine, anthracenylamine, 9-methyl- , Diphenylamine group, ditolylamine group, N-phenyltolylamine group, triphenyleneamine group, N-phenylbiphenylamine group; N-phenylnaphthylamine group; An N-biphenylnaphthylamine group; N-naphthylfluorenylamine group; N-phenylphenanthrenylamine group; An N-biphenyl phenanthrenyl amine group; N-phenylfluorenylamine group; An N-phenyltriphenylamine group; N-phenanthrenyl fluorenylamine group; And an N-biphenylfluorenylamine group, but are not limited thereto.

In the present specification, the phosphine oxide group specifically includes a diphenylphosphine oxide group, dinaphthylphosphine oxide, and the like, but is not limited thereto.

In the present specification, the aryl group in the aryloxy group, the arylthioxy group, the arylsulfoxy group, the N-arylalkylamine group, and the N-arylheteroarylamine group is the same as the aforementioned aryl group. Specific examples of the aryloxy group include a phenoxy group, a p-tolyloxy group, a m-tolyloxy group, a 3,5-dimethyl-phenoxy group, a 2,4,6- trimethylphenoxy group, a p- Naphthyloxy group, 4-methyl-1-naphthyloxy group, 5-methyl-2-naphthyloxy group, 1-anthryloxy group , 2-anthryloxy group, 9-anthryloxy group, 1-phenanthryloxy group, 3-phenanthryloxy group and 9-phenanthryloxy group and the arylthioxy group includes phenylthio group, 2- Methylphenylthio group, 4-tert-butylphenylthio group and the like, and examples of the arylsulfoxy group include a benzene sulfoxide group and a p-toluenesulfoxy group. However, the present invention is not limited thereto.

In the present specification, examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted triarylamine group. The aryl group in the arylamine group may be a monocyclic aryl group or a polycyclic aryl group. The arylamine group having at least two aryl groups may contain a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group at the same time. For example, the aryl group in the arylamine group may be selected from the examples of the aryl group described above. Specific examples of the arylamine group include phenylamine, naphthylamine, biphenylamine, anthracenylamine, 3-methylphenylamine, 4-methyl-naphthylamine, 2-methyl- But are not limited to, cenylamine, diphenylamine, phenylnaphthylamine, ditolylamine, phenyltolylamine, carbazole and triphenyleneamine groups.

In the present specification, examples of the heteroarylamine group include a substituted or unsubstituted monoheteroarylamine group, a substituted or unsubstituted diheteroarylamine group, or a substituted or unsubstituted triheteroarylamine group. The heteroarylamine group having two or more heteroaryl groups may include a monocyclic heteroaryl group, a polycyclic heteroaryl group, or a monocyclic heteroaryl group and a polycyclic heteroaryl group at the same time. For example, the heteroaryl group in the heteroarylamine group may be selected from the examples of the above-mentioned heteroaryl group.

In the present specification, an arylene group means a divalent group having two bonding positions in an aryl group. The description of the aryl group described above can be applied except that each of these is 2 groups.

In the present specification, the heteroarylene group means that the heteroaryl group has two bonding positions, that is, divalent. The description of the above-mentioned heteroaryl groups can be applied, except that they are each 2 groups.

In one embodiment of the present disclosure, L is a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group.

In one embodiment of the present specification, L is a direct bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted naphthylene group, or a substituted or unsubstituted fluorenyl It is a stove.

In one embodiment of the present specification, L is a phenylene group, a biphenylene group, a naphthylene group, or a fluorenylene group.

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

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

In one embodiment of the present disclosure, L is a naphthylene group.

In one embodiment of the present disclosure, L is a fluorenylene group.

In one embodiment of the present specification, L is a direct bond, a substituted or unsubstituted divalent pyridine group, a substituted or unsubstituted divalent pyrimidine group, a substituted or unsubstituted divalent triazine group, a substituted or unsubstituted A divalent quinoline group, or a substituted or unsubstituted divalent quinazoline group.

In one embodiment of the present specification, L is a divalent pyridine group in which hydrogen, deuterium, a halogen group, a cyano group, an alkyl group, or an aryl group is substituted or unsubstituted.

In one embodiment of the present specification, L is a divalent pyrimidine group in which hydrogen, deuterium, a halogen group, a cyano group, an alkyl group, or an aryl group is substituted or unsubstituted.

In one embodiment of the present specification, L is a divalent triazine group in which hydrogen, deuterium, a halogen group, a cyano group, an alkyl group, or an aryl group is substituted or unsubstituted.

In one embodiment of the present specification, L is a divalent quinoline group in which hydrogen, deuterium, a halogen group, a cyano group, an alkyl group, or an aryl group is substituted or unsubstituted.

In one embodiment of the present specification, L is a divalent quinazoline group in which hydrogen, deuterium, a halogen group, a cyano group, an alkyl group, or an aryl group is substituted or unsubstituted.

In one embodiment of the present specification, L is a divalent pyridine group in which the cyano group is substituted or unsubstituted.

In one embodiment of the present specification, L is a divalent pyridine group in which the phenyl group is substituted or unsubstituted.

In one embodiment of the present specification, L is a divalent pyridine group substituted with a cyano group.

In one embodiment of the present disclosure, L is a divalent pyridine group substituted with a phenyl group.

In one embodiment of the present specification, L is a divalent pyrimidine group in which the cyano group is substituted or unsubstituted.

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

In one embodiment of the present specification, L is a divalent pyrimidine group substituted with a cyano group.

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

In one embodiment of the present specification, L is a divalent triazine group in which the cyano group is substituted or unsubstituted.

In one embodiment of the present specification, L is a divalent triazine group in which the phenyl group is substituted or unsubstituted.

In one embodiment of the present specification, L is a bivalent triazine group substituted with a cyano group.

In one embodiment of the present specification, L is a bivalent triazine group substituted with a phenyl group.

