KR20180027230A - 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-

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), R1 and R2 are the same or different and each independently hydrogen or deuterium, R1 and R2 may be bonded to each other to form a ring,

Ra, Rb, Rc, Rd and Re are the same or different and each independently hydrogen; heavy hydrogen; A halogen group; Cyano; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

l, m and o are each an integer of 0 to 4, n and p are each an integer of 0 to 3, and when 1 to p is 2 or more, the substituents in parentheses are the same or different,

L1 to L3 are the same or different and are each independently a direct bond; Or a substituted or unsubstituted arylene group,

Ar 1 is a substituted or unsubstituted dibenzothiophene group; A substituted or unsubstituted dibenzofurane group; A substituted or unsubstituted carbazole group; A substituted or unsubstituted fluorene group; Or a substituted or unsubstituted triphenylene group,

Ar2 is a substituted or unsubstituted phenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted dibenzothiophene group; A substituted or unsubstituted dibenzofurane group; Or a substituted or unsubstituted fluorene group,

Provided that when Ar1 is a substituted or unsubstituted fluorene group, Ar2 is a substituted or unsubstituted dibenzothiophene group; A substituted or unsubstituted dibenzofurane group; And a substituted or unsubstituted fluorene 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; An alkyl group; A cycloalkyl group; An alkenyl group; An alkoxy group; An aryl group; And a heterocyclic group, or that two or more of the substituents in the above-exemplified substituents are substituted with a substituent to which they are linked, 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, and specifically includes cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, But are not limited to, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert- butylcyclohexyl, cycloheptyl, Do not.

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

In the present specification, the 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, 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, but are not limited to, a naphthyl group, an anthracene group, a phenanthryl group, a pyrenyl group, a perylenyl group, a klycenyl group and a fluorene group.

In the present specification, the fluorene 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, 퀴놀린기, 퀴나졸린기, 퀴녹살리닐기, 프탈라지닐기, 피리도피리미디닐기, 피리도피라지닐기, 피라지노피라지닐기, 이소퀴놀리닐기, 인돌기, 카바졸기, 벤즈옥사졸기, 벤즈이미다졸기, 벤조티아졸기, 벤조카바졸기, 디벤조카바졸기, 벤조티오펜기, 디벤조티오펜기, 벤조퓨란기, 디벤조퓨란기; 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 thiophene group, a furan group, a pyrrolyl group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridine group, a bipyridine group, a pyrimidine group, , Hydroacridyl groups (e.g.,

), A pyridazinyl group, a pyrazinyl group, a quinoline group, a quinazoline group, a quinoxalinyl group, a phthalazinyl group, a pyridopyrimidinyl group, a pyridopyrimidinyl group, a pyrazinopyrazinyl group, an isoquinolinyl group, An indole group, a carbazole group, a benzoxazole group, a benzimidazole group, a benzothiazole group, a benzocarbazole group, a dibenzocarbazole group, a benzothiophene group, a dibenzothiophene group, a benzofurane group, a dibenzofurane 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 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 invention, Ra, Rb, Rc, Rd and Re are the same or different, and each independently hydrogen or deuterium.

In one embodiment of the present specification, Ra, Rb, Rc, Rd, and Re are hydrogen.

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

(2)

(3)

In Formulas (2) and (3), L1 to L3, Ar1 and Ar2 are as defined in Formula (1).

In one embodiment of the present invention, the formula 1 may be represented by any one of the following formulas 2-1 to 2-4 and 3-1 to 3-4.

[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

[Chemical Formula 2-4]

[Formula 3-1]

[Formula 3-2]

[Formula 3-3]

[Chemical Formula 3-4]

In Formulas (2-1) to (2-4) and (3-1) to (3-4), L1 to L3, Ar1 and Ar2 are as defined in Formula (1).

In one embodiment of the present invention, L1 to L3 are the same or different from each other, and each independently is a direct bond; A substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylene group; A substituted or unsubstituted naphthalene group; Or a substituted or unsubstituted fluorenylene group.

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

In one embodiment of the present specification, L2 and L3 are the same or different and are each independently a direct bond; A substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylene group; A substituted or unsubstituted naphthalene group; Or a substituted or unsubstituted fluorenylene group.

In one embodiment of the present specification, L2 and L3 are the same or different and are each independently a direct bond; Or a substituted or unsubstituted phenylene group.

