KR20150012906A - COMPOUND, ORGANIC LiGHT EMITTING DIODE INCLUDING THE SAME, COMPOSITION INCLUDING THE SAME AND DISPLAY INCLUDING THE ORGANIC LiGHT EMITTING DIODE - Google Patents

Abstract

The present invention relates to a compound, an organic light emitting diode including the same, a composition for the organic light emitting diode including the same, and a display device comprising the organic light emitting diode. The present invention is to provide a compound which can provide an organic photoelectron diode having high efficiency and long service life. To this end, provided is a compound for an organic photoelectron diode represented by chemical formula 1.

Description

TECHNICAL FIELD [0001] The present invention relates to a compound, an organic electroluminescent device including the same, a composition for an organic electroluminescent device including the same, and a display device including the organic electroluminescent device. }

Compound, an organic light emitting device including the same, a composition for an organic light emitting device including the same, and a display device including the organic light emitting device.

An organic optoelectronic device refers to a device that requires charge exchange between an electrode and an organic material using holes or electrons.

Organic optoelectronic devices can be roughly classified into two types according to the operating principle as described below. First, an exciton is formed in an organic material layer by a photon introduced into an element from an external light source. The exciton is separated into an electron and a hole, and the electrons and holes are transferred to different electrodes to be used as a current source Type electronic device.

The second type is an electronic device in which holes or electrons are injected into an organic semiconductor forming an interface with an electrode by applying a voltage or current to two or more electrodes and operated by injected electrons and holes.

Examples of organic optoelectronic devices include organic optoelectronic devices, organic light-emitting devices, organic solar cells, organic photo conductor drums, and organic transistors, all of which are used for the injection or transport of holes, An injection or transport material, or a luminescent material.

In particular, organic light emitting diodes (OLEDs) have been attracting attention in recent years as the demand for flat panel displays increases. In general, organic light emission phenomenon refers to a phenomenon in which an organic material is used to convert electric energy into light energy.

Such an organic light emitting device is a device that converts electric energy into light by applying an electric current to an organic light emitting material, and is usually composed of a structure in which a functional organic layer is interposed between an anode and a cathode. Here, in order to enhance the efficiency and stability of the organic light emitting device, the organic material layer may have a multi-layered structure composed of different materials and may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer.

When a voltage is applied between the two electrodes in the structure of such an organic light emitting device, holes are injected into the anode and electrons are injected into the organic layer through the cathode, and injected holes and electrons are recombined Energy excitons are formed. At this time, the exciton formed again moves to the ground state, and light having a specific wavelength is generated.

In recent years, it is known that not only a fluorescent light emitting material but also a phosphorescent emitting material can be used as a light emitting material of an organic light emitting device. Such phosphorescent emitting is a phenomenon in which electrons transition from a ground state to an excited state, cross-linking of the triplet exciton to the triplet exciton, and then the triplet exciton transitions to the ground state.

As described above, a material used as an organic material layer in an organic light emitting device can be classified into a light emitting material and a charge transporting material such as a hole injecting material, a hole transporting material, an electron transporting material, and an electron injecting material depending on functions.

Further, the light emitting material can be classified into blue, green, and red light emitting materials and yellow and orange light emitting materials required to realize better natural color depending on the luminescent color.

On the other hand, when only one material is used as a light emitting material, there arises a problem that the maximum light emission wavelength shifts to a long wavelength due to intermolecular interaction, the color purity decreases, or the efficiency of the device decreases due to the light emission attenuating effect. A host / dopant system can be used as a light emitting material in order to increase the light emitting efficiency and stability through the light emitting layer.

In order for the organic luminescent device to fully exhibit the above-described excellent characteristics, a host material and / or a dopant such as a hole injecting material, a hole transporting material, a luminescent material, an electron transporting material, an electron injecting material, The organic material layer for organic light emitting devices has not been sufficiently developed yet. Therefore, development of new materials has been continuously required. The necessity of developing such a material is the same in other organic optoelectronic devices described above.

In addition, the low-molecular organic light-emitting device has good efficiency and long life performance because it is manufactured in the form of a thin film by a vacuum deposition method. The polymer organic light-emitting device uses an inkjet or spin coating method, There is an advantage that the large area is advantageous.

Low molecular organic light emitting devices and polymer organic light emitting devices are attracting attention as next generation displays because they have advantages such as self-emission, fast response, wide viewing angle, ultra-thin, high image quality, durability and wide driving temperature range. Compared to conventional liquid crystal displays (LCDs), it is self-luminous and has good visibility even when dark or external light enters. It can reduce thickness and weight to 1/3 of that of LCD without backlight.

In addition, the response speed is 1000 times faster than that of LCD, so it is possible to realize perfect video without residual image. Therefore, it is anticipated that it will be seen as an optimal display in accordance with the multimedia age in recent years. Based on these advantages, after the first development in the late 1980s, the efficiency has been rapidly increased to 80 times and the life span of 100 times. And organic light-emitting device panels have been announced, and the size of the organic light-emitting device panel is rapidly increasing.

In order to increase the size, it is necessary to increase the luminous efficiency and the lifetime of the device. Therefore, it is necessary to develop a stable and efficient organic material layer material for an organic light emitting device.

High efficiency, long life, and the like.

An organic light emitting device including the compound, and a display device including the organic light emitting device.

In one embodiment of the present invention, there is provided a compound represented by the following formula (1).

[Chemical Formula 1]

In the above formula (1), the definition of each substituent is as described in the following "Detailed Description of the Invention ".

Another embodiment of the present invention provides an organic light emitting device comprising an anode and a cathode facing each other, and at least one organic layer positioned between the anode and the cathode, wherein the organic layer comprises the compound.

The organic layer may include a light emitting layer, and the light emitting layer may include the compound.

The compound may be included as a host of the light emitting layer. More specifically, the compound may be included as a phosphorescent green hose.

In another embodiment of the present invention, there is provided a display device including the above-described organic optoelectronic device.

It is possible to provide an organic optoelectronic device having excellent electrochemical and thermal stability, excellent lifetime characteristics, and high luminous efficiency even at a low driving voltage.

In addition, compounds suitable for solution processes can be provided.

1 and 2 are cross-sectional views illustrating various embodiments of an organic light emitting diode according to an embodiment of the present invention.

Hereinafter, embodiments of the present invention will be described in detail. However, it should be understood that the present invention is not limited thereto, and the present invention is only defined by the scope of the following claims.

As used herein, unless otherwise defined, at least one of the substituents or at least one hydrogen in the compound is substituted with one or more substituents selected from the group consisting of deuterium, a halogen group, a hydroxy group, an amino group, a substituted or unsubstituted C1 to C30 amine group, a nitro group, C1 to C10 alkyl groups such as a C1 to C40 silyl group, a C1 to C30 alkyl group, a C1 to C10 alkylsilyl group, a C3 to C30 cycloalkyl group, a C6 to C30 aryl group, a C1 to C20 alkoxy group, a fluoro group, A trifluoroalkyl group or a cyano group.

