KR20180032471A - Organic compound and organic optoelectronic device and display device - Google Patents

Abstract

The present invention relates to an organic compound represented by chemical formula 1, an organic optoelectronic device including the organic compound, and a display device. In the chemical formula 1, L^1, Ar^1, Ar^2, and R^1 to R^8 are the same 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 diode is an element that can switch between electric energy and light 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 the following general formula (1).

[Chemical Formula 1]

In formula (1)

L ¹ is a substituted or unsubstituted C6 to C18 arylene group,

Ar ¹ is a substituted or unsubstituted C2 to C30 heteroaryl group,

Ar ² is a substituted or unsubstituted C 2 to C 18 aryl group,

R ¹ to R ⁸ are each independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C20 alkyl groups, substituted or unsubstituted C6 to C30 aryl groups, or combinations thereof.

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, 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 trifluoro 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, a trifluoromethyl group, An alkyl group or a cyano group. "Substitution" in the context of the present invention means that at least one of the substituents or the hydrogen in the compound is deuterium, a substituted or unsubstituted C1 to C30 amine group, a C1 to C30 alkyl group, a C1 to C10 alkylsilyl group, a C6 to C30 aryl group, Substituted with a C2 to C30 heterocyclic group. In addition, in the present invention, "substitution" means that at least one hydrogen in the substituent or the compound is substituted with deuterium, C1 to C30 alkyl group, C6 to C30 aryl group or C2 to C30 heterocyclic 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 carbazolyl group, a combination thereof, or a substituted or unsubstituted benzothiophenyl group, Combinations of these may be in fused form, but are not limited thereto.

In this specification, a single bond means a bond directly connected to a carbon atom or a carbon atom other than a carbon atom or a hetero atom other than carbon. For example, L means a single bond means that a substituent connected to L is directly connected to a center core do. That is, in the present specification, a single bond does not mean methylene or the like via carbon.

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 is represented by the following formula (1).

[Chemical Formula 1]

In formula (1)

L ¹ is a substituted or unsubstituted C6 to C18 arylene group,

Ar ¹ is a substituted or unsubstituted C 2 to C 18 aryl group,

Ar ² is a substituted or unsubstituted C2 to C30 heteroaryl group,

R ¹ to R ⁸ are each independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C20 alkyl groups, substituted or unsubstituted C6 to C30 aryl groups, or combinations thereof.

The organic compound according to an embodiment includes the indolecarbazole moiety represented by the formula (1), and includes a substituent such as an aryl group or a heteroaryl group in the para direction centering on the central phenyl of indolocarbazole.

Generally, indolocarbazole can be formed in various structures depending on the bonding position of the carbazole moiety and is suitable for use in a hole transport host since the HOMO energy level is high. Various indole-carbazole structures have similar energy levels, but various HOMO characteristics can be realized depending on the substituent type and substitution position. In particular, the indolocarbazole moiety as shown in the above formula (1) has electron paramagnetism (para) facing each other, and thus has a higher HOMO energy level than indolecarbazole of another structure, . Therefore, in the case of the device using the organic compound according to one embodiment, it is possible to lower the driving voltage and improve the lifetime and the efficiency characteristic.

The organic compound of formula (1) can realize an organic compound in which the energy level of HOMO and LUMO can be easily controlled by locating indolecarbazole as a core and a functional group such as a central phenyl aryl group or a heteroaryl group in the para direction Lt; RTI ID = 0.0 > aryl, < / RTI > or heteroaryl groups. Accordingly, when the organic compound is applied to a device, it is possible to realize an organic optoelectronic device having a low driving voltage, a high efficiency and a long life.

L ^{1, which} is located in the central phenyl group of the indolo-carbazole moiety, is a substituted or unsubstituted C6 to C18 arylene group.

For example, L ¹ in the above formula (1) may be a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted terphenylene group.

In one example, L < ¹ > may be a substituted or unsubstituted phenylene group or a substituted or unsubstituted biphenylene group.

In one example, L ¹ may be a substituted or unsubstituted m-phenylene group or a substituted or unsubstituted m-biphenylene group.

Ar ¹ in the para direction to L ^{1 in the} above formula (1) is a substituted or unsubstituted C6 to C18 aryl group.

In one example, Ar ¹ may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group.