In one embodiment of the present specification, Ar 1 is a dibenzothiophene group substituted or unsubstituted with an alkyl group or an aryl group; A dibenzofurane group substituted or unsubstituted with an alkyl group or an aryl group; A carbazole group substituted or unsubstituted with an alkyl group or an aryl group; A fluorene group substituted or unsubstituted with an alkyl group or an aryl group; Or a triphenylene group substituted or unsubstituted with an alkyl group or an aryl group.

In one embodiment of the present specification, Ar1 is a dibenzothiophene group; A dibenzofurane group; A carbazole group substituted or unsubstituted with a phenyl group; A fluorene group substituted or unsubstituted with a methyl group or a phenyl group; A spirobifluorene group; Or a triphenylene group.

In one embodiment of the present specification, Ar2 represents a phenyl group substituted or unsubstituted with an alkyl group or an aryl group; A naphthyl group substituted or unsubstituted with an alkyl group or an aryl group; A biphenyl group substituted or unsubstituted with an alkyl group or an aryl group; A dibenzothiophene group substituted or unsubstituted with an alkyl group or an aryl group; A dibenzofurane group substituted or unsubstituted with an alkyl group or an aryl group; Or a fluorene group substituted or unsubstituted with an alkyl group or an aryl group.

In one embodiment of the present specification, Ar2 represents a phenyl group; Naphthyl group; A biphenyl group; A dibenzothiophene group; A dibenzofurane group; A fluorene group substituted or unsubstituted with a methyl group or a phenyl group; Or a spirobifluorene group.

In one embodiment of the present disclosure, -L2-Ar1 is selected from among the following structures:

In the above formula, a dotted line means a moiety bonded to the formula (1).

In one embodiment of the present disclosure, -L3-Ar2 is selected from the following formulas.

In the above formula, a dotted line means a moiety bonded to the formula (1).

In one embodiment of the present invention, N (L2-Ar1) (L3-Ar2) in Formula 1 is selected from the following structural formulas.

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.

For example, the compound of Formula 1 may be prepared as a core structure as shown in Schemes 1 to 3 below. Substituent groups may be attached by methods known in the art, and the type, position or number of substituent groups may be varied according to techniques known in the art.

[Reaction Scheme 1]

[Reaction Scheme 2]

[Reaction Scheme 3]

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 understood that it may include other components as well, without departing from the other components unless specifically stated otherwise.

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

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

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

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

[A-1]

In the above formula (A-1)

q is an integer of 1 or more,

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

L4 is a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,

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

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

According to one embodiment of the present invention, the organic layer includes a light emitting layer, and the light emitting layer includes the compound represented by the above formula (A-1) as a dopant in the light emitting layer.

According to one embodiment of the present disclosure, L4 is a direct bond.

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

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

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

According to one embodiment of the present invention, Ar 4 and Ar 5 are the same or different and each independently represent a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

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

According to one embodiment of the present invention, Ar4 and Ar5 are the same or different and are each independently a phenyl group substituted or unsubstituted with a tert-butyl group; A dibenzofurane group; Or a dibenzothiophene group.

According to one embodiment of the present invention, Ar4 and Ar5 are the same or different and are each independently a phenyl group substituted or unsubstituted with a tert-butyl group; Or a dibenzofurane group.

According to one embodiment of the present disclosure, the formula (A-1) is represented by the following compound.

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

[A-2]

In the above formula (A-2)

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

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

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

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

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

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

According to one embodiment of the present invention, Ar6 and Ar7 are the same or different and are each independently a substituted or unsubstituted 1-naphthyl group or 2-naphthyl group.

According to one embodiment of the present invention, Ar6 is a 1-naphthyl group, and Ar7 is a 2-naphthyl group.

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

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

According to one embodiment of the present invention, the organic layer includes a light emitting layer, and the light emitting layer includes the compound represented by the formula A-1 as a dopant of the light emitting layer, and the compound represented by the formula A- .

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

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

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

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

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

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

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

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

The electron injection layer is a layer for injecting electrons from the electrode. The electron injection layer has the ability to transport electrons, has an electron injection effect from the cathode, and has an excellent electron injection effect with respect to the light emitting layer or the light emitting material. A compound which prevents migration to a layer and is excellent in a thin film forming ability is preferable. Specific examples thereof include fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, 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.

