KR101918386B1 - Compound and organic light emitting device comprising the same - Google Patents

Abstract

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

Description

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

This application claims the benefit of Korean Patent Application No. 10-2016-0012922 filed on February 2, 2016, the entire contents of which are incorporated herein by reference.

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a compound and an organic light emitting device including the same.

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 ₁ to X ₁₆ are the same or different and are each independently N or CR,

X ₁ to X ₄ is the ring forming, at least two or more of X ₁ to X ₄ is or N, X ₁ to X ₄ is CR,

In ring X ₅ to X ₈ forms, X ₅ to X ₈ is either at least two or more of N, and X ₅ to X ₈ is CR,

And X ₉ to X ₁₂ are in the ring forming, X ₉ to X _12, at least two or more of the N, X ₉ to X ₁₂ is CR,

In ring X ₁₃ to X ₁₆ forms, X ₁₃ to X _16, at least two of the above, or N, X ₁₃ to X ₁₆ is CR,

Each R is the same or different from each other and is independently selected from the group consisting of hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, at least one of R is a substituted or unsubstituted arylamine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

Also, the present specification discloses a plasma display panel comprising a first electrode; A second electrode facing the first electrode; And at least one organic 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 invention can be 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.
3 shows HPLC data and MS spectrum of Compound 1 according to Synthesis Example 1. Fig.

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

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

In one embodiment of the present invention, the compound represented by Formula 1 is a compound consisting of 6 rings, wherein the 6 rings are the same or different and are independently substituted or unsubstituted benzene rings; Substituted or unsubstituted pyrimidines; Or substituted or unsubstituted triazine. All of the six rings of the present invention are not pyridine, and the benzene ring, pyrimidine, and triazine have a good charge mobility.

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 "Cyano; A nitro group; An alkyl 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, 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 amine group may be selected from the group consisting of -NH ₂ , a monoalkylamine group, a dialkylamine group, a N-alkylarylamine group, a monoarylamine group, a diarylamine group, an N-arylheteroarylamine group, An arylamine group, a monoheteroarylamine group, and a diheteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include methylamine, dimethylamine, ethylamine, diethylamine, phenylamine, naphthylamine, biphenylamine, anthracenylamine, 9-methyl- , Diphenylamine group, ditolylamine group, N-phenyltolylamine group, triphenylamine group, N-phenylbiphenylamine group, N-phenylnaphthylamine group, N-biphenylnaphthylamine group, N- Naphthylphenylenediamine amine group, N-phenylphenanthrenylamine group, N-biphenylphenanthrenylamine group, N-phenylfluorenylamine group, N-phenyltriphenylamine group, Naphthylamine group, an naphthylamine group, an oleylamine group and an N-biphenylfluorenylamine group, but are not limited thereto.

In the present specification, an arylamine group means an amine group in which an N in the amine group is substituted with an aryl group.

In the present specification, examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted triarylamine group. The aryl group in the arylamine group may be a monocyclic aryl group or a polycyclic aryl group. The arylamine group having at least two aryl groups may contain a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group at the same time. For example, the aryl group in the arylamine group may be selected from the examples of the aryl group described above.

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), 티아졸릴기, 이소옥사졸릴기, 옥사디아졸릴기, 티아디아졸릴기, 벤조티아졸릴기, 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 and at least one hetero atom. Specifically, the hetero atom may include at least one atom selected from the group consisting of O, N, Se, Si and S have. 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 a thiophenyl group, a furanyl group, a pyrrolyl group, an imidazolyl group, an oxazolyl group, a triazolyl group, a pyridyl group, a bipyridyl group, a pyrimidyl group, a triazinyl group, an acridyl 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; Benzosyl group; Dibenzosilyl groups; A phenanthrolinyl group, a thiazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiadiazolyl group, a benzothiazolyl group, a phenothiazinyl group, a phenoxazinyl group, and condensation structures thereof , But are not limited thereto. In addition, examples of the heterocyclic group include a heterocyclic structure including a sulfonyl group,

,

.

In one embodiment of the present specification, R is the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted arylamine group having 6 to 30 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; At least one of R is a substituted or unsubstituted arylamine group having 6 to 30 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

In one embodiment of the present specification, at least one of X ₁ to X ₁₆ is CR, and R is a substituted or unsubstituted arylamine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group. An arylamine group in which the present compound is substituted or unsubstituted; A substituted or unsubstituted aryl group; And a substituted or unsubstituted heterocyclic group, the substituents have an effect of imparting a hole or electron mobility characteristic to the material itself.