A substituted or unsubstituted C1 to C20 amine group, a nitro group, a substituted or unsubstituted C3 to C40 silyl group, a C1 to C30 alkyl group, a C1 to C10 alkylsilyl group, a C3 to C10 alkylsulfinyl group, A C1 to C10 trifluoroalkyl group such as a C30 cycloalkyl group, a C6 to C30 aryl group, a C1 to C20 alkoxy group, a fluoro group or a trifluoromethyl group, or a cyano group may be fused together to form a ring . Specifically, the substituted C6 to C30 aryl group may be fused with another adjacent substituted C6 to C30 aryl group to form a substituted or unsubstituted fluorene ring.

Means one to three heteroatoms selected from the group consisting of N, O, S and P in one functional group, and the remainder is carbon, unless otherwise defined.

As used herein, unless otherwise defined, the term "alkyl group" means an aliphatic hydrocarbon group. The alkyl group may be a "saturated alkyl group" which does not contain any double or triple bonds.

The alkyl group may be an alkyl group having from 1 to 20 carbon atoms. More specifically, the alkyl group may be a C1 to C10 alkyl group or a C1 to C6 alkyl group. For example, C1 to C4 alkyl groups mean that from 1 to 4 carbon atoms are included in the alkyl chain and include methyl, ethyl, propyl, iso-propyl, n-butyl, iso-butyl, sec- Indicating that they are selected from the group.

Specific examples of the alkyl group include a methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, t-butyl group, pentyl group, hexyl group, cyclopropyl group, cyclobutyl group, cyclopentyl group, And the like.

The term "aryl group" used herein means a substituent in which all the elements of the cyclic substituent have p-orbital and the p-orbital forms a conjugation, and the monocyclic or fused-ring polycyclic (I. E., A ring that divides adjacent pairs of carbon atoms) functional groups.

As used herein, the term " heteroaryl group "means that the aryl group contains 1 to 3 heteroatoms selected from the group consisting of N, O, S and P, and the remainder is carbon. When the heteroaryl group is a fused ring, it may contain 1 to 3 heteroatoms in each ring.

More specifically, the substituted or unsubstituted C6 to C30 aryl group and / or the substituted or unsubstituted C2 to C30 heteroaryl group may be substituted or unsubstituted phenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted anthra A substituted or unsubstituted naphthacenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted p-terphenyl group, a substituted or unsubstituted naphthacenyl group, a substituted or unsubstituted pyrenyl group, A substituted or unsubstituted aryl group, a substituted m-terphenyl group, a substituted or unsubstituted chrysenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted perylenyl group, a substituted or unsubstituted indenyl group, a substituted or unsubstituted furanyl group , A substituted or unsubstituted thiophenyl group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted imidazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted pyrazolyl group, A substituted or unsubstituted thiazolyl group, a substituted or unsubstituted thiadiazolyl group, a substituted or unsubstituted thiadiazolyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidyl group, Substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted thiazinyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted benzimidazolyl, A substituted or unsubstituted quinolinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinazolinyl group, Substituted or unsubstituted pyrazinyl groups, substituted or unsubstituted pyrazinyl groups, substituted or unsubstituted benzoxazinyl groups, substituted or unsubstituted benzothiazyl groups, substituted or unsubstituted acridinyl groups, A substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbonyl group, or a substituted or unsubstituted arylthio group, or a substituted or unsubstituted arylthio group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted arylthio group, But are not limited thereto.

In the present specification, a fused ring means a ring form in which two or more rings are formed by sharing one or more atoms. The fused ring may be aromatic or non-aromatic.

For example, the fused ring may be a carbazole, dibenzofuran, dibenzothiophene, triphenylene, naphthalene, anthracene, phenanthrene, tetraline, quinoline, indene, indane, indole, isoindole, indoline, indolizine, Benzofuran, benzothiophene, benzimidazole, fluorene, pyrene and the like.

In the present specification, the hole property means a property of facilitating the injection into the light emitting layer and the movement in the light emitting layer of the hole formed in the anode due to conduction characteristics along the HOMO level. Specifically, it may be similar to the characteristic of pushing electrons. More specifically, it is similar to the ability to give electrons when an electric field is applied.

Further, the electron characteristic means a property of facilitating the injection of electrons formed in the anode into the luminescent layer and the movement in the luminescent layer due to conduction characteristics along the LUMO level. Specifically, it may be similar to the characteristic of attracting electrons. More specifically, it is analogous to the ability to receive electrons when an electric field is applied.

In one embodiment of the present invention, a compound represented by the following general formula (1) can be provided.

[Chemical Formula 1]

In Formula 1, X ¹ is O, S, SO _2, SiR'R ", or NR ', and wherein R' and R" are independently, hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl groups each other, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or a substituted or unsubstituted silyl group unsubstituted, X ² to X ⁹ are each independently, is N or CR ', wherein R 'is hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or a substituted or unsubstituted silyl group, At least one of X ² to X ⁹ is N, Ar ¹ is a substituted or unsubstituted C6 to C30 arylamine group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 hetero Lt; ¹ > is a substituted or unsubstituted C6 to C30 arylene group or a substituted or unsubstituted C6- And n is an integer of 0 to 3; R ¹ to R ⁴ are, independently of each other, hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C30 heteroarylene group, A substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or a substituted or unsubstituted silyl group.

The compound according to one embodiment of the present invention may have a hole property in a continuous fused ring part of hexagonal. Alternatively, a compound having a bipolar structure as a whole can be selectively formed by introducing a substituent having an electron characteristic and / or a substituent having a hole property into Ar ¹ . Also, at least one of X ² to X ⁹ may be N, so that the T 1 value can be improved by about 0.2 eV. Whereby the compound may have an appropriate energy band value as a phosphorescent green host.

In addition, the compound represented by Formula 1 may be a compound having various energy bandgaps by introducing various substituents.

By using a compound having an appropriate energy level according to the substituent of the compound in an organic optoelectronic device, the hole transporting ability or the electron transporting ability is enhanced to have an excellent effect in terms of efficiency and driving voltage, and excellent electrochemical and thermal stability. The lifetime characteristics can be improved when the device is driven.

More specifically, the compound may be represented by any one of the following general formulas (2), (3) and (4).

[Chemical Formula 2] [Chemical Formula 3], [Chemical Formula 4]

In Formula 2 to 4, X ¹ is O, S, SO _2, SiR'R ", or NR ', and wherein R' and R" are independently, hydrogen, deuterium, a substituted or unsubstituted C1 to C30 each other alkyl group, a substituted or unsubstituted, and a C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or a substituted or unsubstituted silyl group unsubstituted, X ² to X ⁹ are independently of one another, N or CR ', and , R 'represents hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or a substituted or unsubstituted silyl group At least one of X ² to X ⁹ is N, Ar ¹ is a substituted or unsubstituted C6 to C30 arylamine group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 aryl group, C30 hetero aryl group, R ¹ to R ⁴ are each independently hydrogen, deuterium, substituted again An unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group or a substituted or unsubstituted silyl group.

