KR20180010808A - Compound for organic optoelectronic device, composition for organic optoelectronic device and organic optoelectronic device and display device - Google Patents

Abstract

The present invention relates to: a compound for an organic optoelectronic device represented by chemical formula 1; a composition for an organic optoelectronic device; an organic optoelectronic device using the same; and a display device. The details of the chemical formula 1 are the same as defined in the specification. One embodiment provides the compound for the organic optoelectronic device capable of implementing a high-efficiency and long-lived organic optoelectronic device.

Description

Technical Field The present invention relates to a compound for organic optoelectronic devices, a composition for organic optoelectronic devices, an organic optoelectronic device, and a display device. BACKGROUND OF THE INVENTION 1. Field of the Invention [0001]

Compounds for organic optoelectronic devices, compositions for organic optoelectronic devices, 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. The organic light emitting diode is a device for converting electrical energy into light by applying an electric current to the organic light emitting material, and usually has an organic layer inserted between an anode and a cathode. The organic layer may include a light emitting layer and an optional auxiliary layer. The auxiliary layer may include, for example, a hole injecting layer, a hole transporting layer, an electron blocking layer, an electron transporting layer, an electron injecting layer, Lt; RTI ID = 0.0 > layer. ≪ / RTI >

The performance of the organic light-emitting device is greatly affected by the characteristics of the organic layer, and the organic light-emitting device is highly affected by the organic material contained in the organic layer.

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

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

Another embodiment provides a composition for an organic optoelectronic device including the compound for an organic optoelectronic device.

Yet another embodiment provides an organic optoelectronic device comprising such a compound.

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

According to one embodiment, there is provided a compound for an organic optoelectronic device represented by the following formula (1).

[Chemical Formula 1]

In formula (1)

X ¹ to X ³ are each independently N or CR ^a ,

At least one of X ¹ to X ³ is N,

Y is O or S,

Ar ¹ is a substituted or unsubstituted C6 to C30 aryl group,

R ^a and R ¹ to R ¹² are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group,

L ¹ and L ² are each independently a single bond or a substituted or unsubstituted C6 to C30 arylene group.

According to another embodiment, the organic light emitting device includes 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 is a compound for the organic optoelectronic device or a composition And an organic electroluminescent device.

According to another embodiment, there is provided a display device including the organic optoelectronic device.

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

1 and 2 are cross-sectional views illustrating an organic light emitting device according to one 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 hydrogen in the substituent or compound is replaced with a substituent selected from the group consisting of deuterium, a halogen group, a hydroxyl group, an amino group, a substituted or unsubstituted C1 to C30 amine group, a nitro group, A C1 to C30 alkyl group, a C1 to C10 alkylsilyl group, a C6 to C30 arylsilyl group, a C3 to C30 cycloalkyl group, a C3 to C30 heterocycloalkyl group, a C6 to C30 aryl group, a C2 to C30 aryl group, Substituted with a C1-C20 alkyl group, a C1-C20 alkoxy group, a fluoro group, a C1-C10 trifluoroalkyl group, a cyano group, or a combination thereof.

In one embodiment of the invention, "substituted" means that at least one of the substituents or the hydrogen in the compound is deuterium, a C1 to C30 alkyl group, a C1 to C10 alkylsilyl group, a C6 to C30 arylsilyl group, a C3 to C30 cycloalkyl group, A heterocycloalkyl group, a C6 to C30 aryl group, or a C2 to C30 heteroaryl group. In a specific example of the present invention, "substituted" means that at least one hydrogen in the substituent or the compound is substituted with deuterium, a C1 to C20 alkyl group, a C6 to C30 aryl group, or a C2 to C30 heteroaryl group. In a specific embodiment of the present invention, the "substitution" means that at least one hydrogen is substituted with a substituent selected from the group consisting of deuterium, a C1 to C20 alkyl group, a C6 to C30 aryl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted quinolinyl group, Or an unsubstituted isoquinolinyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

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

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

The alkyl group may be an alkyl group of C1 to C30. More specifically, the alkyl group may be a C1 to C20 alkyl group or a C1 to C10 alkyl group. For example, C1 to C4 alkyl groups mean that from 1 to 4 carbon atoms are included in the alkyl chain and include methyl, ethyl, propyl, iso-propyl, n-butyl, iso-butyl, sec- Indicating that they are selected from the group.