In one embodiment of the present specification, L is a divalent quinoline group in which the cyano group is substituted or unsubstituted.

In one embodiment of the present specification, L is a divalent quinoline group in which the phenyl group is substituted or unsubstituted.

In one embodiment of the present disclosure, L is a divalent quinoline group substituted with a cyano group.

In one embodiment of the present disclosure, L is a divalent quinoline group substituted with a phenyl group.

In one embodiment of the present specification, L is a divalent quinazoline group in which the cyano group is substituted or unsubstituted.

In one embodiment of the present specification, L is a divalent quinazoline group in which the phenyl group is substituted or unsubstituted.

In one embodiment of the present specification, L is a divalent quinazoline group substituted with a cyano group.

In one embodiment of the present disclosure, L is a divalent quinazoline group substituted with a phenyl group.

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

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

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

In one embodiment of the present disclosure, L is a divalent quinoline group.

In one embodiment of the present disclosure, L is a divalent quinazoline group.

In one embodiment of the present specification, n is an integer of 0 to 2, and when n is 2 or more, plural Ls are the same or different from each other.

In one embodiment of the present specification, Ar and R ₁ to R ₃ are the same or different and each independently hydrogen; heavy hydrogen; A halogen group; Cyano; A nitro group; A hydroxy group; A carbonyl group; An ester group; Imide; An amino group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

In one embodiment of the present specification, Ar is a substituted or unsubstituted aryl group having 6 to 50 carbon atoms.

In one embodiment of the present specification, Ar is an aryl group having 6 to 50 carbon atoms which is substituted or unsubstituted with an alkyl group or an aryl group.

In one embodiment of the present specification, Ar is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted triphenylene group , Or a fluorenyl group substituted or unsubstituted with an alkyl group.

In one embodiment of the present invention, Ar is phenyl, biphenyl, terphenyl, naphthyl, triphenylene or dimethylfluorenyl.

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

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

In one embodiment of the present disclosure, Ar is a terphenyl group.

In one embodiment of the present specification, Ar is a naphthyl group.

In one embodiment of the present specification, Ar is a triphenylene group.

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

In one embodiment of the present specification, Ar is a substituted or unsubstituted heteroaryl group having 6 to 50 carbon atoms.

In one embodiment of the present specification, Ar is a heteroaryl group having 6 to 50 carbon atoms substituted or unsubstituted with deuterium, cyano group, alkyl group, aryl group or heteroaryl group.

In one embodiment of the present specification, Ar represents a substituted or unsubstituted pyridine group, a substituted or unsubstituted pyrimidine group, a substituted or unsubstituted triazine group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted di A substituted or unsubstituted dibenzofurane group, a substituted or unsubstituted quinoline group, or a substituted or unsubstituted quinazoline group.

In one embodiment of the present specification, Ar is a pyridine group in which a deuterium, a cyano group, an aryl group, or a heteroaryl group is substituted or unsubstituted.

In one embodiment of the present specification, Ar is a pyridine group in which a phenyl group, biphenyl group, terphenyl group, naphthyl group, carbazole group, dibenzofurane group, or dibenzothiophene group is substituted or unsubstituted.

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

In one embodiment of the present specification, Ar is a pyridine group substituted with a carbazole group.

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

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

In one embodiment of the present invention, Ar is a pyrimidine group in which a cyano group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a carbazole group, a dibenzofurane group, or a dibenzothiophene group is substituted or unsubstituted.

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

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

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

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

In one embodiment of the present specification, Ar is a triazine group in which a deuterium, a cyano group, an aryl group, or a heteroaryl group is substituted or unsubstituted.

In one embodiment of the present specification, Ar is a triazine group in which a phenyl group, biphenyl group, terphenyl group, naphthyl group, carbazole group, dibenzofurane group, or dibenzothiophene group is substituted or unsubstituted.

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

In one embodiment of the present specification, Ar is a triazine group substituted with a biphenyl group.

In one embodiment of the present specification, Ar is a triazine group substituted with a dibenzofurane group.

In one embodiment of the present specification, Ar is a triazine group substituted with a carbazole group.

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

In one embodiment of the present specification, Ar is a carbazole group in which a deuterium, a cyano group, an aryl group, or a heteroaryl group is substituted or unsubstituted.

In one embodiment of the present specification, Ar is a carbazole group in which a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a carbazole group, a dibenzofurane group, or a dibenzothiophene group is substituted or unsubstituted.

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

In one embodiment of the present specification, Ar is a quinoline group in which a deuterium, a cyano group, an aryl group, or a heteroaryl group is substituted or unsubstituted.

In one embodiment of the present specification, Ar is a quinoline group in which a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a carbazole group, a dibenzofurane group, or a dibenzothiophene group is substituted or unsubstituted.

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

In one embodiment of the present specification, Ar is a quinolinyl group substituted with a carbazole group.

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

In one embodiment of the present specification, Ar is a quinazoline group in which a deuterium, a cyano group, an aryl group, or a heteroaryl group is substituted or unsubstituted.

In one embodiment of the present specification, Ar represents a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a carbazole group substituted or unsubstituted with a phenyl group, a dibenzofurane group, or a quinazoline substituted or unsubstituted dibenzothiophene group .

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

In one embodiment of the present specification, Ar is a quinazoline group substituted with a biphenyl group.

In one embodiment of the present specification, Ar is a quinazoline group substituted with a naphthyl group.

In one embodiment of the present specification, Ar is a quinazoline group substituted with a carbazole group.

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

In one embodiment of the present specification, Ar is a quinoxaline group in which a deuterium, a cyano group, an aryl group, or a heteroaryl group is substituted or unsubstituted.

In one embodiment of the present specification, Ar is a quinoxaline group in which a phenyl group, biphenyl group, terphenyl group, naphthyl group, carbazole group, dibenzofurane group, or dibenzothiophene group is substituted or unsubstituted.

