KR101877678B1 - Compound and organic light emitting device using the same - Google Patents

Abstract

The present invention provides a compound of Formula 1 and an organic light emitting device using the same.

Description

TECHNICAL FIELD [0001] The present invention relates to a compound and an organic light emitting device using the compound.

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a compound and an organic light emitting device using the same. This specification claims the benefit of Korean Patent Application No. 10-2016-0071789 filed on June 9, 2016 with the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference.

The organic light emitting device has a structure in which an organic thin film is disposed between two electrodes. When a voltage is applied to the organic light emitting device having such a structure, electrons and holes injected from the two electrodes couple to each other in the organic thin film and form a pair, which then extinguishes and emits light. The organic thin film may be composed of a single layer or a multilayer, if necessary.

The material of the organic thin film may have a light emitting function as needed. For example, as the organic thin film material, a compound capable of forming a light emitting layer by itself may be used, or a compound capable of serving as a host or a dopant of a host-dopant light emitting layer may be used. In addition, as the material of the organic thin film, a compound capable of performing a role such as hole injection, hole transport, electron blocking, hole blocking, electron transport or electron injection may be used.

In order to improve the performance, life or efficiency of an organic light emitting device, development of materials for organic thin films is continuously required.

International Patent Application Publication No. 2003-012890

The present invention provides a compound and an organic light emitting device comprising the same.

An embodiment of the present invention provides a compound represented by the following formula (1).

 [Chemical Formula 1]

In Formula 1, X is O or S,

Ar1 is a substituted or unsubstituted aryl group,

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

R1 and R2 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

a is an integer of 0 to 4, b is an integer of 0 to 2, and when a and b are each 2 or more, the substituents in the parentheses are the same as or different from each other,

X ₁ to X ₃ are the same or different and each independently N or CH,

At least one of X ₁ to X ₃ is N,

At least one of Y ₁ to Y ₄ is C bonded to L and the other is N or CR,

R is hydrogen; heavy hydrogen; A halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, and when CR is 2 or more, Rs are the same or different from each other,

Ar2 and Ar3 are the same or different and each independently represents a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

The present application also includes a first electrode; A second electrode facing the first electrode; And at least one organic compound layer disposed between the first electrode and the second electrode, wherein at least one of the organic compound layers includes the compound described above.

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

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; A cycloalkyl group; An alkenyl group; An alkoxy group; A substituted or unsubstituted phosphine oxide 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, " a substituent to which at least two 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. 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 60 carbon atoms. Specific examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, 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 20 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 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 phosphine oxide group specifically includes a diphenylphosphine oxide group, dinaphthylphosphine oxide, and the like, but is not limited thereto.

In the present specification, when the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 6 to 25 carbon atoms. Specific examples of the monocyclic aryl group include a phenyl group, a biphenyl group, a terphenyl group, and the like, but are not limited thereto.

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.

), 피리다지닐기, 피라지닐기, 퀴놀리닐기, 퀴나졸리닐기, 퀴녹살리닐기, 프탈라지닐기, 피리도피리미디닐기, 피리도피라지닐기, 피라지노피라지닐기, 이소퀴놀리닐기, 인돌기, 카바졸릴기, 벤즈옥사졸릴기, 벤즈이미다졸릴기, 벤조티아졸릴기, 벤조카바졸릴기, 디벤조카바졸릴기, 벤조티오페닐기, 디벤조티오페닐기, 벤조퓨라닐기, 디벤조퓨라닐기; 벤조실롤기, 디벤조실롤기, 페난트롤리닐기(phenanthrolinyl group), 이소옥사졸릴기, 티아디아졸릴기, 페노티아지닐기, 페노옥사지닐기, 및 이들의 축합구조 등이 있으나, 이들에만 한정되는 것은 아니다. 이외에도 헤테로고리기의 예로서, 술포닐기를 포함하는 헤테로고리 구조, 예컨대,

,

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, Group, an acridyl group, a hydroacridyl group (e.g.,

), A pyridazinyl group, a pyrazinyl group, a quinolinyl group, a quinazolinyl group, a quinoxalinyl group, a phthalazinyl group, a pyridopyrimidinyl group, a pyridopyranyl group, a pyrazinopyrazinyl 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 dibenzothiophenyl group, a benzofuranyl group, A furanyl group; A benzothiazolyl group, a benzothiazolyl group, a phenothiazyl group, a phenoxazinyl group, a condensed structure thereof, and the like, but are not limited thereto It is not. In addition, examples of the heterocyclic group include a heterocyclic structure including a sulfonyl group,

,

.

In the present specification, the aryl group in the arylalkyl group, arylalkenyl group, alkylaryl group and arylamine group can be applied to the description of the aryl group described above.

In the present specification, the alkyl group, the alkylaryl group and the alkyl group in the alkylamine group may be the same as the alkyl group described above.

In the present specification, the heteroaryl among the heteroarylamines can be applied to the aforementioned heterocyclic group.

In the present specification, the alkenyl group in the arylalkenyl group can be applied to the description of the alkenyl group described above.

In the present specification, the description of the aryl group described above can be applied except that arylene is a divalent group.

In the present specification, the description of the above-mentioned heterocyclic group can be applied except that the heteroarylene is a divalent group.

In one embodiment of the present specification, Ar1 represents 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 phenanthrene group; A substituted or unsubstituted anthracene group; A substituted or unsubstituted fluorenyl group; Or a substituted or unsubstituted triphenylene group.

In one embodiment of the present specification, Ar1 represents a phenyl group; A biphenyl group; A terphenyl group; Naphthyl group; Phenanthrene; Anthracene group; A dimethylfluorene group or a triphenylene group.

In one embodiment of the present specification, Ar1 represents a phenyl group; A biphenyl group; Or a terphenyl group.