In one example, Ar ¹ may be a substituted or unsubstituted phenyl group.

Ar ² in Formula 1 is a substituted or unsubstituted C2 to C30 heteroaryl group.

For example, Ar ² is a heteroaryl group containing at least one nitrogen, for example, a substituted or unsubstituted pyridine group, a substituted or unsubstituted pyridazine group, a substituted or unsubstituted pyrimidine group, a substituted or unsubstituted pyrimidine group, A substituted or unsubstituted quinoline, a substituted or unsubstituted quinazoline, a substituted or unsubstituted quinoxaline, a substituted or unsubstituted quinoline, a substituted or unsubstituted quinoline, a substituted or unsubstituted quinazoline, or a substituted or unsubstituted quinoxaline.

R ¹ to R ⁸ in Formula 1 are each independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C20 alkyl groups, substituted or unsubstituted C6 to C30 aryl groups, or combinations thereof.

As an example, R ¹ to R ⁴ may each independently be hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl groups, substituted or unsubstituted C6 to C18 aryl groups, or combinations thereof.

As an example, each of R ¹ to R ⁴ may independently be hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C4 alkyl group, substituted or unsubstituted phenyl group, or combinations thereof.

In one example, each of R ⁵ to R ⁸ may independently be hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl group, or combinations thereof.

In one example, each of R ⁵ to R ⁸ may independently be hydrogen, deuterium, cyano group, substituted or unsubstituted C1 to C4 alkyl group, or combinations thereof.

For example, R ¹ to R ⁸ are each independently preferably hydrogen, deuterium, cyano, or a combination thereof. For example, R ¹ to R ⁸ may each be hydrogen.

The organic compound according to one embodiment may be represented by any one of the following Chemical Formulas (2) to (4).

(2)  (3) [Chemical Formula 4]

In formulas (2) to (4)

Ar ² is a substituted or unsubstituted C2 to C30 heteroaryl group,

R ¹ to R ¹² are each independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C20 alkyl group, substituted or unsubstituted C6 to C30 aryl group, or combinations thereof.

In one example, each of R ⁹ to R ¹² in the general formulas (2) to (4) may independently be hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl group, or combinations thereof.

In one example, each of R ⁹ to R ¹² may independently be hydrogen, deuterium, cyano group, substituted or unsubstituted C1 to C4 alkyl group, or combinations thereof.

For example, R ⁹ to R ¹² are each independently preferably hydrogen, deuterium, cyano, or a combination thereof. For example, R ⁹ to R ¹² may each be hydrogen.

In one example, Ar ² is located in the ortho, meta, and para directions with indolocarbazole. For example, Ar ² is preferably located in the meta direction with the indolocarbazole.

Particularly, when Ar ² is located in the meta direction with indolocarbazole to phenyl, the conjugation between indolocarbazole and Ar ² can be broken to increase the triplet energy. In particular, when Ar ² is an electron transport moiety , The stability of the compound can be achieved by separating HOMO and LUMO.

The organic compound may be represented, for example, by the following formula (5).

[Chemical Formula 5]

In formula (5)

Z ¹ to Z ⁵ are each independently N or CR ^a ,

At least one of Z ¹ to Z ⁵ is N,

R ¹ to R ¹² each independently represent hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C20 alkyl group, substituted or unsubstituted C6 to C30 aryl group, or combinations thereof,

R ^a is each independently selected from the group consisting of hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl groups, substituted or unsubstituted C6 to C30 aryl groups, substituted or unsubstituted C2 to C30 heteroaryl groups, ego,

At least one R ^< a > is independently present, or adjacent groups are connected to form a substituted or unsubstituted aliphatic, aromatic or heteroaromatic monocyclic or polycyclic ring.

For example, at least one of Z ¹ to Z ⁵ in Formula 5 may be N.

For example, at least two of Z ¹ to Z ⁵ in Formula 5 may be N.

For example, at least three of Z ¹ to Z ⁵ in Formula 5 may be N.

R ^a in Formula 5 may each independently be hydrogen, a substituted or unsubstituted C6 to C18 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or a combination thereof.

In one example, each R ^a may independently be hydrogen, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, or a substituted or unsubstituted biphenylene group.