The linking group corresponding to L ¹ in the general formula (1) may be a phenylene group and the linking sites on both sides of the phenylene group may be para, meta, or ortho. However, the present invention is not limited thereto.

When the linking group corresponding to L ¹ in the formula (1) is a phenylene group and the connecting sites on both sides of the phenylene group are meta or oline as shown in the formula (3) or (4), the T1 value of the device can be increased. In addition, the conjugation between a substituent having a hole characteristic and a substituent having an electron characteristic can be interrupted so that the bipolar characteristic can be improved and the molecular structure can be made amorphous, thereby improving the deposition property of the compound.

In one embodiment of the present invention, X ¹ is O, S, SO ₂ , SiR'R "or NR ', wherein R' and R" are independently of each other hydrogen, deuterium, unsubstituted C1 to C30 alkyl group, or a substituted or unsubstituted C6 to C30 aryl group unsubstituted and, X ² to X ⁹ are independently of one another, N or CR ', and wherein R' is hydrogen or deuterium, the X ² to X ⁹ is N, Ar ¹ is a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heteroaryl group, and R ¹ to R ⁴ are each independently of the other hydrogen, Or a substituted or unsubstituted C1 to C30 alkyl group.

When Ar ¹ is a substituted or unsubstituted C 2 to C 30 heteroaryl group, it is preferably a substituted or unsubstituted pyridinyl, pyrimidinyl, triazinyl, carbazolyl, dibenzofuranyl, or dibenzothiophenyl .

More specifically, Ar ¹ may be a substituent represented by the following formula (X-1). However, the present invention is not limited thereto.

[Chemical Formula X-1]

In Formula (X-1), X ¹⁰ to X ¹² are independently of each other N or CR ', and R' is hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C6 to C30 aryl A substituted or unsubstituted C2 to C30 heteroaryl group or a substituted or unsubstituted silyl group, at least one of X ¹⁰ to X ¹² is N, R ⁵ and R ⁶ are each independently of the other hydrogen, A substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group or a substituted or unsubstituted silyl group, .

Specifically, for example, Ar ¹ is a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted quinolinyl group, or a substituted or unsubstituted quinolinyl group An isoquinolinyl group.

As another example, the Ar ¹ may be a substituent represented by the following formula (X-2).

[Formula X-2]

In Formula (X-2), X ¹³ to X ¹⁸ are independently of each other N or CR ', and R' is hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted, and a C2 to C30 heteroaryl group, or a substituted or unsubstituted silyl group unsubstituted ring, wherein X ¹³ to X ^15, at least either one of which is N, wherein X ¹⁶ to X ^18, at least any one of the N And * denotes the connecting position of the substituent.

In the case of the substituent group as shown in the above formula (X-2), the electron cloud of the electron characteristic substituent such as the substituent having the hole characteristic and the electron characteristic such as X-2 can be well separated and the bipolar characteristic can be improved.

More specifically, Ar1 may be a substituent represented by the following formula (X-3).

[Formula X-3]

In the above formula (X-3), Ar ² and Ar ³ independently represent a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, A substituted or unsubstituted phenanthrenyl group, or a substituted or unsubstituted fluorenyl group, and * denotes a connecting position of a substituent.

As described above, when Ar ¹ is an amine group, hole characteristics of the whole compound are increased, and the lifetime and efficiency of the device can be improved. More specifically, when the above compound and another different compound are mixed and used as a host material, the lifetime and efficiency of the device can be further improved.

Thus, in one embodiment of the present invention, the C6 to C30 amine group, for example, in the case of the arylamine of the formula X-3 compound, or a substituted or unsubstituted two Ar ¹ unsubstituted or substituted in the formula (1) A C6 to C30 aryl group as a first host, and other host compounds for an organic light emitting device as a second host.

More specifically, Ar ¹ may be a substituent represented by the following formula (X-4).

[Chemical Formula X-4]

In the formula 4, X ¹⁹ is O, S, SO ₂ , NR 'or SiR'R ", and R' and R" are independently selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted C1- Or a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or a substituted or unsubstituted silyl group, and R ⁷ to R ⁹ are each independently of the other hydrogen, deuterium, A substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or a substituted or unsubstituted silyl group, and * denotes a connecting position of a substituent.

As described above, when Ar ¹ is substituted or unsubstituted dibenzofuranyl group and / or substituted or unsubstituted dibenzothiophenyl group, the hole characteristics of the whole compound are increased, and the lifetime and efficiency of the device can be improved. More specifically, when the above compound and another different compound are mixed and used as a host material, the lifetime and efficiency of the device can be further improved.

Thus, in one embodiment of the invention, when Ar ¹ is a substituted or unsubstituted dibenzo furanoid group, or a substituted or unsubstituted dibenzo thio phenyl ring in Formula 1, the organic light-emitting device other than this, a first host, And a second host having a second host compound for the second host.

More specifically, for example, at least one of X ⁵ and X ³ may be N, and the remaining X ² , X ⁴ , and X ⁶ to X ⁹ may independently be CR '. Alternatively, X ⁵ and X ³ may be N, and the remaining X ² , X ⁴ , and X ⁶ to X ⁹ may independently be CR '. The position of N as described above may be advantageous in terms of synthesis.

More specifically, X ¹ may be S. However, the present invention is not limited thereto.

In one embodiment of the present invention, L < ¹ > may be a substituted or unsubstituted C2 to C30 heteroarylene group. In this case, the electronic properties in the compound are reinforced, and the intramolecular bipolar characteristics can be improved.

More specifically, for example, L ¹ may be a substituted or unsubstituted pyridinylene group, a substituted or unsubstituted pyrimidinylene group, or a substituted or unsubstituted tridienylene group. However, the present invention is not limited thereto.

Further, the conjugation length of the entire compound can be determined by selectively controlling the L ¹ , and the triplet energy bandgap can be controlled therefrom. This makes it possible to realize the characteristics of the materials required in organic optoelectronic devices. Further, the triplet energy bandgap can be controlled by changing the bonding position of the ortho, para, and meta.

At the same time, L < ¹ > may be a substituted or unsubstituted C6 to C30 arylene group, in which case the compound may have suitable hole and / or electronic properties.

Specific examples of the L ¹ include a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted anthracenylene group , A substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted pyrenylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted p-terphenyl group, a substituted or unsubstituted m-terphenyl group, a substituted Or an unsubstituted perylenyl group.

Specific examples of the compound according to one embodiment of the present invention include, but are not limited to, the following compounds.

Hereinafter, an organic optoelectronic device to which the above-described compound is applied will be described.

The organic optoelectronic device is not particularly limited as long as it is an element capable of converting electric energy and optical energy. Examples of the organic optoelectronic device include organic light emitting devices, organic solar cells, and organic photoconductor drums.