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

In one embodiment of the present specification, Ar is a quinoxaline group substituted with a naphthyl group.

In one embodiment of the present disclosure, Ar is benzo [h] quinazoline wherein the deuterium, cyano group, aryl group, or heteroaryl group is substituted or unsubstituted.

In one embodiment of the present specification, Ar represents a benzo [h] quinazoline group substituted or unsubstituted with a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a carbazole group, a dibenzofurane group, or a dibenzothiophene group [h] quinazoline).

In one embodiment of the present disclosure, Ar is benzo [h] quinazoline substituted phenyl group.

In one embodiment of the present specification, Ar is benzofuro [3,2-d] pyrimidine group in which deuterium, cyano, aryl or heteroaryl groups are substituted or unsubstituted, pyrimidine.

In one embodiment of the present specification, Ar is benzopyrro [3,2-d (benzyloxy) benzo [b] thiopyranyl which is substituted or unsubstituted with a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a carbazole group, a dibenzofurane group, ] Benzofuro [3,2-d] pyrimidine.

In one embodiment of the present specification, Ar is benzofuro [3,2-d] pyrimidine substituted with a phenyl group.

In one embodiment of the present disclosure, Ar is benzofuro [3,2-d] pyrimidine substituted with a biphenyl group.

In one embodiment of the present specification, Ar is benzofuro [3,2-d] pyrimidine substituted with a naphthyl group.

In one embodiment of the present specification, Ar is a 5,5-dimethyl-5H-indeno [1,2-d] pyrimidine group (5) substituted or unsubstituted with deuterium, cyano group, aryl group, or heteroaryl group , 5-dimethyl-5H-indeno [1,2-d] pyrimidine).

In one embodiment of the present specification, Ar is 5,5-dimethyl-5H-, in which a phenyl group, biphenyl group, terphenyl group, naphthyl group, carbazole group, dibenzofurane group or dibenzothiophene group is substituted or unsubstituted 5-dimethyl-5H-indeno [l, 2-d] pyrimidine.

In one embodiment of the present specification, Ar represents a 5,5-dimethyl-5H-indeno [1,2-d] pyrimidine group substituted with a phenyl group, d] pyrimidine.

In one embodiment of the present specification, Ar is a 5,5-dimethyl-5H-indeno [1,2-d] pyrimidine group substituted with a biphenyl group -d] pyrimidine).

In one embodiment of the present disclosure, Ar is a 5,5-dimethyl-5H-indeno [1,2-d] pyrimidine group substituted with a naphthyl group -d] pyrimidine).

In one embodiment of the present specification, Ar is a pyrido [3,2-b] pyrazine group in which a deuterium, a cyano group, an aryl group, or a heteroaryl group is substituted or unsubstituted, to be.

In one embodiment of the present specification, Ar is pyrido [3,2-b] pyrimidinyl substituted or unsubstituted phenyl, biphenyl, terphenyl, naphthyl, carbazole, dibenzofurane, Pyrazine (pyrido [3,2-b] pyrazine).

In one embodiment of the present disclosure, Ar is a pyrido [3,2-b] pyrazine substituted with a phenyl group.

In one embodiment of the present specification, Ar is a pyrazino [2,3-b] pyrazine group in which a deuterium, a cyano group, an aryl group, or a heteroaryl group is substituted or unsubstituted, to be.

In one embodiment of the present specification, Ar is a pyrazino [2,3-b] thiophene substituted or unsubstituted phenyl, biphenyl, terphenyl, naphthyl, carbazole, dibenzofurane, Pyrazino [2,3-b] pyrazine.

In one embodiment of the present disclosure, Ar is a pyrazino [2,3-b] pyrazine substituted with a phenyl group.

In one embodiment of the present specification, Ar is benzothieno [2,3-d] pyrimidine group substituted or unsubstituted with deuterium, cyano group, aryl group, or heteroaryl group, pyrimidine.

In one embodiment of the present specification, Ar represents a benzothieno [2,3-d (benzyloxycarbonyl) benzo [b] thiophene substituted or unsubstituted phenyl group, biphenyl group, terphenyl group, naphthyl group, carbazole group, dibenzofurane group, ] Pyrimidine group (benzothieno [2,3-d] pyrimidine).

In one embodiment of the present specification, Ar is benzothieno [2,3-d] pyrimidine substituted with a phenyl group.

In one embodiment of the present specification, Ar is benzothieno [2,3-d] pyrimidine substituted with a biphenyl group.

In one embodiment of the present specification, Ar is benzothieno [2,3-d] pyrimidine substituted with a naphthyl group.

In one embodiment of the present specification, Ar is a pyridine group.

In one embodiment of the present specification, Ar is a pyrimidine group.

In one embodiment of the present specification, Ar is a triazine group.

In one embodiment of the present specification, Ar is a carbazole group.

In one embodiment of the present specification, Ar is a dibenzofurane group.

In one embodiment of the present specification, Ar is a dibenzothiophene group.

In one embodiment of the present disclosure, Ar is a quinoline group.

In one embodiment of the present specification, Ar is a quinazoline group.

In one embodiment of the present specification, Ar is an amine group.

In one embodiment of the present specification, Ar is an arylamine group or a heteroarylamine group.

In one embodiment of the present specification, Ar is an amine group in which a phenyl group, biphenyl group, naphthyl group, fluorenyl group, triphenylene group, dibenzofurane group, or dibenzothiophene group is substituted or unsubstituted.

In one embodiment of the present disclosure, Ar is an amine group substituted with a phenyl group.

In one embodiment of the present specification, Ar is an amine group substituted with a biphenyl group.

In one embodiment of the present disclosure, Ar is an amine group substituted with a fluorenyl group.

In one embodiment of the present disclosure, Ar is an amine group substituted with a triphenylene group.