In one example, each R ^a independently represents hydrogen, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted dibenzofuranyl group, A substituted or unsubstituted dibenzothiophenyl group, or a combination thereof.

For example, each R ^a independently represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzo A thiophene group, or a combination thereof.

For example, the organic compound may be represented by any one of the following Chemical Formulas (6) to (8).

[Chemical Formula 6] (7)     [Chemical Formula 8]

In formulas (6) to (8)

Z ¹ to Z ⁵ are each independently N or CR ^a ,

At least one of Z ¹ to Z ⁵ is N,

R ¹ to R ¹² each independently represent hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C20 alkyl group, substituted or unsubstituted C6 to C30 aryl group, or combinations thereof,

R ^a is each independently selected from the group consisting of hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl groups, substituted or unsubstituted C6 to C30 aryl groups, substituted or unsubstituted C2 to C30 heteroaryl groups, ego,

At least one R ^< a > is independently present, or adjacent groups are connected to form a substituted or unsubstituted aliphatic, aromatic or heteroaromatic monocyclic or polycyclic ring.

For example, R ^a in the above formulas (5) to (8) may form a monocyclic or polycyclic ring of an aliphatic, aromatic or heteroaromatic group in which adjacent groups are connected to each other to form a substituted or unsubstituted aliphatic, aromatic or heteroaromatic ring, Can be expressed.

[Chemical Formula 10]

In formulas (9) and (10)

Y ¹ is O or S,

Z ⁶ to Z ⁸ are each independently N or CR ^b ,

At least one of Z ⁶ to Z ⁸ is N,

R ^b and R ¹ to R ¹⁴ are each independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C20 alkyl groups, substituted or unsubstituted C6 to C30 aryl groups, or combinations thereof.

For example, at least two of Z ⁶ to Z ⁸ in the above formulas (9) and (10) may be N.

For example, Z ⁶ to Z ⁸ in the above formulas (9) and (10) may all be N.

R ^b in each of formulas (9) and (10) may independently be hydrogen, deuterium, cyano group, substituted or unsubstituted C6 to C18 aryl group, or combinations thereof.

In one example, each R ^b may independently be hydrogen, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, or a combination thereof.

In one embodiment, R ¹³ and R ¹⁴ of the general formula 9 and 10 are, each independently, may be a hydrogen, a deuterium, a cyano group, a substituted or unsubstituted C1 to C10 alkyl group, or a combination thereof, for example, R ¹³ and R ¹⁴ may all be hydrogen.

The organic compound may be, for example, compounds listed in Groups 1, 2, and 3, but is not limited thereto.

 [Group 1]

[Group 2]

[Group 3]

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.

In one embodiment of the present invention, the organic layer may include a light-emitting layer including a plurality of hosts, wherein the light-emitting layer comprises a triazine dianiline group containing the organic compound as a first host and substituted or unsubstituted as a second host, A substituted or unsubstituted pyrimidinyl group, and the like. Preferably, the light emitting layer may include a compound containing the organic compound as a first host and a triazine dianil group as a second host.

For example, the compound containing a triazinyl group or a pyrimidinyl group as the second host may be a compound in which at least one C6 to C60 aryl group is substituted in the triazine group, or a compound in which at least one C6 to C60 aryl group is substituted in the pyrimidinyl group Lt; / RTI >

For example, the second host may be in a form in which the triazinyl group is substituted with at least one selected from a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthracene group, a triphenylene group, a quaterphenyl group and a pentaphenyl group.

For example, the second host may be in the form of a pyrimidine or triazine group substituted with two or three C6 to C60 aryl groups, preferably three C6 to C60 aryl groups. Also optionally, the aryl group may be further substituted with a heteroaryl group or an aryl group.

As described above, by using a compound containing a triazine diisocyanate or a pyrimidine diisocyanate having high electron characteristics as the second host, it is possible to balance with the organic compound of the present invention having a strong hole characteristic, so that it is possible to exhibit more excellent device characteristics.

For example, the organic layer may include a light emitting layer, at least one auxiliary layer disposed 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 auxiliary layer of the at least one auxiliary layer adjacent to the light emitting layer may include the organic compound.

For example, the organic layer may include a light emitting layer, a hole transporting layer disposed between the anode and the light emitting layer, and a hole transporting auxiliary layer positioned adjacent to the light emitting layer between the light emitting layer and the hole transporting layer, Organic compounds.

