KR20180088262A - Novel amine-based compound and organic light emitting device comprising the same - Google Patents

Abstract

Provided are a novel amine-based compound and an organic light emitting device comprising the same. The amine compound is represented by chemical formula 1. The compound represented by the chemical formula 1 can be used as a material of an organic material layer of an organic light emitting device, and can improve the efficiency, the driving voltage and/or the lifetime characteristic in the organic light emitting device.

Description

TECHNICAL FIELD The present invention relates to a novel amine compound and an organic light emitting device using the same.

The present invention relates to a novel amine compound and an organic light emitting device comprising the same.

In general, organic light emission phenomenon refers to a phenomenon in which an organic material is used to convert electric energy into light energy. The organic light emitting device using the organic light emitting phenomenon has a wide viewing angle, excellent contrast, fast response time, excellent characteristics of luminance, driving voltage and response speed, and much research has been conducted.

The organic light emitting device generally has a structure including an anode and a cathode, and an organic layer between the anode and the cathode. In order to increase the efficiency and stability of the organic light emitting device, the organic material layer may have a multilayer structure composed of different materials. For example, the organic material layer may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. When a voltage is applied between the two electrodes in the structure of such an organic light emitting device, holes are injected in the anode, electrons are injected into the organic layer in the cathode, excitons are formed when injected holes and electrons meet, When it falls back to the ground state, the light comes out.

There is a continuing need for the development of new materials for the organic materials used in such organic light emitting devices.

Korean Patent Publication No. 10-2000-0051826

The present invention relates to a novel amine compound and an organic light emitting device comprising the same.

The present invention provides a compound represented by the following formula (1): < EMI ID =

[Chemical Formula 1]

In Formula 1,

X is O or S,

A and B each independently represent hydrogen; Substituted or unsubstituted C _6-60 aryl; Or substituted or unsubstituted C _2-60 heteroaryl containing 1 to 3 heteroatoms selected from the group consisting of N, O and S, except that when A and B are both hydrogen,

L is a single bond; Substituted or unsubstituted C _6-60 arylene; Or substituted or unsubstituted C _2-60 heteroarylene containing at least one heteroatom selected from the group consisting of O, N, Si and S,

Ar ₁ and Ar ₂ are each independently a substituted or unsubstituted C _6-60 aryl; Or substituted or unsubstituted C _2-60 heteroaryl containing 1 to 3 heteroatoms selected from the group consisting of N, O and S,

R ₁ is hydrogen; heavy hydrogen; halogen; Cyano; Nitro; Amino; Substituted or unsubstituted C _1-6 alkyl; Substituted or unsubstituted C _1-6 haloalkyl; Substituted or unsubstituted C _1-60 alkoxy; Substituted or unsubstituted C _1-60 haloalkoxy; Substituted or unsubstituted C _3-60 cycloalkyl; Substituted or unsubstituted C _2-60 alkenyl; Substituted or unsubstituted C _6-60 aryl; Substituted or unsubstituted C _6-60 aryloxy; Or a substituted or unsubstituted C _2-60 heterocyclic group containing at least one heteroatom selected from the group consisting of N, O and S,

a1 is an integer of 0 to 4;

The present invention also provides 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 a compound represented by Formula 1 .

The compound represented by the general formula (1) can be used as a material of an organic material layer of an organic light emitting device and can improve the efficiency, the driving voltage and / or the lifetime of the organic light emitting device.

Fig. 1 shows an example of an organic light-emitting device comprising a substrate 1, an anode 2, a light-emitting layer 3 and a cathode 4. Fig.
2 shows an example of an organic light emitting element comprising a substrate 1, an anode 2, a hole injecting layer 5, a hole transporting layer 6, a light emitting layer 7, an electron transporting layer 8 and a cathode 4 It is.

Hereinafter, the present invention will be described in detail in order to facilitate understanding of the present invention.

는 다른 치환기에 연결되는 결합을 의미하고, 단일 결합은 L로 표시되는 부분에 별도의 원자가 존재하지 않은 경우를 의미한다. In the present specification,

Means a bond connected to another substituent, and a single bond means a case where no separate atom exists in a portion represented by L. [

As used herein, the term " substituted or unsubstituted " A halogen group; Cyano; A nitro group; A hydroxy group; A carbonyl group; An ester group; Imide; An amino group; Phosphine oxide groups; An alkoxy group; An aryloxy group; An alkyloxy group; Arylthioxy group; An alkylsulfoxy group; Arylsulfoxy group; Silyl group; Boron group; An alkyl group; Cycloalkyl groups; An alkenyl group; An aryl group; Aralkyl groups; An aralkenyl group; An alkylaryl group; An alkylamine group; An aralkylamine group; A heteroarylamine group; An arylamine group; Arylphosphine groups; Or a heterocyclic group containing at least one of N, O and S atoms, or a substituted or unsubstituted group in which at least two of the above-exemplified substituents are connected to each other . 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, or may be interpreted as a substituent in which two phenyl groups are connected.

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

In the present specification, the ester group may be substituted with a straight-chain, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms in the ester group. Specifically, it may be a compound of the following structural formula, but is not limited thereto.

In the present specification, the number of carbon atoms of the imide group is not particularly limited, but is preferably 1 to 25 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

In the present specification, the silyl group specifically includes a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, But are not limited thereto.

In the present specification, the boron group specifically includes, but is not limited to, a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, and a phenylboron group.

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 40. According to one embodiment, the alkyl group has 1 to 20 carbon atoms. According to another embodiment, the alkyl group has 1 to 10 carbon atoms. According to another embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an isopropyl group, a n-butyl group, an isobutyl group, a tert-butyl group, But are not limited to, pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, , n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, But are not limited to, dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl and 5-methylhexyl.