< Synthetic example  1>

< Manufacturing example  1>

One) Synthesis of Compound (1)

                                                     [Compound 1]

Compound (A) (6.5 g, 13.42 mmol), N- (4- (dibenzo [b, d] furan-4-yl) phenyl) - [1,1'- 4-amine (5.80g, 14.09mmol), and then completely dissolved in 160ml of xylene was added sodium tert- butoxide (NaOtBu) (1.55g, 16.10mmol) and bis (tri - tert - butylphosphine) palladium (0) (Pd (t-Bu ₃ P ₂ )) (0.07 g, 0.13 mmol) was added thereto, followed by heating and stirring for 5 hours. The temperature was lowered to room temperature, and the base was removed by filtration. The xylene was concentrated under reduced pressure and recrystallized from ethyl acetate (250 ml) to obtain Compound 1 (8.46 g, yield: 77%).

MS [M + H] &lt; ⁺ &gt; = 815

< Manufacturing example  2>

One) Synthesis of Compound 2 below

                                                    [Compound 2]

To a 500 ml round bottom flask in a nitrogen atmosphere was added compound B (6.5 g, 13.36 mmol), N- (4- (dibenzo [b, d] furan- 4-amine (5.77 g, 14.03 mmol) was dissolved in 160 ml of xylene and sodium tert-butoxide (1.54 g, 16.04 mmol) was added and bis (tri- tert-butylphosphine) palladium , 0.13 mmol) were added, and the mixture was heated and stirred for 3 hours. After the temperature was lowered to room temperature and the salts were removed by filtration, the xylene was concentrated under reduced pressure and recrystallized from ethyl acetate (200 ml) to give Compound 2 (7.16 g, yield: 66%).

MS [M + H] &lt; ⁺ &gt; = 817

< Manufacturing example  3>

One) Synthesis of Compound 3 below

                                                 [Compound 3]

Compound A (5.0 g, 10.28 mmol), N- (4- (dibenzo [b, d] furan-4-yl) phenyl) -9,9-dimethyl-9H-fluorene (Tert-butylphosphine) palladium (0) (0.05%) was added to a solution of the compound of Example 1 (2.9 g, 10.79 mmol) g, 0.10 mmol), and the mixture was heated with stirring for 4 hours. After the temperature was lowered to room temperature and the salts were removed by filtration, the xylene was concentrated under reduced pressure and recrystallized from ethyl acetate (300 ml) to give Compound 3 (7.08 g, yield: 81%).

MS [M + H] &lt; ⁺ &gt; = 855

< Manufacturing example  4>

One) Synthesis of Compound (4)

                                                      [Compound 4]

(5.0 g, 10.28 mmol), N- (4- (dibenzo [b, d] furan-4-yl) phenyl) -9,9-dimethyl-9H-fluorene in a 500 ml round- (Tert-butylphosphine) palladium (0) (0.05%) was added to a solution of the compound of Example 1 (2.9 g, 10.79 mmol) g, 0.10 mmol), and the mixture was heated with stirring for 4 hours. After the temperature was lowered to room temperature and the salts were removed by filtration, the xylene was concentrated under reduced pressure and recrystallized from ethyl acetate (300 ml) to obtain Compound 4 (6.37 g, yield: 72%).

MS [M + H] &lt; ⁺ &gt; = 857

< Manufacturing example  5>

One) Synthesis of Compound 5 below

                                                [Compound 5]

Compound (A) (6.5 g, 13.42 mmol), N- (4- (dibenzo [b, d] furan-2-yl) phenyl- [1,1'- biphenyl] - 4-amine (5.80 g, 14.09 mmol) was completely dissolved in 160 ml of xylene, sodium tert-butoxide (1.55 g, 16.10 mmol) was added and bis (tri- tert- butylphosphine) palladium , 0.13 mmol), and the mixture was heated and stirred for 4 hours. The temperature was lowered to room temperature, and the salt was removed by filtration. The xylene was concentrated under reduced pressure and recrystallized from ethyl acetate (260 ml) to prepare the above compound 5 (7.58 g, yield: 70%).