In one embodiment of the present specification, Ar is an amine group substituted with a dibenzofurane group.

In one embodiment of the present disclosure, Ar is an amine group substituted with a dibenzothiophene group.

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

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

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

In one embodiment of the present specification, Ar represents a phenyl group; Biphenyl group; A terphenyl group; Naphthyl group; A dimethylfluorene group; A dibenzothiophene group; A pyrimidine group substituted with a carbazole group, cyano group or phenyl group substituted or unsubstituted with a phenyl group; A triazine group substituted or unsubstituted with a phenyl group, a biphenyl group, or a dibenzofurane group; A carbazole group substituted or unsubstituted with a phenyl group; A phenyl group, a biphenyl group, a naphthyl group, or a quinazoline group substituted or unsubstituted with a carbazole group substituted or unsubstituted with a phenyl group; A quinoxaline group substituted or unsubstituted with a phenyl group or a naphthyl group; A benzo [h] quinazoline group substituted with a phenyl group; A benzofura [3,2-d] pyrimidine group substituted or unsubstituted with a phenyl group, a biphenyl group, or a naphthyl group; A 5,5-dimethyl-5H-indeno [1,2-d] pyrimidine group substituted or unsubstituted with a phenyl group, a biphenyl group, or a naphthyl group; A pyrido [3,2-b] pyrazine group substituted with a phenyl group; A pyrazino [2,3-b] pyrazine group substituted with a phenyl group; A benzothieno [2,3-d] pyrimidine group substituted or unsubstituted with a phenyl group, a biphenyl group or a naphthyl group; A biphenyl group, a dimethylfluorene group, a dibenzofurane group, or an amine group substituted or unsubstituted with a triphenylene group; Or a phosphine oxide group substituted with a phenyl group.

In one embodiment of the present invention, the formula (1) may be represented by any one of the following formulas (2) to (4).

(2)

(3)

[Chemical Formula 4]

In the above formulas 2 to 4,

L, n, Ar, and R ₁ to R ₃ are the same as defined in the above formula (1).

In one embodiment of the present disclosure, the compound 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 below. Exemplary examples are described below in the preparation examples, but substituents can be added or removed as needed, and the position of the substituent can be changed. In addition, based on techniques known in the art, starting materials, reactants, reaction conditions, and the like can be changed.

The compounds of the present invention were prepared by using Suzuki coupling reaction, Buchwald-Hartwig coupling reaction, cadogan carbazole synthesis, etc. as typical reactions.

Production Examples 1. Preparation of Formulas (2-1) and (2)

To 100.00 g (1.0 eq) of 3-bromofluoranthene was added 135.48 g (1.5 eq) of bis (pinacolato) diboron, Pd (dba) ₂ 4.09 g (0.02 eq), PCy ₃ 3.8 g (0.04 eq) of KOAc and 98.31 g (2.00 eq) of KOAc were placed in 800 mL of dioxane, and the mixture was refluxed and stirred. After 3 hours, the solution was concentrated under reduced pressure. This was dissolved in CHCl ₃ and completely washed with water. The solution in which the product was dissolved was further concentrated under reduced pressure and purified by column chromatography. 88.72 g (yield 76%) of formula 2-3 was obtained

Formula 2-3 88.72 g (1.0 eq), 1- bromo-2-nitro-naphthalene 74.95 g (1.1 eq), Pd (t-Bu 3 P) 2 0.69 g (0.005 eq) of 74.71 g (2.00 eq) of K ₂ CO ₃ dissolved in water was added to 700 ml of THF, and the mixture was refluxed and stirred. After 2 hours, the aqueous layer was removed and the solution was concentrated under reduced pressure. This was dissolved in CHCl ₃ and completely washed with water. The solution in which the product was dissolved was further concentrated under reduced pressure and purified by column chromatography. 71.66 g (71%) of the compound of the formula 2-2 was obtained.

71.66 g (1.0 eq) of Formula 2-2 was dissolved in 350 ml of triethylphosphite (P (OEt) ₃ ), refluxed and stirred. After 5 hours, when the reaction was completed, the solvent was removed by vacuum decompression to remove 50% of the solvent, and crystals were dropped. After filtration, the solution was completely dissolved in ethyl acetate and then washed with water. The solution was concentrated under reduced pressure at about 70%, cooled, cooled, and filtered. 45.86 g (yield 70%) of the compound represented by the formula (2-1) was obtained.

The compound of the present invention was synthesized by Buchwald-Hartwig coupling reaction with various Ar-L-X (X is Cl or Br) using the formula (2-1) as a starting material.

Production Example 2. Preparation of Formula 3-1

(3-1) was synthesized by the same synthetic method using 2-bromo-3-nitronaphthalene instead of 1-bromo-2-nitronaphthalene in Preparation Example 1.

Preparation Example 3. Preparation of the formula 4-1

4-1 was synthesized by the same synthetic method using 2-bromo-1-nitronaphthalene instead of 1-bromo-2-nitronaphthalene in Preparation Example 1 above.

Synthetic example

Synthesis Example 1. Synthesis of Compound 2-1-A

Formula 2-1 10.0 g (1.0 eq), 2- chloro-4-phenyl-quinazoline 7.75 g (1.1 eq), K 3 PO 4 12.43 g (2.0 eq), Pd (t-Bu 3 P) 2 0.07 g ( 0.005 eq) was dissolved in 70 ml of xylene, refluxed and stirred. When the reaction was completed after 3 hours, the solvent was removed by decompression. After that, it was completely dissolved in CHCl ₃ , washed with water and decompressed again to remove about 50% of the solvent. Ethyl acetate was added in the refluxing state, and the crystals were dropped and cooled, followed by filtration. This was subjected to column chromatography to obtain 11.02 g (yield: 87%) of the compound 2-1-A.

Fig. 3 is LC / MS synthesis confirmation data of the formula 2-1-A.