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

As used herein, the term " aryl group "is intended to encompass groups having one or more hydrocarbon aromatic moieties, in which all the elements of the hydrocarbon aromatic moiety have a p-orbital, Such as a biphenyl group, a terphenyl group, a quaterphenyl group, and the like, which include two or more hydrocarbon aromatic moieties including a phenyl group, a naphthyl group, and the like, in which two or more hydrocarbon aromatic moieties are connected through a sigma bond, May also include non-aromatic fused rings fused directly or indirectly. For example, a fluorenyl group and the like.

The aryl groups include monocyclic, polycyclic or fused ring polycyclic (i. E., Rings that divide adjacent pairs of carbon atoms) functional groups.

As used herein, the term " heterocyclic group "is a superordinate concept including a heteroaryl group, and includes N, O, and S substituents in the ring compound such as an aryl group, a cycloalkyl group, a fused ring thereof, Means at least one heteroatom selected from the group consisting of S, P and Si. When the heterocyclic group is a fused ring, the heterocyclic group or the ring may include one or more heteroatoms.

As used herein, the term " heteroaryl group "means containing at least one heteroatom selected from the group consisting of N, O, S, P and Si in the aryl group. Two or more heteroaryl groups may be directly connected through a sigma bond, or when the heteroaryl group includes two or more rings, two or more rings may be fused together. When the heteroaryl group is a fused ring, it may contain 1 to 3 heteroatoms in each ring.

The heterocyclic group may include, for example, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group and the like.

More specifically, the substituted or unsubstituted C6 to C30 aryl group and / or the substituted or unsubstituted C2 to C30 heterocyclic group may be substituted or unsubstituted phenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted anthra Substituted or unsubstituted phenanthrenyl groups, substituted or unsubstituted naphthacenyl groups, substituted or unsubstituted pyrenyl groups, substituted or unsubstituted biphenyl groups, substituted or unsubstituted p-terphenyl groups, substituted or unsubstituted naphthacenyl groups, A substituted or unsubstituted naphthyl group, a substituted m-terphenyl group, a substituted or unsubstituted o-terphenyl group, a substituted or unsubstituted chrysenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted perylenyl group, A substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted pyrazolyl group, Substituted or unsubstituted oxadiazole groups, substituted or unsubstituted thiadiazole groups, substituted or unsubstituted thiadiazole groups, substituted or unsubstituted thiadiazole groups, substituted or unsubstituted thiadiazole groups, substituted or unsubstituted thiadiazole groups, A substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted thiazinyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted pyrazinyl 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 benzoxazinyl group, a substituted or unsubstituted benzothiazine group, a substituted or unsubstituted azo group A substituted or unsubstituted phenanthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted phenothiazyl group, a substituted or unsubstituted phenothiazyl group, a substituted or unsubstituted dibenzofuranyl group, Thiophene group, or a combination thereof, but is 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 compounds for organic optoelectronic devices according to one embodiment will be described below.

The compound for organic optoelectronic devices according to one embodiment is represented by the following formula (1).

[Chemical Formula 1]

In formula (1)

X ¹ to X ³ are each independently N or CR ^a ,

At least one of X ¹ to X ³ is N,

Y is O or S,

Ar ¹ is a substituted or unsubstituted C6 to C30 aryl group,

R ^a and R ¹ to R ¹² are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group,

L ¹ and L ² are each independently a single bond or a substituted or unsubstituted C6 to C30 arylene group.

The compound for organic optoelectronic devices represented by Formula 1 according to an embodiment includes a carbazole substituted carbazole group, and a heterocyclic group containing at least one nitrogen is substituted with dibenzofuran or dibenzofuran As a basic skeleton, a structure which is bonded at position 3 of dibenzothiophen.