In one embodiment of the present specification, Ar2 and Ar3 are the same or different and each independently represents a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; An unsubstituted or unsubstituted naphthyl group; A substituted or unsubstituted fluorenyl group; Or a substituted or unsubstituted pyridine group.

In one embodiment of the present specification, Ar2 and Ar3 are the same or different and each independently represents a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; An unsubstituted or unsubstituted naphthyl group; A substituted or unsubstituted fluorenyl group; Or a substituted or unsubstituted pyridine group, and the substitution is substituted with a cyano group or an aryl group.

In one embodiment of the present specification, Ar2 and Ar3 are the same or different and each independently represents a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; An unsubstituted or unsubstituted naphthyl group; A substituted or unsubstituted fluorenyl group; Or a substituted or unsubstituted pyridine group, and the substitution is substituted with a cyano group or a phenyl group.

In one embodiment of the present specification, L is a direct bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylylene group, a substituted or unsubstituted dimethylfluorenyl group, a substituted or unsubstituted diphenyl A substituted or unsubstituted divalent pyridine group, a substituted or unsubstituted divalent dibenzothiophene group, or a substituted or unsubstituted divalent dibenzofurane group.

In one embodiment of the present invention, L is a direct bond, a phenylene group, a biphenylrenylene group, a dimethylfluorenyl group, a diphenylfluorenyl group, a divalent pyridine group, a divalent dibenzothiophene group, Dibenzofurane group.

In one embodiment of the present specification, R1 and R2 are the same or different from each other and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted methyl group; A substituted or unsubstituted ethyl group; A substituted or unsubstituted propyl group; A substituted or unsubstituted butyl group; A substituted or unsubstituted cyclohexyl group; A substituted or unsubstituted phenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted triphenylene group; A substituted or unsubstituted carbazole group; A substituted or unsubstituted dibenzofurane group; A substituted or unsubstituted dibenzothiophene group; A substituted or unsubstituted benzocarbazole group; A substituted or unsubstituted N-phenylcarbazole group; A substituted or unsubstituted N-phenylbenzocarbazole group; A substituted or unsubstituted pyridone ring; A substituted or unsubstituted benzopyropyridine group; A substituted or unsubstituted benzothienopyrimidine group; The substitution degree is an unsubstituted benzothienopyridine group; Or a substituted or unsubstituted benzopyrimidine group.

In one embodiment of the present disclosure, R 2 is hydrogen.

In one embodiment of the present specification, R 1 is selected from the group consisting of hydrogen, a substituted or unsubstituted phenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted cyclohexyl group, An unsubstituted naphthyl group, a substituted or unsubstituted N-phenylcarbazole group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted dibenzofurane group, a substituted or unsubstituted dibenzothiophene group, a substituted or unsubstituted naphthyl group, Substituted benzopyrimidine groups, substituted or unsubstituted benzophenylene groups, substituted benzopyrimidine groups, substituted or unsubstituted benzophenylene groups, substituted benzopyrimidine groups, substituted or unsubstituted benzophenone groups, substituted or unsubstituted benzophenone groups, Or a substituted or unsubstituted benzothienopyridine group. The substituent may be substituted or unsubstituted with a cyano group, a phenyl group, or a phenylcarbazole group.

In one embodiment of the present specification, R 1 is selected from the group consisting of hydrogen, a substituted or unsubstituted phenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted cyclohexyl group, An unsubstituted naphthyl group, a substituted or unsubstituted N-phenylcarbazole group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted dibenzofurane group, a substituted or unsubstituted dibenzothiophene group, a substituted or unsubstituted naphthyl group, Substituted benzopyrimidine groups, substituted or unsubstituted benzophenylene groups, substituted benzopyrimidine groups, substituted or unsubstituted benzophenylene groups, substituted benzopyrimidine groups, substituted or unsubstituted benzophenone groups, substituted or unsubstituted benzophenone groups, Or a substituted or unsubstituted benzothienopyridine group, and the substituent may be substituted or unsubstituted with cyano group, phenyl group, N-phenylcarbazole group.

In one embodiment of the present disclosure, X is O.

In one embodiment of the present disclosure, X is S.

In one embodiment of the present invention, the formula (1) is represented by the following formula (2) or (3).

(2)

(3)

In the general formulas (2) and (3)

Ar 1 to Ar 3, R 1, R 2, Y ₁ to Y ₄ , X ₁ to X ₃ , L, a and b are the same as defined in formula (1).

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

In one embodiment of the present disclosure, X ₁ is CH and X ₂ and X ₃ are N.

In one embodiment of the present disclosure, X ₂ is CH, and X ₁ and X ₃ are N.

In one embodiment of the present disclosure, X ₃ is CH and X ₁ and X ₂ are N.

In one embodiment of the present disclosure, X ₁ is N, X ₂ and X ₃ are CH.

In one embodiment of the present disclosure, X ₂ is N, X ₁ and X ₃ are CH.

In one embodiment of the present disclosure, X ₃ is N, X ₁ and X ₂ are CH.

In one embodiment of the present disclosure, Y ₁ is bonded to L and the remainder is N or CR.

In one embodiment of the present disclosure, Y ₂ is combined with L and the remainder is N or CR.

In one embodiment of the present disclosure, Y ₃ is combined with L and the remainder is N or CR.

In one embodiment of the present disclosure, Y < ₄ > is bonded to L and the remainder is N or CR.

In one embodiment of the present invention, the formula (1) is represented by any one of the following formulas (4) to (7).

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

(7)

In the above formulas 4 to 7,

Ar 1 to Ar 3, R 1, R 2, X, X ₁ to X ₃ , L, a and b are the same as defined in formula (1)

R11 to R14 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

In one embodiment of the present invention, the formula (1) is represented by any one of the following formulas (8) to (10).