 Synthesis Example 2. Synthesis of Compound 2-1-B

12.50 g (1.1 eq) of 2- (4-bromophenyl) -4,6-diphenyl-1,3,5-triazine, 5.62 g (2.0 eq) of NaOtBu, 10.0 g (1.0 eq) And 0.07 g (0.005 eq) of Pd (t-Bu ₃ P) ₂ were dissolved in 70 ml of xylene, refluxed and stirred. When the reaction was completed after 3 hours, the solvent was removed by decompression. After that, it was completely dissolved in CHCl ₃ , washed with water and decompressed again to remove about 50% of the solvent. Ethyl acetate was added in the refluxing state, and the crystals were dropped and cooled, followed by filtration. This was subjected to column chromatography to obtain 14.06 g (yield 74%) of the compound 2-1-B.

FIG. 4 is LC / MS synthesis confirmation data of the formula (2-1-B).

Synthesis Example 3. Synthesis of Compound 3-1-A

Formula 3-1 10.0 g (1.0 eq), 2- chloro-4- (naphthalen-2-yl) quinazoline 9.36 g (1.1 eq), K 3 PO 4 12.43 g (2.0 eq), Pd (t-Bu 3 P) ₂ (0.05 g, 0.005 eq) was dissolved in 70 ml of xylene, refluxed and stirred. When the reaction was completed after 3 hours, the solvent was removed by decompression. After that, it was completely dissolved in CHCl ₃ , washed with water and decompressed again to remove about 50% of the solvent. Ethyl acetate was added in the refluxing state, and the crystals were dropped and cooled, followed by filtration. This was subjected to column chromatography to obtain 11.69 g (yield 67%) of the compound 3-1-A.

FIG. 5 is an LC / MS synthesis confirmation data of the formula 3-1-A.

Synthesis Example 4. Synthesis of Compound 3-1-B

12.50 g (1.1 eq) of 2- (4-bromophenyl) -4,6-diphenyl-1,3,5-triazine and 5.62 g (2.0 eq) of NaOtBu were added to 10.0 g (1.0 eq) And 0.07 g (0.005 eq) of Pd (t-Bu ₃ P) ₂ were dissolved in 70 ml of xylene, refluxed and stirred. When the reaction was completed after 3 hours, the solvent was removed by decompression. After that, it was completely dissolved in CHCl ₃ , washed with water and decompressed again to remove about 50% of the solvent. Ethyl acetate was added in the refluxing state, and the crystals were dropped and cooled, followed by filtration. This was subjected to column chromatography to obtain 14.25 g (yield 75%) of the compound 3-1-B.

Synthesis Example 5. Synthesis of Compound 4-1-A

12.50 g (1.1 eq) of 2- (4-bromophenyl) -4,6-diphenyl-1,3,5-triazine and 5.62 g (2.0 eq) of NaOtBu were added to 10.0 g (1.0 eq) And 0.07 g (0.005 eq) of Pd (t-Bu ₃ P) ₂ were dissolved in 70 ml of xylene, refluxed and stirred. When the reaction was completed after 3 hours, the solvent was removed by decompression. After that, it was completely dissolved in CHCl ₃ , washed with water and decompressed again to remove about 50% of the solvent. Ethyl acetate was added in the refluxing state, and the crystals were dropped and cooled, followed by filtration. This was subjected to column chromatography to obtain 13.30 g (yield 70%) of the compound 4-1-A.

Synthesis Example 6. Synthesis of Compound 4-1-B

Formula 4-1 10.0 g (1.0 eq), 4 - ([1,1'- biphenyl] -4-yl) -2-chloro-quinazoline 10.20 g (1.1 eq), K 3 PO 4 12.43 g (2.0 eq ) And 0.07 g (0.005 eq) of Pd (t-Bu ₃ P) ₂ were dissolved in 70 ml of xylene, refluxed and stirred. When the reaction was completed after 3 hours, the solvent was removed by decompression. After that, it was completely dissolved in CHCl ₃ , washed with water and decompressed again to remove about 50% of the solvent. Ethyl acetate was added in the refluxing state, and the crystals were dropped and cooled, followed by filtration. This was subjected to column chromatography to obtain 11.83 g (yield 65%) of the compound 4-1-B.

Fig. 6 is LC / MS synthesis confirmation data of the formula 4-1-B.

Further, the present invention provides an organic electronic device comprising the above-mentioned compounds.

In one embodiment of the present disclosure, the first electrode; A second electrode facing the first electrode; And at least one organic compound layer provided between the first electrode and the second electrode, wherein at least one of the organic compound layers includes the compound.

When a member is referred to herein as being "on " another member, it includes not only a member in contact with another member but also another member between the two members.

Whenever a component is referred to as "comprising ", it is to be understood that the component may include other components as well, without departing from the scope of the present invention.

The organic material layer of the organic electronic device in this specification may have a single layer structure, but may have a multi-layer structure in which two or more organic material layers are stacked. For example, as a representative example of the organic electronic device of the present invention, the organic light emitting device may have a structure including a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, an electron injecting layer, etc. as an organic material layer. 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 invention, the organic electronic device may be selected from the group consisting of an organic light emitting device, an organic phosphor device, an organic solar cell, an organic photoconductor (OPC), and an organic transistor.

Hereinafter, the organic light emitting device will be described.

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

In one embodiment of the present invention, 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 invention, the organic layer includes an electron transporting layer or an electron injecting layer, and the electron transporting layer or the electron injecting layer includes the compound.

In one embodiment of the present invention, the organic light emitting element is a hole injection layer, a hole transport layer, An electron transport layer, an electron injection layer, and a light emitting layer.

In one embodiment of the present invention, the organic light emitting device includes a first electrode; A second electrode facing the first electrode; And a light emitting layer provided between the first electrode and the second electrode; At least one of the two or more organic layers includes two or more organic layers disposed between the light emitting layer and the first electrode or between the light emitting layer and the second electrode. In one embodiment of the present invention, the two or more organic layers may be selected from the group consisting of an electron transport layer, an electron injection layer, a layer that simultaneously transports electrons and an electron injection layer, and a hole blocking layer.