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.

Referring to FIG. 1, an organic light emitting device 200 according to an embodiment includes an anode 110 and a cathode 120 facing each other, and an organic layer 105 between the anode 110 and the cathode 120 .

The anode 110 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 110 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 120 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 120 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 a light emitting layer 130.

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.

For example, the organic compound may be used as a first host, and an organic compound different from the organic compound may be used as a second host. For example, the second host may be an organic compound having electronic characteristics, but is not limited thereto.

The light emitting layer 130 may further include a dopant. The dopant may be a red, green or blue dopant, for example a blue 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 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, for example, a chemical vapor deposition method, sputtering, plasma plating, or ion plating, 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.

The organic layer 105 includes a hole-assist layer 140 positioned between the light-emitting layer 130 and the anode 110. The hole assist layer 140 may improve injection and / or movement of holes between the anode 110 and the light emitting layer 130, and may block and / or reduce the entry of electrons.

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

The hole-assist layer 140 may include the above-described organic compounds.

2, an organic light emitting diode 300 according to an embodiment includes an anode 110 and a cathode 120 facing each other, and an organic layer 105 located between the anode 110 and the cathode 120 .

The organic layer 105 includes a light emitting layer 130 and a hole auxiliary layer 140 positioned between the light emitting layer 130 and the anode 110.

The hole-assist layer 140 includes a hole-transport layer 141 and a hole-transport-assisting layer 142.

The hole transport layer 141 can facilitate hole transport from the anode 110 to the light emitting layer 130. [ The hole transport layer 141 may include a material having a HOMO energy level between the work function of the conductive material forming the anode 110 and the HOMO energy level of the material forming the light emitting layer 130.

The hole transporting layer 141 is not particularly limited, but may include, for example, a compound represented by the following formula (A).

(A)

In the above formula (A)

R ²¹ to R ²⁴ each independently represent hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof ,

R ²¹ and R ²² are each independently present or form a fused ring with each other,

R ²³ and R ²⁴ are each independently present or form a fused ring with each other,

Ar ³ to Ar ⁵ each independently represent a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,

L ² to L ⁵ each independently represent a single bond, a substituted or unsubstituted C2 to C10 alkylene group, a substituted or unsubstituted C2 to C10 alkenylene group, a substituted or unsubstituted C2 to C10 alkynylene group, A substituted or unsubstituted C6 to C30 arylene group, a divalently substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof.

For example, Ar ⁵ in the formula (A) may be a substituted or unsubstituted phenyl group, or a substituted or unsubstituted biphenyl group. In the formula (A), Ar ³ and Ar ⁴ each independently represent a substituted or unsubstituted phenyl group, A substituted or unsubstituted thiophene group, a substituted or unsubstituted thiophene group, a substituted or unsubstituted anthracene group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted thiophene group, A substituted or unsubstituted dibenzofurane group, or a substituted or unsubstituted dibenzothiophenyl group.

The hole transporting auxiliary layer 142 may be located adjacent to the light emitting layer 130 and may include the above-described organic compounds. The injection and / or movement of the holes transferred from the hole transport layer 141 at the interface between the light emitting layer 130 and the hole assisting layer 140 can be more effectively improved by including the above-described organic compound in the hole transport assisting layer 142, The efficiency and lifetime of the organic light emitting device can be improved by effectively blocking and / or reducing the entry of the organic light emitting device.

1 and 2, the organic layer 105 may further include at least one electron assist layer (not shown) positioned between the cathode 120 and the light emitting layer 130.

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.

Synthesis of organic compounds

The starting materials and reactants used in the synthesis examples and examples were purchased from Sigma-Aldrich, TCI, Alfa Aesar or other subcontractors unless otherwise noted.

Synthesis of indolecarbazole core

[Reaction Scheme 1]

To three types of indole carbazole core is the same synthesis method: the process proceeds through (reference J. Org Chem, 72, 19, 2007, Eur J. Org Chem 2010, 2576.....).