[Chemical Formula 8]

[Chemical Formula 9]

[Chemical formula 10]

In the general formulas (8) to (10)

Ar 1 to Ar 3, R 1, R 2, X, X ₁ to X ₃ , L, a and b are the same as defined in formula (1)

R12 to R14 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

In one embodiment of the present disclosure, R is hydrogen; heavy hydrogen; A halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, and when CR is 2 or more, Rs are the same or different from each other.

In one embodiment of the present disclosure, R is hydrogen; heavy hydrogen; Or a substituted or unsubstituted aryl group, and when CR is 2 or more, Rs are the same or different from each other.

In one embodiment of the present disclosure, R is hydrogen; heavy hydrogen; Or an aryl group, and when CR is 2 or more, Rs are the same or different from each other.

In one embodiment of the present disclosure, R is hydrogen; heavy hydrogen; Or a phenyl group, and when CR is 2 or more, Rs are the same or different from each other.

In one embodiment of the present disclosure, Formula 1 is selected from the following formulas.

The compound according to one embodiment of the present application can be produced by a production method described below.

<Reaction Scheme 1>

The present invention also provides an organic light emitting device comprising the above-described compound.

In one embodiment of the present application, the first electrode; A second electrode facing the first electrode; And at least one organic compound layer disposed 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 light emitting device of the present application may have a single layer structure, but may have a multilayer structure in which two or more organic material layers are stacked. For example, as a typical example of the organic light emitting 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, and an electron injecting layer as organic layers. However, the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers.

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

In one embodiment of the present application, the light emitting layer is a phosphorescent light emitting layer.

In one embodiment of the present application, the light emitting layer further comprises a phosphorescent material.

In one embodiment of the present application, the thickness of the organic material layer including the compound of Formula 1 is 1 to 1000 Å, more preferably 1 to 500 Å.

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

In one embodiment of the present application, the organic layer includes a light emitting layer, and the light emitting layer includes the compound as a host material, and further includes another host material.

In one embodiment of the present application, the organic layer includes a light emitting layer, the light emitting layer includes the compound as a host material, and further includes another host material, and the compound and the other host material have a ratio of 1: 9 to 9: 1 &lt; / RTI &gt;

In one embodiment of the present application, the organic layer comprises a light emitting layer, wherein the light emitting layer comprises the compound as a host material and further comprises another host material, wherein the heterocyclic compound and the other host material have a ratio of 5: 5 .

In one embodiment of the present application, the other host material is a material comprising a carbazole.

In one embodiment of the present application, the other host material may be represented by the following formula (B).

[Chemical Formula B]

In the formula (B), R200 and R201 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

In one embodiment of the present application, R200 and R201 are the same or different and each independently a substituted or unsubstituted aryl group.

In one embodiment of the present application, R200 and R201 are the same or different and each independently represents a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Or a substituted or unsubstituted naphthyl group.

In one embodiment of the present application, R200 and R201 are the same or different and each independently represents a substituted or unsubstituted phenyl group; Or a substituted or unsubstituted biphenyl group.

In one embodiment of the present application, R200 and R201 are the same or different from each other and are each independently a phenyl group; Or a biphenyl group.

In one embodiment of the present application, R200 is a phenyl group, and R201 is a biphenyl group.

In one embodiment of the present application, the compound of formula (B) is a compound selected from the following structural formulas.

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

In one embodiment of the present application, the dopant compound is a phosphorescent dopant compound.

In one embodiment of the present application, the dopant compound is a metal complex.

In one embodiment of the present application, the dopant compound is an iridium complex.

In one embodiment of the present application, the organic layer includes a light emitting layer, and the light emitting layer contains the compound and the dopant compound in a weight ratio of 100: 1 to 5: 5. In one embodiment of the present application, The organic material layer includes a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer includes the above 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 material layer includes an electron transport layer, an electron injection layer, or an electron injection and transport layer, and the electron transport layer, the electron injection layer, or the electron injection and transport layer includes the above compound

In one embodiment of the present application, the organic layer includes an electron blocking layer or a hole blocking layer, and the electron blocking layer or the hole blocking layer includes the compound.

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 containing 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 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 light emitting 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 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 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 include 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 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-hydroxyquinoline 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.

As the electron transporting material, a material capable of transferring electrons from the cathode well into the light emitting layer, which is suitable for electrons, 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.

The electron injection layer is a layer for injecting electrons from the electrode. The electron injection layer has an 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.

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.

&Lt; Preparation Example > Preparation of Compound 1A

Iodo-2-nitrobenzene (42.8 g, 171.9 mmol) and potassium carbonate (K ₂ CO ₃ ) (71.2 g, 171.9 mmol) were added to a solution of 9- 515.7 mmol) was dissolved in toluene (800 mL) and H ₂ O (300 mL) and heated to 100 ° C. After addition of tetrakis (triphenylphosphine) palladium _{(Pd (PPh 3) 4)} (3.98g, 3.4mmol) and the mixture was refluxed for 4 hr. After cooling to room temperature, the water layer was removed. Magnesium sulfate (MgSO ₄ ) was added to the organic layer, followed by filtration. Concentrated, and then purified by column chromatography to obtain 1-bromo-8- (2-nitrophenyl) -dibenzofurane (50 g, yield 79%).