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

In addition, in one embodiment of the present specification, when the compound is contained in each of the two or more electron transporting layers, the materials other than the above compounds may be the same or different from each other.

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

In another embodiment, the organic light emitting device may be a normal type organic light emitting device in which an anode, at least one organic layer, and a cathode are sequentially stacked on a substrate.

 In another embodiment, the organic light emitting device may be an inverted type organic light emitting device in which a cathode, at least one organic material layer, and an anode are sequentially stacked on a substrate.

For example, the structure of the organic light emitting device according to one embodiment of the present disclosure is illustrated in FIGS.

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

2 shows a structure in which a first electrode 30, a hole injecting layer 60, a hole transporting layer 70, an electron blocking layer 80, a light emitting layer 40, an electron transporting layer 90, 100 and a second electrode 50 are sequentially laminated on a transparent substrate 100. In this case,

2 is an exemplary structure according to an embodiment of the present invention, and may further include another organic layer.

According to an embodiment of the present invention, the organic material layer includes a hole transporting layer, and the hole transporting layer includes a compound represented by the general formula (1).

According to an embodiment of the present invention, the organic material layer includes an electron blocking layer, and the electron blocking layer includes a compound represented by the general formula (1).

According to one embodiment of the present invention, the organic material layer includes an electron transporting layer, and the electron transporting layer includes a compound represented by the general formula (1).

According to an embodiment of the present invention, the organic layer includes a light emitting layer, and the light emitting layer includes a compound represented by the general formula (1).

According to one embodiment of the present invention, the organic layer includes a light emitting layer, and the light emitting layer includes the compound represented by Formula 1 as a host of the light emitting layer.

According to one embodiment of the present invention, the organic material layer of the organic light emitting device in the present specification includes an electron transporting layer or a light emitting layer, wherein the substituent Ar in the electron transporting layer or the light emitting layer is a phenyl group; Biphenyl group; A terphenyl group; Naphthyl group; A dimethylfluorene group; A dibenzothiophene group; A pyrimidine group substituted with a carbazole group, cyano group or phenyl group substituted or unsubstituted with a phenyl group; A triazine group substituted or unsubstituted with a phenyl group, a biphenyl group, or a dibenzofurane group; A carbazole group substituted or unsubstituted with a phenyl group; A phenyl group, a biphenyl group, a naphthyl group, or a quinazoline group substituted or unsubstituted with a carbazole group substituted or unsubstituted with a phenyl group; A quinoxaline group substituted or unsubstituted with a phenyl group or a naphthyl group; A benzo [h] quinazoline group substituted with a phenyl group; A benzofura [3,2-d] pyrimidine group substituted or unsubstituted with a phenyl group, a biphenyl group, or a naphthyl group; A 5,5-dimethyl-5H-indeno [1,2-d] pyrimidine group substituted or unsubstituted with a phenyl group, a biphenyl group, or a naphthyl group; A pyrido [3,2-b] pyrazine group substituted with a phenyl group; A pyrazino [2,3-b] pyrazine group substituted with a phenyl group; A benzothieno [2,3-d] pyrimidine group substituted or unsubstituted with a phenyl group, a biphenyl group or a naphthyl group; A biphenyl group, a dimethylfluorene group, a dibenzofurane group, or an amine group substituted or unsubstituted with a triphenylene group; Or a phosphine oxide group substituted with a phenyl group.

According to one embodiment of the present invention, the organic material layer of the organic light emitting device in the present specification includes an electron blocking layer or a hole transporting layer, and the electron blocking layer or the hole transporting layer is formed by substituting the substituent Ar of the above formula Or an amine group substituted or unsubstituted with an aryl group.

In one embodiment of the present invention, the organic material layer includes the compound represented by Formula 1 as a host, and may include other organic compounds, metals, or metal compounds as a dopant.

The dopant may be at least one selected from the following compounds, but is not limited thereto.

In such a structure, the compound may be contained in at least one of the hole injecting layer, the hole transporting layer, the light emitting layer, and the electron transporting layer.

The organic light emitting device of the present invention can be manufactured by materials and methods known in the art, except that one or more of the organic layers includes the compound of the present invention, i.e., the compound.

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

 The organic light emitting device of the present invention can be manufactured by materials and methods known in the art, except that one or more of the organic layers include the compound, i.e., the compound represented by the above formula (1).

For example, the organic light emitting device of the present invention can be manufactured by sequentially laminating a first electrode, an organic material layer, and a second electrode on a substrate. At this time, by using a PVD (physical vapor deposition) method such as a sputtering method or an e-beam evaporation method, a metal or a metal oxide having conductivity or an alloy thereof is deposited on the substrate to form a positive electrode Forming an organic material layer including a hole injecting layer, a hole transporting layer, a light emitting layer and an electron transporting layer thereon, and depositing a material usable as a cathode thereon. In addition to such a method, an organic light emitting device can be formed by sequentially depositing a cathode material, an organic material layer, and a cathode material on a substrate.

In addition, the compound of Formula 1 may be formed into an organic material layer by a solution coating method as well as a vacuum evaporation method in the production of an organic light emitting device. Here, the solution coating method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating and the like, but is not limited thereto.

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

In one embodiment of the present invention, 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 a cathode.

As the anode material, a material having a large work function is preferably used so that hole injection can be smoothly conducted into the organic material layer. Specific examples of the cathode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO: Al or SnO _2: a combination of a metal and an oxide such as Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole and polyaniline.