Synthesis Example 1: Synthesis of IDCBZ-m

3-Chlorobenzaldehyde (50.0 g, 356 mmol), indole (87.5 g, 747 mmol) and iodine (27.1 g, 107 mmol) were added to 1 L of acetonitrile and stirred at room temperature for 6 hours. Once the first reaction is complete, it is extracted once with saturated aqueous sodium sulfite solution and ethyl acetate. After evaporation of the organic layer solvent, the precipitated solid is dissolved in 400 mL of methyl alcohol together with triethylorthoformate (59.2 mL, 356 mmol). Methanesulfonic acid (46.2 mL, 711 mmol) is slowly added to this solution and stirred at room temperature for 12 hours. After the second reaction is over, the solution is put into excess water to precipitate a solid. The solid is filtered and extracted once with dichloromethane and water. The organic layer was purified by column chromatography and further recrystallized with a dichloromethane: n- hexane mixed solution to obtain IDCBZ-m (15.1 g, Y = 11.6%).

Synthesis Example 2: Synthesis of PhIDCBZ-m

(13.8 g, 87 mmol), bis (dibenzylideneacetone) palladium (0) (1.3 g, 2 mmol) and sodium tert-butoxide (10.85 g, 113 mmol) And then tri-tert-butylphosphine solution (5.37 mL, 11 mmol) was slowly added thereto, followed by reflux stirring at 140 ° C for 12 hours. When the reaction was completed, all the solvent was evaporated and purified by column chromatography with n- hexane: dichloromethane mixed solution to obtain PhIDCBZ-m (13.2 g, Y = 67.6%).

Synthesis Example 3: Synthesis of compound a-m

After dissolving PhIDCBZ-m (10.0 g, 19 mmol) in 500 mL tetrahydrofuran: DIW = 5: 2 mixture, slowly add iron (III) bromide (17.1 g, 58 mmol) and stir at room temperature for 20 hours. After the reaction was completed, the reaction mixture was extracted with ethyl acetate and the organic layer was evaporated. Compound a-m (8.8 g, Y = 76.4%) was obtained through column chromatography.

Synthesis Example 4: Synthesis of compound b-m

To a solution of compound am (5 g, 8 mmol), phenylboronic acid (1.43 g, 12 mmol), tetrakis (triphenylphosphine) palladium (0) (0.48 g, 0.4 mmol) and potassium carbonate (2.89 g, : DIW = 2: 1 mixed solution, and the mixture was refluxed and stirred at 80 ° C for 12 hours. After the reaction was completed, the organic layer was extracted and the solvent was evaporated. Compound bm (4.0 g, Y = 80.4%) was obtained by recrystallization from dichloromethane: n- hexane mixed solution.

Synthesis Example 5: Synthesis of compound c-m

(2.5 g, 10 mmol), potassium acetate (1.98 g, 20 mmol) and [1,1'-bis (diphenylphosphino) ferrocene] -dichloropalladium (II) (0.27 g, 0.3 mmol) were added to 30 mL of N , N- dimethylformamide and the mixture was refluxed at 150 ° C for 12 hours. When the reaction is complete, the solution is placed in an excess of DIW to form a precipitate. The precipitate is filtered, boiled in toluene and dissolved in silica gel. And recrystallized from the filtered solution to obtain yellow compound cm (4.1 g, Y = 88.8%).

Synthesis Example 6: Synthesis of compound c-p

4-chlorobenzaldehyde as a starting material, proceeding in the same manner as the whole synthesis process of compound c-m to obtain yellow compound c-p.

Synthesis Example 7: Synthesis of compound c-o

2-chlorobenzaldehyde as a starting material, proceeding in the same manner as the whole synthesis process of the compound c-m to obtain a yellow compound c-o.

Synthesis Example 8: Synthesis of Compound m-1

[Reaction Scheme 2]

Compound (10.0 g, 15 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (5.07 g, 19 mmol), tetrakis (triphenylphosphine) palladium (0) Then, potassium carbonate (5.03 g, 36 mmol) was dissolved in 110 mL of a tetrahydrofuran: DIW = 2: 1 mixed solution and refluxed at 80 ° C. for 12 hours. After the reaction was completed, the organic layer was extracted and the solvent was evaporated. The residue was recrystallized from toluene to obtain m-1 (8.7 g, Y = 75.4%).