The intermediate compound (50 g, 135.8 mmol) was dissolved in triethyl ester phosphoric acid (700 ml) and refluxed at 150 ° C for 12 hours to obtain 1-bromo-7- benzopureocarbazole (40 g, 86% (25 g, 119 mmol), CuI and K ₃ PO ₄ were added to toluene (500 mL) and refluxed at 80 ° C. for 12 hours. After cooling to room temperature, the solid was filtered and washed several times with toluene and ethanol to obtain 1-bromo-7-phenyl-benzofukarbazole (45g, yield 91.8%). The compound (45 g, 109 mmol) thus obtained and bispinolate diboron (83 g, 327.4 mmol) were charged in dioxane (1500 ml) and dissolved by heating at 130 캜. P (Cy) ₃ and Pd (dba) ₂ were mixed at a molar ratio of 2: 1 (1.88 g), and the mixture was refluxed for 4 hours. After cooling to room temperature, the solution was concentrated and purified by column chromatography to obtain Compound 1A (42 g, yield 84%). MS: [M + H] &lt; ⁺ &gt; = 459

1B, 1C, 1D, 1E, 1F, 2A, 2B, 2C, 3A, and 3B were prepared by using other compounds instead of 9-bromo-2-dibenzofuranylboronic acid and iodobenzene in the above- 3B and 4A can be prepared. For example, Compound 2A can be prepared by using 8-bromo-2-dibenzofuranylboronic acid in place of 9-bromo-2-dibenzofuranylboronic acid in the above preparation example, Compound IB can be prepared using iodobiphenyl in place of dodecylbenzene.

Synthesis Example 1 Synthesis of Compound 1

Compound 1A (16g, 34.8mmol) and chloro-diphenyl-triazine (9.78g, 36.5mmol) and potassium carbonate _{(K 2 CO 3) (14.4g} , 104.4mmol) of tetrahydrofuran (THF) (300mL), H 2 O (100 ml) and heated to 90 &lt; 0 &gt; C. After addition of tetrakis (triphenylphosphine) palladium _{(Pd (PPh 3) 4)} (0.8g, 0.70mmol) and the mixture was refluxed for 4 hr. After cooling to room temperature, the water layer was removed. Magnesium sulfate (MgSO ₄ ) was added to the organic layer, followed by filtration. Concentrated, and then purified by column chromatography to obtain Compound 1 (15 g, yield 77%).

MS: [M + H] &lt; ⁺ &gt; = 564

Synthesis Example 2 Preparation of Compound 2

Except that 4-bromophenyldiphenyltriazine (14.2 g, 36.5 mmol) was used instead of chlorodiphenyltriazine in Synthesis Example 1 to obtain Compound 2 (18 g, yield: 81%) .

MS: [M + H] &lt; ⁺ &gt; = 640

SYNTHESIS EXAMPLE 3 Preparation of Compound 3

Except that chlorophenylnaphthalenetriazine (11.6 g, 36.5 mmol) was used instead of chlorodiphenyltriazine in Synthesis Example 1 to obtain Compound 3 (18 g, yield 84%).

MS: [M + H] &lt; ⁺ &gt; = 614

Synthesis Example 4 Preparation of Compound 4

The procedure of Synthesis Example 1 was repeated except that chloropyridine (9.7 g, 36.5 mmol) was used instead of chlorodiphenyltriazine to obtain Compound 4 (13 g, yield 66%).

MS: [M + H] &lt; ⁺ &gt; = 564

SYNTHESIS EXAMPLE 5 Preparation of Compound 5

Compound 5 (21 g, yield 75%) was prepared in the same manner as in Synthesis Example 1, except that chlorophenyldiphenylfluorene triazine (18.5 g, 36.5 mmol) was used instead of chlorochlorodiphenyltriazine .

MS: [M + H] &lt; ⁺ &gt; = 804

&Lt; Synthesis Example 6 > Preparation of Compound 6

(14 g, 104.4 mmol) and 4-bromodibenzothiophenyldiphenyltriazine (18 g, 36.5 mmol) and potassium carbonate (K ₂ CO ₃ ) (16 g, 34.8 mmol) were dissolved in tetrahydrofuran (THF) 300 mL) was dissolved in H ₂ O (100 mL) and heated to 90 ° C. After addition of tetrakis (triphenylphosphine) palladium _{(Pd (PPh 3) 4)} (0.8g, 0.70mmol) and the mixture was refluxed for 4 hr. After cooling to room temperature, the water layer was removed. Magnesium sulfate (MgSO ₄ ) was added to the organic layer, followed by filtration. Concentrated, and then purified by column chromatography to obtain Compound 6 (19 g, yield 73%).

MS: [M + H] &lt; ⁺ &gt; = 746

Synthesis Example 7 Preparation of Compound 7

Compound 2A (16g, 34.8mmol) and 4-bromo-modify-benzo furanyl-diphenyl-triazine (17.5g, 36.5mmol) and potassium carbonate _{(K 2 CO 3) (14.4g} , 104.4mmol) in tetrahydrofuran (THF) (300 mL), H ₂ O (100 mL) and heated to 90 ° C. After addition of tetrakis (triphenylphosphine) palladium _{(Pd (PPh 3) 4)} (0.8g, 0.70mmol) and the mixture was refluxed for 4 hr. After cooling to room temperature, the water layer was removed. Magnesium sulfate (MgSO ₄ ) was added to the organic layer, followed by filtration. Concentrated, and then purified by column chromatography to obtain Compound 7 (18 g, yield 71%).

MS: [M + H] &lt; ⁺ &gt; = 730

SYNTHESIS EXAMPLE 8 Preparation of Compound 8

A solution of compound 2B (18.6 g, 34.8 mmol), chlorodiphenyltriazine (9.8 g, 36.5 mmol) and potassium carbonate (K ₂ CO ₃ ) (14.4 g, 104.4 mmol) in tetrahydrofuran (THF) ₂ O (100 ml) and heated to 90 &lt; 0 &gt; C. After addition of tetrakis (triphenylphosphine) palladium _{(Pd (PPh 3) 4)} (0.8g, 0.70mmol) and the mixture was refluxed for 4 hr. After cooling to room temperature, the water layer was removed. Magnesium sulfate (MgSO ₄ ) was added to the organic layer, followed by filtration. Concentrated, and then purified by column chromatography to obtain Compound 8 (15 g, yield 68%).