Here, an organic light emitting device, which is an example of an organic optoelectronic device, will be described with reference to the drawings.

1 and 2 are cross-sectional views illustrating an organic light emitting device according to an embodiment.

1, an organic light emitting device 100 according to an exemplary embodiment includes an anode 120 and a cathode 110 facing each other, and an organic layer 105 disposed between the anode 120 and the cathode 110 .

The anode 120 may be made of a conductor having a high work function to facilitate, for example, hole injection, and may be made of, for example, a metal, a metal oxide, and / or a conductive polymer. The anode 120 is made of a metal such as nickel, platinum, vanadium, chromium, copper, zinc, gold, or an alloy thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); A combination of ZnO and Al or a metal and an oxide such as SnO ₂ and Sb; Conductive polymers such as poly (3-methylthiophene), poly (3,4- (ethylene-1,2-dioxy) thiophene), polypyrrole and polyaniline, It is not.

The cathode 110 may be made of a conductor having a low work function, for example, to facilitate electron injection, and may be made of, for example, a metal, a metal oxide, and / or a conductive polymer. The cathode 110 is made of a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium or the like or an alloy thereof; Layer structure materials such as LiF / Al, LiO ₂ / Al, LiF / Ca, LiF / Al and BaF ₂ / Ca.

The organic layer 105 includes the light emitting layer 130 including the above-described compound.

The light-emitting layer 130 may include, for example, the above-described compounds alone or may be a mixture of at least two of the above-described compounds, or may include a mixture of the above-described compounds and other compounds. When the above-mentioned compound is mixed with another compound, it may be contained in the form of, for example, a host and a dopant, and the above-mentioned compound may be included, for example, as a host. The host may be, for example, a phosphorescent host or a fluorescent host, for example a green phosphorescent host.

When the above-mentioned compound is included as a host, the dopant may be an inorganic, organic, or organic compound and may be selected from among known dopants.

Referring to FIG. 2, the organic light emitting diode 200 further includes a hole assist layer 140 in addition to the light emitting layer 230. The hole assist layer 140 can further enhance the hole injection and / or hole mobility between the anode 120 and the light emitting layer 230 and block the electrons. The hole-assist layer 140 may be, for example, a hole transport layer, a hole injection layer, and / or an electron blocking layer, and may include at least one layer. The above-described compounds may be included in the light emitting layer 230 and / or the hole assist layer 140. 1 or 2, the organic thin film layer 105 may further include an electron injection layer, an auxiliary electron transport layer, an electron transport layer, a hole transport layer, an auxiliary hole transport layer, and a hole injection layer, though not shown.

1 and 2, the light emitting layers 130 and 230, the hole transport layer 140, the electron injection layer, the auxiliary electron transport layer, the electron transport layer, and the auxiliary layer (not shown) Any one selected from the group consisting of a hole transporting layer, a hole injecting layer, and combinations thereof includes the above compounds. In particular, the compound can be used as a host in the light emitting layer.

The organic light emitting devices 100 and 200 may be formed by forming an anode or a cathode on a substrate and then performing a dry deposition method such as evaporation, sputtering, plasma plating, and ion plating; Or a wet film formation method such as spin coating, dipping or flow coating, and then forming a cathode or anode on the organic layer.

The above-described organic light emitting element can be applied to a display device.

Hereinafter, specific embodiments of the present invention will be described. However, the embodiments described below are only intended to illustrate or explain the present invention, and thus the present invention should not be limited thereto.

(Preparation of compound for organic optoelectronic device)

For organic optoelectronic devices  Synthesis of compounds

[ 1 ] X1 When this is S

[ Formula 2 ] X1 When this is O

[ Formula 3 ] X1 this NR ' when

[ Formula 4 ] X1 this SiR'R "when

Specific compounds according to one embodiment of the present invention prepared according to the above synthesis method are shown in Table 1 below.

Example Compound Intermediate Reactant yield
(%) MS data

A-125

A-125

75 583.70 g / mol

A-217

68 583.70 g / mol

A-121

80 582.72 g / mol

A-209

67 582.72 g / mol

A-126

63 567.2 g / mol

A-218

50 567.2 g / mol

A-122

69 566.2 g / mol

A-210

57 566.2 g / mol

A-21

68 566.2 g / mol

A-17

71 565.2 g / mol

A-22

72 533.2 g / mol

A-18

77 532.2 g / mol

[Intermediate synthesis]

[Reaction Scheme 1]

A first step; Synthesis of intermediate product (A)

(319.51 mmol) of 2-amino-benzenethiol, 50.65 g (319.51 mmol) of 2-chloro-3-nitropyridine, 0.71 g (12.78 mmol) of KOH and 1.2 L of EtOH were stirred at room temperature for 3 hours under a stream of nitrogen. After completion of the reaction, the reaction mixture was extracted with dichloromethane and distilled water, and the organic layer was subjected to silica gel filtration. The organic solvent was removed and silica gel column chromatography with hexane: ethyl acetate = 7: 3 (v / v) gave 63.21 g (yield: 80%) of the intermediate product (A).

A second step; Synthesis of intermediate product (B)

60 g (242.65 mmol) of the intermediate product (A) and 86 g (849.27 mmol) of acetic anhydride were stirred at 100 DEG C for 5 hours in a stream of nitrogen. After completion of the reaction, the reaction mixture was extracted with dichloromethane and distilled water, and the organic layer was subjected to silica gel filtration. The organic solvent was removed and silica gel column chromatography with hexane: ethyl acetate = 8: 2 (v / v) yielded 41.42 g (yield: 59%) of the intermediate product (B).

A third step; Synthesis of intermediate product (C)

40.0 g (138.26 mmol) of the intermediate product (B) and 0.71 g (12.78 mmol) of KOH were suspended in 270 mL of EtOH and 270 mL of Acetone, and the mixture was refluxed at 70 DEG C for 12 hours under a stream of nitrogen. After completion of the reaction, the reaction mixture was extracted with dichloromethane and distilled water, and the organic layer was subjected to silica gel filtration. The organic solvent was removed and silica gel column chromatography with hexane: ethyl acetate = 8: 2 (v / v) yielded 18.43 g (yield: 55%) of the intermediate product (C).

Step 4; Synthesis of intermediate product (D)

(119.82 mmol) of the intermediate product (C) and 4.36 g (119.82 mmol) of HCl were suspended in 470 mL of EtOH, and the mixture was refluxed at 70 DEG C for 12 hours under a nitrogen stream. After completion of the reaction, the reaction mixture was extracted with dichloromethane and distilled water, and the organic layer was subjected to silica gel filtration. The organic solvent was removed and silica gel column chromatography with hexane: ethyl acetate = 7: 3 (v / v) yielded 20.64 g (yield: 86%) of the intermediate product (D).