In one embodiment of the present specification, at least one of R is a substituted or unsubstituted diphenylamine group; 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 pyridine group; A substituted or unsubstituted pyrimidine group; A substituted or unsubstituted triazine group; Or a substituted or unsubstituted carbazole group, and the remaining R are the same or different from each other and each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted alkyl group.

In one embodiment of the present disclosure, at least one of R is a diphenylamine group; A phenyl group substituted or unsubstituted with a cyano group or a pyridine group; Biphenyl group; A terphenyl group; Naphthyl group; Phenanthrene; A pyridine group; A pyrimidine group; A triazine group substituted or unsubstituted with an aryl group; Or a carbazole group, and the remaining R's are the same or different from each other and each independently hydrogen; heavy hydrogen; Or a methyl group.

In one embodiment of the present specification, X ₁ to X ₁₆ are the same as or different from each other, and each independently CR.

In one embodiment of the present disclosure, in the ring, the X ₁ to X ₄ forms, X ₁ to X ₄ is at least two or more of the N.

In one embodiment of the description, X ₁ to the ring X ₄ is forming, X ₁ to X, and _4, at least two or more of the N, X ₁ to X ₄ N rest and X non-of ₅ to X ₁₆ are mutually Are the same or different, and each independently CR.

In one embodiment of the present disclosure, in the ring, the X ₁ to X ₄ forms, at least two or more of X ₁ to X ₄ is N, the ring is X ₅ to X ₈ forms, at least one of X ₅ to X ₈ 2 The above is N.

In one embodiment of the present disclosure, in the ring, the X ₁ to X ₄ forms, at least two or more of X ₁ to X ₄ is N, the ring is X ₅ to X ₈ forms, at least one of X ₅ to X ₈ 2 And the others are N, and the remaining X ₁ to X ₁₆ are the same or different from each other, and each independently CR.

In one embodiment of the description, X ₁ to the ring X ₄ is forming, X ₁ to X, and _4, at least three or more of the N, the ring is X ₅ to X ₈ forms, X ₅ to X ₈ at least three of the The above is N.

In one embodiment of the description, X ₁ to the ring X ₄ is forming, X ₁ to X, and _4, at least three or more of the N, the ring is X ₅ to X ₈ forms, X ₅ to X ₈ at least three of the And the others are N, and the remaining X ₁ to X ₁₆ are the same or different from each other, and each independently CR.

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

(2)

(3)

[Chemical Formula 4]

In the above formula (2), R ₁ to R ₁₆ are as defined for R in formula (1).

In Formula 3, R ₂ and R ₅ to R ₁₆ are defined as R in formula (1).

In Formula 4, R ₂ , R ₆ and R ₉ to R ₁₆ have the same definition as R in formula (1).

In one embodiment of the present invention, R ₉ to R ₁₆ are the same as or different from each other and each independently hydrogen or deuterium.

In one embodiment of the present invention, at least one of R ₁ to R ₈ is a substituted or unsubstituted diphenylamine group; 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 pyridine group; A substituted or unsubstituted pyrimidine group; A substituted or unsubstituted triazine group; Or a substituted or unsubstituted carbazole group, and the remaining R ₁ to R _{8 which} are not substituted with the substituent group are the same or different from each other and each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted alkyl group.

In one embodiment of the present invention, at least one of R ₁ to R ₈ is a diphenylamine group; A phenyl group substituted or unsubstituted with a cyano group or a pyridine group; Biphenyl group; A terphenyl group; Naphthyl group; Phenanthrene; A pyridine group; A pyrimidine group; A triazine group substituted or unsubstituted with an aryl group; Or a carbazole group, and the remaining R ₁ to R _{8 which} are not substituted with the substituent are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or a methyl group.

In one embodiment of the present specification, one or both of R ₂ and R ₆ is a substituted or unsubstituted arylamine group; A substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group.

In one embodiment of the present specification, one or both of R ₂ and R ₆ is a substituted or unsubstituted diphenylamine group; 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 pyridine group; A substituted or unsubstituted pyrimidine group; A substituted or unsubstituted triazine group; Or a substituted or unsubstituted carbazole group.