MS [M + H] &lt; ⁺ &gt; = 815

< Manufacturing example  6>

One) Synthesis of Compound 6 below

                                                       [Compound 6]

To a 500 ml round-bottom flask in a nitrogen atmosphere was added compound B (6.5 g, 13.36 mmol), N- (4- (dibenzo [b, d] furan-2-yl) 4-amine (5.77 g, 14.03 mmol) was dissolved in 160 ml of xylene and sodium tert-butoxide (1.54 g, 16.04 mmol) was added and bis (tri- tert-butylphosphine) palladium , 0.13 mmol) were added thereto, followed by heating and stirring for 2 hours. After the temperature was lowered to room temperature and the salts were removed by filtration, the xylene was concentrated under reduced pressure and recrystallized from ethyl acetate (230 ml) to obtain Compound 6 (6.82 g, yield: 62%).

MS [M + H] &lt; ⁺ &gt; = 817

< Manufacturing example  7>

One) Synthesis of Compound 7 below

                                                   [Compound 7]

Compound A (5.0 g, 10.28 mmol), N- (4- (dibenzo [b, d] furan-2-yl) phenyl) -9,9-dimethyl-9H-fluorene (Tert-butylphosphine) palladium (0) (0.05%) was added to a solution of the compound of Example 1 (2.9 g, 10.79 mmol) g, 0.10 mmol), and the mixture was heated and stirred for 3 hours. After the temperature was lowered to room temperature and the salts were removed by filtration, the xylene was concentrated under reduced pressure and recrystallized from ethyl acetate (220 ml) to obtain Compound 7 (7.08 g, yield: 81%).

MS [M + H] &lt; ⁺ &gt; = 855

< Manufacturing example  8>

One) Synthesis of Compound 8 below

                                                        [Compound 8]

(5.0 g, 10.28 mmol), N- (4- (dibenzo [b, d] furan-2-yl) phenyl) -9,9-dimethyl-9H-fluorene in a 500 ml round- (Tert-butylphosphine) palladium (0) (0.05%) was added to a solution of the compound of Example 1 (2.9 g, 10.79 mmol) g, 0.10 mmol), and the mixture was heated and stirred for 3 hours. After the temperature was lowered to room temperature and the salts were removed by filtration, the xylene was concentrated under reduced pressure and recrystallized from ethyl acetate (200 ml) to obtain the above compound 8 (5.76 g, yield 65%).

MS [M + H] &lt; ⁺ &gt; = 857

< Manufacturing example  Preparation of the following compounds 9 to 16

One) Synthesis of the following compounds 9 to 16

The compounds 9 to 16 were prepared in the same manner as in the preparation of the above compounds 1 to 8 except that the compounds C and D were used instead of the compounds A and B in Production Examples 1 to 8.

< Manufacturing example  Preparation of the following compounds 17 to 24

One) Synthesis of the following compounds 17 to 24

The compounds 17 to 24 were prepared in the same manner as in the preparation of the above compounds 1 to 8 except that the compounds E and F were used instead of the compounds A and B in Production Examples 1 to 8.

< Manufacturing example  11>

One) Synthesis of the following compound 25

                                    [Compound 25]

Compound A (6.5 g, 13.40 mmol), N- (4- (dibenzo [b, d] diphen-2-yl) phenyl) - [1,1'- biphenyl] - 4-amine (6.01 g, 14.07 mmol) was completely dissolved in 210 ml of xylene, sodium tert-butoxide (1.55 g, 16.08 mmol) was added and bis (tri- tert-butylphosphine) palladium , 0.13 mmol) were added, and the mixture was heated and stirred for 5 hours. After the temperature was lowered to room temperature and the salts were removed by filtration, the xylene was concentrated under reduced pressure and recrystallized from ethyl acetate (290 ml) to obtain Compound 25 (8.26 g, yield: 74%).

MS [M + H] &lt; ⁺ &gt; = 831

< Manufacturing example  12>

One) Synthesis of Compound 26

                                                 [Compound 26]

To a 500 ml round bottom flask in a nitrogen atmosphere was added a solution of compound B (6.5 g, 13.40 mmol), N- (4- (dibenzo [b, d] thiophen-2-yl) phenyl) - [ -4-amine (6.01 g, 14.07 mmol) was completely dissolved in 180 ml of xylene, sodium tert-butoxide (1.55 g, 16.08 mmol) was added and bis (tri- tert- butylphosphine) palladium g, 0.13 mmol), and the mixture was heated with stirring for 3 hours. After the temperature was lowered to room temperature and the salts were removed by filtration, the xylene was concentrated under reduced pressure and recrystallized from ethyl acetate (280 ml) to obtain Compound 26 (7.79 g, yield: 70%).