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. According to one embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, Butenyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, (Diphenyl-1-yl) vinyl-1-yl, stilbenyl, stilenyl, and the like.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms. According to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specific examples include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3- 4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but are not limited thereto.

In the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a phenyl group, a biphenyl group, a terphenyl group or the like as the monocyclic aryl group, but is not limited thereto. Examples of the polycyclic aryl group include, but are not limited to, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a klycenyl group and a fluorenyl group.

등이 될 수 있다. 다만, 이에 한정되는 것은 아니다.In the present specification, a fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure. When the fluorenyl group is substituted,

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

In the present specification, the heterocyclic group is a hetero ring group containing at least one of O, N, Si and S as a hetero atom, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms. Examples of the heterocyclic group include a thiophene group, a furane group, a furyl group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, a bipyridyl group, a pyrimidyl group, A pyridazinyl group, a pyrazinopyrazinyl group, an isoquinoline group, a pyrazinyl group, a pyrazinyl group, a pyrazinyl group, a pyrazinyl group, a quinolinyl group, a quinazolinyl group, a quinoxalinyl group, a phthalazinyl group, a pyridopyrimidinyl group, , An indole group, a carbazole group, a benzoxazole group, a benzoimidazole group, a benzothiazole group, a benzocarbazole group, a benzothiophene group, a dibenzothiophene group, a benzofuranyl group, a phenanthroline, An isoxazolyl group, an oxadiazolyl group, a thiadiazolyl group, a benzothiazolyl group, a phenothiazinyl group, and a dibenzofuranyl group, but is not limited thereto.

In the present specification, the aryl group in the aralkyl group, the aralkenyl group, the alkylaryl group and the arylamine group is the same as the aforementioned aryl group. In the present specification, the alkyl group in the aralkyl group, the alkylaryl group, and the alkylamine group is the same as the alkyl group described above. In the present specification, the heteroaryl among the heteroarylamines can be applied to the aforementioned heterocyclic group. In the present specification, the alkenyl group in the aralkenyl group is the same as the above-mentioned alkenyl 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 the present specification, the description of the above-mentioned aryl group or cycloalkyl group can be applied except that the hydrocarbon ring is not a monovalent group and two substituents are bonded to each other. In the present specification, the description of the above-mentioned heterocyclic group can be applied except that the heterocyclic ring is not a monovalent group and two substituents are bonded to each other.

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

In Formula 1, A and B each independently represent hydrogen, or any one selected from the group consisting of That is, in the above formula (1), one of A and B is hydrogen and the other is selected from the group consisting of A and B may be any one selected from the group consisting of:

In the above,

Y ₁ is O, S, or CZ ₄ Z ₅ ,

Z ₁ to Z ₅ each independently represent hydrogen; heavy hydrogen; halogen; Cyano; Nitro; Amino; C _1-20 alkyl; C _1-20 haloalkyl; C _6-20 aryl; _Lt ; / RTI > heteroaryl containing one or more heteroatoms of O or S,

n1 to n3 each independently represent an integer of 0 to 3;

For example, A and B may each independently be hydrogen, or any one selected from the group consisting of:

Specifically, in the organic light-emitting device manufactured by using a compound in which A and B are both hydrogen as the electron suppressing layer or the hole transporting layer, the efficiency is 10% or more and the lifetime is limited to 30% or more. Accordingly, when A and B are independently selected from the group consisting of hydrogen and the group consisting of the above-mentioned formula (1), the efficiency of the device can be increased and the stability can be greatly increased.

L is a single bond, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted phenanthrenylene, substituted or unsubstituted anthracenylene, Substituted or unsubstituted fluorenylene, substituted or unsubstituted fluorenylene, substituted or unsubstituted fluorenenylene, substituted or unsubstituted triphenylenylene, substituted or unsubstituted pyrenylene, substituted or unsubstituted carbazolylene, substituted or unsubstituted fluorenylene, It may be an unsubstituted spiro-fluorenylene.

For example, L may be a single bond, or any one selected from the group consisting of:

Specifically, for example, L may be a single bond, or any one selected from the group consisting of:

When the L has a long chain as described below, the distance between the core and the arylamine group in Formula 1 may become too great, and the characteristics of the organic light emitting device may be significantly deteriorated.

Ar ₁ and Ar ₂ are each independently a substituted or unsubstituted C _6-20 aryl; Or a C _2-20 heteroaryl containing 1 to 3 hetero atoms of substituted or unsubstituted O or S.

For example, Ar ₁ and Ar ₂ may each independently be selected from the group consisting of:

In the above,

Y ₂ is O, S, or CZ ₁₄ Z ₁₅ ,

Z ₁₁ to Z ₁₅ each independently represent hydrogen; heavy hydrogen; halogen; Cyano; Nitro; Amino; Silyl; C _1-20 alkyl; C _1-20 haloalkyl; C _6-20 aryl; O or are a C _2-20 heteroaryl group containing one or more heteroatoms of S, Z ₁₄ and Z ₁₅ may combine to form a monocyclic or polycyclic ring are connected to each other,

m1 to m3 each independently represent an integer of 0 to 3;

Z ₁₁ to Z ₁₃ are each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, trimethylsilyl, methyl, tert-butyl, phenyl, naphthyl, triphenylenyl, dibenzofuranyl or dibenzothiophenyl ,

Z < ₁₄ > and Z < ₁₅ > are each independently methyl, or are connected to each other to form a monocyclic or polycyclic ring,

m1 to m3 each independently represent 0 or 1;

Specifically, for example, Ar ₁ and Ar ₂ each independently may be any one selected from the group consisting of:

R < ₁ > is hydrogen; heavy hydrogen; halogen; Cyano; Nitro; C _1-20 alkyl; Or C _6-20 aryl.