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

The hole injecting material is a layer for injecting holes from the electrode. The hole injecting material has a hole injecting effect, a hole injecting effect in the anode, and an excellent hole injecting effect in the light emitting layer or the light emitting material. A compound which prevents the exciton from migrating to the electron injection layer or the electron injection material and is also excellent in the thin film forming ability is preferable. It is preferable that the highest occupied molecular orbital (HOMO) of the hole injecting material be between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injecting material include metal porphyrin, oligothiophene, arylamine-based organic materials, hexanitrile hexaazatriphenylene-based organic materials, quinacridone-based organic materials, and perylene- , Anthraquinone, polyaniline and polythiophene-based conductive polymers, but the present invention is not limited thereto.

The hole transport layer is a layer that transports holes from the hole injection layer to the light emitting layer. The hole transport material is a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer. The material is suitable. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers having a conjugated portion and a non-conjugated portion together, but are not limited thereto.

The light emitting material is preferably a material capable of emitting light in the visible light region by transporting and receiving holes and electrons from the hole transporting layer and the electron transporting layer, respectively, and having good quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; Compounds of the benzoxazole, benzothiazole and benzimidazole series; Polymers of poly (p-phenylenevinylene) (PPV) series; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited thereto.

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

The electron transporting material of the electron transporting layer is a layer that transports electrons from the electron injecting layer to the electron transporting layer and transports electrons from the cathode to the light emitting layer. This large material is suitable. Specific examples include an Al complex of 8-hydroxyquinoline; Complexes containing Alq ₃ ; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited thereto. The electron transporting layer can be used with any desired cathode material as used according to the prior art. In particular, an example of a suitable cathode material is a conventional material having a low work function followed by an aluminum layer or a silver layer. Specifically cesium, barium, calcium, ytterbium and samarium, in each case followed by an aluminum layer or a silver layer.

When the organic compound layer containing the compound of Formula 1 is an electron transporting layer, the electron transporting layer may further include 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 an example, the electron transport layer containing the compound of Formula 1 may further include LiQ.

The electron injection layer is a layer for injecting electrons from the electrode. The electron injection layer has the ability to transport electrons, has an electron injection effect from the cathode, and has an excellent electron injection effect with respect to the light emitting layer or the light emitting material. A compound which prevents migration to a layer and is excellent in a thin film forming ability is preferable. Specific examples thereof include fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, A complex compound and a nitrogen-containing five-membered ring derivative, but are not limited thereto.

Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, bis (8- Tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8- hydroxyquinolinato) gallium, bis (10- Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8- quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) (2-naphtholato) gallium, and the like, But is not limited thereto.

The hole blocking layer prevents holes from reaching the cathode, and may be formed under the same conditions as those of the hole injecting layer. Specific examples thereof 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 invention may be of a top emission type, a back emission type, or a both-side emission type, depending on the material used.

In one embodiment of the present invention, the compound may be included in an organic solar cell or an organic transistor in addition to the organic light emitting device.

The compound according to the present invention can act on a principle similar to that applied to organic light emitting devices in organic electronic devices including organic phosphorescent devices, organic solar cells, organic photoconductors, organic transistors and the like.

Hereinafter, the present invention will be described in detail by way of examples with reference to the drawings. However, the embodiments according to the present disclosure can be modified in various other forms, and the scope of the present specification is not construed as being limited to the embodiments described below. Embodiments of the present disclosure are provided to more fully describe the present disclosure to those of ordinary skill in the art.

< Example 1 >

A thin glass substrate coated with ITO (indium tin oxide) at a thickness of 1,300 Å was immersed in distilled water containing detergent and washed with ultrasonic waves. At this time, a Fischer Co. product was used as a detergent, and distilled water, which was filtered with a filter of Millipore Co., was used as distilled water. The ITO was washed for 30 minutes and then washed twice with distilled water and ultrasonically cleaned for 10 minutes. After the distilled water was washed, it was ultrasonically washed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. Further, the substrate was cleaned using oxygen plasma for 5 minutes, and then the substrate was transported by a vacuum evaporator. The HAT-CN compound as described above was thermally vacuum deposited on the ITO transparent electrode to a thickness of 500 Å to form a hole injection layer. The HT1 compound was thermally vacuum deposited on the hole injection layer to a thickness of 800 Å, and HT2 compound was vacuum deposited thereon to a thickness of 500 Å to form a hole transport layer. Compound 2-1-A and dopant Dp-7 compound were vacuum-deposited as a host to a thickness of 300 Å in the light emitting layer. The amount of the dopant was 3 wt% based on the total amount of the host and the dopant. An ET-1 material was vacuum deposited on the light emitting layer to form a hole blocking layer to form a hole blocking layer. An ET-2 material and LiQ were vacuum deposited on the hole blocking layer at a weight ratio of 1: 1 to form an electron transporting layer of 250 ANGSTROM . Lithium fluoride (LiF) was sequentially deposited on the electron transporting layer to a thickness of 10 Å, and aluminum was deposited thereon to a thickness of 1000 Å to form a cathode. The deposition rate of the organic material was maintained at 0.4 to 0.7 Å / sec, the lithium fluoride at the cathode was maintained at a deposition rate of 0.3 Å / sec, and the deposition rate of aluminum was maintained at 2 Å / sec. ^-7 to 5 x 10 &lt; ^-8 &gt; torr.

< Example  2>

An organic luminescent device was fabricated in the same manner as in Example 1, except that the compound 2-1-B was used instead of the compound 2-1-A in Example 1 above.

< Example  3>

An organic light emitting device was fabricated in the same manner as in Example 1 except that the compound 3-1-A was used instead of the compound 2-1-A in Example 1,

< Example  4>

An organic luminescent device was fabricated in the same manner as in Example 1, except that the compound 3-1-B was used instead of the compound 2-1-A in Example 1 above.

< Example  5>

An organic luminescent device was fabricated in the same manner as in Example 1 except that the compound 4-1-A was used in place of the compound 2-1-A in Example 1 above.