MS: [M + H] &lt; ⁺ &gt; = 640

Synthesis Example 9 Synthesis of Compound 9

Compound 3A (18.8g, 34.8mmol) and chloro-diphenyl-triazine (9.8g, 36.5mmol) and potassium carbonate _{(K 2 CO 3) (14.4g} , 104.4mmol) of tetrahydrofuran (THF) (300mL), H ₂ O (100 ml) and heated to 90 &lt; 0 &gt; C. After addition of tetrakis (triphenylphosphine) palladium _{(Pd (PPh 3) 4)} (0.8g, 0.70mmol) and the mixture was refluxed for 4 hr. After cooling to room temperature, the water layer was removed. Magnesium sulfate (MgSO ₄ ) was added to the organic layer, followed by filtration. Concentrated, and then purified by column chromatography to obtain Compound 9 (16 g, yield 72%).

MS: [M + H] &lt; ⁺ &gt; = 646

Synthesis Example 10 Preparation of Compound 10

Except that Compound 1B (18.6 g, 34.8 mmol) was used instead of Compound 1A in Synthesis Example 1 to obtain Compound 10 (21 g, yield 84%).

MS: [M + H] &lt; ⁺ &gt; = 716

Synthesis Example 11 Synthesis of Compound 11

(13.4 g, 36.5 mmol) and potassium carbonate (K ₂ CO ₃ ) (14.4 g, 104.4 mmol) were dissolved in tetrahydrofuran (THF) (300 mL ), Dissolved in H ₂ O (100 ml) and heated to 90 ° C. After addition of tetrakis (triphenylphosphine) palladium _{(Pd (PPh 3) 4)} (0.8g, 0.70mmol) and the mixture was refluxed for 4 hr. After cooling to room temperature, the water layer was removed. Magnesium sulfate (MgSO ₄ ) was added to the organic layer, followed by filtration. Concentrated, and then purified by column chromatography to obtain Compound 11 (25 g, yield 80%).

MS: [M + H] &lt; ⁺ &gt; = 906

Synthesis Example 12 Preparation of Compound 12

Compound 1D (27g, 34.8mmol) and chloro-diphenyl-triazine (9.8g, 36.5mmol) and potassium carbonate _{(K 2 CO 3) (14.4g} , 104.4mmol) of tetrahydrofuran (THF) (300mL), H 2 O (100 ml) and heated to 90 &lt; 0 &gt; C. After addition of tetrakis (triphenylphosphine) palladium _{(Pd (PPh 3) 4)} (0.8g, 0.70mmol) and the mixture was refluxed for 4 hr. After cooling to room temperature, the water layer was removed. Magnesium sulfate (MgSO ₄ ) was added to the organic layer, followed by filtration. Concentrated, and then purified by column chromatography to obtain Compound 12 (26 g, yield 85%).

MS: [M + H] &lt; ⁺ &gt; = 884

Synthesis Example 13: Preparation of Compound 13

Compound 1E (24g, 34.8mmol) and chloro-diphenyl-triazine (9.8g, 36.5mmol) and potassium carbonate _{(K 2 CO 3) (14.4g} , 104.4mmol) of tetrahydrofuran (THF) (300mL), H 2 O (100 ml) and heated to 90 &lt; 0 &gt; C. After addition of tetrakis (triphenylphosphine) palladium _{(Pd (PPh 3) 4)} (0.8g, 0.70mmol) and the mixture was refluxed for 4 hr. After cooling to room temperature, the water layer was removed. Magnesium sulfate (MgSO ₄ ) was added to the organic layer, followed by filtration. Concentrated, and then purified by column chromatography to obtain Compound 13 (21 g, yield 77%).

MS: [M + H] &lt; ⁺ &gt; = 790

Synthesis Example 14: Preparation of Compound 14

Compound 2C (24.5g, 34.8mmol) and chloro-diphenyl-triazine (9.8g, 36.5mmol) and potassium carbonate _{(K 2 CO 3) (14.4g} , 104.4mmol) of tetrahydrofuran (THF) (300mL), H ₂ O (100 ml) and heated to 90 &lt; 0 &gt; C. After addition of tetrakis (triphenylphosphine) palladium _{(Pd (PPh 3) 4)} (0.8g, 0.70mmol) and the mixture was refluxed for 4 hr. After cooling to room temperature, the water layer was removed. Magnesium sulfate (MgSO ₄ ) was added to the organic layer, followed by filtration. Concentrated, and then purified by column chromatography to obtain Compound 14 (20 g, yield 71%).

MS: [M + H] &lt; ⁺ &gt; = 808

Synthesis Example 15: Preparation of Compound 15

Except that 4-bromopyridine diphenyltriazine (14.2 g, 36.5 mmol) was used instead of chlorodiphenyltriazine in Synthesis Example 1 to obtain Compound 15 (17 g, yield 76%). .

MS: [M + H] &lt; ⁺ &gt; = 641

Synthesis Example 16: Preparation of Compound 16

A solution of compound 4A (18.7 g, 34.8 mmol), m, m-chlorobiphenyldiphenyltriazine (15.3 g, 36.5 mmol) and potassium carbonate (K ₂ CO ₃ ) (14.4 g, 104.4 mmol) in tetrahydrofuran ) (300 mL), H ₂ O (100 mL) and heated to 90 ° C. After addition of tetrakis (triphenylphosphine) palladium _{(Pd (PPh 3) 4)} (0.8g, 0.70mmol) and the mixture was refluxed for 4 hr. After cooling to room temperature, the water layer was removed. Magnesium sulfate (MgSO ₄ ) was added to the organic layer, followed by filtration. Concentrated, and then purified by column chromatography to obtain Compound 16 (21 g, yield 76%).