MS [M + H] &lt; ⁺ &gt; = 833

< Manufacturing example  13>

One) Synthesis of Compound (27)

                                                   [Compound 27]

Compound A (5.0 g, 10.28 mmol), N- (4- (dibenzo [b, d] furan-2-yl) phenyl) -9,9-dimethyl-9H-fluorene (Tert-butylphosphine) palladium (0) (0.05) (0.05 g, 10.82 mmol) was dissolved in 120 ml of xylene and sodium tert-butoxide (1.19 g, 12.34 mmol) g, 0.10 mmol), and the mixture was heated and stirred for 3 hours. After the temperature was lowered to room temperature and the salts were removed by filtration, the xylene was concentrated under reduced pressure and recrystallized from ethyl acetate (220 ml) to give Compound 27 (6.22 g, yield 69%).

MS [M + H] &lt; ⁺ &gt; = 871

< Manufacturing example  14>

One) Synthesis of Compound 28

                                                  [Compound 28]

(5.0 g, 10.31 mmol), N- (4- (dibenzo [b, d] thiophen-2-yl) phenyl) -9,9-dimethyl-9H- Amine (5.06 g, 10.82 mmol) was dissolved in 150 ml of xylene, sodium tert-butoxide (1.19 g, 12.37 mmol) was added and bis (tri- tert-butylphosphine) palladium 0.05 g, 0.10 mmol), and the mixture was heated with stirring for 5 hours. After the temperature was lowered to room temperature and the salts were removed by filtration, the xylene was concentrated under reduced pressure and recrystallized from ethyl acetate (230 ml) to obtain the compound 28 (7.19 g, yield: 80%).

MS [M + H] &lt; ⁺ &gt; = 873

< Manufacturing example  15>

One) Synthesis of the compound of the following compound 29

                                              [Compound 29]

Compound A (8.0 g, 16.52 mmol) and bis (9,9-dimethyl-9H-fluoren-2-yl) amine (6.95 g, 17.34 mmol) were completely dissolved in 180 ml of xylene in a 500 ml round- (Tert-butylphosphine) palladium (0) (0.08 g, 0.17 mmol) was added thereto, followed by heating and stirring for 6 hours. After the temperature was lowered to room temperature and the salts were removed by filtration, the xylene was concentrated under reduced pressure and recrystallized from ethyl acetate (260 ml) to obtain the above compound 29 (9.16 g, yield: 79%).

MS [M + H] &lt; ⁺ &gt; = 805

< Manufacturing example  16>

One) Synthesis of Compound 30 below

                                                  [Compound 30]

Compound (B) (7.0 g, 14.39 mmol) and bis (9,9-dimethyl-9H-fluoren-2-yl) amine (6.06 g, 15.11 mmol) were completely dissolved in 160 ml of xylene in a 500 ml round- (Tert-butylphosphine) palladium (0) (0.07 g, 0.14 mmol) was added thereto, followed by heating and stirring for 4 hours. After the temperature was lowered to room temperature and the salts were removed by filtration, the xylene was concentrated under reduced pressure and recrystallized from 210 ml of ethyl acetate to obtain Compound 30 (7.48 g, yield: 64%).

MS [M + H] &lt; ⁺ &gt; = 807

< Experimental Example  1>

The glass substrate coated with ITO (indium tin oxide) thin film with a thickness of 1,000 Å was immersed in distilled water containing detergent and washed with ultrasonic waves. In this case, Fischer Co. 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.

On this ITO transparent electrode, hexanitrile hexaazatriphenylene (HAT) of the following chemical formula was thermally vacuum deposited to a thickness of 500 Å to form a hole injection layer.

[LINE]

The following compounds N4, N4, N4 ', N4'-tetra ([1,1'-biphenyl] -4-yl) - [1,1'- 4,4'-diamine (HTL) (300 ANGSTROM) was vacuum-deposited to form a hole transport layer.

[HTL]

Subsequently, an electron blocking layer was formed on the hole transport layer by vacuum evaporation of the following compound EBL, which is a substance suppressing electrons, to a thickness of 100 ANGSTROM.

