KR20170022940A - Compound and organic electronic device comprising the same - Google Patents

Abstract

The present invention relates to a compound and an organic electronic device comprising the same. The compound is represented by chemical formula 1. The compound can exhibit high light-emitting efficiency.

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 application relates to compounds and organic electronic devices comprising them. The present application claims the benefit of Korean Patent Application No. 10-2015-0117897 filed on August 21, 2015 with the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference.

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 enhance the efficiency and stability of the organic light emitting device, the organic material layer may have a multi-layered 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 invention provides a compound and an organic electronic device comprising the same.

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

[Chemical Formula 1]

In formula (1)

Z is C, Si or Ge,

X ₁ to X ₃ are the same or different from each other, at least one of X ₁ to X ₃ is N, and the others are CR,

L is a direct bond; A substituted or unsubstituted arylene group; A substituted or unsubstituted divalent heterocyclic group; Or -NR'-,

R and R 'are the same or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

Ar ₁ and Ar ₂ may be the same or different from each other and each independently selected from the group consisting of deuterium, halogen, cyano, nitro, substituted or unsubstituted silyl, C ₁ to C ₄₀ alkyl, C ₆ to C ₄₀ cycloalkyl , A C ₆ to C ₄₀ aryl group, and a C ₂ to C ₄₀ heterocyclic group; A substituted or unsubstituted aryl group, a substituted or unsubstituted silyl group, a C ₆ to C ₄₀ cycloalkyl group, a C ₆ to C ₄₀ aryl group, and a C ₂ to C ₄₀ heterocyclic group, from the group consisting of a halogen atom, a halogen atom, a cyano group, An aryl group substituted or unsubstituted with at least one selected; Or a deuterium, a halogen group, a cyano group, a nitro group, a substituted or unsubstituted silyl group, an alkyl group of C ₁ to about C _40, cycloalkyl group of C ₆ to C _40, C ₆ to C ₄₀ aryl, and C ₂ to and at least one substituted or unsubstituted heterocycle selected from the group consisting of a heterocycle of the C _40,

R ₁ to R ₄ are the same or different from each other, and each independently hydrogen; heavy hydrogen; A C ₁ to C ₁₀ alkyl group; Or a C ₆ to C ₁₂ aryl group,

n is an integer of 0 to 4, and when n is an integer of 2 or more, plural Ls are the same or different from each other,

p is an integer of 0 to 4, and when p is an integer of 2 or more, plural R < ₁ > s are the same or different,

q, r and s are each an integer of 0 to 5, and when q, r and s are each an integer of 2 or more, plural R ₂ to R ₄ are the same or different from each other.

The present application also includes 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 application can be used in an organic electronic device including an organic light emitting device, and can exhibit a low driving voltage, a high luminous efficiency, and / or a long life effect.

1 shows an example of an organic light emitting device in which a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4 are sequentially laminated.
2 shows an organic light emitting device in which a substrate 1, an anode 2, a hole injecting layer 5, a hole transporting layer 6, a light emitting layer 3, an electron transporting layer 7 and a cathode 4 are sequentially laminated FIG.

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.

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; An alkyl group; An alkenyl group; An alkoxy group; A cycloalkyl group; An amine group; An aryl group; And a heterocyclic group, or that at least two of the substituents exemplified in the above exemplified substituents are substituted with a connected substituent, or have no substituent. For example, the "substituent group to which two or more substituents are connected" may be a biphenyl group. That is, the biphenyl group may be an aryl group, and may be interpreted as a substituent in which two phenyl groups are connected.

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

In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 50, and more preferably 1 to 40. 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 alkenyl group may be straight-chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. 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 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 20 carbon atoms. Specific examples include methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, N-hexyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, But is not limited thereto.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and more preferably 6 to 40 carbon atoms. Specific examples include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but are 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 it is preferably 6 to 40 carbon atoms, more preferably 6 to 25 carbon atoms. Specific examples of the monocyclic aryl group include, but are not limited to, a phenyl group, a biphenyl group, a terphenyl 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 24 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.

등이 있다.In the present specification, the heterocyclic group includes at least one non-carbon atom or hetero atom, and specifically, the hetero atom may include at least one atom selected from the group consisting of O, N, Se, and S, and the like. The number of carbon atoms of the heterocyclic group is not particularly limited, but is preferably 2 to 60 carbon atoms. Examples of the heterocyclic group include thiophenyl group, furanyl group, pyrrolyl group, imidazolyl group, thiazolyl group, oxazolyl group, oxadiazolyl group, triazolyl group, pyridyl group, bipyridyl group, pyrimidyl group, A pyridazinyl group, a pyridazinyl group, a pyridazinyl group, a pyridazinyl group, a pyridazinyl group, a pyridazinyl group, a pyridazinyl group, a pyridazinyl group, a pyrazinyl group, a quinolizinyl group, a quinazolinyl group, A benzoyl group, a benzoyl group, a benzoyl group, an isoquinolinyl group, an indole group, a carbazolyl group, a benzoxazolyl group, a benzimidazolyl group, a benzothiazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a benzothiophenyl group, A phenanthrolinyl group, a phenanthrolinyl group, a thiazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiadiazolyl group, a benzothiazolyl group, a phenothiazinyl group, a phenoxazinyl group, a dibenzofurane group and the like , And a condensation structure of < RTI ID = 0.0 > . In addition, examples of the heterocyclic group include a heterocyclic structure including a sulfonyl group,

.

,

,

등이 될 수 있으나, 이에 한정되는 것은 아니다.In the present specification, the condensed structure may be a structure in which an aromatic carbon-hydrogen ring is condensed with the substituent. For example, as a condensation ring of benzimidazole

,

,

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

As used herein, the term "adjacent" means that the substituent is a substituent substituted on an atom directly connected to the substituted atom, a substituent stereostructically closest to the substituent, or another substituent substituted on the substituted atom . For example, two substituents substituted at the ortho position in the benzene ring and two substituents substituted at the same carbon in the aliphatic ring may be interpreted as "adjacent" groups to each other.

