KR20170081438A

KR20170081438A - Organic compound and organic optoelectronic device and display device

Info

Publication number: KR20170081438A
Application number: KR1020160000480A
Authority: KR
Inventors: 장유나; 홍진석; 유은선; 정성현
Original assignee: 삼성에스디아이 주식회사
Priority date: 2016-01-04
Filing date: 2016-01-04
Publication date: 2017-07-12
Also published as: KR101962757B1

Abstract

An organic compound represented by a combination of the following formulas (1) and (2), an organic optoelectronic device including the organic compound, and a display device.
[Chemical Formula 1] < EMI ID =

In Formula 1 or 2, X ¹ , X ² , L ^a , L ^b , R ^a , R ^b , and R ¹ to R ⁴ are as defined in the specification.

Description

Technical Field [0001] The present invention relates to an organic compound, an organic optoelectronic device,

Organic optoelectronic devices, and display devices.

An organic optoelectronic device is an element capable of converting electrical energy to optical energy.

Organic optoelectronic devices can be roughly classified into two types according to the operating principle. One is an optoelectronic device in which an exciton formed by light energy is separated into an electron and a hole, the electron and hole are transferred to different electrodes to generate electric energy, and the other is a voltage / Emitting device that generates light energy from energy.

Examples of organic optoelectronic devices include organic optoelectronic devices, organic light emitting devices, organic solar cells, and organic photo conductor drums.

In recent years, organic light emitting diodes (OLEDs) have attracted considerable attention due to the demand for flat panel display devices. BACKGROUND ART 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 typically has a structure in which an organic layer is interposed between an anode and a cathode.

The performance of an organic light emitting device is greatly influenced by the characteristics of the organic layer, and the organic light emitting device is most affected by the organic materials contained in the organic layer.

In particular, in order to apply the organic light emitting device to a large-sized flat panel display device, it is necessary to develop an organic material capable of increasing the hole and electron mobility and increasing the electrochemical stability.

One embodiment provides an organic compound capable of realizing a high-efficiency and long-lived organic optoelectronic device.

Another embodiment provides an organic optoelectronic device comprising the organic compound.

Another embodiment provides a display device comprising the organic opto-electronic device.

According to one embodiment, there is provided an organic compound represented by a combination of the following formulas (1) and (2).

[Chemical Formula 1] (2)

In the above formula (1) or (2)

Wherein ^{one of} X < ¹ ^> and X < ² > is N,

And the other of X ¹ and X ² is NL ^b -R ^b ,

L ^a and L ^b are each independently a single bond or a substituted or unsubstituted C6 to C30 arylene group,

R ^a and R ^b are each independently a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heterocyclic group, or a combination thereof,

R ¹ to R ⁴ are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted A substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heterocyclic group, a substituted or unsubstituted C6 to C30 arylamine group, a halogen, a cyano group, a silyl group,

R ¹ and R ² are each independently present or bonded to each other to form a ring,

R ³ and R ⁴ are each independently present or bonded to each other to form a ring,

Two adjacent * in formula (1) combine with two of * in formula (2) to form a fused ring.

According to another embodiment, there is provided an organic optoelectronic device including 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 includes the organic compound.

According to another embodiment, there is provided a display device including the organic opto-electronic device.

High-efficiency long-lived organic optoelectronic devices can be realized.

1 is a cross-sectional view illustrating an organic light emitting device according to one embodiment,
2 is a cross-sectional view illustrating another organic light emitting device according to another embodiment.

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, the term "substitution" means that at least one hydrogen in the substituent or the compound is substituted with at least one substituent selected from the group consisting of deuterium, a halogen group, a hydroxyl group, an amino group, a C1- A C1 to C10 trifluoroalkyl group such as a C1 to C40 silyl group, a C1 to C30 alkyl group, a C1 to C10 alkylsilyl group, a C6 to C30 aryl group, a C2 to C30 heterocyclic group, a C1 to C20 alkoxy group, and a trifluoromethyl group Or cyano group.

In one embodiment of the present invention, 'substituted' means that at least one hydrogen in the substituent or compound is substituted with deuterium, an arylamine group having from C6 to C24, a C1 to C10 alkyl group, a C6 to C24 aryl group, or a C3 to C24 heterocyclic group . In yet another embodiment of the present invention, "substituted" means that at least one hydrogen in the substituent or compound is substituted with deuterium, a C1 to C10 alkyl group, a C6 to C24 aryl group, or a C3 to C24 heterocyclic group. In another embodiment of the present invention, "substituted" means that at least one hydrogen in the substituent or compound is substituted with deuterium, a C1 to C10 alkyl group, or a C6 to C24 aryl 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 C6 to C10 alkylsulfinyl group, A C1 to C10 trifluoroalkyl group such as a C30 aryl group, a C3 to C30 heterocyclic group, a C1 to C20 alkoxy group, and a trifluoromethyl group, or a cyano group may be fused to form a ring. For example, 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.

As used herein, unless otherwise defined, it is meant that at least one heteroatom is contained in one functional group and the remainder is carbon. The heteroatom may be selected from N, O, S, P, and Si.