For example, R ₁ can be hydrogen, deuterium, halogen, cyano, nitro, methyl, or phenyl, and a 1 can be 0 or 1.

Here, a1 represents the number of R ₁ , and when a ₁ is 2 or more, two or more R _{1 s} may be the same or different from each other. n1 to n3 and m1 to m3 can be understood with reference to the description of a1 and the structure of the above formula (1).

On the other hand, the compound may be represented by the following formula (1A) or (1B):

≪ EMI ID =

≪ RTI ID = 0.0 &

In the above formulas 1A and 1B,

X, A, B, L, Ar < _{1 >} and Ar < ₂ >

For example, the compound may be any one selected from the group consisting of the following compounds:

The compound represented by Formula 1 has a structure in which A or B and an arylamine substituent are connected to specific positions of dibenzofuran / dibenzothiophene core, and thus the organic light emitting device using the same has high efficiency, low driving voltage, And longevity.

The compound represented by the formula (1A) can be prepared, for example, according to the following reaction scheme 1, and the compound represented by the formula (1B) can be prepared, for example, according to the following reaction scheme 2.

[Reaction Scheme 1]

[Reaction Scheme 2]

In the above Reaction Schemes 1 and 2, X, A, B, L, Ar ₁ and Ar ₂ are as defined in Formula 1 above.

The compound represented by the formula (1) can be prepared by appropriately substituting the starting material according to the structure of the compound to be prepared with reference to the schemes 1 and 2.

Meanwhile, the present invention provides an organic light emitting device comprising the compound represented by Formula 1. In one embodiment, the present invention provides a liquid crystal display 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 a compound represented by Formula 1 .

The organic material layer may include a hole injecting layer, a hole transporting layer, or a layer simultaneously injecting and transporting holes.

In addition, the organic layer may include a light emitting layer, and the light emitting layer may include a compound represented by the general formula (1).

Further, the electron transport layer, the electron injection layer, or the layer that simultaneously performs electron transport and electron injection may be included.

In addition to the organic layer, the organic light emitting diode may further include an electron blocking layer (EBL) disposed between the hole transport layer and the light emitting layer and / or a hole blocking layer between the emission layer and the electron transport layer, layer: HBL). The electron blocking layer and the hole blocking layer may be organic layers adjacent to the light emitting layer, respectively.

At this time, the compound represented by Formula 1 may be included in the hole transport layer and / or the electron blocking layer.

The organic material layer of the organic light emitting device of the present invention may have a single layer structure, but may have a multilayer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present invention 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 an organic material layer. 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 of the present invention may have a single layer structure, but may have a multilayer structure in which two or more organic material layers are stacked. For example, in the organic light emitting device of the present invention, in addition to the light emitting layer as the organic material layer, a hole injecting layer and a hole transporting layer between the first electrode and the light emitting layer, and an electron transporting layer and an electron injecting layer between the light emitting layer and the second electrode are further included . ≪ / RTI > However, the structure of the organic light emitting device is not limited thereto, and may include fewer or more organic layers.

The organic light emitting device according to the present invention 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 addition, the organic light emitting device according to the present invention may be an inverted type organic light emitting device in which an anode, one or more organic compound layers and an anode are sequentially stacked on a substrate. For example, the structure of an organic light emitting diode according to an embodiment of the present invention is illustrated in FIGS.

Fig. 1 shows an example of an organic light-emitting device comprising a substrate 1, an anode 2, a light-emitting layer 3 and a cathode 4. Fig. In such a structure, the compound represented by Formula 1 may be included in the light emitting layer.

2 shows an example of an organic light emitting element comprising a substrate 1, an anode 2, a hole injecting layer 5, a hole transporting layer 6, a light emitting layer 7, an electron transporting layer 8 and a cathode 4 It is. In such a structure, the compound represented by Formula 1 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 according to the present invention may be manufactured by materials and methods known in the art, except that at least one of the organic layers includes the compound represented by Formula 1. [ In addition, 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.

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

The compound represented by Formula 1 may be formed into an organic 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 can be manufactured by sequentially depositing an organic material layer and a cathode material from a cathode material on a substrate (WO 2003/012890). However, the manufacturing method is not limited thereto.

In one example, the first electrode is an anode, the second electrode is a cathode, or 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 positive electrode material 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 as described above. The host material may further include 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 the heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

Examples of the dopant material include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specific examples of the aromatic amine derivatives include condensed aromatic ring derivatives having substituted or unsubstituted arylamino groups, and examples thereof include pyrene, anthracene, chrysene, and peripherrhene having an arylamino group. Examples of the styrylamine compound include substituted or unsubstituted Wherein at least one aryl vinyl group is substituted with at least one aryl vinyl group, and at least one substituent selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group is substituted or unsubstituted. Specific examples thereof include, but are not limited to, styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like. Examples of the metal complex include iridium complex, platinum complex, and the like, but are not limited thereto.

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

The electron injection layer is a layer for injecting electrons from the electrode. The electron injection layer has 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 nitrogen-containing 5-membered ring derivative, and the like, 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 organic light emitting device according to the present invention may be a front emission type, a back emission type, or a both-sided emission type, depending on the material used.

In addition, the compound represented by Formula 1 may be included in an organic solar cell or an organic transistor in addition to an organic light emitting device.