< Example  6>

An organic luminescent device was fabricated in the same manner as in Example 1, except that the compound 4-1-B was used instead of the compound 2-1-A in Example 1 above.

< Comparative Example  1>

An organic luminescent device was fabricated in the same manner as in Example 1, except that H-1 was used instead of the compound 2-1-A in Example 1.

< Comparative Example  2>

An organic luminescent device was fabricated in the same manner as in Example 1 except that H-2 was used instead of the compound 2-1-A in Example 1.

Table 1 shows the results of the organic light-emitting device manufactured by the above-described Examples 1 to 6 and Comparative Examples 1 and 2. Voltage, efficiency, and emission color are data at 5000 nit brightness. The lifetime was 100% of the initial photocurrent value, and the time was 98% of the photocurrent value.

division matter The driving voltage (V) Efficiency (cd / A) Life span T98 (hr) Luminous color Example 1  Compound 2-1-A 4.2 35.8 87 Red Example 2 Compound 2-1-B 3.9 37.6 68 Red Example 3 Compound 3-1-A 4.0 36.5 83 Red Example 4 Compound 3-1-B 3.8 38.0 66 Red Example 5 Compound 4-1-A 3.9 36.2 34 Red Example 6 Compound 4-1-B 4.1 30.7 61 Red Comparative Example 1 H-1 4.2 26.3 40 Red Comparative Example 2 H-2 4.2 28.6 49 Red

Compared to the previously known comparative materials, the material of the present invention has a wider HOMO region of the molecular orbital function. This has the advantage that the hole transport can be well transferred to the host material since the energy level can be adjusted to a level similar to that of the hole transport layer. It can be seen from Table 1 that the organic EL device using the compound of the present invention has improved luminous efficiency while lowering the driving voltage and shows all the red luminescence. The material of the present invention exhibited an improvement of more than 70% in terms of efficiency in comparison with the comparative materials H-1 and H-2, and the driving voltage was advantageous as a whole. The life span of Comparative Example 1 and Comparative Example 2 is very short. Therefore, the compound of the present invention can be considered to have the advantages of high efficiency, low driving voltage and long life in an organic light emitting device.

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 (10)

A compound represented by the following formula (1):
[Chemical Formula 1]

In Formula 1,
L is a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
n is an integer of 0 to 2,
When n is 2 or more, the plural Ls are the same or different from each other,
Ar, and R ₁ to R ₃ are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; Cyano; A nitro group; A hydroxy group; A carbonyl group; An ester group; Imide; An amino group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
a is an integer of 1 to 4,
b is an integer of 1 to 4,
c is an integer of 1 to 6,
When a is 2 or more, a plurality of R &lt; ₁ &gt; s are the same or different from each other,
When b is 2 or more, a plurality of R &lt; ₂ &_gt; s are the same or different from each other,
When c is 2 or more, a plurality of R ₃ are the same or different from each other. The compound according to claim 1, wherein the compound represented by Formula 1 is represented by any one of the following Formulas 2 to 4:
(2)

(3)

[Chemical Formula 4]

In the above formulas 2 to 4,
L, n, Ar, and R ₁ to R ₃ are the same as defined in the above formula (1). [2] The compound according to claim 1, wherein Ar in Formula 1 is a substituted or unsubstituted aryl group having 6 to 50 carbon atoms; A substituted or unsubstituted C6 to C30 heteroaryl group; An arylamine group; A heteroarylamine group; Or the aryl group is a substituted or unsubstituted phosphine oxide group. [2] The compound according to claim 1, wherein Ar in Formula 1 is a phenyl group; Biphenyl group; A terphenyl group; Naphthyl group; A dimethylfluorene group; A dibenzothiophene group; A pyrimidine group substituted with a carbazole group, cyano group or phenyl group substituted or unsubstituted with a phenyl group; A triazine group substituted or unsubstituted with a phenyl group, a biphenyl group, or a dibenzofurane group; A carbazole group substituted or unsubstituted with a phenyl group; A phenyl group, a biphenyl group, a naphthyl group, or a quinazoline group substituted or unsubstituted with a carbazole group substituted or unsubstituted with a phenyl group; A quinoxaline group substituted or unsubstituted with a phenyl group or a naphthyl group; A benzo [h] quinazoline group substituted with a phenyl group; A benzofura [3,2-d] pyrimidine group substituted or unsubstituted with a phenyl group, a biphenyl group, or a naphthyl group; A 5,5-dimethyl-5H-indeno [1,2-d] pyrimidine group substituted or unsubstituted with a phenyl group, a biphenyl group, or a naphthyl group; A pyrido [3,2-b] pyrazine group substituted with a phenyl group; A pyrazino [2,3-b] pyrazine group substituted with a phenyl group; A benzothieno [2,3-d] pyrimidine group substituted or unsubstituted with a phenyl group, a biphenyl group or a naphthyl group; A biphenyl group, a dimethylfluorene group, a dibenzofurane group, or an amine group substituted or unsubstituted with a triphenylene group; Or a phosphine oxide group substituted with a phenyl group. The compound according to claim 1, wherein the compound of formula (1) is any one selected from the following compounds:

A first electrode; A second electrode facing the first electrode; And at least one organic compound layer provided between the first electrode and the second electrode, wherein at least one of the organic compound layers comprises a compound according to any one of claims 1 to 5. 2. The organic electronic device according to claim 1, Electronic device. The organic electronic device according to claim 6, wherein the organic layer includes a light emitting layer, and the light emitting layer comprises the compound. The organic electronic device according to claim 6, wherein the organic material layer includes a hole transporting layer, and the hole transporting layer comprises the compound. 7. The organic electronic device according to claim 6, wherein the organic layer comprises an electron blocking layer, and the electron blocking layer comprises the compound. 7. The organic electronic device according to claim 6, wherein the organic layer comprises an electron transporting layer, and the electron transporting layer comprises the compound.

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