[Reaction Scheme 2]

A first step; Synthesis of intermediate product (E)

40.0 g (287.54 mmol) of 3-Nitro-pyridin-2-ylamine, 36.96 g (287.54 mmol) of 2-Chloro-phenol, 28.30 g (345.04 mmol) of NaOAc and 1.1 L of EtOH were refluxed under nitrogen stream for 24 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane and distilled water, and the organic layer was subjected to silica gel filtration. The organic solvent was removed and silica gel column chromatography with hexane: ethyl acetate = 7: 3 (v / v) yielded 46.53 g (yield: 70%) of the intermediate product (E).

A second step; Synthesis of intermediate product (F)

(287.54 mmol) of the intermediate product (E), 28.69 g (207.60 mmol) of K ₂ CO _{3 and} 0.7 L of DMF were stirred under reflux for 12 hours under a stream of nitrogen. After completion of the reaction, the reaction mixture was extracted with dichloromethane and distilled water, and the organic layer was subjected to silica gel filtration. The organic solvent was removed and silica gel column chromatography with hexane: ethyl acetate = 7: 3 (v / v) yielded 34.42 g (yield: 65%) of the intermediate product (F).

[Reaction Scheme 3]

A first step; Synthesis of intermediate product (G)

(232.53 mmol) of 2-bromo-phenylamine, 40.23 g (232.53 mmol) of 3-bromo-pyridin-2-ylamine, 83.33 g (255.78 mmol) of Cs2CO3, 1.05 g (4.65 mmol) Was refluxed and stirred at 120 DEG C for 24 hours in a stream of nitrogen. After completion of the reaction, the reaction mixture was extracted with dichloromethane and distilled water, and the organic layer was subjected to silica gel filtration. The organic solvent was removed and silica gel column chromatography with hexane: ethyl acetate = 7: 3 (v / v) yielded 29.49 g (yield: 70%) of the intermediate product (G).

A second step; Synthesis of intermediate product (H)

29.49 g (162.77 mmol) of the intermediate product (G), phenyl lithium in cyclohexanes-ether (200 ml) and 160 ml of o-xylene were stirred at room temperature for 4 hours under a nitrogen stream. After completion of the reaction, the reaction mixture was extracted with dichloromethane and distilled water, and the organic layer was subjected to silica gel filtration. The organic solvent was removed and silica gel column chromatography with hexane: ethyl acetate = 9: 1 (v / v) yielded 26.59 g (yield: 63%) of the intermediate product (H).

[Reaction Scheme 4]

A first step; Synthesis of intermediate product (I)

(110.44 mmol) of Chloro-trimethyl-silane, 5.17 g (132.53 mmol) of NaNH2, 220 mL of benzene , and toluene (220 mL) were stirred under reflux for 10 hours in a stream of nitrogen. After completion of the reaction, the reaction mixture was extracted with dichloromethane and distilled water, and the organic layer was subjected to silica gel filtration. The organic solvent was removed and silica gel column chromatography with hexane: ethyl acetate = 7: 3 (v / v) yielded 8.83 g (yield: 20%) of the intermediate product ( I ).

A second step; Synthesis of intermediate product (J)

20 g (49.97 mmol) of the intermediate product (I), 4 g (49.97 mmol) of Dichloro-dimethyl-silane 6.4 g (54.96 mmol) of Na and 200 ml of toluene were refluxed with stirring in a nitrogen stream for 10 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane and distilled water, and the organic layer was subjected to silica gel filtration. The organic solvent was removed and silica gel column chromatography with hexane: ethyl acetate = 8: 2 (v / v) yielded 11.99 g (yield: 80%) of the intermediate product (J).

A third step; Synthesis of intermediate product (K)

10 g (31.35 mmol) of the intermediate product (J) and 2.82 g (47.02 mmol) of AcOH were suspended in 270 mL of EtOH, and the mixture was refluxed at 70 DEG C for 12 hours under a stream of nitrogen. After completion of the reaction, the reaction mixture was extracted with dichloromethane and distilled water, and the organic layer was subjected to silica gel filtration. The organic solvent was removed and silica gel column chromatography with hexane: ethyl acetate = 8: 2 (v / v) yielded 5.81 g (yield: 82%) of the intermediate product (K).

Synthetic example  1: Synthesis of A-125

[Reaction Scheme 5]

4-yl) -4,6-diphenyl- [1,3,5] triazine (2-Chloro-4,4-dihydroxyphenyl) 25.50 g (54.92 mmol) of NaO (t-Bu) and 14.39 g (149.79 mmol) of 4-Bromo-4-biphenyl boronic acid were synthesized by Suzuki coupling. (1.99 mmmol) of Pd2 (dba) 3 was suspended in 200 mL of toluene, and 0.96 mL (3.99 mmol) of P (t-Bu) 3 was added thereto and stirred under reflux for 24 hours under a nitrogen stream. Extraction is carried out with dichloromethane and distilled water, and the organic layer is subjected to silica gel filtration. The organic solution was removed, and the residue was subjected to silica gel column chromatography with hexane: dichloromethane = 7: 3 (v / v), followed by recrystallization from dichloromethane and ethyl acetate to obtain 21.85 g (yield: 75%) of A-125.

Synthetic example  2: Synthesis of A-217

[Reaction Scheme 6]

10.0 g (49.93 mmol) of the intermediate product (D) of Scheme 1 and 2- (3'-Chloro-biphenyl-3-yl) -4,6-diphenyl- [1,3,5] 23.06 g (54.92 mmol) of NaO (t-Bu) and 149.39 g of NaOH (t-Bu) were synthesized by Suzuki coupling with 6-diphenyl- [1,3,5] triazine and 4'-boronicacid- ) And 1.82 g (1.99 mmmol) of Pd2 (dba) 3 were suspended in 200 mL of toluene. Then, 0.96 mL (3.99 mmol) of P (t-Bu) 3 was added and the mixture was refluxed under nitrogen atmosphere for 24 hours. Extraction is carried out with dichloromethane and distilled water, and the organic layer is subjected to silica gel filtration. The organic solution was removed, and the residue was subjected to silica gel column chromatography with hexane: dichloromethane = 7: 3 (v / v), followed by recrystallization from dichloromethane and ethyl acetate to obtain 19.81 g (yield: 68%) of A-217.

Synthetic example  3: Synthesis of A-121

[Reaction Scheme 7]

10.0 g (49.93 mmol) of the intermediate product (D) of Scheme 1 and 2- (4'-Bromo-biphenyl-4-yl) -4,6-diphenyl-pyrimidine (2-Chloro-4,6- 25.44 g (54.92 mmol) of NaB (t-Bu) 14.39 g (149.79 mmol) and 1.82 g (1.99 mmmol) of Pd2 (dba) 3 were dissolved in toluene , And 0.96 mL (3.99 mmol) of P (t-Bu) 3 was added thereto, followed by reflux stirring for 24 hours under a nitrogen stream. Extraction is carried out with dichloromethane and distilled water, and the organic layer is subjected to silica gel filtration. The organic solution was removed, and the residue was subjected to silica gel column chromatography with hexane: dichloromethane = 7: 3 (v / v), followed by recrystallization from dichloromethane and ethyl acetate to obtain 23.27 g (yield: 80%) of A-121.