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 invention, and the scope of the present invention is not limited thereto.

Production Example A: Preparation of Intermediate Compound A

Production Example B: Preparation of Intermediate Compound B

Production Example C: Preparation of Intermediate Compound C

Production Example D: Preparation of Intermediate Compound D

Preparation Example E: Preparation of intermediate compound E

Preparation Example F: Preparation of Intermediate Compound F

Preparation Example G: Preparation of Intermediate Compound G

Production Example H: Preparation of Intermediate Compound H

Preparation Example I: Preparation of Intermediate Compound I

Production Example J: Preparation of Intermediate Compound J

Preparation Example K: Preparation of Intermediate Compound K

Production Example L: Preparation of Intermediate Compound L

Preparation Example M: Preparation of Intermediate Compound M

Production Example 1: Preparation of Compound 1

                                                        [Compound 1]

Compound A (7.56 g, 31.11 mmol) and di ([1,1'-biphenyl] -4-yl) amine (10.99 g, 34.22 mmol) were completely dissolved in 220 ml of xylene in a 500 ml round- (12.13 g, 37.33 mmol) was added, and Bis (tri- tert- butylphosphine) palladium (0) (0.08 g, 0.16 mmol) was added and the mixture was heated with stirring for 3 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 (180 ml) to give Compound 1 (12.46 g, yield: 71%).

MS [M + H] < ⁺ > = 564

Production Example 2: Preparation of Compound 2

                                                            [Compound 2]

Compound A (8.22 g, 33.83 mmol), N - ([1,1'-biphenyl] -4-yl) -9,9-dimethyl-9H-fluoren- g, 37.21 mmol) was dissolved in 250 ml of xylene, followed by the addition of Caesium carbonate (13.19 g, 40.59 mmol) and bis (tri- tert- butylphosphine) palladium (0) (0.09 g, 0.17 mmol) Followed by heating and stirring. 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 (130 ml) to obtain Compound 2 (10.45 g, yield: 51%).

MS [M + H] < ⁺ > = 604

Production Example 3: Preparation of Compound 3

                                                           [Compound 3]

Compound A (6.73 g, 27.70 mmol), N- (4- (dibenzo [b, d] furan-4-yl) phenyl) -9,9-dimethyl-9H- -amine (13.74g, 30.47mmol) was completely dissolved in 300ml of xylene and then Caesium carbonate (10.80g, 33.23mmol) was added and bis (tri- tert- butylphosphine) palladium (0) (0.07g, 0.14mmol) The mixture was heated and stirred for 6 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 260 ml of tetrahydrofuran to obtain Compound 3 (13.29 g, yield 69%).

MS [M + H] < ⁺ > = 694

Production Example 4: Preparation of Compound 4

                                                        [Compound 4]

(4.96 g, 15.55 mmol) and di ([1,1'-biphenyl] -4-yl) amine (5.49 g, 17.10 mmol) were completely dissolved in 260 ml of xylene in a 500 ml round- (6.06 g, 18.66 mmol) was added, and Bis (tri- tert- butylphosphine) palladium (0) (0.04 g, 0.08 mmol) was added and the mixture was heated with stirring for 6 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 (220 ml) to obtain the above compound 4 (7.19 g, yield 67%).

MS [M + H] < ⁺ > = 640

Production Example 5: Preparation of Compound 5

                                                       [Compound 5]

(4.96 g, 15.55 mmol) and N-phenyl- [1,1 ': 4', 1 "-terphenyl] -4-amine (5.49 g, 17.10 mmol) were added to a 500 ml round- (6.06 g, 18.66 mmol) was added. Bis (tri- tert- butylphosphine) palladium (0) (0.04 g, 0.08 mmol) was added thereto and the mixture was heated with 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 give Compound 5 (6.08 g, yield: 56%).

MS [M + H] < ⁺ > = 640

Preparation Example 6: Preparation of Compound 6

                                                       [Compound 6]

(5.13 g, 17.51 mmol) and di ([1,1'-biphenyl] -4-yl) amine (6.18 g, 19.26 mmol) were completely dissolved in 190 ml of xylene in a 500 ml round- ( Tert- butylphosphine) palladium (0) (0.04 g, 0.09 mmol) was added thereto, followed by heating and stirring for 4 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 6 (7.82 g, yield: 73%).

MS [M + H] < ⁺ > = 614

Production Example 7: Preparation of Compound 7

                                                       [Compound 7]

(4.29 g, 14.64 mmol) and N - ([1,1'-biphenyl] -4-yl) -9,9-dimethyl-9H-fluoren- g, 16.11 mmol) was dissolved in 280 ml of xylene, and then Ca (5.71 g, 17.57 mmol) was added and bis (tri- tert- butylphosphine) palladium (0) (0.04 g, 0.07 mmol) Followed by heating and stirring. 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 (130 ml) to obtain Compound 7 (5.17 g, yield: 58%).

MS [M + H] < ⁺ > = 604

Production Example 8: Preparation of Compound 8

                                                          [Compound 8]

Compound D (7.38 g, 15.19 mmol) and phenylboronic acid (2.13 g, 17.46 mmol) were completely dissolved in 240 ml of tetrahydrofuran in a 500 ml round-bottomed flask under nitrogen atmosphere, and 2M aqueous potassium carbonate solution (120 ml) (Triphenylphosphine) palladium (0.62 g, 0.58 mmol) was added thereto, followed by heating and stirring for 5 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from ethyl acetate (250 ml) to give Compound 8 (6.27 g, yield: 73%).