As used herein, "aryl group" means a group having one or more carbocyclic aromatic moieties and broadly refers to carbocyclic aromatic moieties linked by a single bond, and carbocyclic aromatic moieties are referred to as " But also includes non-aromatic fused rings fused indirectly. The aryl groups include monocyclic, polycyclic or fused polycyclic (i. E., Rings that divide adjacent pairs of carbon atoms) functional groups.

As used herein, the term "heterocyclic group" refers to a heterocyclic group having at least one heteroatom selected from N, O, S, P and Si in a ring compound such as an aryl group, a cycloalkyl group, a fused ring thereof, And the remainder is carbon. When the heterocyclic group is a fused ring, the heterocyclic group or the ring may include one or more heteroatoms.

More specifically, the substituted or unsubstituted aryl group and / or the substituted or unsubstituted heterocyclic group may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, A substituted or unsubstituted naphthacenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted quaterphenyl group, a substituted or unsubstituted pyrazinyl group, A substituted or unsubstituted thienyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted thienyl group, Or an unsubstituted pyrrolyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted imidazolyl group, a substituted or unsubstituted triazolyl group, a substituted or unsubstituted oxazolyl group, A substituted or unsubstituted thiadiazolyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted thiadiazolyl group, a substituted or unsubstituted thiadiazolyl group, a substituted or unsubstituted thiadiazolyl group, A substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted thiazinyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted indolyl group , A substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted quinazolinyl group, A substituted or unsubstituted benzothiazyl group, a substituted or unsubstituted acridinyl group, a substituted or unsubstituted phenazinyl group, a substituted or unsubstituted phenothiazine group, a substituted or unsubstituted benzothiazyl group, a substituted or unsubstituted benzothiazyl group, A substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazole group, a combination thereof, or a combination thereof, or a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazolyl group, May be in a fused form, but are not limited thereto.

For example, the substituted or unsubstituted aryl group may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted A naphthacenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted quaterphenyl group, a substituted or unsubstituted triphenylenyl group, or a substituted or unsubstituted fluorenyl group.

For example, the substituted or unsubstituted heterocyclic group may be a substituted or unsubstituted indenyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, A substituted or unsubstituted benzyl group, a substituted or unsubstituted benzyl group, a substituted or unsubstituted benzyl group, a substituted or unsubstituted benzyl group, a substituted or unsubstituted benzyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothiophenyl group, , A substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted quinazolinyl group, Or an unsubstituted carbazole group, a combination thereof, or a combination thereof may be in a fused form.

In the present specification, the hole property refers to a property of forming holes by donating electrons when an electric field is applied, and has a conduction property along the HOMO level so that the injection of holes formed in the anode into the light emitting layer, Quot; refers to the property of facilitating the movement of the hole formed in the light emitting layer to the anode and the movement of the hole in the light emitting layer.

In addition, the electron characteristic refers to a characteristic that electrons can be received when an electric field is applied. The electron characteristic has a conduction characteristic along the LUMO level so that electrons formed in the cathode are injected into the light emitting layer, electrons formed in the light emitting layer migrate to the cathode, It is a characteristic that facilitates movement.

The organic compounds according to one embodiment will be described below.

The organic compound according to one embodiment may be represented by a combination of the following formulas (1) and (2).

[Chemical Formula 1] (2)

In the above formula (1) or (2)

Wherein ^{one of} X < ¹ ^> and X < ² > is N,

And the other of X ¹ and X ² is NL ^b -R ^b ,

The organic compound may have high hole transportability by including a core having a wide and flat hole characteristic in which at least six 5-membered and 6-membered rings are fused.

Further, it is possible to form a hole-transporting property of the organic optoelectronic device to which the organic compound is applied by bonding a substituent having a hole characteristic to the core of the hole characteristic to form a stronger hole-transporting compound.

Further, it is possible to form a bipolar structure by binding substituents having an electron characteristic to the hole core of the hole characteristic, and thus to appropriately balance the flow of holes and electrons, and accordingly, the organic optoelectronic device The efficiency can be improved.

For example, R ^a and R ^b in the above formula (1) or (2) independently represent a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted terphenyl group, A substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted quaterphenyl group or a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, A substituted or unsubstituted thiazolyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted thiazolyl group, Or an unsubstituted dibenzothiophenyl group or a combination thereof.

For example, at least one of R ^a and R ^b in Formula 1 or 2 may be a substituent having a hole property. Examples of the substituent having a hole property include a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted naphthacenyl group A substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted quaterphenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted fluorenyl group, A dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazolyl group, or a combination thereof.

For example, at least one of R ^a and R ^b in Formula 1 or 2 may be a substituent having an electron characteristic. Here, the substituent having an electron characteristic may be a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted triazinyl group, A substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted quinoxalinyl group, or a combination thereof.

For example, any one of R ^a and R ^b in Formula 1 or 2 may be a substituted or unsubstituted C6 to C30 aryl group, and the other of R ^a and R ^b may be a substituent having a hole property.