In the present specification, the adjacent groups bonded to each other to form a ring means that adjacent groups are bonded to each other to form a 5-membered to 8-membered hydrocarbon ring or a 5-to 8-membered heterocyclic ring as described above , Monocyclic or polycyclic, and may be aliphatic, aromatic, or condensed forms thereof, but is not limited thereto.

As used herein, the hydrocarbon ring or heterocycle may be selected from the examples of cycloalkyl groups, aryl groups or heterocyclic groups described above, except monovalent, and may be monocyclic or polycyclic, aliphatic or aromatic, or a condensed form thereof Yes. But is not limited thereto.

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

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

According to one embodiment of the present application, X ₁ is N.

According to one embodiment of the present application, X ₂ is N.

According to one embodiment of the present application, X ₃ is N.

According to one embodiment of the present application, X ₁ is CR.

According to one embodiment of the present application, X ₂ is CR.

According to one embodiment of the present application, X ₃ is CR.

According to one embodiment of the present application, X ₁ and X ₂ are N.

According to one embodiment of the present application, X ₁ and X ₃ are N.

According to one embodiment of the present application, X ₂ and X ₃ are N.

According to one embodiment of the present application, X ₁ to X ₃ are N.

According to one embodiment of the present application, L is a direct bond; Or a substituted or unsubstituted arylene group.

According to one embodiment of the present application, L is a direct bond; A substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylene group; A substituted or unsubstituted naphthylene group; A substituted or unsubstituted anthracenylene group; A substituted or unsubstituted fluorenylene group; A substituted or unsubstituted phenanthrenylene group; A substituted or unsubstituted pyrenylene group; And a substituted or unsubstituted chryshenylene group.

According to one embodiment of the present application, L is a direct bond; A phenylene group; Biphenylene group; Naphthylene group; Anthracenylene group; A fluorenylene group; Phenanthrenylene group; Pyrenylene group; And a chlorenylene group.

According to one embodiment of the present application, L is a direct bond; Or a substituted or unsubstituted phenylene group.

According to one embodiment of the present application, L is a direct bond; Or a phenylene group.

또는

이다. 상기 구조식에서 점선은 화학식 1의 N 포함 헤테로고리 및 벤젠고리에 결합되는 위치이다.According to one embodiment of the present application, L is a direct bond;

or

to be. In the above formula, the dotted line is a position at which the N-containing heterocyclic ring and the benzene ring of formula (1) are bonded.

According to one embodiment of the present application, n is 1 or 2.

According to one embodiment of the present application, n is 3 and the three Ls are the same or different from each other.

According to one embodiment of the present application, n is 4 and the four Ls are the same or different.

According to one embodiment of the present application, Ar ₁ and Ar ₂ are the same or different and each independently represents a substituted or unsubstituted C ₆ to C ₂₀ aryl group; Or a substituted or unsubstituted C ₂ to C ₂₀ heterocyclic group.

According to one embodiment of the present application, Ar ₁ and Ar ₂ are the same or different from each other and each independently selected from the group consisting of deuterium, a halogen group, a cyano group, a nitro group, a trimethylsilyl group, a C ₆ to C ₄₀ cycloalkyl group, A C ₆ to C ₂₀ aryl group which is substituted or unsubstituted with at least one member selected from the group consisting of a C ₆ to C ₄₀ aryl group and a C ₂ to C ₄₀ heterocyclic group; Or a deuterium, a halogen group, a cyano group, a nitro group, trimethylsilyl group, C ₁ to alkyl groups of C _40, C ₆ to C ₄₀ cycloalkyl group, C ₆ to C ₄₀ aryl group, and heteroaryl of C ₂ to C ₄₀ And a C ₂ to C ₂₀ heterocyclic group which is substituted or unsubstituted with at least one selected from the group consisting of halogen atoms.

According to one embodiment of the present application, Ar ₁ and Ar ₂ may be the same or different from each other and each independently selected from the group consisting of deuterium, a halogen group, a cyano group, a nitro group, a trimethylsilyl group, a C ₆ to C ₂₀ aryl group, A C ₆ to C ₂₀ aryl group which is substituted or unsubstituted with at least one selected from the group consisting of C ₂ to C ₂₀ heterocyclic groups; Or at least one selected from the group consisting of deuterium, a halogen group, a cyano group, a nitro group, a trimethylsilyl group, a C ₁ to C ₂₀ alkyl group, a C ₆ to C ₂₀ aryl group, and a C ₂ to C ₂₀ heterocyclic group Substituted or unsubstituted C ₂ to C ₂₀ heterocyclic group.

According to one embodiment of the present application, Ar ₁ and Ar ₂ are the same or different and are each independently selected from the group consisting of deuterium, a halogen group, a cyano group, a nitro group, a trimethylsilyl group, a phenyl group, and a biphenyl group A substituted or unsubstituted C ₆ to C ₂₀ aryl group; Or at least one member selected from the group consisting of deuterium, halogen, cyano, nitro, trimethylsilyl, methyl, ethyl, propyl, i-propyl, butyl, t-butyl, Or an unsubstituted C ₂ to C ₂₀ heterocyclic group.

According to one embodiment of the present application, the C ₆ to C ₂₀ aryl group is a phenyl group; Biphenyl group; Naphthyl group; Anthracenyl group; A phenanthrenyl group; A crycenyl group; Pyrenyl; A triphenylrenyl group; Or a fluorenyl group.