MS [M + H] < ⁺ > = 564

Production Example 9: Preparation of Compound 9

                                                             [Compound 9]

Compound D (7.38 g, 15.19 mmol) and naphthalen-2-ylboronic acid (2.13 g, 17.46 mmol) were dissolved in 280 ml of tetrahydrofuran in a 500 ml round-bottomed flask under nitrogen atmosphere and 2M aqueous potassium carbonate solution (140 ml) , And tetrakis- (triphenylphosphine) palladium (0.61 g, 0.57 mmol) were added thereto, followed by heating and stirring for 4 hours. The temperature was lowered to room temperature, and the water layer was removed. The organic layer was dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from ethyl acetate (250 ml) to give Compound 9 (7.01 g, yield 75%).

MS [M + H] < ⁺ > = 614

Production Example 10: Preparation of Compound 10

                                                         [Compound 10]

Compound E (7.38 g, 15.19 mmol) and phenylboronic acid (2.13 g, 17.46 mol) were completely dissolved in 240 ml of tetrahydrofuran in a 500 ml round bottom flask under a nitrogen atmosphere, and 2M aqueous potassium carbonate solution (120 ml) (Triphenylphosphine) palladium (0.49 g, 0.46 mmol) was added thereto, followed by heating and stirring for 6 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from ethyl acetate (240 ml) to obtain Compound 10 (8.26 g, yield: 79%).

MS [M + H] < ⁺ > = 604

Production Example 11: Preparation of Compound 11

                                                     [Compound 11]

*

Compound F (7.77 g, 13.49 mmol) and phenylboronic acid (1.89 g, 15.51 mol) were completely dissolved in 200 ml of tetrahydrofuran in a 500 ml round-bottomed flask under nitrogen atmosphere, and 2M potassium carbonate aqueous solution (100 ml) (Triphenylphosphine) palladium (0.47 g, 0.40 mmol) were added thereto, followed by heating and stirring for 6 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was recrystallized from ethyl acetate (260 ml) to obtain the above compound 11 (8.26 g, yield 79%).

MS [M + H] < ⁺ > = 654

Production Example 12: Preparation of Compound 12

[Compound 12]

Compound G (6.64 g, 11.22 mmol) and (9,9-dimethyl-9H-fluoren-2-yl) boronic acid (3.07 g, 12.90 mmol) were completely dissolved in 240 ml of tetrahydrofuran in a 500 ml round- Then, 2M aqueous potassium carbonate solution (120 ml) was added, tetrakis- (triphenylphosphine) palladium (0.39 g, 0.34 mmol) was added, and the mixture was heated and stirred for 4 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from ethyl acetate (310 ml) to obtain Compound (12) (8.26 g, yield 79%).

MS [M + H] < ⁺ > = 786

Production Example 13: Preparation of Compound 13

                                                      [Compound 13]

To a 500 ml round-bottomed flask in a nitrogen atmosphere was added H (5.39 g, 20.81 mmol), N - ([1,1'-biphenyl] -4-yl) - [1,1 ': 4', 1 " -4-amine (9.17 g, 23.10 mmol) was completely dissolved in 250 ml of xylene, followed by the addition of Caesium carbonate (8.66 g, 27.05 mmol) and bis (tri- tert- butylphosphine) palladium (0) (0.11 g, 0.21 mmol) Followed by heating and stirring for 5 hours. After the temperature was lowered to room temperature and the base was removed by filtration, the xylene was concentrated under reduced pressure and recrystallized from 250 ml of tetrahydrofuran to obtain Compound 13 (11.67 g, yield: 70%).

MS [M + H] < ⁺ > = 656

Production Example 14: Preparation of Compound 14

                                                       [Compound 14]

Compound I (7.16 g, 20.81 mmol) and N-phenyl- [1,1'-biphenyl] -4-amine (5.81 g, 23.72 mmol) were completely dissolved in 300 ml of xylene in a 500 ml round- ( Tert- butylphosphine) palladium (0) (0.11 g, 0.21 mmol) was added thereto, followed by heating and stirring for 3 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 200 ml of tetrahydrofuran to obtain the compound 14 (8.88 g, yield: 72%).

MS [M + H] < ⁺ > = 580

Production Example 15: Preparation of Compound 15

                                                       [Compound 15]

(4.28 g, 13.85 mmol), N - ([1,1'-biphenyl] -4-yl) -9,9-dimethyl-9H-fluoren- bis (tri- tert- butylphosphine) palladium (0) (0.07g, 0.14mmol) was added to the reaction mixture, and the mixture was stirred for 4 hours Followed by heating and stirring. After the temperature was lowered to room temperature and the base was removed by filtration, the xylene was concentrated under reduced pressure and recrystallized from 220 ml of tetrahydrofuran to obtain the compound 15 (4.39 g, yield: 46%).

MS [M + H] < ⁺ > = 696

Production Example 16: Preparation of Compound 16

                                                      [Compound 16]

Compound K (9.68 g, 19.28 mmol) and phenylboronic acid (2.61 g, 21.40 mmol) were completely dissolved in 240 ml of tetrahydrofuran in a 500 ml round-bottomed flask under nitrogen atmosphere, and 2M potassium carbonate aqueous solution (120 ml) (Triphenylphosphine) palladium (0.67 g, 0.58 mmol) were added thereto, followed by heating and stirring for 4 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was recrystallized from ethyl acetate (220 ml) to give Compound 16 (6.09 g, yield: 54%).