For example, any one of R ^a and R ^b in Formula 1 or 2 may be a substituted or unsubstituted C6 to C30 aryl group, and the other of R ^a and R ^b may be a substituent having an electron characteristic.

For example, any one of R ^a and R ^b in Formula 1 or 2 is a substituted or unsubstituted C6 to C30 aryl group, and R ^a and R ^b The other is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenan A substituted or unsubstituted thiazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted thiophenyl group, a substituted or unsubstituted thiophenyl group, a substituted or unsubstituted thiophenyl group, A substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, Or a combination thereof.

For example, any one of R ^a and R ^b in Formula 1 or 2 may be a substituted or unsubstituted phenyl group, and the other of R ^a and R ^b may be a substituent having a hole property.

For example, any one of R ^a and R ^b in Formula 1 or 2 may be a substituted or unsubstituted phenyl group, and the other of R ^a and R ^b may be a substituent having an electron characteristic.

For example, any one of R ^a and R ^b in Formula 1 or 2 may be a substituted or unsubstituted phenyl group, and R ^a and R ^b The other is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenan A substituted or unsubstituted thiazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted thiophenyl group, a substituted or unsubstituted thiophenyl group, a substituted or unsubstituted thiophenyl group, A substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, Or a combination thereof.

For example, at least one of R ^a and R ^b in the above formula (1) or (2) may be a group represented by the following formula (9).

[Chemical Formula 9]

In the above formula (9)

Z ¹ to Z ⁹ are each independently N or CR ^c ,

At least one of Z ¹ to Z ⁹ is N,

L ^c is a single bond or a substituted or unsubstituted C6 to C30 arylene group,

R ⁵ to R ⁸ and R ^c are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C20 aryl group or a combination thereof,

n1 and n2 are each independently 0 or 1;

In one example, at least two of Z ¹ to Z ⁹ may be nitrogen.

In one example, at least one of Z ¹ to Z ³ may be nitrogen.

In one example, at least two of Z ¹ to Z ³ may be nitrogen.

In one example, L ^c may be a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted naphthylene group.

In one example, L ^c may be a single bond, a substituted or unsubstituted m-phenylene group or a substituted or unsubstituted p-phenylene group.

The group represented by the formula (9) may be, for example, a group listed in the following group 1, but is not limited thereto.

[Group 1]

For example, R ^a and R ^b May be a substituted or unsubstituted phenyl group, and R & lt ^; ^a & gt ^; and R < ^b & gt ^; May be a group represented by the formula (9).

For example, R ^a and R ^b May be a substituted or unsubstituted phenyl group, and R & lt ^; ^a & gt ^; and R < ^b & gt ^; Lt; / RTI > may be one of the groups listed in group 1 above.

In one example, L ^a and L ^b may each independently be a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted naphthyl group.

In one example, L ^a and L ^b may each independently be a single bond, a substituted or unsubstituted m-phenylene group or a substituted or unsubstituted p-phenylene group.

In one example of the present invention, the organic compound of the present invention may have an absolute value of the HOMO energy level of 4.9 eV or more and less than 5.3 eV.

The organic compound may be represented, for example, by any of the following formulas (3) to (8).

(3) [Chemical Formula 4]

[Chemical Formula 5] [Chemical Formula 6]

(7) [Chemical Formula 8]

In the above formulas 3 to 8, L ^a , L ^b , R ^a , R ^b and R ¹ to R ⁴ are as described above.

For example, R ^a and R ^b in formulas (3) to (8) each independently represent a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted terphenyl group, A substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted quaterphenyl group or a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, A substituted or unsubstituted thiazolyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted substituted or unsubstituted di A benzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a combination thereof.

For example, at least one of R ^a and R ^b in the above formulas 3 to 8 may be a substituent having a hole property.

For example, at least one of R ^a and R ^b in the above formulas 3 to 8 may be a substituent having an electron characteristic.

For example, any one of R ^a and R ^b in the above formulas 3 to 8 may be a substituted or unsubstituted C6 to C30 aryl group, and the other of R ^a and R ^b may be a substituent having a hole property.

For example, any one of R ^a and R ^b in the above formulas 3 to 8 may be a substituted or unsubstituted C6 to C30 aryl group, and the other of R ^a and R ^b may be a substituent having an electron characteristic.

For example, any one of R ^a and R ^b in the above formulas 3 to 8 is a substituted or unsubstituted C6 to C30 aryl group, and R ^a and R ^b The other is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenan A substituted or unsubstituted thiazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted thiophenyl group, a substituted or unsubstituted thiophenyl group, a substituted or unsubstituted thiophenyl group, A substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, Or a combination thereof.

For example, any one of R ^a and R ^b in the above formulas 3 to 8 may be a substituted or unsubstituted phenyl group, and the other of R ^a and R ^b may be a substituent having a hole property.

For example, any one of R ^a and R ^b in the above formulas 3 to 8 may be a substituted or unsubstituted phenyl group, and the other of R ^a and R ^b may be a substituent having an electron characteristic.