Synthesis Example 9: Synthesis of Compound m-7

[Reaction Scheme 3]

Compound (10.0 g, 15 mmol), 2-chloro-4- (dibenzo [b, d] furan-3-yl) -6- (0.83 g, 1 mmol) of tetrakis (triphenylphosphine) palladium (5.03 g, 36 mmol) in tetrahydrofuran: DIW (2: 1) is stirred at reflux for 12 hours. After the reaction was completed, the organic layer was extracted and the solvent was evaporated. The residue was recrystallized with monochlorobenzene to obtain m-7 (11.3 g, Y = 88.0%).

Synthesis Example 10: Synthesis of Compound m-29

[Reaction Scheme 4]

Compound c-m2 was synthesized in the same manner as in the synthesis of compound c-m except that 3-biphenylboronic acid was used instead of phenylboronic acid in the synthesis of compound b in the above scheme 1. Potassium carbonate (4.53 g, 33 mmol) and tetrakis (triphenylphosphine) palladium (0) (0.76 g, 13 mmol) were added to a solution of Compound c-m2 (10.0 g, 13 mmol), 4-chloro-2,6-diphenylpyrimidine , 1 mmol) were dissolved in 100 mL of a tetrahydrofuran: DIW = 2: 1 mixed solution, and the mixture was refluxed and stirred at 80 ° C for 12 hours. After the reaction was completed, the organic layer was extracted and the solvent was evaporated, and recrystallized with monochlorobenzene to obtain m-29 (9.37 g, Y = 82.4%).

Synthesis Example 11: Synthesis of Compound m-50

[Reaction Scheme 5]

Compound (10.0 g, 15 mmol), 4-chloro-2,6-diphenylpyrimidine (4.75 g, 16 mmol), potassium carbonate (5.03 g, 36 mmol) and tetrakis (triphenylphosphine) palladium mmol) is dissolved in 110 mL of a tetrahydrofuran: DIW = 2: 1 mixed solution, and the mixture is refluxed and stirred at 80 ° C for 12 hours. When the reaction was completed, the organic layer was extracted and the solvent was evaporated. The residue was recrystallized with monochlorobenzene to obtain m-50 (8.84 g, Y = 73.9%).

Synthesis Example 12: Synthesis of Compound p-1

[Reaction Scheme 6]

Tetrakis (triphenylphosphine) palladium (0) (0.42 g, 0.5 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (2.54 g, Then, potassium carbonate (5.03 g, 18 mmol) was dissolved in 60 mL of a tetrahydrofuran: DIW = 2: 1 mixed solution, and the mixture was refluxed at 80 ° C. for 12 hours. After the reaction was completed, the organic layer was extracted and the solvent was evaporated. The solvent was recrystallized from monochlorobenzene to obtain p-1 (4.6 g, Y = 79.73%).

Synthesis Example 13: Synthesis of Compound p-5

[Reaction Scheme 7]

Compound (10.0 g, 15 mmol), 2-chloro-4- (dibenzo [b, d] furan-3-yl) -6- (0.83 g, 1 mmol) of tetrakis (triphenylphosphine) palladium (5.03 g, 36 mmol) in tetrahydrofuran: DIW (2: 1) is stirred at reflux for 12 hours. After the reaction was completed, the organic layer was extracted and the solvent was evaporated. The residue was recrystallized with monochlorobenzene to obtain m-7 (11.3 g, Y = 88.0%).

Synthesis Example 14: Synthesis of compound o-1

[Reaction Scheme 8]

Compound 2.c (5.0 g, 7 mmol), 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine (2.83 g, 7 mmol), tetrakis (triphenylphosphine) palladium (0) , 0.5 mmol) and potassium carbonate (2.52 g, 18 mmol) were dissolved in 60 mL of a tetrahydrofuran: DIW = 2: 1 mixed solution and refluxed at 80 ° C for 12 hours. After the reaction was completed, the organic layer was extracted and the solvent was evaporated. The residue was recrystallized with monochlorobenzene to obtain o-1 (2.8 g, Y = 44.30%).

Fabrication of organic light emitting device

Example 1

An organic light emitting device was fabricated using the compound m-1 obtained in Synthesis Example 8 as a host and acetylacetonatobis (2-phenylquinolinato) iridium (Ir (pq) ₂ acac) as a dopant.