MS [M + H] < ⁺ > = 580

Production Example 17: Preparation of Compound 17

                                                  [Compound 17]

(5.72 g, (4- (di ([1,1'-biphenyl] -4-yl) amino) phenyl) boronic acid (10.72 g, 24.30 mmol) was dissolved in tetrahydrofuran (Triphenylphosphine) palladium (0.76 g, 0.66 mmol) was added thereto, and the mixture was heated with stirring for 4 hours. After the temperature was lowered to room temperature, a water layer The organic layer was dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from ethyl acetate (250 ml) to obtain Compound (17) (7.12 g, yield: 51%).

MS [M + H] < ⁺ > = 640

Production Example 18: Preparation of Compound 18

                                                    [Compound 18]

Compound A (6.67 g, 27.45 mmol), (4 - ([1,1'-biphenyl] -4-yl (9,9-dimethyl-9H- fluoren- 2- yl) amino ) phenylboronic acid (10.72 g, 24.30 mol) was completely dissolved in 240 ml of tetrahydrofuran. To the mixture was added 2M potassium carbonate aqueous solution (120 ml), tetrakis- (triphenylphosphine) palladium (0.76 g, 0.66 mmol) And the mixture was heated and stirred for 4 hours. The temperature was lowered to room temperature, and the water layer was removed. The organic layer was dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from ethyl acetate (250 ml) to prepare the compound 18 (7.12 g, yield: 51%).

MS [M + H] < ⁺ > = 680

Production Example 19: Preparation of Compound 19

                                                      [Compound 19]

To a 500 ml round-bottom flask in a nitrogen atmosphere was added compound C (7.75 g, 27.45 mmol), (4 - ([1,1'-biphenyl] -4-yl ) phenyl boronic acid (13.41 g, 30.42 mol) was completely dissolved in 280 ml of tetrahydrofuran, followed by addition of 2M aqueous potassium carbonate solution (140 ml) and tetrakis- (triphenylphosphine) palladium (0.92 g, Followed by heating and stirring for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from ethyl acetate (250 ml) to obtain Compound 19 (15.26 g, yield: 84%).

MS [M + H] < ⁺ > = 690

Production Example 20: Preparation of Compound 20

                                   [Compound 20]

The compound L (5.47 g, 17.15 mmol) and di ([1,1'-biphenyl] -4-yl) amine (6.33 g, 19.72 mmol) were completely dissolved in 180 ml of xylene in a 500 ml round- (8.38 g, 25.72 mmol) was added, and Bis (tri- tert- butylphosphine) palladium (0) (0.09 g, 0.17 mmol) was added thereto and the mixture was heated with stirring for 6 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 20 (6.77 g, yield 62%).

MS [M + H] < ⁺ > = 640

Production Example 21: Preparation of Compound 21

                                   [Compound 21]

(7.54 g, 22.51 mmol), N - ([1,1'-biphenyl] -4-yl) -9,9-dimethyl-9H- fluoren- 2 -amine g, 25.88 mmol) was completely dissolved in 220 ml of xylene, followed by the addition of Caesium carbonate (11.00 g, 33.76 mmol), bis (tri- tert- butylphosphine) palladium (0) (0.12 g, 0.23 mmol) Followed by heating and stirring. 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 (180 ml) to obtain Compound 21 (10.07 g, yield: 64%).

MS [M + H] < ⁺ > = 696

Example 1-1

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 formula was thermally vacuum deposited to a thickness of 150 Å to form a hole injection layer.

[LINE]

The following compound HT1 (1150 ANGSTROM), which is a material for transporting holes, was vacuum deposited on the hole injection layer to form a hole transport layer.

[HT1]

Subsequently, Compound 1 prepared in Preparation Example 1 was vacuum deposited on the hole transport layer to a thickness of 150 ANGSTROM to form an electron blocking layer.

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]

[ET]

[LiQ]

The compound ET 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 transport layer having a thickness of 300 ANGSTROM. Aluminum was sequentially deposited on the electron transport layer to a thickness of 12 Å and a thickness of 2,000 Å to form an electron injection layer and 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 < ^-6 > torr, thereby fabricating an organic light emitting device.

Examples 1-2 to 1-15

The organic light emitting devices of Examples 1-2 to 1-15 were fabricated in the same manner as in Example 1-1, except that Compound 1 was changed as shown in Table 1 below in forming the electron blocking layer. Respectively.

Comparative Example 1-1

An organic light emitting device was fabricated in the same manner as in Example 1-1 except that EB-1 was used instead of Compound 1 in the formation of the electron blocking layer

[EB-1]

Comparative Example 1-2

An organic light emitting device was fabricated in the same manner as in Example 1-1 except that EB-2 was used instead of Compound 1 in the formation of the electron blocking layer

[EB-2]

Comparative Example 1-3

An organic light emitting device was fabricated using the same method as in Example 1-1 except that EB-3 was used instead of Compound 1 in forming the electron blocking layer

[EB-3]

Comparative Example 1-4

An organic light emitting device was fabricated using the same method as in Example 1-1 except that EB-4 was used instead of Compound 1 in the formation of the electron blocking layer

[EB-4]

Experimental Example 1

The voltage, efficiency, luminance, color coordinate and lifetime were measured by applying current to the organic light-emitting devices fabricated in Examples 1-1 to 1-13 and Comparative Examples 1-1 to 1-3. The results are shown in the following Table 1 Respectively. T95 means the time required for the luminance to decrease from the initial luminance (650 nits) to 95%.