For example, any one of R ^a and R ^b in the above formulas 3 to 8 may be a substituted or unsubstituted phenyl group, and R ^a and R ^b The other is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenan A substituted or unsubstituted thiazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted thiophenyl group, a substituted or unsubstituted thiophenyl group, a substituted or unsubstituted thiophenyl group, A substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, Or a combination thereof.

For example, L ^a and L ^b in formulas (3) to (8) may independently be a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group or a substituted or unsubstituted naphthyl group, For example, a single bond, a substituted or unsubstituted m-phenylene group or a substituted or unsubstituted p-phenylene group.

The organic compound may be, for example, compounds listed in the following Group 2, but is not limited thereto.

[Group 2]

The organic compound may have an absolute value of HOMO energy level of, for example, about 4.9 eV to less than 5.3 eV. By having the HOMO energy level in the above range, the hole injection characteristics can be enhanced.

The above-described organic compounds can be applied to organic optoelectronic devices. The above-described organic compounds can be applied to organic optoelectronic devices alone or together with other organic compounds.

Hereinafter, an organic optoelectronic device to which the organic compound described above 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.

The organic optoelectronic device may include an anode and a cathode facing each other, and at least one organic layer positioned between the anode and the cathode, and the organic layer may include the organic compound described above.

In one example, the organic layer may include a light emitting layer containing the organic compound.

For example, the organic layer may include a light emitting layer, an auxiliary layer located between the anode and the light emitting layer and / or between the cathode and the light emitting layer, and the auxiliary layer may include the organic compound.

For example, the organic layer may include a light-emitting layer, a hole-assist layer positioned between the anode and the light-emitting layer, and the hole-assist layer may include the organic compound.

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

1 is a cross-sectional view illustrating an organic light emitting device according to one embodiment.

1, an organic light emitting diode 100 according to an embodiment includes an anode 120 and a cathode 110 facing each other, and an organic layer 105 positioned 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 may be 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 may be formed 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 organic compound.

The light emitting layer 130 may include the organic compound as a host and may include the organic compound alone or may be a mixture of at least two of the organic compounds described above, Other organic compounds may be mixed and contained.

The light emitting layer 130 may further include a dopant. The dopant may be a red, green or blue dopant, for example a phosphorescent dopant.

The dopant may be a material such as a metal complex which emits light by a multiple excitation which is excited by a triplet state. The dopant may be, for example, an inorganic, organic, or organic compound, and may include one or more species.

The light emitting layer 130 may be formed by a dry film forming method or a solution process. The dry film forming method may be a chemical vapor deposition method, a sputtering method, a plasma plating method, or an ion plating method, and two or more compounds may be simultaneously deposited or a compound having the same deposition temperature may be mixed to form a film. The solution process may be, for example, ink jet printing, spin coating, slit coating, bar coating and / or dip coating.

2 is a cross-sectional view illustrating an organic light emitting device according to another embodiment.

2, an organic light emitting diode 200 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 organic layer 105 includes a hole-assist layer 140 positioned between the light-emitting layer 230 and the anode 120. The hole assist layer 140 may facilitate injection and movement of holes between the anode 120 and the light emitting layer 230.

The above-described organic compound may be included as a host in the light emitting layer 230. The light emitting layer 230 may include the organic compound alone, or may be a mixture of at least two of the organic compounds described above, or may include a mixture of the organic compound and the other organic compound. The light emitting layer 230 may further include a dopant.

The organic compound described above may be included in the hole-assist layer 140. The hole-assist layer 140 may contain the above organic compound alone or may be a mixture of at least two of the organic compounds described above, or may include a mixture of the above organic compound and another organic compound.

In FIG. 2, the organic layer 105 may further include at least one layer of an electron assist layer (not shown) positioned between the cathode 110 and the light emitting layer 230.

The organic light emitting device described above can be applied to an organic light emitting display.

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.

For organic optoelectronic devices Synthesis of compounds

Synthesis of intermediate compounds

A first step; Synthesis of Intermediate I-A

[Reaction Scheme 1]

1-bromo-3-fluoro-2-nitrobenzene (32.8 g, 149.10 mmol), CuI (56.79 g, 298.20 mmol), 1 H-benzo [d] imidazol- K2CO3 (41.21 g, 298.20 mmol) and 1,10-phenanthroline (2.68 g, 14.91 mmol) were placed in dimethylformamide and refluxed with stirring in 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 normal hexane to obtain 15.66 g of Intermediate I-A (yield: 50%).

A second step; Synthesis of Intermediate I-B

[Reaction Scheme 2]

Intermediate I-A (20.0 g, 59.86 mmol) and SnCl2 (22.70 g, 119.72 mmol) were added to 6N HCl and refluxed for 24 hours under a stream of nitrogen. 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 recrystallized from dichloromethane and n-hexane to obtain 9.65 g (yield: 53%) of Intermediate I-B.

A third step; Synthesis of Intermediate I-C

[Reaction Scheme 3]

Intermediate I-B (20.0 g, 65.76 mmol) was added to Xylene and refluxed under nitrogen stream for 24 hours. The organic solution is removed, extracted 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 = 9: 1 (v / v), followed by recrystallization from dichloromethane and normal hexane to obtain 7.71 g (yield: 41%) of Intermediate I-C.