According to an exemplary embodiment of the present application, the C ₂ to C ₂₀ heterocyclic group is a pyridyl group of; Pyrimidyl; Triazinyl groups; A thiophenyl group; A furanyl group; A benzofuranyl group; A benzothiophenyl group; A dibenzofuranyl group; A dibenzothiophenyl group; A carbazolyl group; Benzocarbazolyl group; Or a dibenzocarbazolyl group.

According to one embodiment of the present application, R1 to R4 are the same or different and each independently hydrogen; heavy hydrogen; Methyl or phenyl.

According to one embodiment of the present application, R1 to R4 are hydrogen.

According to one embodiment of the present application, Z is C and the compound of Formula 1 is symmetrical.

According to one embodiment of the present application, the compound represented by Formula 1 is asymmetric.

According to one embodiment of the present application, Z is C and the compound of Formula 1 is asymmetric.

According to one embodiment of the present application, Z is Si and the compound of Formula 1 is asymmetric. Particularly, a compound in which Z is Si and asymmetric has a low driving voltage, a high luminous index and a long life.

According to one embodiment of the present invention, when Ar 1 and Ar 2 are different from each other or when L is a phenylene group, the compound represented by the general formula (1) is asymmetric, and the bonding position is meta or ortho it means.

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

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

In one embodiment of the present application, 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 of the present application 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 application, the organic electronic device may be selected from the group consisting of an organic light emitting device, an organic phosphorescent device, an organic solar cell, an organic photoconductor (OPC), and an organic transistor.

Hereinafter, the organic light emitting device will be described.

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

In another embodiment, the organic layer includes a light emitting layer, and the light emitting layer includes the compound.

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

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

In one embodiment of the present application, 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 application, 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 electrons, and a hole blocking layer.

In one embodiment of the present application, 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 the embodiment of the present application, 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 application, the organic layer further includes a hole injection layer or a hole transport layer containing a compound including an arylamino group, a carbazole group or a benzocarbazole group in addition to the organic compound layer containing the compound.

In one embodiment of the present application, the organic layer includes a light emitting layer, and the light emitting layer includes a compound represented by the following formula (A-1).

[A-1]

In the above formula (A-1)

m is an integer of 1 or more,

Ar3 is a substituted or unsubstituted monovalent or more benzofluorene group; A substituted or unsubstituted monovalent or more fluoranthene group; A substituted or unsubstituted monovalent or higher valent phenylene group; Or a substituted or unsubstituted monovalent or more chrysene group,

L1 is a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,

Ar 4 and Ar 5 are the same or different and each independently represents a substituted or unsubstituted aryl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted arylalkyl group; Or a substituted or unsubstituted heterocyclic group or may be bonded to each other to form a substituted or unsubstituted ring,

When m is 2 or more, the structures in parentheses two or more are the same or different from each other.

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 above formula (A-1) as a dopant in the light emitting layer.

According to one embodiment of the present disclosure, L1 is a direct bond.

According to one embodiment of the present disclosure, m is 2.

In one embodiment of the present invention, Ar3 is a divalent pyylene group substituted or unsubstituted with deuterium, a methyl group, an ethyl group, an isopropyl group, or a tert-butyl group; Or a divalent cyclic group substituted or unsubstituted with a deuterium, a methyl group, an ethyl group or a tert-butyl group.

In one embodiment of the present specification, Ar3 is a divalent pyylene group substituted or unsubstituted with an alkyl group; Or a divalent cyclic group substituted or unsubstituted with an alkyl group.

In one embodiment of the present invention, Ar3 is a divalent pyylene group substituted or unsubstituted with an alkyl group.

In one embodiment of the present invention, Ar3 is a divalent pyrene group.

According to one embodiment of the present invention, Ar4 and Ar5 are the same or different and each independently represent a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

According to one embodiment of the present invention, Ar4 and Ar5 are the same or different and each independently an aryl group substituted or unsubstituted with an alkyl group, a nitrile group, or a silyl group substituted with an alkyl group.

According to one embodiment of the present invention, Ar 4 and Ar 5 are the same or different and each independently represents a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a nitrile group, a substituted or unsubstituted Lt; / RTI >

According to one embodiment of the present invention, Ar4 and Ar5 are the same or different and each independently an aryl group substituted or unsubstituted with a silyl group substituted with an alkyl group.

According to one embodiment of the present invention, Ar4 and Ar5 are the same or different and each independently an aryl group substituted or unsubstituted with a trimethylsilyl group.

According to one embodiment of the present invention, Ar4 and Ar5 are the same or different and are each independently a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Or a substituted or unsubstituted terphenyl group.

According to one embodiment of the present invention, Ar4 and Ar5 are the same or different and each independently a phenyl group substituted or unsubstituted with a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a nitrile group or a trimethylsilyl group.

According to one embodiment of the present invention, Ar4 and Ar5 are the same or different and each independently a phenyl group substituted or unsubstituted with a trimethylsilyl group.

According to one embodiment of the present invention, Ar 4 and Ar 5 are the same or different and each independently represent a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

According to one embodiment of the present invention, Ar4 and Ar5 are the same or different and each independently represents a methyl group, an ethyl group, a tert-butyl group, a nitrile group, a silyl group substituted with an alkyl group, Lt; / RTI >

According to one embodiment of the present invention, Ar4 and Ar5 are the same or different and each independently represents a dibenzofurane group substituted or unsubstituted with a methyl group, an ethyl group, a tert-butyl group, a nitrile group, a trimethylsilyl group, to be.

According to one embodiment of the present disclosure, the formula (A-1) is selected from the following compounds.

According to one embodiment of the present invention, the organic layer includes a light emitting layer, and the light emitting layer includes a compound represented by the following formula (A-2).