The electron blocking layer
compound Voltage
(V @ 10 mA / cm ² ) efficiency
(cd / A @ 10mA / cm 2) Color coordinates
(x, y) life span
(T95, h) Example 1-1 Compound 1 3.72 5.47 (0.140, 0.045) 225 Examples 1-2 Compound 4 3.86 5.32 (0.140, 0.045) 215 Example 1-3 Compound 5 3.88 5.31 (0.139, 0.046) 210 Examples 1-4 Compound 6 3.87 5.38 (0.139, 0.047) 230 Examples 1-5 Compound 8 3.74 5.41 (0.138, 0.044) 220 Examples 1-6 Compound 9 3.85 5.28 (0.140, 0.042) 200 Examples 1-7 Compound 11 3.81 5.29 (0.140, 0.041) 205 Examples 1-8 Compound 12 3.72 5.45 (0.141, 0.045) 210 Examples 1-9 Compound 13 3.77 5.42 (0.142, 0.045) 205 Example 1-10 Compound 14 3.98 5.11 (0.137, 0.047) 245 Example 1-11 Compound 16 3.94 5.18 (0.136, 0.048) 240 Examples 1-12 Compound 17 3.88 5.31 (0.137, 0.044) 250 Examples 1-13 Compound 19 3.74 5.28 (0.136, 0.045) 215 Examples 1-14 Compound 20 3.68 5.57 (0.142, 0.042) 250 Examples 1-15 Compound 21 3.64 5.58 (0.143, 0.043) 215 Comparative Example 1-1 EB-1 4.05 4.87 (0.136, 0.047) 165 Comparative Example 1-2 EB-2 4.16 4.77 (0.136, 0.048) 170 Comparative Example 1-3 EB-3 4.10 4.82 (0.136, 0.046) 185 Comparative Example 1-4 EB-4 5.12 4.13 (0.136, 0.047) 115

As shown in Table 1, the organic light emitting device manufactured using the compound according to the present invention as an electron blocking layer exhibited superior performance in terms of driving voltage, current efficiency, lifetime, and stability as compared with the organic light emitting device of the comparative example can confirm.

Specifically, the organic light-emitting device manufactured using the compounds of Comparative Examples 1-1 to 1-3, which have the same structure as the core of the present invention and have no substituent in the 1 st and 3 rd directions, as the electron suppressing layer, The contrast efficiency was more than 10%, and the life time was more than 30%.

On the other hand, in the compound of Comparative Example 1-4, the distance between the core and the arylamine group was too large, and the characteristics of the organic light emitting device were greatly deteriorated.

In the case of the compound of the present invention, it was confirmed that the efficiency of the device was increased and the stability was greatly increased.

Example 2-1

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.

The HAT was thermally vacuum deposited on the ITO transparent electrode to a thickness of 150 Å to form a hole injection layer.

Compound 1 prepared in Preparation Example 1 was vacuum-deposited to a thickness of 1150 ANGSTROM as a hole transporting material on the hole injection layer to form a hole transport layer.

Subsequently, the following compound EB was vacuum deposited on the hole transport layer to a thickness of 150 ANGSTROM to form an electron blocking layer.

[EB]

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.

The compound ET 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 transport layer having a thickness of 300 ANGSTROM. Aluminum was sequentially deposited on the electron transport layer to a thickness of 12 Å and a thickness of 2,000 Å to form an electron injection layer and 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 < ^-6 > torr, thereby fabricating an organic light emitting device.

Examples 2-2 to 2-12

The organic light emitting devices of Examples 2-2 to 2-12 were produced in the same manner as in Example 2-1 except that the electron transporting material in the formation of the hole transporting layer was changed as shown in Table 2 instead of the compound 1. Respectively.

Comparative Example 2-1

An organic light emitting device was fabricated using the same method as in Example 2-1, except that HT-1 was used instead of Compound 1 in forming the hole transport layer.

[HT-1]

Comparative Example 2-2

An organic light emitting device was fabricated using the same method as in Example 2-1 except that HT-2 was used instead of Compound 1 in forming the hole transport layer.

[HT-2]

Comparative Example 2-3

An organic light emitting device was fabricated using the same method as in Example 2-1, except that HT-3 was used instead of Compound 1 as an electron transporting material in forming the hole transporting layer.

[HT-3]

Comparative Example 2-4

An organic light emitting device was fabricated using the same method as in Example 2-1 except that HT-4 was used instead of Compound 1 in forming the hole transport layer.

[HT-4]

Experimental Example 2

The voltage, efficiency, luminance, chromaticity coordinate and lifetime were measured by applying current to the organic light-emitting device manufactured in Examples 2-1 to 2-12 and Comparative Examples 2-1 to 2-4, Respectively. T95 means the time required for the luminance to decrease from the initial luminance (650 nits) to 95%.

Hole transport layer
compound Voltage
(V @ 10 mA / cm ² ) efficiency
(cd / A @ 10mA / cm 2) Color coordinates
(x, y) life span
(T95, h) Example 2-1 Compound 1 3.81 5.53 (0.140, 0.045) 260 Example 2-2 Compound 2 3.95 5.42 (0.140, 0.045) 250 Example 2-3 Compound 3 3.94 5.44 (0.139, 0.046) 255 Examples 2-4 Compound 4 3.96 5.45 (0.139, 0.047) 275 Example 2-5 Compound 6 3.87 5.57 (0.138, 0.044) 265 Examples 2-6 Compound 7 3.99 5.38 (0.140, 0.042) 245 Examples 2-7 Compound 9 3.91 5.39 (0.140, 0.041) 240 Examples 2-8 Compound 10 3.82 5.59 (0.141, 0.045) 255 Examples 2-9 Compound 15 3.85 5.55 (0.142, 0.045) 240 Examples 2-10 Compound 18 4.01 5.26 (0.137, 0.047) 280 Examples 2-11 Compound 20 3.86 5.43 (0.142, 0.041) 270 Examples 2-12 Compound 21 3.73 5.42 (0.143, 0.042) 265 Comparative Example 2-1 HT-1 4.13 4.83 (0.136, 0.047) 200 Comparative Example 2-2 HT-2 4.21 4.74 (0.136, 0.048) 215 Comparative Example 2-3 HT-3 4.29 4.87 (0.136, 0.046) 220 Comparative Example 2-4 HT-4 4.92 4.10 (0.143, 0.042) 110

As shown in Table 2, the organic light emitting device manufactured using the compound according to the present invention as a hole transport layer exhibited superior performance in terms of current efficiency, driving voltage, lifetime, and stability compared with the organic light emitting device of the comparative example Can be confirmed.