In one embodiment of the present specification, one or both of R ₂ and R ₆ is a diphenylamine group; A phenyl group substituted or unsubstituted with a cyano group or a pyridine group; Biphenyl group; A terphenyl group; Naphthyl group; Phenanthrene; A pyridine group; A pyrimidine group; A triazine group substituted or unsubstituted with an aryl group; Or a carbazole group.

In one embodiment of the present invention, the compound represented by Formula 1 is any one selected from the following structural formulas.

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.

The organic material layer of the organic light emitting device has a thickness of 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 includes the compound.

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 material layer includes a hole injecting layer, a hole transporting layer, or a layer simultaneously injecting and transporting a hole, and the hole injecting layer, the hole transporting layer, .

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 a layer simultaneously injecting or transporting electrons, and the electron injection layer, the electron transport layer, ≪ / RTI >

In one embodiment of the present application, the compound may include the electron injecting layer, the electron transporting layer, or the layer simultaneously injecting and transporting electrons.

In one embodiment of the present application, the electron injecting layer, the electron transporting layer, or the layer simultaneously injecting and transporting electrons may further include an N-type dopant.

In one embodiment of the present application, the electron injecting layer, the electron transporting layer, or the layer simultaneously injecting and transporting electrons may further include a metal complex.

In one embodiment of the present application, the electron injecting layer, the electron transporting layer, or the layer simultaneously injecting and transporting electrons may further include an alkali metal complex.

In one embodiment of the present application, the electron injecting layer, the electron transporting layer, or the layer simultaneously injecting and transporting electrons may further include lithium quinolate.

In one embodiment of the present application, the electron injecting layer, the electron transporting layer, or the layer simultaneously injecting and transporting electrons may contain the compound of Formula 1 and lithium quinolate in a weight ratio of 1: 9 to 9: 1 .

In one embodiment of the present application, the electron injecting layer, the electron transporting layer, or the layer simultaneously injecting and transporting electrons may contain the compound of Formula 1 and lithium quinolate in a weight ratio of 4: 6 to 6: 4 .

In one embodiment of the present application, the electron injecting layer, the electron transporting layer, or the layer simultaneously injecting and transporting electrons may contain the compound of Formula 1 and lithium quinolate at a weight ratio of 1: 1.

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 compound is a phosphorescent host material or a fluorescent host material of the light emitting 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 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-hydroxy-quinoline aluminum complex (Alq ₃ ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; Compounds of the benzoxazole, benzothiazole and benzimidazole series; Polymers of poly (p-phenylenevinylene) (PPV) series; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited thereto.

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

The electron transporting material 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. 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.

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

< Manufacturing example >

< Synthetic example  1 > - Preparation of compound 1

(1) Preparation of Compound 1A

(3-chlorophenyl) -6-phenyl-1,3,5-triazine (30.0 g, 99.3 mmol) and (3-chlorophenyl) boronic acid mmol) were dissolved in 400 ml of tetrahydrofuran, and the mixture was stirred and refluxed. After that, potassium carbonate (41.2 g, 297.9 mmol) was dissolved in 120 ml of water, and the mixture was sufficiently stirred and then tetrakistriphenylphosphinopalladium (3.4 g, 3.0 mmol) was added thereto. After 12 hours of reaction, the temperature was lowered to room temperature and filtered. The filtrate was extracted with chloroform and water, and then the organic layer was dried with magnesium sulfate. The organic layer was then distilled under reduced pressure and recrystallized using ethyl acetate. The resulting solid was filtered and dried to give Compound 1A (26 g, 70%).

(2) Preparation of Compound 1B

(26.3 g, 69.5 mmol) and bis (pinacolato) diboron (44.7 g, 175.86 mmol) and potassium acetate (KOAc) (40.9 g, 417.2 mmol) were mixed in a nitrogen atmosphere and added to 300 ml of dioxane And heated with stirring. Bis (dibenzylideneacetone naphthyridin-acetone) palladium _{(Pd (dba) 2) (} 2.4g, 4.2mmol) and tri-cyclohexyl-phosphine _{(P (Cy) 3) (} 2.3g, 8.3mmol) is placed for 18 hours at reflux Was heated and stirred. 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 1B (23.0 g, 59%).