Synthetic example  4: Synthesis of A-209

[Reaction Scheme 8]

10.0 g (49.93 mmol) of the intermediate product (D) of Scheme 1 and 2- (3'-Chloro-biphenyl-3-yl) -4,6-diphenyl-pyrimidine (2-Chloro-4,6- (1.99 mmmol) of Pd2 (dba) 3 were added to a solution of 23.00 g (54.92 mmol) of 4'-boronicacid-3-chloro-biphenyl with Suzuki coupling, 14.39 g (149.79 mmol) After suspending in 200 mL of toluene, 0.96 mL (3.99 mmol) of P (t-Bu) 3 was added and the mixture was refluxed with stirring under a nitrogen stream for 24 hours. Extraction is carried out with dichloromethane and distilled water, and the organic layer is subjected to silica gel filtration. The organic solution was removed, and the residue was subjected to silica gel column chromatography with hexane: dichloromethane = 7: 3 (v / v), followed by recrystallization from dichloromethane and ethyl acetate to obtain 19.49 g (yield: 67%) of A-209.

Synthetic example  5: Synthesis of A-126

[Reaction Scheme 9]

10.0 g (54.29 mmol) of intermediate product intermediate product (F) of Scheme 2 and 2- (4'-Bromo-biphenyl-4-yl) -4,6-diphenyl- [1,3,5] 25.50 g (54.92 mmol) of NaO (t-Bu) 14.39 g (149.79 mmol) of 4,6-diphenyl- [1,3,5] triazine and 4'-Bromo-4-Biphenyl boronicacid were synthesized by Suzuki coupling. 1.96 g (1.99 mmmol) of Pd2 (dba) 3 was suspended in 200 mL of toluene, and 0.96 mL (3.99 mmol) of P (t-Bu) 3 was added thereto and stirred under reflux for 24 hours. Extraction is carried out with dichloromethane and distilled water, and the organic layer is subjected to silica gel filtration. The organic solution was removed, and the residue was subjected to silica gel column chromatography with hexane: dichloromethane = 7: 3 (v / v), followed by recrystallization from dichloromethane and ethyl acetate to obtain 19.39 g (yield: 63%) of A-126.

Synthetic example  6: Synthesis of A-218

[Reaction Scheme 10]

10.0 g (54.29 mmol) of the intermediate product (F) in Scheme 2 and 2- (3'-Chloro-biphenyl-3-yl) -4,6-diphenyl- [ 23.06 g (54.92 mmol) of NaO (t-Bu) and 149.39 g of NaOH (t-Bu) were synthesized by Suzuki coupling with 6-diphenyl- [1,3,5] triazine and 4'-boronicacid- ) And 1.82 g (1.99 mmmol) of Pd2 (dba) 3 were suspended in 200 mL of toluene. Then, 0.96 mL (3.99 mmol) of P (t-Bu) 3 was added and the mixture was refluxed under nitrogen atmosphere for 24 hours. Extraction is carried out with dichloromethane and distilled water, and the organic layer is subjected to silica gel filtration. The organic solution was removed, and the residue was subjected to silica gel column chromatography with hexane: dichloromethane = 7: 3 (v / v), followed by recrystallization from dichloromethane and ethyl acetate to obtain 15.39 g (yield: 50%) of A-218.

Synthetic example  7: Synthesis of A-122

[Reaction Scheme 11]

10.0 g (54.29 mmol) of the intermediate product (F) in Scheme 2 and 2- (4'-Bromo-biphenyl-4-yl) -4,6-diphenyl-pyrimidine (2-Chloro-4,6- 25.44 g (54.92 mmol) of NaB (t-Bu) 14.39 g (149.79 mmol) and 1.82 g (1.99 mmmol) of Pd2 (dba) 3 were dissolved in toluene , And 0.96 mL (3.99 mmol) of P (t-Bu) 3 was added thereto, followed by reflux stirring for 24 hours under a nitrogen stream. Extraction is carried out with dichloromethane and distilled water, and the organic layer is subjected to silica gel filtration. The organic solution was removed, and the residue was subjected to silica gel column chromatography with hexane: dichloromethane = 7: 3 (v / v), followed by recrystallization from dichloromethane and ethyl acetate to obtain 21.20 g (yield: 69%) of A-122.

Synthetic example  8: Synthesis of A-210

[Reaction Scheme 12]

10.0 g (54.29 mmol) of the intermediate product (F) in Scheme 2 and 2- (3'-Chloro-biphenyl-3-yl) -4,6-diphenyl- pyrimidine (2-Chloro-4,6- (1.99 mmmol) of Pd2 (dba) 3 were added to a solution of 23.00 g (54.92 mmol) of 4'-boronicacid-3-chloro-biphenyl with Suzuki coupling, 14.39 g (149.79 mmol) After suspending in 200 mL of toluene, 0.96 mL (3.99 mmol) of P (t-Bu) 3 was added and the mixture was refluxed with stirring under a nitrogen stream for 24 hours. Extraction is carried out with dichloromethane and distilled water, and the organic layer is subjected to silica gel filtration. The organic solution was removed, and the residue was subjected to silica gel column chromatography with hexane: dichloromethane = 7: 3 (v / v), followed by recrystallization from dichloromethane and ethyl acetate to obtain 17.52 g (yield: 57%) of A-210.

Synthetic example  9: Synthesis of A-21

[Reaction Scheme 13]

10.0 g (38.56 mmol) of the intermediate product (H) of Scheme 3 and 2- (3-Bromo-phenyl) -4,6-diphenyl- [1,3,5] triazine (2-Bromo-4,6- 16.47 g (42.42 mmol) NaO (t-Bu) 14.39 g (149.79 mmol), Pd2 (3-phenylpyridine) dba) 3 was suspended in 200 mL of toluene, and 0.96 mL (3.99 mmol) of P (t-Bu) 3 was added thereto, followed by reflux stirring for 24 hours in a nitrogen stream. Extraction is carried out with dichloromethane and distilled water, and the organic layer is subjected to silica gel filtration. The organic solution was removed, and the residue was subjected to silica gel column chromatography with hexane: dichloromethane = 7: 3 (v / v), followed by recrystallization from dichloromethane and ethyl acetate to obtain 14.85 g (yield: 68%) of A-21.

Synthetic example  10: Synthesis of A-17

[Reaction Scheme 14]

10.0 g (38.56 mmol) of the intermediate product (H) of Scheme 3 and 2- (3-bromo-phenyl) -4,6-diphenyl-pyrimidine (2-Bromo- Bromo-3-phenyl boronicacid was synthesized by Suzuki coupling. To a solution of 16.42 g (42.42 mmol) of NaB (t-Bu), 1.82 g (1.99 mmmol) of Pd2 (dba) After the suspension, 0.96 mL (3.99 mmol) of P (t-Bu) 3 was added thereto and the mixture was refluxed under nitrogen stream for 24 hours. Extraction is carried out with dichloromethane and distilled water, and the organic layer is subjected to silica gel filtration. The organic solution was removed, and the residue was subjected to silica gel column chromatography with hexane: dichloromethane = 7: 3 (v / v), followed by recrystallization from dichloromethane and ethyl acetate to obtain 15.47 g (yield: 71%) of A-17.