[EBL]

Subsequently, BH and BD were vacuum deposited on the electron blocking layer to a thickness of 300 ANGSTROM at a weight ratio of 25: 1 to form a light emitting layer.

[BH]

[BD]

[ET1]

[LiQ]

The compound ET1 and the 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 300 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.

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, the degree of vacuum upon deposition ⅹ10 2 ^-7 To 5 x 10 &lt; ^-6 &gt; torr, thereby fabricating an organic light emitting device.

<Experimental Example 1-1>

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

<Experimental Example 1-2>

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

 <Experimental Example 1-3>

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

<Experimental Example 1-4>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 4 was used instead of EBL in Experimental Example 1.

<Experimental Example 1-5>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 5 was used instead of EBL in Experimental Example 1.

<Experimental Example 1-6>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 6 was used instead of EBL in Experimental Example 1.

<Experimental Example 1-7>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 7 was used instead of EBL in Experimental Example 1.

<Experimental Example 1-8>

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

 <Experimental Example 1-9>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 9 was used instead of EBL in Experimental Example 1.

<Experimental Example 1-10>

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

<Experimental Example 1-11>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 11 was used instead of EBL in Experimental Example 1.

<Experimental Example 1-12>

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

<Experimental Example 1-13>

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

<Experimental Example 1-14>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 14 was used instead of EBL in Experimental Example 1.

<Experimental Example 1-15>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 15 was used instead of EBL in Experimental Example 1.

<Experimental Example 1-16>

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

<Experimental Example 1-17>

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

<Experimental Example 1-18>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 18 was used instead of EBL in Experimental Example 1.

<Experimental Example 1-19>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 19 was used instead of EBL in Experimental Example 1.

<Experimental Example 1-20>

An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that Compound 20 was used instead of EBL in Experimental Example 1.

<Experimental Example 1-21>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 21 was used instead of EBL in Experimental Example 1.

<Experimental Example 1-22>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 22 was used instead of EBL in Experimental Example 1.

<Experimental Example 1-23>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 23 was used instead of EBL in Experimental Example 1.

<Experimental Example 1-24>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 24 was used instead of EBL in Experimental Example 1.

<Experimental Example 1-25>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 25 was used instead of EBL in Experimental Example 1.

<Experimental Example 1-26>

An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that Compound 26 was used instead of EBL in Experimental Example 1.

<Experimental Example 1-27>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 27 was used instead of EBL in Experimental Example 1.

<Experimental Example 1-28>

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that Compound 28 was used instead of EBL in Experimental Example 1.

&Lt; Comparative Example 1 &

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that the following EB1 compound was used instead of EBL in Experimental Example 1.

[EB1]

&Lt; Comparative Example 2 &

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that the following EB2 compound was used in place of EBL in Experimental Example 1.

[EB2]

&Lt; Comparative Example 3 &

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that the following EB3 compound was used in place of EBL in Experimental Example 1.

[EB3]

&Lt; Comparative Example 4 &

An organic light emitting device was fabricated in the same manner as in Experimental Example 1, except that the following EB4 compound was used in place of EBL in Experimental Example 1.

[EB4]

The voltage, efficiency, color coordinates, and lifetime were measured when current was applied to the organic light-emitting device manufactured in Experimental Example 1, Experimental Examples 1-1 to 1-28 and Comparative Examples 1 to 4, and the results are shown in Table 1 ]. T95 means the time required for the luminance to decrease from the initial luminance (5000 nits) to 95%.