(3) Preparation of Compound 1

In a nitrogen atmosphere, compound 1A (15.0 g, 39.7 mmol) and compound 1B (22.3 g, 39.7 mmol) were added to 200 ml of tetrahydrofuran (THF) and stirred and refluxed. Then, potassium carbonate (16.4 g, 119 mmol) was dissolved in 60 ml of water, and the mixture was sufficiently stirred, and tetrakistriphenylphosphinopalladium (TTP) (1.4 g, 1.2 mmol) was added thereto. After 4 hours of reaction, the temperature was lowered to room temperature and filtered. The filtrate was extracted with chloroform and water, and then the organic layer was dried with magnesium sulfate. The organic layer was then distilled under reduced pressure and recrystallized using ethyl acetate. The resulting solid was filtered and dried to give Compound 1 (16.3 g, 67%).

MS: [M + H] &lt; + &gt; = 615

< Synthetic example  2 > - Preparation of compound 2

(One) Preparation of Compound 2A

4-Bromobenzonitrile (30.0 g, 164.8 mmol) and (3,5-dichlorophenyl) boronic acid (34.6 g, 181.3 mmol) were dissolved in 400 ml of tetrahydrofuran in a nitrogen atmosphere and stirred and refluxed. Subsequently, potassium carbonate (68.3 g, 494.5 mmol) was dissolved in 150 ml of water, and the mixture was sufficiently stirred. Tetraquistriphenylphosphinopalladium (5.7 g, 5.0 mmol) was added thereto. After 12 hours of reaction, the temperature was lowered to room temperature and filtered. The filtrate was extracted with chloroform and water, and then the organic layer was dried with magnesium sulfate. The organic layer was then distilled under reduced pressure and recrystallized using ethyl acetate. The resulting solid was filtered and dried to give Compound 2A (27 g, 66%).

(2) Preparation of compound 2B

(27.0 g, 108.8 mmol), bis (pinacolato) diboron (44.7 g, 175.86 mmol) and potassium acetate (64.1 g, 652.9 mmol) were mixed in a nitrogen atmosphere and added to 300 ml of dioxane. Respectively. Bis (dibenzylidine acetone) palladium (dba ₂ ) (3.8 g, 6.5 mmol) and tricyclohexylphosphine (Pcy ₃ ) (3.7 mg, 6.5 mmol) were added under reflux and heated and stirred for 11 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 2B (40.8 g, 88%).

(3) Preparation of Compound 2C

Compound 2B (40.8 g, 94.6 mmol) and 1-bromo-3-iodobenzene (53.5 g, 189.3 mmol) were dissolved in 400 ml of tetrahydrofuran in a nitrogen atmosphere and stirred and refluxed. After that, potassium carbonate (78.5 g, 567.8 mmol) was dissolved in 200 ml of water, and the mixture was sufficiently stirred and then tetrakistriphenylphosphinopalladium (6.6 g, 5.7 mmol) was added thereto. After the reaction for 3 hours, the temperature was lowered to room temperature, and the water layer and the organic layer were separated, and the organic layer was distilled off under reduced pressure. The distillate was extracted with chloroform and water, and then the organic layer was dried with magnesium sulfate. The organic layer was then distilled under reduced pressure, and then recrystallized using ethyl acetate and ethanol. The resulting solid was filtered and dried to give Compound 2C (32.4 g, 70%).

(4) Preparation of Compound 2

Compound 2C (20.0 g, 40.9 mmol) and compound 1B (22.9 g, 40.9 mmol) were dissolved in tetrahydrofuran (200 ml) under a nitrogen atmosphere, followed by stirring and refluxing. After that, potassium carbonate (17.0 g, 122.7 mmol) was dissolved in 60 ml of water, and the mixture was sufficiently stirred and tetrakistriphenylphosphinopalladium (1.4 g, 1.2 mmol) was added thereto. After 4 hours of reaction, the temperature was lowered to room temperature and filtered. The filtrate was extracted with chloroform and water, and then the organic layer was dried with magnesium sulfate. The organic layer was then distilled under reduced pressure and recrystallized using ethyl acetate. The resulting solid was filtered and dried to give Compound 2 (9.6 g, 37%). MS: [M + H] &lt; + &gt; = 636