MS: [M + H] &lt; ⁺ &gt; = 794

SYNTHESIS EXAMPLE 17 Preparation of Compound 17

Compound 1F (24.4g, 34.8mmol) and chloro-diphenyl-triazine (9.8g, 36.5mmol) and potassium carbonate _{(K 2 CO 3) (14.4g} , 104.4mmol) of tetrahydrofuran (THF) (300mL), H ₂ O (100 ml) and heated to 90 &lt; 0 &gt; C. After addition of tetrakis (triphenylphosphine) palladium _{(Pd (PPh 3) 4)} (0.8g, 0.70mmol) and the mixture was refluxed for 4 hr. After cooling to room temperature, the water layer was removed. Magnesium sulfate (MgSO ₄ ) was added to the organic layer, followed by filtration. Concentrated, and then purified by column chromatography to obtain Compound 17 (20 g, yield 71%).

MS: [M + H] &lt; ⁺ &gt; = 805

Synthesis Example 18: Preparation of Compound 18

Except that Compound 3B (16 g, 34.8 mmol) was used instead of Compound 3A in Synthesis Example 2 to obtain Compound 18 (13 g, yield 59%).

MS: [M + H] &lt; ⁺ &gt; = 640

&Lt; 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 50 Å to form a hole injection layer. HT1 (250 angstroms), which is a material for transporting holes, was vacuum deposited thereon, and a second hole transport layer (HT2) having a thickness of 50 angstroms was deposited thereon.

Compound 1 prepared in Synthesis Example 1 and D1 as a phosphorescent dopant were respectively placed as a phosphorescent host with a film thickness of 300 nm on this film, and then the two materials were evaporated at different rates to deposit a light emitting layer so as to be doped with 12% by weight .

An ET1 compound (250 ANGSTROM) was sequentially vacuum-deposited on the light emitting layer using an electron transport layer. An ET2 compound and LiQ (Lithium Quinolate) were co-deposited on the electron transport layer sequentially to form an electron injection layer having a thickness of 102 ANGSTROM, and then aluminum was deposited to a thickness of 1,000 ANGSTROM to form an anode.

In the above process, the deposition rate of the organic material was maintained at 0.4 to 0.7 Å / sec, the deposition rate of aluminum was maintained at 2 Å / sec, and the vacuum degree during deposition was maintained at 2 × 10 ^-7 to 5 × 10 ^-6 torr To prepare an organic light emitting device.

< Example  1-2>

An organic light emitting device was prepared in the same manner as in Example 1-1 except that Compound 2 was used instead of Compound 1.

< Example  1-3>

An organic light emitting device was prepared in the same manner as in Example 1-1, except that Compound 3 was used instead of Compound 1.

< Example  1-4>

An organic light emitting device was prepared in the same manner as in Example 1-1 except that Compound 4 was used instead of Compound 1.

< Example  1-5>

An organic light emitting device was prepared in the same manner as in Example 1-1 except that Compound 5 was used instead of Compound 1.

< Example  1-6>

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

< Example  1-7>

An organic light emitting device was prepared in the same manner as in Example 1-1 except that Compound 7 was used instead of Compound 1.

< Example  1-8>

An organic light emitting device was prepared in the same manner as in Example 1-1, except that Compound 8 was used instead of Compound 1.

< Example  1-9>

An organic light emitting device was prepared in the same manner as in Example 1-1 except that Compound 9 was used instead of Compound 1.

< Example  1-10>

An organic light emitting device was prepared in the same manner as in Example 1-1, except that Compound 10 was used instead of Compound 1.

< Example  1-11>

An organic light emitting device was prepared in the same manner as in Example 1-1 except that Compound 11 was used instead of Compound 1.

< Example  1-12>

An organic light emitting device was prepared in the same manner as in Example 1-1, except that Compound 12 was used instead of Compound 1.

< Example  1-13>

An organic light emitting device was prepared in the same manner as in Example 1-1, except that Compound 13 was used instead of Compound 1.

< Example  1-14>

An organic light emitting device was prepared in the same manner as in Example 1-1 except that Compound 14 was used instead of Compound 1.

< Example  1-15>

An organic light emitting device was prepared in the same manner as in Example 1-1 except that Compound 15 was used instead of Compound 1.

< Example  1-16>

An organic light emitting device was prepared in the same manner as in Example 1-1, except that Compound 16 was used instead of Compound 1.

< Example  1-17>

An organic light emitting device was prepared in the same manner as in Example 1-1, except that Compound 17 was used instead of Compound 1.

< Example  1-18>

An organic light emitting device was prepared in the same manner as in Example 1-1 except that Compound 18 was used instead of Compound 1.

< Comparative Example  1>

An organic light emitting device was prepared in the same manner as in Example 1-1 except that CBP was used in place of Compound 1.

< Comparative Example  2>

An organic light emitting device was prepared in the same manner as in Example 1-1, except that the following H1 was used instead of the compound 1:

< Comparative Example  3>

An organic light emitting device was prepared in the same manner as in Example 1-1, except that the following H2 was used instead of the compound 1:

< Comparative Example  4>

An organic light emitting device was prepared in the same manner as in Example 1-1, except that Compound H3 was used in place of Compound 1.

Table 1 shows the results of the organic light emitting device manufactured using the respective compounds as phosphorescent host materials as in Examples 1-1 to 1-18 and Comparative Examples 1 to 4.