Specifically, the organic light emitting device manufactured using the compounds of Comparative Examples 2-1 to 2-3, which had the same structure as the core of the present invention and had no substituent in the first and third directions, as the hole transport layer, The efficiency was more than 10%, and the life time was more than 30%.

On the other hand, in the compound of Comparative Example 2-4, the distance between the core and the arylamine group was too far, and the characteristics of the organic light emitting device were greatly deteriorated.

In the case of the compound of the present invention, it was confirmed that the efficiency of the device was increased and the stability was greatly increased.

Therefore, it can be seen that the compound according to the present invention is applicable not only to the electron blocking ability but also to the electron blocking layer and / or the hole transporting layer of the organic light emitting device because of its excellent hole transporting ability.

1: substrate 2: anode
3: light emitting layer 4: cathode
5: Hole injection layer 6: Hole transport layer
7: light emitting layer 8: electron transporting layer

Claims (13)

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

In Formula 1,
X is O or S,
A and B each independently represent hydrogen; Substituted or unsubstituted C _6-60 aryl; Or substituted or unsubstituted C _2-60 heteroaryl containing 1 to 3 heteroatoms selected from the group consisting of N, O and S, except that when A and B are both hydrogen,
L is a single bond; Substituted or unsubstituted C _6-60 arylene; Or substituted or unsubstituted C _2-60 heteroarylene containing at least one heteroatom selected from the group consisting of O, N, Si and S,
Ar ₁ and Ar ₂ are each independently a substituted or unsubstituted C _6-60 aryl; Or substituted or unsubstituted C _2-60 heteroaryl containing 1 to 3 heteroatoms selected from the group consisting of N, O and S,
R ₁ is hydrogen; heavy hydrogen; halogen; Cyano; Nitro; Amino; Substituted or unsubstituted C _1-6 alkyl; Substituted or unsubstituted C _1-6 haloalkyl; Substituted or unsubstituted C _1-60 alkoxy; Substituted or unsubstituted C _1-60 haloalkoxy; Substituted or unsubstituted C _3-60 cycloalkyl; Substituted or unsubstituted C _2-60 alkenyl; Substituted or unsubstituted C _6-60 aryl; Substituted or unsubstituted C _6-60 aryloxy; Or a substituted or unsubstituted C _2-60 heterocyclic group containing at least one heteroatom selected from the group consisting of N, O and S,
a1 is an integer of 0 to 4;
The method according to claim 1,
A and B are each independently selected from the group consisting of:

In the above,
Y ₁ is O, S, or CZ ₄ Z ₅ ,
Z ₁ to Z ₅ each independently represent hydrogen; heavy hydrogen; halogen; Cyano; Nitro; Amino; C _1-20 alkyl; C _1-20 haloalkyl; C _6-20 aryl; _Lt ; / RTI > heteroaryl containing one or more heteroatoms of O or S,
n1 to n3 each independently represent an integer of 0 to 3;
3. The method of claim 2,
A and B are each independently selected from the group consisting of:

The method according to claim 1,
L is a single bond, or any one selected from the group consisting of:

.
5. The method of claim 4,
L is a single bond, or any one selected from the group consisting of:

.
The method according to claim 1,
Ar ₁ and Ar ₂ are each independently any one selected from the group consisting of:

In the above,
Y ₂ is O, S, or CZ ₁₄ Z ₁₅ ,
Z ₁₁ to Z ₁₅ each independently represent hydrogen; heavy hydrogen; halogen; Cyano; Nitro; Amino; Silyl; C _1-20 alkyl; C _1-20 haloalkyl; C _6-20 aryl; O or are a C _2-20 heteroaryl group containing one or more heteroatoms of S, Z ₁₄ and Z ₁₅ may combine to form a monocyclic or polycyclic ring are connected to each other,
m1 to m3 each independently represent an integer of 0 to 3;
The method according to claim 6,
Ar ₁ and Ar ₂ are each independently any one selected from the group consisting of:

The method according to claim 1,
R ₁ is hydrogen, deuterium, halogen, cyano, nitro, methyl, or phenyl,
and a1 is 0 or 1.
The method according to claim 1,
The compound is a compound represented by the following formula (1A) or (1B):
≪ EMI ID =

≪ RTI ID = 0.0 &

In the above formulas 1A and 1B,
X, A, B, L, Ar < _{1 >} and Ar < ₂ >
The method according to claim 1,
Wherein said compound is any one selected from the group consisting of the following compounds:

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 according to any one of claims 1 to 10 The organic light-emitting device.
12. The method of claim 11,
The organic compound layer containing the compound may include a hole injection layer; A hole transport layer; Or a layer which simultaneously injects holes and transports holes.
12. The method of claim 11,
Wherein the organic compound layer containing the compound is an electron blocking layer.

Images