< Synthetic example  3> - Preparation of Compound 3

(One) Preparation of Compound 3A

2- (4-bromophenyl) pyridine (30.0 g, 128.2 mmol) and (3,5-dichlorophenyl) boronic acid (26.6 g, 141.0 mmol) were added to 300 ml of tetrahydrofuran in a nitrogen atmosphere, Respectively. After that, potassium carbonate (53.1 g, 384.5 mmol) was dissolved in 150 ml of water, and the mixture was sufficiently stirred and then tetrakistriphenylphosphinopalladium (4.4 g, 3.8 mmol) was added thereto. After 12 hours of reaction, the temperature was lowered to room temperature and filtered. The filtrate was extracted with chloroform and water, and then the organic layer was dried with magnesium sulfate. The organic layer was then distilled under reduced pressure and recrystallized using ethyl acetate. The resulting solid was filtered and dried to give Compound 3A (21 g, 61%).

(2) Preparation of Compound 3B

(47.1 g, 479.6 mmol) of bis (pinacolato) diboron (44.7 g, 175.86 mmol) and potassium acetate (47.1 g, 479.6 mmol) were mixed in a nitrogen atmosphere and heated to 200 ml with dioxane Respectively. Bis (dibenzylidineacetone) palladium (2.7 g, 4.8 mmol) and tricyclohexylphosphine (2.7 mg, 9.6 mmol) were added under reflux and heated and stirred for 18 hours. After completion of the reaction, the temperature was lowered to room temperature and then filtered. The filtrate was distilled, water was poured out, the mixture was extracted with chloroform, and the organic layer was dried over anhydrous magnesium sulfate. After distillation under reduced pressure, the product was recrystallized with ethanol to obtain Compound 3B (31.3 g, 81%).

(3) Preparation of Compound 3C

Compound 3B (31.3 g, 64.8 mmol) and 1-bromo-3-iodobenzene (36.7 g, 129.6 mmol) were added to 300 ml of tetrahydrofuran in a nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (53.7 g, 388.7 mmol) was dissolved in 150 ml of water, and the mixture was sufficiently stirred. Tetraquistriphenylphosphinopalladium (4.5 g, 3.9 mmol) was added thereto. After the reaction for 3 hours, the temperature was lowered to room temperature, and the water layer and the organic layer were separated, and the organic layer was distilled off under reduced pressure. The distillate was extracted with chloroform and water, and then the organic layer was dried with magnesium sulfate. The organic layer was then distilled under reduced pressure, and then recrystallized using ethyl acetate and ethanol. The resulting solid was filtered and dried to give Compound 3C (27.0 g, 77%).

(4) Preparation of Compound 3

Compound 3C (20.0 g, 37.0 mmol) and compound 1B (20.7 g, 37.0 mmol) were dissolved in 200 ml of tetrahydrofuran in a nitrogen atmosphere, followed by stirring and refluxing. Then, potassium carbonate (15.3 g, 110.9 mmol) was dissolved in 50 ml of water, and the mixture was sufficiently stirred. Tetraquistriphenylphosphinopalladium (2.6 g, 2.2 mmol) was added thereto. After 4 hours of reaction, the temperature was lowered to room temperature and filtered. The filtrate was extracted with chloroform and water, and then the organic layer was dried with magnesium sulfate. The organic layer was then distilled under reduced pressure and recrystallized using ethyl acetate. The resulting solid was filtered and dried to give compound 3 (12.7 g, 50%). MS: [M + H] &lt; + &gt; = 688

< Example >

< Example  1>

A glass substrate coated with ITO (indium tin oxide) having a thickness of 1500 Å was immersed in distilled water containing detergent and washed with ultrasonic waves. At this time, Fischer Co. product was used as a detergent, and distilled water filtered by a filter of Millipore Co. was used as distilled water. The ITO was washed for 30 minutes and then washed twice with distilled water and ultrasonically cleaned for 10 minutes. After the distilled water was washed, it was ultrasonically washed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. Further, the substrate was cleaned using oxygen plasma for 5 minutes, and then the substrate was transported by a vacuum evaporator.

The following compound [HAT] was thermally vacuum deposited on the prepared ITO transparent electrode to a thickness of 50 Å to form a hole injection layer. The following compound [NPB] (1000 Å) and [HT-A] (400 Å) were sequentially vacuum-deposited on the hole injection layer to form a hole transport layer.