[A-2]

In the above formula (A-2)

Ar6 and Ar7 are the same or different and each independently represents a substituted or unsubstituted monocyclic aryl group; Or a substituted or unsubstituted polycyclic aryl group,

G1 to G8 are the same or different from each other, and each independently hydrogen; A substituted or unsubstituted monocyclic aryl group; Or a substituted or unsubstituted polycyclic aryl group.

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 the above formula (A-2) as a host of the light emitting layer.

According to one embodiment of the present invention, Ar6 and Ar7 are the same or different and each independently a substituted or unsubstituted polycyclic aryl group.

According to one embodiment of the present invention, Ar6 and Ar7 are the same or different and each independently a substituted or unsubstituted polycyclic aryl group having 10 to 30 carbon atoms.

According to one embodiment of the present invention, Ar6 and Ar7 are the same or different and each independently a substituted or unsubstituted naphthyl group.

According to one embodiment of the present invention, Ar6 and Ar7 are the same or different and each independently a substituted or unsubstituted 1-naphthyl group.

According to one embodiment of the present invention, Ar6 and Ar7 are 1-naphthyl groups.

According to one embodiment of the present invention, G1 to G8 are hydrogen.

According to one embodiment of the present disclosure, the formula (A-2) is selected from the following compounds.

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 the formula A-1 as a dopant of the light emitting layer, and the compound represented by the formula A- .

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 compound layer, and an anode are sequentially stacked on a substrate.

For example, the structure of an organic light emitting device according to one embodiment of the present application is illustrated in Figs. 1 and 2. Fig.

1 shows a structure of an organic electronic device in which a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4 are sequentially laminated. In such a structure, the compound may be included in the light emitting layer (3).

2 shows an organic electronic device in which a substrate 1, an anode 2, a hole injecting layer 5, a hole transporting layer 6, a light emitting layer 3, an electron transporting layer 7 and a cathode 4 are sequentially stacked Structure is illustrated. In such a structure, the compound may be contained in at least one of the hole injecting layer 5, the hole transporting layer 6, the light emitting layer 3, and the electron transporting layer 7.

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 application may 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 application, 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 application can be produced by materials and methods known in the art, except that one or more of the organic layers include the above compound, that is, the compound represented by the above formula (1).

For example, the organic light emitting device of the present application 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 application, 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 layer is a layer for injecting holes from an electrode. The hole injecting material has a hole injecting effect, and has a hole injecting effect on the light emitting layer or a light emitting material. A compound which prevents the migration of excitons to the electron injecting layer or the electron injecting 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 layer is a layer that receives electrons from the electron injecting layer and transports electrons to the light emitting layer. The electron transporting material is a material capable of transferring electrons from the cathode well to the light emitting layer. 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.

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, perylene tetracarboxylic 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 application, 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 application may 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.

The preparation of the compound represented by Formula 1 and the organic light emitting device comprising the same will be described in detail in the following examples. However, the following examples are intended to illustrate the present specification, and the scope of the present specification is not limited thereto.

<Production Example>

&Lt; Synthesis Example 1 > - Preparation of the compound represented by Compound 1

(1) Preparation of Compound 1A

Reagent 1 (100.0 g, 250.45 mmol) was mixed with reagent 2 (70.0 g, 275.46 mmol) and potassium acetate (73.7 g, 751.26 mmol) in 1000 ml of dioxane and heated with stirring. Bis (dibenzylidineacetone) palladium (4.3 g, 7.51 mmol) and tricyclohexylphosphine (4.2 g, 15.03 mmol) were added under reflux and 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, extracted with chloroform, and the organic layer was dried over anhydrous magnesium sulfate. After distillation under reduced pressure, the product was recrystallized from ethanol to obtain Compound 1A (51 g, 61%).

(2) Preparation of compound 1

Compound 1A (14.3 g, 31.09 mmol) and Intermediate 1 (10.0 g, 29.09 mmol) were dissolved in 300 ml of tetrahydrofuran in a nitrogen atmosphere, followed by stirring and refluxing. After that, potassium carbonate (12.1 g, 87.26 mmol) was dissolved in 100 ml of water, and the mixture was sufficiently stirred and tetrakistriphenylphosphinopalladium (1.0 g, 0.87 mmol) was added thereto. After the reaction for 12 hours, the temperature was lowered to room temperature and the resulting solid was filtered. After filtration, the mixture was washed with 200 ml of tetrahydrofuran, 500 ml of ethyl acetate, 500 ml of water and 200 ml of ethanol. Subsequently, the material was extracted with chloroform and water, and Compound 1 (14.1 g, 77%) was prepared through recrystallization.

MS: [M + H] &lt; + &gt; = 629

&Lt; Synthesis Example 2 > - Preparation of the compound represented by Compound 2

(1) Preparation of compound 2

Compound 1A (11.7 g, 26.20 mmol) and Intermediate 2 (10.0 g, 23.81 mmol) were added to 250 ml of tetrahydrofuran in a nitrogen atmosphere, followed by stirring and refluxing. Thereafter, potassium carbonate (9.9 g, 71.44 mmol) was dissolved in 600 ml of water, and the mixture was sufficiently stirred. Tetraquistriphenylphosphinopalladium (0.8 g, 0.71 mmol) was added thereto. After the reaction for 12 hours, the temperature was lowered to room temperature and the resulting solid was filtered. After filtration, the mixture was washed with 200 ml of tetrahydrofuran, 500 ml of ethyl acetate, 500 ml of water and 200 ml of ethanol. Subsequently, the material was extracted with chloroform and water, and compound 2 (11.1 g, 66%) was prepared through recrystallization.