Step 4; Synthesis of Intermediate I-D

[Reaction Scheme 4]

Intermediate IC (20.0g, 69.90mmol), iodobenzene (14.26g, 69.90mmol), CuI (45.55g, 139.80mmol), CS2CO3 (19.32g, 139.80mmol), 1,10- phenanthroline Dimethylformamide, and the mixture was stirred under reflux for 24 hours under a stream of nitrogen. 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) and then recrystallized with toluene to obtain 11.90 g (yield: 47%) of Intermediate I-D.

Step 5; Synthesis of Intermediate I-E

[Reaction Scheme 5]

Intermediate ID (20.0 g, 55.22 mmol), 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl-2,2'-bi (1,3,2-dioxaborolane) , PdCl2 (dppf) (2.70 g, 3.31 mmol) and KOAc (16.26 g, 165.65 mmol) were added to toluene and 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 using hexane: dichloromethane = 7: 3 (v / v), followed by recrystallization from dichloromethane and normal hexane to obtain 16.95 g (yield: 75%) of Intermediate I-E.

Step 6; Synthesis of Intermediate I-F

[Reaction Scheme 6]

Intermediate IE (20.0 g, 48.87 mmol), 1-bromo-2-nitrobenzene (12.83 g, 63.53 mmol), Pd (PPh3) 4 1.13 g, 0.98 mmol) and K2CO3 (20.26 g, 146.6 mmol) were dissolved in tetrahydrofuran And the mixture was refluxed under nitrogen flow 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) and then recrystallized with toluene to obtain 15.81 g (yield: 80%) of Intermediate I-F.

Step 7; Synthesis of Intermediate I-G

[Reaction Scheme 7]

The intermediate solution IF (20.0 g, 49.45 mmol), PPh3 (59.70 g, 182.98 mmol) was added to dichlorobenzene and refluxed for 48 hours under a stream of nitrogen. The organic solution was removed and hexane: ethyl acetate = ), Followed by recrystallization from dichloromethane and normal hexane to obtain 12.52 g (yield: 68%) of Intermediate IG.

Synthesis of final compound

Synthetic example 1: Synthesis of compound 1

[Reaction Scheme 8]

Pd (dba) 2 (0.62 g, 1.07 mmol), P (t-Bu) 3 (0.33 g, 1.61 mmol), NaO (t -Bu) (7.74 g, 80.55 mmol) were added to toluene, and the mixture was refluxed and stirred 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 recrystallized with toluene to obtain 16.86 g (Yield: 70%) of Compound 1.

Synthetic example 2: Synthesis of Compound 3

[Reaction Scheme 9]

P (t-Bu) 3 (0.33 g, 1.07 mmol), Pd (dba) 2 (0.62 g, 1.07 mmol), 3-bromo-1,1'-biphenyl (12.52 g, 53.70 mmol) g, 1.61 mmol) and NaO (t-Bu) (7.74 g, 80.55 mmol) were added to toluene and 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 normal hexane to obtain 19.72 g of Compound 3 (yield: 70%).

Synthetic example 3: Synthesis of compound 10

[Reaction Scheme 10]

P (t-Bu) 3 (0.33 g, 1.61 mmol), NaO (0.60 g, 1.07 mmol), Pd (dba) 2 (0.62 g, 1.07 mmol), 2-bromotriphenylene (16.49 g, 53.70 mmol) (t-Bu) (7.74 g, 80.55 mmol) were added to toluene, and the mixture was refluxed with stirring in 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 = 8: 2 (v / v) and then recrystallized with toluene to obtain 20.90 g (yield: 65%) of Compound 10.

Synthetic example 4: Synthesis of Compound 23

[Reaction Scheme 11]

P (tBu) 3 (0.33 g, 1.07 mmol), Pd (dba) 2 (0.62 g, 1.07 mmol), 4-bromo-N, N-diphenylaniline (17.41 g, 53.70 mmol) , 1.61 mmol) and NaO (t-Bu) (7.74 g, 80.55 mmol) were put in toluene and refluxed with stirring in 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 = 9: 1 (v / v), followed by recrystallization from dichloromethane and normal hexane to obtain 22.48 g (yield: 68%) of Compound 23.

Synthetic example 5: Synthesis of Compound 27

[Reaction Scheme 12]

A mixture of intermediate IG (20.0 g, 53.70 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (14.38 g, 53.70 mmol), Pd (dba) 2 (0.62 g, 1.07 mmol) t-Bu) 3 (0.33 g, 1.61 mmol) and NaO (t-Bu) (7.74 g, 80.55 mmol) were added to xylene and 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 monochlorobenzene to obtain 25.94 g (yield: 80%) of Example Compound 27.