Subsequently, the following compounds [BH] and [BD] were vacuum deposited on the hole transport layer at a weight ratio of 25: 1 at a thickness of 200 ANGSTROM to form a light emitting layer.

[Compound 1] and the following compound [LiQ] (Lithium quinolate) were vacuum deposited on the light emitting layer at a weight ratio of 1: 1 to form an electron injection and transport layer having a thickness of 350 Å. Lithium fluoride (LiF) and aluminum having a thickness of 1,000 Å were sequentially deposited on the electron injecting and transporting layer to form a cathode.

The deposition rate of the organic material was maintained at 0.4 to 0.9 Å / sec, the lithium fluoride at the cathode was maintained at a deposition rate of 0.3 Å / sec, and the deposition rate of aluminum was maintained at 2 Å / sec. ^-7 to 5 x 10 &lt; ^-8 &gt; torr to produce an organic light emitting device.

< Example  2>

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

< Example  3>

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

< Comparative Example  1>

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

< Comparative Example  2>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that the compound of ET2 was used in place of the compound 1 in Experimental Example 1.

The driving voltage and the luminous efficiency were measured at an electric current density of 10 mA / cm &lt; ² &gt; at an organic light emitting device manufactured by using each compound as an electron injecting and transporting layer material as in Examples 1 to 3 and Comparative Examples 1 and 2, The time to reach 95% of the initial luminance (LT95) at a current density of 20 mA / cm ² was measured. The results are shown in Table 1 below.

division compound
(Electron injection and transport layer) Voltage
(V) Current efficiency
(cd / A) Color coordinates
(x, y) Life Time 95 at 20 mA / cm ² Example 1 Compound 1 3.5 6.90 (0.133, 0.135) 80 Example 2 Compound 2 3.9 5.80 (0.133, 0.137) 120 Example 3 Compound 3 3.6 6.22 (0.134, 0.133) 100 Comparative Example 1 ET1 3.98 5.77 (0.136, 0.162) 80 Comparative Example 2 ET2 4.10 4.00 (0.136, 0.162) 20

As can be seen from the above Table 1, the organic light emitting device manufactured using the compound of the present invention as an electron injecting and transporting layer material exhibited excellent characteristics at similar efficiencies as compared with the case of using the material of Comparative Example 1, 2 material is superior in terms of efficiency and stability.

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

Claims (10)

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

In Formula 1,
X ₁ to X ₈ are the same or different and are each independently N or CR,
And the ring is X ₁ to X ₄ forms, at least two of X ₁ to X ₄ is or N, X ₁ to X ₄ is CR,
In ring X ₅ to X ₈ forms, at least two of X ₅ to X ₈ is either N, and X ₅ to X ₈ is CR,
X ₉ to X ₁₂ are CR,
X ₁₃ to X ₁₆ are CR,
At least two of X ₁ to X ₈ are N,
At least one of the Rs is an aryl group having 6 to 25 carbon atoms which is substituted or unsubstituted with a cyano group or a pyridine group, and the remaining R is hydrogen. 2. The compound according to claim 1, wherein at least one of R is a phenyl group substituted or unsubstituted with a cyano group or a pyridine group; A biphenyl group substituted or unsubstituted with a cyano group or a pyridine group; A terphenyl group substituted or unsubstituted with a cyano group or a pyridine group; A naphthyl group substituted or unsubstituted with a cyano group or a pyridine group; Or a phenanthrene group substituted or unsubstituted with a cyano group or a pyridine group. 2. The compound according to claim 1, wherein at least one of R is a phenyl group substituted or unsubstituted with a cyano group or a pyridine group; Biphenyl group; A terphenyl group; Naphthyl group; Or phenanthrene group, and the remaining R is hydrogen. 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 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 3 and 6 Organic light emitting device. The organic light emitting device according to claim 7, wherein the organic layer includes a light emitting layer, and the light emitting layer comprises the compound. [Claim 7] The organic light emitting device according to claim 7, wherein the organic compound layer comprises a hole injection layer, a hole transport layer or a hole injection and transport layer, and the hole injection layer, the hole transport layer or the hole injection and transport layer comprises the compound. [Claim 7] The organic light emitting device according to claim 7, wherein the organic material layer includes an electron injection layer, an electron transport layer or an electron injection and transport layer, and the electron injection layer, electron transport layer or electron injection and transport layer comprises the compound.

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