MS: [M + H] &lt; + &gt; = 704

&Lt; Synthesis Example 3 > - Preparation of the compound represented by Compound 3

(1) Preparation of Compound 3

Compound 1A (11.7 g, 26.20 mmol) and Intermediate 3 (10.0 g, 23.81 mmol) were added to 250 ml of dioxane in a nitrogen atmosphere, followed by stirring and refluxing. (0.8 g, 0.71 mmol) and tricyclohexylphosphine (0.8 g, 0.71 mmol) were dissolved in 600 ml of water and sufficiently stirred. To the reaction mixture was added potassium bis (dibenzylidineacetone) palladium Respectively. After the reaction for 12 hours, the temperature was lowered to room temperature and the resulting solid was filtered. After filtration, the mixture was washed with 200 ml of tetrahydrofuran, 500 ml of ethyl acetate, 500 ml of water and 200 ml of ethanol. Subsequently, the material was extracted with chloroform and water and recrystallized to obtain Compound 3 (9.9 g, 59%).

MS: [M + H] &lt; + &gt; = 704

&Lt; Synthesis Example 4 > - Preparation of the compound represented by the compound 4

(1) Preparation of Compound (4)

In a nitrogen atmosphere, Compound 1A (18.3 g, 41.09 mmol) and Intermediate 4 (10.0 g, 37.35 mmol) were placed in 300 ml of tetrahydrofuran and stirred and refluxed. Then, potassium carbonate (15.5 g, 112.06 mmol) was dissolved in 100 ml of water, and the mixture was sufficiently stirred and tetrakistriphenylphosphinopalladium (1.3 g, 1.12 mmol) was added thereto. After the reaction for 12 hours, the temperature was lowered to room temperature and the resulting solid was filtered. After filtration, the mixture was washed with 200 ml of tetrahydrofuran, 500 ml of ethyl acetate, 500 ml of water and 200 ml of ethanol. Subsequently, the material was extracted with chloroform and water, and Compound 4 (14.6 g, 71%) was prepared through recrystallization.

MS: [M + H] &lt; + &gt; = 552

&Lt; Synthesis Example 5 > - Preparation of a compound represented by Compound 5

(1) Preparation of Compound 5

Compound 1A (12.6 g, 28.33 mmol) and Intermediate 5 (10.0 g, 25.76 mmol) were dissolved in 300 ml of tetrahydrofuran in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (15.5 g, 112.06 mmol) was dissolved in 100 ml of water, and the mixture was sufficiently stirred. Tetraquistriphenylphosphinopalladium (0.9 g, 0.77 mmol) was added thereto. After the reaction for 12 hours, the temperature was lowered to room temperature and the resulting solid was filtered. After filtration, the mixture was washed with 200 ml of tetrahydrofuran, 500 ml of ethyl acetate, 500 ml of water and 200 ml of ethanol. Subsequently, the material was extracted with chloroform and water and recrystallized to obtain Compound 5 (9.9 g, 61%).

MS: [M + H] &lt; + &gt; = 629

&Lt; Synthesis Example 6 > - Preparation of the compound represented by Compound 6

(1) Preparation of Compound 6

Compound 1A (14.3 g, 31.99 mmol) and Intermediate 6 (10.0 g, 29.09 mmol) were added to 250 ml of dioxane in a nitrogen atmosphere, followed by stirring and refluxing. Then, potassium bis (dibenzylidineacetone) palladium (0.8 g, 0.71 mmol) and tricyclohexylphosphine (0.8 g, 0.71 mmol) were added to the reaction solution after dissolving potassium phosphate (12.1 g, 87.26 mmol) Respectively. After the reaction for 12 hours, the temperature was lowered to room temperature and the resulting solid was filtered. After filtration, the mixture was washed with 200 ml of tetrahydrofuran, 500 ml of ethyl acetate, 500 ml of water and 200 ml of ethanol. Subsequently, the material was extracted with chloroform and water, and Compound 6 (14.6 g, 71%) was prepared through recrystallization.

MS: [M + H] &lt; + &gt; = 629

&Lt; Synthesis Example 7 > - Preparation of the compound represented by Compound 7

(1) Preparation of Compound 7A

Reagent 7-1 (16.2 g, 84.62 mmol) was added to 170 ml of anhydrous tetrahydrofuran and cooled to -78 ° C. Then, while stirring, n-butyllithium (40.6 mL, 101.54 mmol) was slowly added dropwise over 30 minutes and reacted for 1 hour. Then, Reagent 7-2 was put into a solid state. After reacting for 1 hour, the temperature was slowly raised to room temperature and reacted for 2 hours. After the reaction was completed, the reaction mixture was poured into water to separate the water layer and the organic layer. The organic layer was distilled under reduced pressure to obtain a solid and dried to obtain Compound 7A (21.0 g, 92%). From n-butyllithium and Aldrich, reagents 7-1 and 7-2 were purchased from TCI.

(2) Preparation of Compound 7B

Compound 7A (21.0 g, 56.61 mmol) was mixed with reagent 2 (15.8 g, 62.27 mmol) and potassium acetate (16.7 g, 169.83 mmol) in 300 ml of dioxane and heated with stirring. Bis (dibenzylidineacetone) palladium (1.0 g, 1.70 mmol) and tricyclohexylphosphine (1.0 g, 3.40 mmol) were added under reflux and 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, extracted with chloroform, and the organic layer was dried over anhydrous magnesium sulfate. After distillation under reduced pressure, the residue was recrystallized from ethanol to obtain Compound 7B (23 g, 88%).

(3) Preparation of Compound 7

In a nitrogen atmosphere, Compound 7B (14.8 g, 31.99 mmol) and Intermediate 1 (10.0 g, 29.09 mmol) were placed in 300 ml of tetrahydrofuran and stirred and refluxed. After that, potassium carbonate (12.1 g, 87.26 mmol) was dissolved in 100 ml of water, and the mixture was sufficiently stirred and tetrakistriphenylphosphinopalladium (1.0 g, 0.87 mmol) was added thereto. After the reaction for 12 hours, the temperature was lowered to room temperature and the resulting solid was filtered. After filtration, the mixture was washed with 200 ml of tetrahydrofuran, 500 ml of ethyl acetate, 500 ml of water and 200 ml of ethanol. Subsequently, the material was extracted with chloroform and water, and compound 7 (11.4 g, 61%) was prepared through recrystallization.