Synthetic example 6: Synthesis of compound 28

[Reaction Scheme 13]

Intermediate IG (20.0 g, 53.70 mmol), 2 - ([1,1'-biphenyl] -4-yl) -4-chloro-6- phenyl- Bu (3.74 g, 1.61 mmol) and NaO (t-Bu) (7.74 g, 80.55 mmol) were added to xylene and a solution of 24 Lt; / RTI > 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 with monochlorobenzene to obtain 26.28 g (yield: 72%) of Compound 28.

Synthetic example 7: Synthesis of Compound 29

[Reaction Scheme 14]

Pd (dba) 2 (0.62 g, 1.07 mmol), P (t-Bu) 3 (0.33 g, 53.70 mmol), 2-chloro-4,6-diphenylpyrimidine (14.32 g, 53.70 mmol) , 1.61 mmol) and NaO (t-Bu) (7.74 g, 80.55 mmol) were added to xylene and the mixture was refluxed with stirring in 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 = 6: 4 (v / v) and then recrystallized from monochlorobenzene to obtain 23.30 g (yield: 60%) of Compound 29.

Synthetic example 8: Synthesis of Compound 32

[Reaction Scheme 15]

Intermediate IG (20.0 g, 53.70 mmol), 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine (20.85 g, 53.70 mmol), Pd (dba) 2 (0.62 g, 1.07 mmol ), P (t-Bu) 3 (0.33 g, 1.61 mmol) and NaO (t-Bu) (7.74 g, 80.55 mmol) were added to toluene and 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 normal hexane to obtain 21.90 g (yield: 74%) of Compound 32.

Synthetic example 9: Synthesis of Compound 33

[Reaction Scheme 16]

P (t-Bu) 3 (0.33 g, 1.61 mmol), Pd (dba) 2 (0.62 g, 1.07 mmol), 2-chloro-4-phenylquinazoline (12.93 g, 53.70 mmol) mmol) and NaO (t-Bu) (7.74 g, 80.55 mmol) were added to toluene, 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 normal hexane to obtain 20.13 g (yield: 65%) of Compound 33.

Synthetic example 10: Synthesis of Compound 35

[Reaction Scheme 17]

Pd (dba) 2 (0.62 g, 1.07 mmol), P (t-Bu) 3 (20.0 g, 53.70 mmol), 2- (3-chlorophenyl) -4-phenylquinazoline (17.01 g, 53.70 mmol) 0.33 g, 1.61 mmol) and NaO (t-Bu) (7.74 g, 80.55 mmol) were added to toluene and 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) and then recrystallized with ethyl acetate to obtain 30.85 g (yield: 88%) of Compound 35.

Fabrication of organic light emitting device

Example 1

Compound 1 obtained in Synthesis Example 1 was used as a host and Ir (PPy) ₃ was used as a dopant to prepare an organic light emitting device.

As the anode, ITO was used in a thickness of 1000 Å, and as a cathode, aluminum (Al) was used in a thickness of 1000 Å. Specifically, an explanation will be given of a method of manufacturing an organic light emitting device. An ITO glass substrate having a sheet resistance of 15 Ω / cm ² is cut into a size of 50 mm × 50 mm × 0.7 mm, and is cut in acetone, isopropyl alcohol and pure water After ultrasonic cleaning for 15 minutes each, UV ozone cleaning was performed for 30 minutes.

N4, N4'-di (naphthalen-1-yl) -N4 and N4'-diphenylbiphenyl-4,4'-diamine were added on the substrate at a vacuum degree of 650 × 10 ^-7 Pa and a deposition rate of 0.1 to 0.3 nm / (NPB) (80 nm) was deposited thereon to form a 800 Å hole transport layer. Subsequently, the compound 1 obtained in Synthesis Example 1 was deposited under the same vacuum deposition conditions to form a light emitting layer having a thickness of 300 Å. At this time, Ir (PPy) ₃ , which is a phosphorescent dopant, was simultaneously deposited. At this time, the deposition rate of the phosphorescent dopant was controlled so that the total amount of the light emitting layer was 100 wt%, and the phosphorescent dopant content was 7 wt%.

Bis (2-methyl-8-quinolinolate) -4- (phenylphenolato) aluminum (BAlq) was deposited on the light emitting layer using the same vacuum deposition conditions to form a hole blocking layer having a thickness of 50 Å. Subsequently, Alq3 was deposited under the same vacuum deposition conditions to form an electron transport layer having a film thickness of 200 ANGSTROM. LiF and Al were sequentially deposited as an anode on the electron transport layer to fabricate an organic light emitting device.

The structure of the organic light emitting device was ITO / NPB (80 nm) / EML (compound 1 (93 wt%) + Ir (PPy) 3 (7 wt%), 30 nm) / Balq (5 nm) / Alq3 ) / LiF (1 nm) / Al (100 nm).

Example 2

An organic light emitting device was prepared in the same manner as in Example 1, except that Compound 3 obtained in Synthesis Example 2 was used instead of Compound 1 obtained in Synthesis Example 1 as a host for the light emitting layer.

Example 3

An organic light emitting device was prepared in the same manner as in Example 1, except that Compound 10 obtained in Synthesis Example 3 was used instead of Compound 1 obtained in Synthesis Example 1 as a host for the light emitting layer.