Synthetic example  11: Synthesis of A-22

[Reaction Scheme 15]

10.0 g (44.17 mmol) of the intermediate product (K) of Scheme 4 and 2- (3-Bromo-phenyl) -4,6-diphenyl- [1,3,5] triazine (2-Bromo-4,6- 16.47 g (42.42 mmol) NaO (t-Bu) 14.39 g (149.79 mmol), Pd2 (3-phenylpyridine) dba) 3 was suspended in 200 mL of toluene, and 0.96 mL (3.99 mmol) of P (t-Bu) 3 was added thereto, followed by reflux stirring for 24 hours in a nitrogen stream. Extraction is carried out with dichloromethane and distilled water, and the organic layer is subjected to silica gel filtration. The organic solution was removed, and the residue was subjected to silica gel column chromatography with hexane: dichloromethane = 7: 3 (v / v), followed by recrystallization from dichloromethane and ethyl acetate to obtain 16.95 g (yield: 72%) of A-22.

Synthetic example  12: Synthesis of A-18

[Reaction Scheme 16]

Bromo-4,6-diphenyl-pyrimidine and 4'-1- (2-bromo-phenyl) Bromo-3-phenyl boronicacid was synthesized by Suzuki coupling. To a solution of 16.42 g (42.42 mmol) of NaB (t-Bu), 1.82 g (1.99 mmmol) of Pd2 (dba) After the suspension, 0.96 mL (3.99 mmol) of P (t-Bu) 3 was added thereto and the mixture was refluxed under nitrogen stream for 24 hours. Extraction is carried out with dichloromethane and distilled water, and the organic layer is subjected to silica gel filtration. The organic solution was removed, and the residue was subjected to silica gel column chromatography with hexane: dichloromethane = 7: 3 (v / v), followed by recrystallization from dichloromethane and ethyl acetate to obtain 18.10 g (yield: 77%) of A-18.

(Fabrication of organic light emitting device)

Example  One

The glass substrate coated with ITO (Indium tin oxide) thin film with thickness of 1500 Å was washed with distilled water ultrasonic wave. After the distilled water was washed, the substrate was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, or methanol, dried, and transferred to a plasma cleaner. Then, the substrate was cleaned using oxygen plasma for 5 minutes, and then the substrate was transferred to a vacuum deposition machine. HTM (see figure below) was vacuum deposited on the ITO substrate using the prepared ITO transparent electrode as an anode to form a 1200 Å thick hole injection layer.

[HTM]

The material synthesized in Synthesis Example 1 was used as a host on the hole transporting layer, doped with PhGD (see FIG. 7) as a phosphorescent green dopant, and a 300 Å thick light emitting layer was formed by vacuum deposition.

[PhGD]

Then, 50 Å of BAlq [Bis (2-methyl-8-quinolinolato-N1, O8) - (1,1'-Biphenyl-4-olato)] and 250 Å of Alq3 [Tris (8-hydroxyquinolinato) aluminum] Were successively laminated to form an electron transporting layer. LiF 5 Å and Al 1000 Å were sequentially vacuum-deposited on the electron transport layer to form a cathode, thereby preparing an organic light emitting device.

[Balq] [Alq3]

Example  2

An organic photoelectric device was fabricated in the same manner as in Example 1 except that the compound synthesized in Synthesis Example 2 was used as the light emitting layer.

Example  3

An organic photoelectric device was fabricated in the same manner as in Example 1 except that the compound synthesized in Synthesis Example 3 was used as the light emitting layer.

Example  4

An organic photoelectric device was fabricated in the same manner as in Example 1 except that the compound synthesized in Synthesis Example 4 was used as the light emitting layer.

Example  5

An organic photoelectric device was fabricated in the same manner as in Example 1 except that the compound synthesized in Synthesis Example 5 was used as the light emitting layer.

Example  6

An organic optoelectronic device was fabricated in the same manner as in Example 1 except that the compound synthesized in Synthesis Example 6 was used as a light emitting layer.

Example  7

An organic photoelectric device was fabricated in the same manner as in Example 1 except that the compound synthesized in Synthesis Example 7 was used as the light emitting layer.

Example  8

An organic optoelectronic device was fabricated in the same manner as in Example 1 except that the compound synthesized in Synthesis Example 8 was used as a light emitting layer.

Example  9

An organic photoelectric device was fabricated in the same manner as in Example 1 except that the compound synthesized in Synthesis Example 9 was used as the light emitting layer.

Example  10

An organic photoelectric device was fabricated in the same manner as in Example 1 except that the compound synthesized in Synthesis Example 10 was used as the light emitting layer.

Example  11

An organic photoelectric device was fabricated in the same manner as in Example 1 except that the compound synthesized in Synthesis Example 11 was used as the light emitting layer.

Example  12

An organic photoelectric device was fabricated in the same manner as in Example 1 except that the compound synthesized in Synthesis Example 12 was used as the light emitting layer.

Comparative Example  One

An organic photoelectric device was fabricated in the same manner as in Example 1 except that the following Comparative Example 1 (Formula R-1) was used as a light emitting layer.

[Chemical formula R-1]

Comparative Example  2

An organic photoelectric device was fabricated in the same manner as in Example 1 except that the following Comparative Example 2 was used as the light emitting layer.

[Chemical formula R-2]

(Performance Measurement of Organic Light Emitting Device)

For each of the organic light emitting devices manufactured in Examples 1 to 12, Comparative Examples 1 and 2, the current density change, the luminance change and the luminous efficiency were measured according to the voltage. The specific measurement method is as follows, and the results are shown in Table 2 below.

1) Measurement of change of current density with voltage change

For each of the organic light emitting devices manufactured in Examples 1 to 12 and Comparative Example 1 and Comparative Example 2, the current value flowing through the unit device was measured using a current-voltage meter (Keithley 2400) while increasing the voltage, The current density was measured by dividing the current value by the area.

2) Measurement of luminance change according to voltage change

For each of the organic light emitting devices manufactured in Examples 1 to 12, Comparative Example 1 and Comparative Example 2, luminance was measured using a luminance meter (keithley 2635B) while increasing the voltage.

3) Measurement of luminous efficiency and power efficiency

The luminous efficiency and the power efficiency were calculated using the luminance value, the current density and the voltage (V) measured in "Measurement of change of current density according to 1) Voltage change" and "Measurement of luminance change with voltage change" , And the results are summarized in Table 2, respectively.

4) Color coordinates ( CIE ) Measure

For each of the organic light emitting devices manufactured in Examples 1 to 12, Comparative Examples 1 and ² , color coordinates were measured using a luminance meter (keithley 2635B) at 6000 cd / m ² .