As the anode, ITO was used to a thickness of 1500 Å, and aluminum (Al) was used as a cathode to 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, UV ozone cleaning was used for 30 minutes.

N, N-bis (3-methylphenyl) amino} -phenyl] -benzonitrile was deposited on the substrate at a vacuum degree of 650 × 10-7 Pa and a deposition rate of 0.1 to 0.3 nm / -N-phenylamino] biphenyl [DNTPD] was vacuum-deposited to form a hole injection layer having a thickness of 600 Å. Subsequently, HT-1 was vacuum vapor deposited under the same vacuum deposition conditions to form a 300 Å thick hole transport layer. Next, using the m-1 obtained in Synthesis Example 8 in the same vacuum deposition conditions were the film to form a light emitting layer having a thickness of 300 Å, a phosphorescent dopant acetylacetonatobis (2-phenylquinolinato) iridium ( Ir (pq) 2 acac) at the same time deposition Respectively. At this time, the deposition rate of the phosphorescent dopant was adjusted so that the phosphorescent dopant content was 7% by weight when the total amount of the light emitting layer was 100% by weight.

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, Tris (8-hydroxyquinolinato) aluminum (Alq3) was deposited under the same vacuum deposition conditions to form an electron transport layer having a thickness of 250 ANGSTROM. LiF and Al were sequentially deposited as an anode on the electron transporting layer to prepare an organic light emitting device.

The structure of the organic photoelectric device is ITO / DNTPD (60 nm) / HT-1 (30 nm) / EML ( Compound m-1 (93 _{wt%) + Ir (pq) 2} acac (7 wt%), 30 nm) / Balq (5 nm) / Alq ₃ (25 nm) / LiF (1 nm) / Al (100 nm).

Examples 2 to 7

The organic light emitting devices of Examples 2 to 7 were fabricated in the same manner as in Example 1 except that the compound described in [Table 1] was used instead of the compound m-1 in Example 1.

Comparative Example 1

An organic light emitting device was fabricated in the same manner as in Example 1 except that CBP was used as a light emitting layer instead of the compound m-1 in Example 1.

Comparative Example 2

An organic light emitting device was fabricated in the same manner as in Comparative Example 1, except that the compound compound d was used in place of the compound CBP in the light emitting layer.

The structures of HT-1 and Compound d used in the production of the organic light emitting device are as follows.

[HT-1]   [Compound d]

evaluation

The current density change, the luminance change, and the light emitting efficiency of the organic light emitting device according to Examples 1 to 7 and Comparative Examples 1 and 2 were measured according to the voltage. The specific measurement method is as follows, and the results are shown in Table 1.

(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 luminous efficiency (cd / A) was calculated using the luminance, current density and voltage measured from the above (1) and (2), and the results are summarized in Table 1, respectively.

No. compound The driving voltage (V) color
(EL color) Luminous efficiency
(cd / A) Example 1 m-1 4.3 Green 56.8 Example 2 m-7 4.1 Green 60.2 Example 3 m-29 4.3 Green 56.5 Example 4 m-50 4.4 Green 55.9 Example 5 p-1 3.9 Green 53.7 Example 6 p-5 3.9 Green 54.2 Example 7 o-1 4.3 Green 63.2 Comparative Example 1 CBP 4.8 Green 31.3 Comparative Example 2 Compound d 4.5 Green 51.6

Referring to Table 1, it can be seen that the organic electroluminescent device according to Examples 1 to 7 has significantly improved driving voltage as compared with the organic electroluminescent device according to Comparative Example 1, and the luminous efficiency is remarkably improved . Particularly, the electrons and hole injections used in Examples 2 and 7 are well balanced and thus the luminous efficiency is particularly high.

The device of Example 2 in which the compound m-7 in which the phenyl group as the substituent of triazine was substituted with dibenzofuran in the compound m-1 of Example 1 was used as the light emitting host, Which is better in terms of driving voltage and efficiency.

In Examples 1 to 4, in which the compound contained in Group 1 (meta) was used as a luminescent host, as compared with Examples 5 and 6 in which the compound contained in Group 2 (para) was used as a luminescent host, , And Examples 5 and 6 using a compound contained in Group 2 as a light emitting material are found to be dominant on the driving surface.