Example 4

An organic light emitting device was fabricated in the same manner as in Example 1, except that Compound 23 obtained in Synthesis Example 4 was used instead of Compound 1 obtained in Synthesis Example 1 as a host for the light emitting layer.

Example 5

An organic light emitting device was fabricated in the same manner as in Example 1, except that Compound 27 obtained in Synthesis Example 5 was used instead of Compound 1 obtained in Synthesis Example 1 as a host for the light emitting layer.

Example 6

An organic light emitting device was fabricated in the same manner as in Example 1, except that Compound 28 obtained in Synthesis Example 6 was used in place of Compound 1 obtained in Synthesis Example 1 as a host for the light emitting layer.

Example 7

An organic light emitting device was fabricated in the same manner as in Example 1 except that the compound 29 obtained in Synthesis Example 7 was used instead of the compound 1 obtained in Synthesis Example 1 as a host for the light emitting layer.

Example 8

An organic light emitting device was fabricated in the same manner as in Example 1 except that the compound 32 obtained in Synthesis Example 8 was used instead of the compound 1 obtained in Synthesis Example 1 as a host for the light emitting layer.

Example 9

Except for using Compound 33 obtained in Synthesis Example 9 instead of Compound 1 obtained in Synthesis Example 1 and using [(piq) ₂ Ir (acac)] instead of Ir (PPy) 3 as a dopant in the light emitting layer, 1, an organic light emitting device was fabricated.

Example 10

Except for using Compound 35 obtained in Synthesis Example 10 instead of Compound 1 obtained in Synthesis Example 1 and using [(piq) ₂ Ir (acac)] instead of Ir (PPy) 3 as a dopant in the light emitting layer, 1, an organic light emitting device was fabricated.

Comparative Example One

An organic light emitting device was prepared in the same manner as in Example 1, except that the following compound (BASF) was used in place of the compound 1 obtained in Synthesis Example 1 as a host for the light emitting layer.

Comparative Example 2

Evaluation I: Comparison of simulation characteristics of compounds

The energy levels of the compounds obtained in Synthesis Examples 1 and 5 and the compounds used in Comparative Examples 1 and 2 were calculated by the Gaussian 09 method using a super computer GAIA (IBM power 6), and the results are shown in Table 1 below.

rescue HOMO LUMO T1 S1 Comparative Example 1

-5.324 -0.537 3.39 4.17 Example 1
(Synthesis Example 1)

-4.954 -0.676 2.98 3.73 Comparative Example 2

-5.631 -1.910 3.077 3.2037 Example 5
(Synthesis Example 5)

-5.175 -1.816 2.85 2.92

Referring to Table 1, it can be seen that the HOMO energy level of the compound obtained in Synthesis Example 1 is higher than that of the compound used in Comparative Example 1, and that the compound obtained in Synthesis Example 2 is HOMO The energy level is greatly increased.

For example, the HOMO energy level of the compound used in Comparative Example 1 is about -5.32 eV, which is considered to be somewhat lacking in hole characteristics when used as a core having hole characteristics, and furthermore, in the same core of the compound used in Comparative Example 1, The compound used in Comparative Example 2 in which the 2,4-biphenyltriazine diaryl group having a heteroaryl group having a heteroaryl group is substituted has a lower HOMO value of about -5.63 eV, so that the compound used in Comparative Example 2 requires a bipolar characteristic It can be expected that the hole transporting ability is significantly lowered for use as the host of the light emitting layer.

On the contrary, the compound obtained in Synthesis Example 1 had a HOMO energy level of about -4.95 eV and a strong hole property, and the same core as the compound obtained in Synthesis Example 1 had a heteroaryl group having electronic properties such as 2,4-biphenyltriazine It is expected that the compound obtained in Synthesis Example 5 in which diaryl substitution is also suitable for use as a host of a light emitting layer which requires a bipolar characteristic due to the hole property of a strong core at a HOMO energy level of about -5.17 eV.

Evaluation II: Evaluation of organic light emitting device

The driving voltage and the luminous efficiency of the organic light emitting device according to Examples 1 to 8 and Comparative Examples 1 and 2 were evaluated.

The specific measurement method is as follows, and the results are shown in Table 2.

(1) Measurement of change in current density with voltage change

For the organic light emitting device manufactured, the current flowing through the unit device was measured using a current-voltmeter (Keithley 2400) while raising the voltage from 0 V to 10 V, and the measured current value was divided by the area to obtain the result.

(2) Measurement of luminance change according to voltage change

For the organic light-emitting device manufactured, luminance was measured using a luminance meter (Minolta Cs-1000A) while increasing the voltage from 0 V to 10 V, and the result was obtained.

(3) Measurement of luminous efficiency

The current efficiency (cd / A) at the same current density (10 mA / cm ² ) was calculated using the luminance, current density and voltage measured from the above (1) and (2).