compound
(Electronic blocking layer) Voltage
(V @ 10 mA / cm ² ) efficiency
(cd / A @ 10mA / cm 2) Color coordinates
(x, y) T95 (h) Experimental Example 1
(Comparative Example) EBL 4.42 5.79 (0.138, 0.127) 75 Experimental Example 1-1 Compound 1 3.64 6.65 (0.139, 0.122) 118 Experimental Example 1-2 Compound 2 3.65 6.66 (0.138, 0.126) 105 Experimental Example 1-3 Compound 3 3.86 6.41 (0.138, 0.127) 126 Experimental Examples 1-4 Compound 4 3.74 6.55 (0.137, 0.125) 130 Experimental Examples 1-5 Compound 5 3.62 6.69 (0.136, 0.125) 112 Experimental Example 1-6 Compound 6 3.63 6.68 (0.136, 0.127) 106 Experimental Example 1-7 Compound 7 3.77 6.55 (0.136, 0.125) 124 Experimental Examples 1-8 Compound 8 3.84 6.45 (0.137, 0.125) 135 Experimental Examples 1-9 Compound 9 3.67 6.63 (0.138, 0.125) 113 Experimental Example 1-10 Compound 10 3.65 6.62 (0.136, 0.125) 108 Experimental Example 1-11 Compound 11 3.81 6.52 (0.137, 0.125) 122 Experimental Example 1-12 Compound 12 3.79 6.40 (0.136, 0.125) 133 Experimental Example 1-13 Compound 13 3.61 6.64 (0.138, 0.126) 119 Experimental Example 1-14 Compound 14 3.63 6.62 (0.137, 0.125) 102 Experimental Example 1-15 Compound 15 3.80 6.40 (0.136, 0.127) 127 Experimental Example 1-16 Compound 16 3.81 6.45 (0.135, 0.127) 136 Experimental Example 1-17 Compound 17 3.62 6.67 (0.138, 0.127) 113 Experimental Example 1-18 Compound 18 3.63 6.65 (0.137, 0.125) 102 Experimental Example 1-19 Compound 19 3.79 6.40 (0.137, 0.125) 121 Experimental Example 1-20 Compound 20 3.75 6.42 (0.136, 0.125) 131 Experimental Example 1-21 Compound 21 3.62 6.69 (0.138, 0.126) 112 Experimental Example 1-22 Compound 22 3.66 6.65 (0.137, 0.125) 107 Experimental Example 1-23 Compound 23 3.84 6.42 (0.136, 0.127) 127 Experimental Example 1-24 Compound 24 3.80 6.40 (0.137, 0.125) 136 Experimental Example 1-25 Compound 25 3.69 6.67 (0.136, 0.125) 114 Experimental Example 1-26 Compound 26 3.63 6.62 (0.138, 0.126) 108 Experimental Example 1-27 Compound 27 3.71 6.64 (0.137, 0.125) 125 Experimental Example 1-28 Compound 28 3.75 6.50 (0.136, 0.127) 136 Comparative Example 1 EB1 3.95 6.15 (0.136, 0.127) 84 Comparative Example 2 EB2 4.15 5.95 (0.136, 0.127) 66 Comparative Example 3 EB3 4.25 5.92 (0.135, 0.125) 74 Comparative Example 4 EB3 4.48 5.34 (0.135, 0.125) 95

As shown in Table 1, the organic light emitting device manufactured using the compound of the present invention as an electron blocking layer has characteristics of excellent efficiency and driving voltage of an organic light emitting device. It also has excellent stability and long life.

In Experimental Examples 1-1 to 1-28, lifetime was 20% or more higher than that of Comparative Example 1 in which Ar1 is a fluorene group and Ar2 is a biphenyl-amine. It can be seen that morphology is well formed when the compound of the present invention having dibenzofuran, dibenzothiophene, and fluorene groups is deposited rather than linear biphenyl, which is superior in terms of stability.

Comparative Examples 2 and 3 in which two substituents are symmetrically connected in the core of the present invention showed relatively low life span and Comparative Example 4 in which two amines were connected was measured to have a very high voltage. This is because the homo value of the material is relatively higher than that of the compound of the present invention due to the presence of two amines, which is different from the homo value of the neighboring light emitting layer material, so that a barrier is formed and hole injection becomes difficult.

In the case where Ar1 is biphenyl, it has a strength in terms of life and has a strength in terms of voltage when Ar1 is fluorene. This is because the fluorene group is generally richer in electrons than the biphenyl group, and has relatively high electron mobility, thus serving to supply holes to the light emitting layer a little faster.

As shown in Table 1, it was confirmed that the compounds of the present invention are excellent in electron blocking ability and applicable to organic light emitting devices.

Although the preferred embodiments of the present invention have been described with reference to the accompanying drawings, it should be understood that the present invention is not limited thereto, but can be variously modified and embodied within the scope of the claims and the detailed description of the invention. .