MS: [M + H] &lt; + &gt; = 645

&Lt; Synthesis Example 8 > - Preparation of the compound represented by Compound 8

(1) Preparation of Compound 8

In a nitrogen atmosphere, Compound 7B (12.1 g, 26.20 mmol) and Intermediate 2 (10.0 g, 23.81 mmol) were added to 300 ml of dioxane and stirred and refluxed. Then, potassium bis (dibenzylidineacetone) palladium (0.4g, 0.71mmol) and tricyclohexylphosphine (0.4g, 1.43mmol) were added to the reaction solution after dissolving potassium phosphate (15.2g, 71.44mmol) Respectively. After the reaction for 12 hours, the temperature was lowered to room temperature and the resulting solid was filtered. After filtration, the mixture was washed with 200 ml of tetrahydrofuran, 500 ml of ethyl acetate, 500 ml of water and 200 ml of ethanol. Subsequently, the material was extracted with chloroform and water, and Compound 8 (13.5 g, 79%) was prepared through recrystallization.

MS: [M + H] &lt; + &gt; = 721

&Lt; Synthesis Example 9 > - Preparation of the compound represented by Compound 9

(1) Preparation of Compound 9

In a nitrogen atmosphere, Compound 7B (12.1 g, 26.20 mmol) and Intermediate 3 (10.0 g, 23.81 mmol) were placed in 300 ml of dioxane and stirred and refluxed. Then, potassium bis (dibenzylidineacetone) palladium (0.4g, 0.71mmol) and tricyclohexylphosphine (0.4g, 1.43mmol) were added to the reaction solution after dissolving potassium phosphate (15.2g, 71.44mmol) Respectively. After the reaction for 12 hours, the temperature was lowered to room temperature and the resulting solid was filtered. After filtration, the mixture was washed with 200 ml of tetrahydrofuran, 500 ml of ethyl acetate, 500 ml of water and 200 ml of ethanol. Subsequently, the material was extracted with chloroform and water, and then Compound 9 (10.3 g, 60%) was prepared through recrystallization.

MS: [M + H] &lt; + &gt; = 721

&Lt; Synthesis Example 10 > - Preparation of the compound represented by Compound 10

(1) Preparation of Compound 10

Compound 7B (14.8 g, 31.99 mmol) and Intermediate 4 (10.0 g, 37.35 mmol) were dissolved in 300 ml of tetrahydrofuran in a nitrogen atmosphere, followed by stirring and refluxing. After that, potassium carbonate (12.1 g, 87.26 mmol) was dissolved in 100 ml of water, and the mixture was sufficiently stirred and tetrakistriphenylphosphinopalladium (1.3 g, 1.12 mmol) was added thereto. After the reaction for 12 hours, the temperature was lowered to room temperature and the resulting solid was filtered. After filtration, the mixture was washed with 200 ml of tetrahydrofuran, 500 ml of ethyl acetate, 500 ml of water and 200 ml of ethanol. Subsequently, the material was extracted with chloroform and water, and compound 10 (14.0 g, 66%) was prepared through recrystallization.

MS: [M + H] &lt; + &gt; = 568

&Lt; Synthesis Example 11 > - Preparation of the compound represented by Compound 11

(1) Preparation of Compound 11

Compound 13B (13.1 g, 31.99 mmol) and Intermediate 5 (10.0 g, 37.35 mmol) were added to 300 ml of tetrahydrofuran in a nitrogen atmosphere, followed by stirring and refluxing. Then, potassium carbonate (10.7 g, 77.27 mmol) was dissolved in 100 ml of water, and the mixture was sufficiently stirred. Tetraquistriphenylphosphinopalladium (0.9 g, 0.77 mmol) was added thereto. After the reaction for 12 hours, the temperature was lowered to room temperature and the resulting solid was filtered. After filtration, the mixture was washed with 200 ml of tetrahydrofuran, 500 ml of ethyl acetate, 500 ml of water and 200 ml of ethanol. Subsequently, the material was extracted with chloroform and water, and then Compound 11 (13.2 g, 71%) was prepared through recrystallization.

MS: [M + H] &lt; + &gt; = 719

&Lt; Synthesis Example 12 > - Preparation of the compound represented by Compound 12

(1) Preparation of Compound (12)

Compound 7B (14.8 g, 31.99 mmol) and Intermediate 6 (10.0 g, 29.09 mmol) were added to 300 ml of dioxane in a nitrogen atmosphere, followed by stirring and refluxing. After that, potassium bis (dibenzylidineacetone) palladium (0.5 g, 0.87 mmol) and tricyclohexylphosphine (0.5 g, 1.75 mmol) were dissolved in 100 ml of water, Respectively. After the reaction for 12 hours, the temperature was lowered to room temperature and the resulting solid was filtered. After filtration, the mixture was washed with 200 ml of tetrahydrofuran, 500 ml of ethyl acetate, 500 ml of water and 200 ml of ethanol. Subsequently, the material was extracted with chloroform and water, and compound 12 (10.3 g, 60%) was prepared through recrystallization.

MS: [M + H] &lt; + &gt; = 644

<Examples>

<Experimental Example 1-1>

A glass substrate (corning 7059 glass) coated with ITO (indium tin oxide) at a thickness of 1000 Å was immersed in distilled water containing a dispersant and washed with ultrasonic waves. The detergent was a product of Fischer Co. The distilled water was supplied by Millipore Co. Distilled water, which was secondly filtered with a filter of the product, was used. After the ITO was washed for 30 minutes, ultrasonic washing was repeated 10 times with distilled water twice. After the distilled water was washed, ultrasonic washing was performed in the order of isopropyl alcohol, acetone, and methanol solvent, followed by drying.