No. compound The driving voltage (V) Color coordinates
(CIEx, CIEy) Efficiency (cd / A) Example 1

Compound 1 4.35 green 43.86 Comparative Example 1

5.25 green 40.12 Example 2

Compound 3 4.35 green 45.21 Example 3

Compound 10 4.19 green 50.31 Example 4

Compound 23 4.30 green 48.34 Example 5

Compound 27 3.89 green 57.02 Comparative Example 2

4.60 green 42.98 Example 6

Compound 28 3.80 green 55.08 Example 7

Compound 29 4.30 green 50.32 Example 8

Compound 32 4.22 green 52.22

Referring to Table 2, it can be seen that the organic light emitting device according to the embodiments exhibits a low driving voltage and a high efficiency. In addition, the organic light emitting device according to Example 1 showed significantly improved driving voltage and efficiency as compared with the organic light emitting device according to Comparative Example 1, and the organic light emitting device according to Example 5 had organic It can be confirmed that the driving voltage and efficiency are greatly improved as compared with the light emitting device. This can be expected due to the difference in energy level of the above-mentioned compounds.

Evaluation III

The luminescent colors of the organic luminescent devices according to Examples 1 to 10 were evaluated.

The results are shown in Table 3.

No. compound The driving voltage (V) Color coordinates
(CIEx, CIEy) Example 1 Compound 1 4.35 green Example 2 Compound 3 4.35 green Example 3 Compound 10 4.19 green Example 4 Compound 23 4.30 green Example 5 Compound 27 3.89 green Example 6 Compound 28 3.80 green Example 7 Compound 29 4.30 green Example 8 Compound 32 4.22 green Example 9 Compound 33 4.00 Red Example 10 Compound 35 4.21 Red

Referring to Table 3, it can be seen that the organic light emitting device according to the embodiments can vary the luminescent color depending on the substituent.

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

Claims

An organic compound represented by a combination of the following formulas (1) and (2):
[Chemical Formula 1] < EMI ID =

In the above formula (1) or (2)
Wherein ^{one of} X < ¹ ^> and X < ² > is N,
And the other of X ¹ and X ² is NL ^b -R ^b ,
L ^a and L ^b are each independently a single bond or a substituted or unsubstituted C6 to C30 arylene group,
R ^a and R ^b are each independently a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heterocyclic group, or a combination thereof,
R ¹ to R ⁴ are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted A substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heterocyclic group, a substituted or unsubstituted C6 to C30 arylamine group, a halogen, a cyano group, a silyl group,
R ¹ and R ² are each independently present or bonded to each other to form a ring,
R ³ and R ⁴ are each independently present or bonded to each other to form a ring,
Two adjacent * in formula (1) combine with two of * in formula (2) to form a fused ring.

The method of claim 1,
An organic compound represented by any one of the following formulas (3) to (8):
[Chemical Formula 3]

[Chemical Formula 5]

[Chemical Formula 7]

In the above Formulas 3 to 8,
L ^a and L ^b are each independently a single bond or a substituted or unsubstituted C6 to C30 arylene group,
R ^a and R ^b are each independently a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heterocyclic group, or a combination thereof,
R ¹ to R ⁴ are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted A substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heterocyclic group, a substituted or unsubstituted C6 to C30 arylamine group, a halogen, a cyano group, a silyl group, or a combination thereof.

The method of claim 1,
R ^a and R ^b are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted anthracenyl group, a substituted Or a substituted or unsubstituted thiophenyl group, a substituted or unsubstituted thiophene group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted thienyl group, A substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinazolinyl group, A dibenzothiophenyl group, or a combination thereof.

The method of claim 1,
R ^a and R ^b Is a substituted or unsubstituted phenyl group,
R ^a and R ^b The other is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenan A substituted or unsubstituted thiazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted thiophenyl group, a substituted or unsubstituted thiophenyl group, a substituted or unsubstituted thiophenyl group, A substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, Organic compounds which are combinations thereof.

The method of claim 1,
R ^a and R ^b Is a group represented by the following formula (9).
[Chemical Formula 9]

In the above formula (9)
Z ¹ to Z ⁹ are each independently N or CR ^c ,
At least one of Z ¹ to Z ⁹ is N,
L ^c is a single bond or a substituted or unsubstituted C6 to C30 aryl group,
R ⁵ to R ⁸ and R ^c are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C20 aryl group or a combination thereof,
n1 and n2 are each independently 0 or 1;

The method of claim 5,
R ^a and R ^b Is a substituted or unsubstituted phenyl group,
R ^a and R ^b And the other is a group represented by the formula (9).

The method of claim 1,
An organic compound having an absolute value of HOMO energy level of 4.9 eV or more and less than 5.3 eV.

The method of claim 1,
Organic compounds listed in group 2 below.
[Group 2]

The anode and the cathode facing each other, and
At least one organic layer positioned between the anode and the cathode
/ RTI >
Wherein the organic layer comprises the organic compound according to any one of claims 1 to 8.

The method of claim 9,
Wherein the organic layer comprises a light-emitting layer containing the organic compound.

The method of claim 9,
The organic layer
A light emitting layer, and
A hole-assisted layer disposed between the anode and the light-emitting layer and containing the organic compound,
/ RTI >

A display device comprising the organic opto-electronic device according to claim 9.