Experimental Example
10 mA / cm 2 compound Voltage
(V) Current efficiency
(cd / A) Color coordinates
(x, y) Example 1-1 Compound 1 2.82 64.71 (0.460, 0.531) Examples 1-2 Compound 2 2.82 65.81 (0.459, 0.533) Example 1-3 Compound 3 2.95 66.14 (0.456, 0.531) Examples 1-4 Compound 4 3.01 63.21 (0.461, 0.531) Examples 1-5 Compound 5 2.93 67.20 (0.457, 0.533) Examples 1-6 Compound 6 2.91 66.56 (0.458, 0.529) Examples 1-7 Compound 7 2.88 66.61 (0.464, 0.531) Examples 1-8 Compound 8 2.86 64.25 (0.460, 0.532) Examples 1-9 Compound 9 2.91 65.55 (0.457, 0.531) Example 1-10 Compound 10 2.83 68.11 (0.458, 0.533) Example 1-11 Compound 11 3.05 70.12 (0.461, 0.532) Examples 1-12 Compound 12 2.90 73.70 (0.462, 0.529) Examples 1-13 Compound 13 2.99 74.10 (0.460, 0.531) Examples 1-14 Compound 14 2.92 72.13 (0.459, 0.532) Examples 1-15 Compound 15 2.79 63.20 (0.457, 0.531) Examples 1-16 Compound 16 3.02 68.1 (0.460, 0.531) Examples 1-17 Compound 17 2.95 75.2 (0.460, 0.529) Example 1-18 Compound 18 2.99 69.98 (0.460, 0.531) Comparative Example 1 CBP 4.02 41.30 (0.463, 0.525) Comparative Example 2 H1 3.32 58.56 (0.461, 0.535) Comparative Example 3 H2 3.41 54.11 (0.446, 0.543) Comparative Example 4 H3 4.12 59.61 (0.451, 0.528)

&Lt; Example 2-1 >

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 50 Å to form a hole injection layer. HT1 (250 angstroms), which is a material for transporting holes, was vacuum deposited thereon, and a second hole transport layer (HT2) having a thickness of 50 angstroms was deposited thereon.

Compound 1 prepared in Synthesis Example 1 was vacuum-deposited as a first host compound and P-1 as a second host compound in a weight ratio of 1: 1 as a phosphorescent host with a film thickness of 300 nm on this film. At the same time, as the phosphorescent dopant, D1 was vaporized at different rates to deposit the light emitting layer so as to be doped with 12% by weight.

An ET1 compound (250 ANGSTROM) was sequentially vacuum-deposited on the light emitting layer using an electron transport layer. An ET2 compound and LiQ (Lithium Quinolate) were co-deposited on the electron transport layer sequentially to form an electron injection layer having a thickness of 102 ANGSTROM, and then aluminum was deposited to a thickness of 1,000 ANGSTROM to form an anode.

In the above process, the deposition rate of the organic material was maintained at 0.4 to 0.7 Å / sec, the deposition rate of aluminum was maintained at 2 Å / sec, and the vacuum degree during deposition was maintained at 2 × 10 ^-7 to 5 × 10 ^-6 torr To prepare an organic light emitting device.

< Example  2-2>

An organic light emitting device was prepared in the same manner as in Example 2-1 except that Compound 2 was used instead of Compound 1.

< Example  2-3>

An organic light emitting device was prepared in the same manner as in Example 2-1 except that Compound 5 was used instead of Compound 1.

< Example  2-4>

An organic light emitting device was prepared in the same manner as in Example 2-1 except that Compound 8 was used instead of Compound 1.

< Example  2-5>

An organic light emitting device was prepared in the same manner as in Example 2-1 except that Compound 10 was used instead of Compound 1.

< Example  2-6>

An organic light emitting device was prepared in the same manner as in Example 2-1 except that Compound 13 was used instead of Compound 1.

< Example  2-7>

An organic light emitting device was prepared in the same manner as in Example 2-1 except that Compound 14 was used instead of Compound 1.

< Example  2-8>

An organic light emitting device was prepared in the same manner as in Example 2-1 except that Compound 17 was used instead of Compound 1.

< Example  2-9>

An organic light emitting device was prepared in the same manner as in Example 2-1 except that Compound 18 was used instead of Compound 1.

< Comparative Example  5>

An organic light emitting device was prepared in the same manner as in Example 2-1 except that CBP was used instead of the compound 1.

< Comparative Example  6>

An organic luminescent device was prepared in the same manner as in Example 2-1, except that the following H1 was used in place of the compound 1:

< Comparative Example  7>

An organic light emitting device was prepared in the same manner as in Example 2-1, except that the following H2 was used instead of the compound 1:

< Comparative Example  8>

An organic luminescent device was prepared in the same manner as in Example 2-1, except that the following H3 was used in place of the compound 1:

Table 2 shows the results of the experiment of the organic light emitting device manufactured using the respective compounds as phosphorescent host materials as in Examples 2-1 to 2-9 and Comparative Examples 5 to 8.

Experimental Example
10 mA / cm 2 compound Voltage
(V) Current efficiency
(cd / A) Color coordinates
(x, y) Example 2-1 Compound 1 3.12 74.81 (0.459, 0.531) Example 2-2 Compound 2 3.05 75.65 (0.459, 0.530) Example 2-3 Compound 5 3.19 76.18 (0.456, 0.534) Examples 2-4 Compound 8 2.96 73.26 (0.460, 0.533) Example 2-5 Compound 10 3.00 78.01 (0.459, 0.531) Examples 2-6 Compound 13 3.19 81.10 (0.461, 0.531) Examples 2-7 Compound 14 3.22 82.45 (0.459, 0.531) Examples 2-8 Compound 17 3.14 84.01 (0.460, 0.528) Examples 2-9 Compound 18 3.09 78.88 (0.460, 0.530) Comparative Example 5 CBP 4.35 50.10 (0.459, 0.525) Comparative Example 6 H1 3.70 64.85 (0.460, 0.534) Comparative Example 7 H2 3.71 59.22 (0.446, 0.544) Comparative Example 8 H3 4.40 65.52 (0.451, 0.530)

&Lt; Example 3-1 >

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 transport material, was vacuum deposited on the hole transport layer, and host BH1 and dopant D2 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. Lithium fluoride (LiF) and aluminum were deposited to a thickness of 2000 Å on the electron injecting and transporting layer sequentially to form a cathode. Thereby preparing an organic light emitting device.

Was maintained at the deposition rate was 0.4 ~ 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.

< Example  3-2>

An organic light emitting device was prepared in the same manner as in Example 3-1 except that Compound 3 was used instead of Compound 1.