Hexanitrile hexaazatriphenylene was thermally vacuum deposited on the prepared ITO transparent electrode to a thickness of 500 Å to form a hole injection layer. HT1 (400 Å), which is a hole transporting material, was vacuum deposited on the hole transporting layer, and a host H1 and a dopant D1 compound were vacuum deposited as a light emitting layer to a thickness of 300 Å. Compound 1 prepared in Synthesis Example 1 and LiQ (Lithium Quinolate) were vacuum deposited on the light emitting layer at a weight ratio of 1: 1 to form an electron injecting and transporting layer having a thickness of 350 Å. Aluminum was sequentially deposited on the electron injecting and transporting layer to a thickness of 12 Å and lithium aluminum fluoride (LiF) to a thickness of 2,000 Å to form an anode, thereby preparing an organic light emitting device.

Was maintained at a vapor deposition rate of 0.4 to 0.7Å / sec for organic material in the above process, the lithium fluoride of the cathode was 0.3Å / sec, aluminum is deposited at a rate of 2Å / sec, During the deposition, a vacuum 2 × 10 ^{- 7} to 5 x 10 &lt; ^-6 &gt; torr to manufacture an organic light emitting device.

<Experimental Example 1-2>

The same experiment was conducted except that Compound 2 was used instead of Compound 1 as the electron transporting layer in Experimental Example 1-1.

<Experimental Example 1-3>

The same experiment was conducted except that Compound 3 was used instead of Compound 1 as the electron transporting layer in Experimental Example 1-1.

<Experimental Example 1-4>

The same experiment was carried out except that Compound 4 was used instead of Compound 1 as the electron transporting layer in Experimental Example 1-1.

<Experimental Example 1-5>

The same experiment was conducted except that Compound 5 was used instead of Compound 1 as the electron transporting layer in Experimental Example 1-1.

<Experimental Example 1-6>

The same experiment was conducted except that Compound 6 was used instead of Compound 1 as the electron transporting layer in Experimental Example 1-1.

<Experimental Example 1-7>

The same experiment was conducted except that Compound 7 was used instead of Compound 1 as the electron transporting layer in Experimental Example 1-1.

<Experimental Example 1-8>

The same experiment was conducted except that Compound 8 was used instead of Compound 1 as the electron transporting layer in Experimental Example 1-1.

<Experimental Example 1-9>

The same experiment was conducted except that Compound 9 was used instead of Compound 1 as the electron transporting layer in Experimental Example 1-1.

<Experimental Example 1-10>

The same experiment was conducted except that Compound 10 was used instead of Compound 1 as the electron transporting layer in Experimental Example 1-1.

<Experimental Example 1-11>

The same experiment was conducted except that Compound 11 was used instead of Compound 1 as the electron transporting layer in Experimental Example 1-1.

<Experimental Example 1-12>

The same experiment was conducted except that Compound 12 was used instead of Compound 1 as the electron transporting layer in Experimental Example 1-1.

&Lt; Comparative Example 1 &

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that the compound of ET1 was used instead of the compound 1 in Experimental Example 1-1.

&Lt; Comparative Example 2 &

An organic light emitting device was fabricated in the same manner as in Experimental Example 1-1, except that the compound of Formula 1 was used in Experimental Example 1-1.

Experimental Example 1-1 to 1-12 and Comparative Examples 1 and 2 and as each of the compound to measure the drive voltage and luminous efficiency at a current density of the organic light-emitting device ² to 10 mA / cm produced by using as the electron transport material (LT95), which is 95% of the initial luminance at a current density of 20 mA / cm &lt; ^{2 &} gt ;. The results are shown in Table 1 below.

Experimental Example
@ 10 mA / cm ² compound Voltage
(V) Current efficiency
(cd / A) Color coordinates
(x, y) LT 95% (hr)
@ 20 mA / cm ² Example 1 Compound 1 3.80 7.60 (0.133, 0.135) 36.0 Example 2 Compound 2 3.85 7.68 (0.133, 0.133) 52.0 Example 3 Compound 3 3.81 8.10 (0.133, 0.135) 37.0 Example 4 Compound 4 4.17 7.45 (0.133, 0.138) 32.4 Example 5 Compound 5 4.21 7.76 (0.133, 0.135) 38.1 Example 6 Compound 6 4.18 8.21 (0.132, 0.136) 36.5 Example 7 Compound 7 3.85 7.88 (0.132, 0.124) 88 Example 8 Compound 8 3.88 7.99 (0.132, 0.123) 95 Example 9 Compound 9 3.85 8.20 (0.132, 0.126) 90 Example 10 Compound 10 4.17 7.53 (0.132, 0.125) 79.3 Example 11 Compound 11 4.00 7.07 (0.132, 0.127) 72.3 Example 12 Compound 12 3.95 7.90 (0.132, 0.128) 86 Comparative Example 1 ET1 4.03 5.16 (0.134, 0.132) 80 Comparative Example 2 ET2 4.00 7.20 (0.132, 0.128) 40

As can be seen from Table 1, the organic light emitting device manufactured using the compound of the present invention as an electron transport layer material exhibited excellent characteristics in terms of efficiency and stability as compared with the case of using the materials of Comparative Examples 1 and 2 Able to know.

While the present invention has been particularly shown and described with reference to exemplary embodiments thereof, it is to be understood that the invention is not limited to the disclosed exemplary embodiments, but, on the contrary, is intended to cover various modifications and equivalent arrangements included within the spirit and scope of the appended claims. .