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

Claims (13)

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

In formula (1), R1 and R2 are the same or different and each independently hydrogen or deuterium, R1 and R2 may be bonded to each other to form a ring,
Ra, Rb, Rc, Rd and Re are the same or different and each independently hydrogen; heavy hydrogen; A halogen group; Cyano; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
l, m and o are each an integer of 0 to 4, n and p are each an integer of 0 to 3, and when 1 to p is 2 or more, the substituents in parentheses are the same or different,
L1 to L3 are the same or different and are each independently a direct bond; Or a substituted or unsubstituted arylene group,
Ar 1 is a substituted or unsubstituted dibenzothiophene group; A substituted or unsubstituted dibenzofurane group; A substituted or unsubstituted carbazole group; A substituted or unsubstituted fluorene group; Or a substituted or unsubstituted triphenylene group,
Ar2 is a substituted or unsubstituted phenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted dibenzothiophene group; A substituted or unsubstituted dibenzofurane group; Or a substituted or unsubstituted fluorene group,
Provided that when Ar1 is a substituted or unsubstituted fluorene group, Ar2 is a substituted or unsubstituted dibenzothiophene group; A substituted or unsubstituted dibenzofurane group; And a substituted or unsubstituted fluorene group. The compound according to claim 1, wherein the compound represented by Formula 1 is represented by Formula 2 or 3:
(2)

(3)

In Formulas (2) and (3), L1 to L3, Ar1 and Ar2 are as defined in Formula (1). The compound according to claim 1, wherein the compound represented by Formula 1 is represented by any one of the following Formulas (2-1) to (2-4) and (3-1) to (3-4)
[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

[Chemical Formula 2-4]

[Formula 3-1]

[Formula 3-2]

[Formula 3-3]

[Chemical Formula 3-4]

In Formulas (2-1) to (2-4) and (3-1) to (3-4), L1 to L3, Ar1 and Ar2 are as defined in Formula (1). [3] The compound according to claim 1, wherein L1 to L3 are the same or different from each other, and each independently is a direct bond; A substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylene group; A substituted or unsubstituted naphthalene group; Or a substituted or unsubstituted fluorenylene group. The compound according to claim 1, wherein N (L2-Ar1) (L3-Ar2) in Formula 1 is selected from the following structural formulas:

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 to 6, device. The organic light emitting device according to claim 7, wherein the organic layer includes an electron blocking layer, and the electron blocking layer includes the compound. [Claim 7] The organic light emitting device of claim 7, wherein the organic layer comprises a light emitting layer, and the light emitting layer comprises a compound represented by the following formula (A-1)
[A-1]

In the above formula (A-1)
q is an integer of 1 or more,
Ar3 is a substituted or unsubstituted monovalent or more benzofluorene group; A substituted or unsubstituted monovalent or more fluoranthene group; A substituted or unsubstituted monovalent or higher valent phenylene group; Or a substituted or unsubstituted monovalent or more chrysene group,
L4 is a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
Ar 4 and Ar 5 are the same or different and each independently represents a substituted or unsubstituted aryl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted germanium group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted arylalkyl group; Or a substituted or unsubstituted heterocyclic group or may be bonded to each other to form a substituted or unsubstituted ring,
When q is 2 or more, the structures in parentheses two or more are the same or different from each other. [10] The compound according to claim 9, wherein L4 is a direct bond, Ar3 is a divalent phenylene group, Ar4 and Ar5 are the same or different and are each independently a phenyl group substituted or unsubstituted with a tert-butyl group; Or a dibenzofurane group, and q is 2. [Claim 7] The organic light emitting device of claim 7, wherein the organic layer comprises a light emitting layer, and the light emitting layer comprises a compound represented by the following formula (A-2)
[A-2]

In the above formula (A-2)
Ar6 and Ar7 are the same or different and each independently represents a substituted or unsubstituted monocyclic aryl group; Or a substituted or unsubstituted polycyclic aryl group,
G1 to G8 are the same or different from each other, and each independently hydrogen; A substituted or unsubstituted monocyclic aryl group; Or a substituted or unsubstituted polycyclic aryl group. 12. The organic electroluminescent device according to claim 11, wherein Ar6 is a 1-naphthyl group, and Ar7 is a 2-naphthyl group. [Claim 11] The organic light emitting device according to claim 9, wherein the light emitting layer comprises a compound represented by the following formula (A-2)
[A-2]

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

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