< Example  3-3>

An organic light emitting device was prepared in the same manner as in Example 3-1 except that Compound 4 was used instead of Compound 1.

< Example  3-4>

An organic light emitting device was prepared in the same manner as in Example 3-1 except that Compound 6 was used instead of Compound 1.

< Example  3-5>

An organic light emitting device was prepared in the same manner as in Example 3-1 except that Compound 8 was used instead of Compound 1.

< Example  3-6>

An organic light emitting device was prepared in the same manner as in Example 3-1 except that Compound 10 was used instead of Compound 1.

< Example  3-7>

An organic electroluminescent device was prepared in the same manner as in Example 3-1, except that the compound 11 was used instead of the compound 1.

< Example  3-8>

An organic light emitting device was prepared in the same manner as in Example 3-1 except that Compound 15 was used instead of Compound 1.

< Example  3-9>

An organic light emitting device was prepared in the same manner as in Example 3-1 except that Compound 18 was used instead of Compound 1.

< Comparative Example  9>

An organic light emitting device was prepared in the same manner as in Example 3-1 except that ET1 was used instead of the compound 1.

< Comparative Example  10>

An organic light emitting device was prepared in the same manner as in Example 3-1 except that H1 was used instead of the compound 1.

< Comparative Example  11>

An organic light emitting device was prepared in the same manner as in Example 3-1 except that H2 was used instead of the compound 1.

< Comparative Example  12>

An organic light emitting device was prepared in the same manner as in Example 3-1 except that H3 was used instead of the compound 1.

Table 3 shows the results of experiments of the organic light emitting devices manufactured using the respective compounds as the electron injecting and transporting layer materials as in Examples 3-1 to 3-9 and Comparative Examples 9 to 11.

Experimental Example
10 mA / cm 2 compound Voltage
(V) Current efficiency
(cd / A) Color coordinates
(x, y) Example 3-1 Compound 1 3.82 5.28 (0.137, 0.124) Example 3-2 Compound 3 3.84 5.34 (0.139, 0.124) Example 3-3 Compound 4 3.70 5.48 (0.138, 0.127) Example 3-4 Compound 6 3.75 5.35 (0.138, 0.129) Example 3-5 Compound 8 3.71 5.45 (0.137, 0.162) Examples 3-6 Compound 10 3.88 5.30 (0.137, 0.124) Examples 3-7 Compound 11 3.98 5.34 (0.137, 0.162) Examples 3-8 Compound 15 4.02 5.66 (0.137, 0.162) Examples 3-9 Compound 18 4.06 5.30 (0.137, 0.162) Comparative Example 9 ET1 4.22 5.01 (0.140, 0.129) Comparative Example 10 H1 4.15 5.12 (0.140, 0.129) Comparative Example 11 H2 4.21 5.12 (0.139, 0.129) Comparative Example 12 H3 4.17 4.7 (0.137, 0.162)

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

Claims (12)

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

In Formula 1, X is O,
Ar1 is a phenyl group,
L is a direct bond; A phenylene group; Biphenyllylene groups; A divalent pyridine group; A divalent dibenzothiophene group; Or a divalent dibenzofurane group,
R1 is hydrogen; A phenyl group substituted or unsubstituted with a phenyl group or a carbazole group; A cyclohexyl group substituted or unsubstituted with a phenyl group or a carbazole group; A benzofuropyridine group substituted or unsubstituted with a phenyl group or a carbazole group; A triphenylene group substituted or unsubstituted with a phenyl group or a carbazole group; A carbazole group substituted or unsubstituted with a phenyl group or a carbazole group; Or a benzofuropyrimidine group substituted or unsubstituted with a phenyl group or a carbazole group,
a is 0 or 1, b is 0,
X ₁ to X ₃ are the same or different and each independently N or CH,
At least one of X ₁ to X ₃ is N,
At least one of Y ₁ to Y ₄ is C bonded to L and the other is N or CR,
Wherein R is hydrogen or a phenyl group,
Ar 2 and Ar 3 are the same or different and are a phenyl group substituted or unsubstituted with a cyano group or a phenyl group; A biphenyl group substituted or unsubstituted with cyano group or phenyl group; A naphthyl group substituted or unsubstituted with cyano group or phenyl group; A fluorenyl group substituted or unsubstituted with cyano group or phenyl group; Or a pyridine group substituted or unsubstituted with cyano group or phenyl group. delete The compound according to claim 1, wherein the compound represented by Formula 1 is represented by any one of the following Formulas 4 to 7:
[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

(7)

In the above formulas 4 to 7,
Ar 1 to Ar 3, R 1, R 2, X, X ₁ to X ₃ , L, a and b are the same as defined in formula (1)
R11 to R14 are the same or different from each other, and each independently hydrogen; Or a phenyl group. The compound according to claim 1, wherein the compound represented by formula (1) is represented by any one of the following formulas (8) to (10):
[Chemical Formula 8]

[Chemical Formula 9]

[Chemical formula 10]

In the general formulas (8) to (10)
Ar 1 to Ar 3, R 1, R 2, X, X ₁ to X ₃ , L, a and b are the same as defined in formula (1)
R12 to R14 are the same or different from each other, and each independently hydrogen or a phenyl group. delete delete delete delete 2. The compound according to claim 1, wherein said formula (1) is selected from the following structural formulas:

A first electrode; A second electrode facing the first electrode; And at least one organic compound layer disposed between the first electrode and the second electrode, wherein at least one of the organic compound layers includes a compound according to any one of claims 1, 3, 4, and 9 . 11. The organic light emitting device according to claim 10, wherein the organic material layer includes an electron transport layer, an electron injection layer or an electron injection and transport layer, and the electron injection layer, the electron injection layer or the electron injection and transport layer comprises the compound. 11. The organic light emitting device according to claim 10, wherein the organic layer includes a light emitting layer, and the light emitting layer comprises the compound.

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