1: substrate
2: anode
3: light emitting layer
4: cathode
5: Hole injection layer
6: hole transport layer
7: Electron transport layer

Claims (18)

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

In formula (1)
Z is C, Si or Ge,
X ₁ to X ₃ are the same or different from each other, at least one of X ₁ to X ₃ is N, and the others are CR,
L is a direct bond; A substituted or unsubstituted arylene group; A substituted or unsubstituted divalent heterocyclic group; Or -NR'-,
R and R 'are the same or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
Ar ₁ and Ar ₂ may be the same or different from each other and each independently selected from the group consisting of deuterium, halogen, cyano, nitro, substituted or unsubstituted silyl, C ₁ to C ₄₀ alkyl, C ₆ to C ₄₀ cycloalkyl , A C ₆ to C ₄₀ aryl group, and a C ₂ to C ₄₀ heterocyclic group; A substituted or unsubstituted aryl group, a substituted or unsubstituted silyl group, a C ₆ to C ₄₀ cycloalkyl group, a C ₆ to C ₄₀ aryl group, and a C ₂ to C ₄₀ heterocyclic group, from the group consisting of a halogen atom, a halogen atom, a cyano group, An aryl group substituted or unsubstituted with at least one selected; Or a deuterium, a halogen group, a cyano group, a nitro group, a substituted or unsubstituted silyl group, an alkyl group of C ₁ to about C _40, cycloalkyl group of C ₆ to C _40, C ₆ to C ₄₀ aryl, and C ₂ to and at least one substituted or unsubstituted heterocycle selected from the group consisting of a heterocycle of the C _40,
R ₁ to R ₄ are the same or different from each other, and each independently hydrogen; heavy hydrogen; A C ₁ to C ₁₀ alkyl group; Or a C ₆ to C ₁₂ aryl group,
n is an integer of 0 to 4, and when n is an integer of 2 or more, plural Ls are the same or different from each other,
p is an integer of 0 to 4, and when p is an integer of 2 or more, plural R &lt; ₁ &gt; s are the same or different,
q, r and s are each an integer of 0 to 5, and when q, r and s are each an integer of 2 or more, a plurality of R ₂ to R ₄ are the same or different from each other. The compound according to claim 1, wherein the compound represented by Formula 1 is asymmetric. The compound according to claim 1, wherein X ₁ to X ₃ are N. 2. The compound of claim 1, wherein L is a direct bond; Or a substituted or unsubstituted C ₁ to C ₂₀ arylene group. The compound according to claim 1, wherein Ar ₁ and Ar ₂ are the same or different and each independently represents a substituted or unsubstituted C ₆ to C ₂₀ aryl group; Or a substituted or unsubstituted C ₂ to C ₂₀ heterocyclic group. The compound according to claim 1, wherein R ₁ to R ₄ are hydrogen. The compound according to claim 1, wherein the compound represented by Formula 1 is any one selected from the following structural formulas:

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 7. The organic electronic device according to claim 1, Electronic device. The method of claim 8,
Wherein the organic material layer includes a hole injection layer or a hole transport layer,
Wherein the hole injection layer or the hole transport layer comprises the compound. The method of claim 8,
Wherein the organic layer includes a light emitting layer,
Wherein the light emitting layer comprises the compound. The method of claim 8,
Wherein the organic material layer includes an electron transport layer or an electron injection layer,
Wherein the electron transporting layer or the electron injecting layer comprises the compound. The method of claim 8,
Wherein the organic electronic device is a hole injection layer, a hole transport layer, An electron transport layer, an electron injection layer, an electron blocking layer, and a hole blocking layer. 11. The organic electronic device according to claim 10, wherein the organic electronic device is 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. 9. The organic electroluminescent device according to claim 8, wherein the organic layer includes a light emitting layer,
Wherein the light emitting layer comprises a compound represented by the following formula (A-1): &lt; EMI ID =
[A-1]

In the above formula (A-1)
m is an integer of 1 or more,
Ar3 is a substituted or unsubstituted monovalent or more benzofluorene group; A substituted or unsubstituted monovalent or more fluoranthene group; A substituted or unsubstituted monovalent or higher valent phenylene group; Or a substituted or unsubstituted monovalent or more chrysene group,
L1 is a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
Ar 4 and Ar 5 are the same or different and each independently represents a substituted or unsubstituted aryl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted arylalkyl group; Or a substituted or unsubstituted heterocyclic group or may be bonded to each other to form a substituted or unsubstituted ring,
When m is 2 or more, the structures in parentheses two or more are the same or different from each other. 15. The method of claim 14, wherein L1 is a direct bond,
Ar3 is a divalent pyrene group,
Ar4 and Ar5 are the same or different and each independently an aryl group substituted or unsubstituted with a silyl group substituted with an alkyl group, and m is 2; The method of claim 8,
Wherein the organic layer comprises a light emitting layer, and the light emitting layer comprises a compound represented by the following formula (A-2):
[A-2]

In the above formula (A-2)
Ar6 and Ar7 are the same or different and each independently represents a substituted or unsubstituted monocyclic aryl group; Or a substituted or unsubstituted polycyclic aryl group,
G1 to G8 are the same or different from each other, and each independently hydrogen; A substituted or unsubstituted monocyclic aryl group; Or a substituted or unsubstituted polycyclic aryl group. 18. The method of claim 16,
Wherein Ar6 and Ar7 are 1-naphthyl groups, and G1 to G8 are hydrogen. 15. The method of claim 14,
Wherein the light emitting layer comprises a compound represented by the following formula (A-2): &lt; EMI ID =
[A-2]

In the above formula (A-2)
Ar6 and Ar7 are the same or different and each independently represents a substituted or unsubstituted monocyclic aryl group; Or a substituted or unsubstituted polycyclic aryl group,
G1 to G8 are the same or different from each other, and each independently hydrogen; A substituted or unsubstituted monocyclic aryl group; Or a substituted or unsubstituted polycyclic aryl group.

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