As compared with the organic light emitting device according to Comparative Example 2, Examples 1 to 4 using Group 1 having the same skeleton as the light emitting layer were remarkably improved in terms of driving voltage and luminous efficiency, And the effect of introducing a phenyl group into the compound is shown.

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.

200, 300: Organic light emitting device
105: organic layer 110: anode
120: cathode 130: light emitting layer
140: hole-assist layer 141: hole-transport layer
142: hole transporting auxiliary layer

Claims (12)

An organic compound represented by the following Formula 1:
[Chemical Formula 1]

In formula (1)
L ¹ is a substituted or unsubstituted C6 to C18 arylene group,
Ar ¹ is a substituted or unsubstituted C 2 to C 18 aryl group,
Ar ² is a substituted or unsubstituted C2 to C30 heteroaryl group,
R ¹ to R ⁸ are each independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C20 alkyl groups, substituted or unsubstituted C6 to C30 aryl groups, or combinations thereof. The method of claim 1,
L ¹ is a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group or a substituted or unsubstituted terphenylene group,
Ar ¹ is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group. The method of claim 1,
R ¹ to R ⁴ are each independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl groups, substituted or unsubstituted C6 to C18 aryl groups, or combinations thereof,
R ⁵ to R ⁸ are each independently hydrogen, deuterium, cyano group, substituted or unsubstituted C1 to C10 alkyl group, or combinations thereof. The method of claim 1,
An organic compound represented by any one of the following Chemical Formulas 2 to 4:
[Chemical Formula 2] < EMI ID =

In formulas (2) to (4)
Ar ² is a substituted or unsubstituted C2 to C30 heteroaryl group,
R ¹ to R ¹² are each independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C20 alkyl group, substituted or unsubstituted C6 to C30 aryl group, or combinations thereof. 5. The method of claim 4,
R ⁹ to R ¹² each independently represent hydrogen, deuterium, cyano group, substituted or unsubstituted C1 to C10 alkyl group, or combinations thereof. The method of claim 1,
An organic compound represented by the following formula (5):
[Chemical Formula 5]

In formula (5)
Z ¹ to Z ⁵ are each independently N or CR ^a ,
At least one of Z ¹ to Z ⁹ is N,
R ^a and R ¹ to R ¹² are each independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C20 alkyl groups, substituted or unsubstituted C6 to C30 aryl groups, or combinations thereof,
At least one R ^a is independently selected from the group consisting of hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C20 alkyl groups, substituted or unsubstituted C6 to C30 aryl groups, substituted or unsubstituted C2 to C30 heteroaryl groups, A combination thereof,
The R ^a may be independently present, or adjacent groups may be connected to form a substituted or unsubstituted aliphatic, aromatic or heteroaromatic monocyclic or polycyclic ring. The method of claim 6,
An organic compound represented by any one of the following formulas (6) to (8):
[Chemical Formula 7] < EMI ID =

In formulas (6) to (8)
Z ¹ to Z ⁵ are each independently N or CR ^a ,
At least one of Z ¹ to Z ⁵ is N,
R ¹ to R ¹² each independently represent hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C20 alkyl group, substituted or unsubstituted C6 to C30 aryl group, or combinations thereof,
At least one R ^a is independently selected from the group consisting of hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C20 alkyl groups, substituted or unsubstituted C6 to C30 aryl groups, substituted or unsubstituted C2 to C30 heteroaryl groups, A combination thereof,
The R ^a may be independently present, or adjacent groups may be connected to form a substituted or unsubstituted aliphatic, aromatic or heteroaromatic monocyclic or polycyclic ring. The method of claim 6,
An organic compound represented by the following formula (9) or (10):
[Chemical Formula 10]

In formulas (9) and (10)
Y ¹ is O or S,
Z ⁶ to Z ⁸ are each independently N or CR ^b ,
At least one of Z ⁶ to Z ⁸ is N,
R ^b and R ¹ to R ¹⁴ are each independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C20 alkyl groups, substituted or unsubstituted C6 to C30 aryl groups, or combinations thereof. The method of claim 1,
Organic compounds listed in Groups 1 to 3 below.
[Group 1]

[Group 2]

[Group 3]

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 9. 11. The method of claim 10,
Wherein the organic layer comprises a light-emitting layer containing the organic compound. A display device comprising the organic opto-electronic device according to claim 10.

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