Luminance 500 cd / m ² Driving voltage
(V) Luminous efficiency
(cd / A) Power efficiency
(lm / W) CIE x y Example 1 4.48 62.91 44.10 0.322 0.631 Example 2 4.73 68.99 45.80 0.337 0.632 Example 3 4.52 61.89 43.00 0.335 0.640 Example 4 4.82 68.15 44.40 0.340 0.627 Example 5 4.50 58.81 41.04 0.321 0.630 Example 6 4.68 65.84 44.18 0.335 0.636 Example 7 4.72 57.75 38.42 0.333 0.639 Example 8 4.61 63.54 43.28 0.339 0.625 Example 9 4.57 58.18 39.98 0.335 0.641 Example 10 4.98 60.29 38.02 0.336 0.621 Example 11 4.59 62.21 42.56 0.329 0.620 Example 12 4.67 62.47 42.01 0.338 0.628 Comparative Example 1 6.90 49.53 22.54 0.333 0.623 Comparative Example 2 5.04 49.58 30.89 0.339 0.637

As can be seen from Table 2, the organic light emitting devices of Examples 1 to 12 exhibited improved characteristics in terms of driving voltage, luminous efficiency, and / or power efficiency as compared with Comparative Examples 1 and 2.

Specifically, it can be seen that the structure containing at least one N in X ² to X ^{9 in the} above formula (1) has more improved properties as a host material than the structure not containing it.

It will be understood by those skilled in the art that various changes in form and details may be made therein without departing from the spirit and scope of the present invention as defined by the following claims. As will be understood by those skilled in the art. It is therefore to be understood that the above-described embodiments are illustrative in all aspects and not restrictive.

100, 200: organic light emitting element 105: organic layer
110: cathode 120: anode
130: light emitting layer 140: hole assist layer
230: light emitting layer

Claims (15)

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

In Formula 1,
X ¹ is O, S, SO ₂ , SiR'R "or NR ', wherein R' and R" are independently of each other hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, A C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or a substituted or unsubstituted silyl group,
X ² to X ⁹ are, independently of each other, N or CR ', R' is hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C6 to C30 aryl group, C2 to C30 heteroaryl group, or a substituted or unsubstituted silyl group ring, at least any one of X ² to X ⁹ is N,
Ar ¹ is a substituted or unsubstituted C6 to C30 amine group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heteroaryl group,
L ¹ is a substituted or unsubstituted C6 to C30 arylene group or a substituted or unsubstituted C2 to C30 heteroarylene group,
n is an integer of 0 to 3,
R ¹ to R ⁴ are, independently of each other, hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, Lt; / RTI >
The method according to claim 1,
Wherein said compound is represented by any one of the following Chemical Formulas 2, 3 or 4:
[Chemical Formula 2] < EMI ID =

In the above Chemical Formulas 2 to 4,
X ¹ is O, S, SO ₂ , SiR'R "or NR ', wherein R' and R" are independently of each other hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, A C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or a substituted or unsubstituted silyl group,
X ² to X ⁹ are, independently of each other, N or CR ', R' is hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C6 to C30 aryl group, C2 to C30 heteroaryl group, or a substituted or unsubstituted silyl group ring, at least any one of X ² to X ⁹ is N,
Ar ¹ is a substituted or unsubstituted C6 to C30 arylamine group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heteroaryl group,
R ¹ to R ⁴ are, independently of each other, hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, Lt; / RTI >
The method according to claim 1,
In Formula 1,
X ¹ is O, S, SO ₂ , SiR'R "or NR ', wherein R' and R" are independently of each other hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, C 6 -C 30 aryl group,
X ² to X ⁹ are independently of each other N or CR ', R' is hydrogen or deuterium, at least one of X ² to X ⁹ is N,
Ar ¹ is a substituted or unsubstituted C6 to C30 arylamine group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heteroaryl group,
R ¹ to R ⁴ are, independently from each other, hydrogen, deuterium, or a substituted or unsubstituted C1 to C30 alkyl group.
The method according to claim 1,
Wherein Ar < ¹ > is a substituent represented by the following formula X-1:
[Chemical Formula X-1]

In the above formula (X-1)
X ¹⁰ to X ¹² are independently of each other N or CR 'and R' is hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, C2 to C30 heteroaryl group, or a substituted or unsubstituted silyl group ring, wherein X ¹⁰ to X ^12, at least any one is N,
R ⁵ and R ⁶ are each independently of the other hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, A substituted silyl group,
* Denotes the connecting position of the substituent.
The method according to claim 1,
Wherein Ar < ¹ > is a substituent represented by the following formula X-2:
[Formula X-2]

In the above formula (X-2)
X ¹³ to X ¹⁸ are independently of each other N or CR 'and R' is hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, C2 to C30 heteroaryl group, or a substituted or unsubstituted silyl group ring, wherein X ¹³ to X ^15, at least any one is N, and wherein X ¹⁶ to X ^18, at least one of which is N,
* Denotes the connecting position of the substituent.
The method according to claim 1,
Wherein Ar < ¹ > is a substituent represented by the following formula X-3:
[Formula X-3]

In the above formula (X-3)
Ar ² and Ar ³ independently represent a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group , Or a substituted or unsubstituted fluorenyl group,
* Denotes the connecting position of the substituent.
The method according to claim 1,
Wherein Ar < ¹ > is a substituent represented by the following formula X-4:
[Chemical Formula X-4]

In Formula 4,
X ¹⁹ is O, S, SO ₂ , NR 'or SiR'R ", wherein R' and R" are independently of each other hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C6 To C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or a substituted or unsubstituted silyl group,
R ⁷ to R ⁹ independently represent hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, An unsubstituted silyl group,
* Denotes the connecting position of the substituent.
The method according to claim 1,
At least one of X ⁵ and X ³ is N, and the remaining X ² , X ⁴ , and X ⁶ to X ⁹ are independently of each other CR '.
The method according to claim 1,
Wherein X ⁵ and X ³ are N and the remaining X ² , X ⁴ , and X ⁶ to X ⁹ are independently of each other CR '.
The method according to claim 1,
Ar ¹ represents a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted quinolinyl group, or a substituted or unsubstituted isoquinolinyl group Lt; / RTI >
A compound wherein Ar ¹ is a substituted or unsubstituted C6 to C30 amine group or a substituted or unsubstituted C6 to C30 aryl group in the formula (1) of claim 1 is used as a first host and the other host compound for an organic light- As a host.
Anode, cathode and
And at least one organic thin film layer interposed between the anode and the cathode,
Wherein at least one of the organic thin film layers comprises the compound according to any one of claims 1 to 10.
The method of claim 12,
Wherein the organic thin film layer is an electron injecting layer, an electron transporting layer, a hole injecting layer, a hole transporting layer, or a light emitting layer.
The method of claim 12,
Wherein the organic thin film layer is a light emitting layer.
13. A display device comprising the organic light-emitting device of claim 12.

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