The nitrogen-containing heterocyclic group according to an embodiment includes dibenzofuran or dibenzothiophen with a substituent which is directly connected to the nitrogen atom-containing heterocyclic group and the dibenzothiophen at the 3-position of dibenzofuran Or dibenzothiophene is coupled to the structure, so that the orbit of LUMO is extended on the structure, so that it is possible to obtain a structure which is easy to receive electrons when an electric field is applied. Accordingly, the driving voltage of the organic optoelectronic device to which the compound for an organic optoelectronic device is applied can be lowered.

In addition, the compound for organic optoelectronic devices according to an embodiment is a compound having a triple-energy and is electrochemically stable, is bonded to a nitrogen-containing heterocyclic ring substituted at the 3-position of dibenzofuran or dibenzothiophene, , Electron withdrawing group (EWG), and electron donating group (EDG), all of the molecules exhibit bipolar characteristics and have high bonding strength to holes and electrons. Therefore, It is not only advantageous as a host in the light emitting layer of the device but also applicable to the hole transporting layer and the hole injecting layer.

Therefore, when the compound represented by Formula 1 of the present invention is used as a material for a hole injection layer, a hole transporting layer, or a light emitting layer of an organic light emitting device, the efficiency and lifetime of the organic light emitting device can be improved.

In Formula 1, at least two of X ¹ to X ³ are N, and preferably all of X ¹ to X ³ are N.

The compound for an organic optoelectronic device according to an embodiment may be represented by the following formulas 1-1 to 1-3:

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

In Formulas 1-1 to 1-3,

X ¹ to X ³ are each independently N or CR ^a ,

At least one of X ¹ to X ³ is N,

Ar ¹ is a substituted or unsubstituted C6 to C30 aryl group,

Y is O or S,

R ^a and R ¹ to R ¹² are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group,

L ¹ and L ² are each independently a single bond or a substituted or unsubstituted C6 to C18 arylene group,

a and b are each independently an integer of 1 to 3;

In one example, X ¹ to X ³ in the general formulas 1-1 to 1-3 may all be N.

In one example, X ¹ and X ³ in Formulas 1-1 through 1-3 may be N and X ² may be CH.

In one example, X ¹ and X ² in Formulas 1-1 through 1-3 may be N and X ³ may be CH.

In one example, X ² and X ³ in Formulas 1-1 through 1-3 may be N and X ¹ may be CH.

In one example, X ¹ in Formulas 1-1 through 1-3 may be N, and X ² and X ³ may be CH.

In one example, X ² in Formulas 1-1 through 1-3 may be N, and X ¹ and X ³ may be CH.

In one example, X ³ in Formulas 1-1 through 1-3 may be N, and X ¹ and X ² may be CH.

In one example, Ar ¹ in the above Chemical Formulas 1-1 to 1-3 may be a phenyl group, a naphthyl group, a biphenyl group, a triphenyl group, or a fluorenyl group.

In one example, L ¹ and L ² in Formulas 1-1 through 1-3 may be a single bond.

In one example, L ¹ in Formulas 1-1 to 1-3 is a single bond, L ² is a phenylene group, or L ² is a single bond, and L ¹ is a phenylene group.

In one example, L ¹ and L ² in the above Formulas 1-1 to 1-3 may be a phenylene group.

When the nitrogen-containing heterocyclic group includes a substituent directly connected to the nitrogen atom at the 3-position of the dibenzofuranyl group or the dibenzothiophen yl group as in the above formulas 1-1 to 1-3, the electron cloud of the LUMO is located on one plane , It is possible to maximize the effect of enlarging the organic EL device. Therefore, when the compound is applied to the organic light emitting device, optimum effects can be obtained in terms of driving reduction and lifetime increase. A compound in which a nitrogen-containing heterocyclic group and dibenzofuran or dibenzothiophene are connected to another position other than the 3-position, or a compound in which a nitrogen-containing heterocyclic group is bonded to dibenzofuran or dibenzothiophene, When applied to an organic light emitting device, the driving reduction effect through expansion of the LUMO electron cloud is reduced.

In Formula 1, Ar ¹ is a substituted or unsubstituted C6 to C30 aryl group.

Examples of the substituted or unsubstituted C6 to C30 aryl group in Formula 1 include a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted A phenanthryl 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 For example, a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a 2-naphthyl group, a 2-substituted naphthyl group, Naphthyl group, 2-biphenyl group, 3-biphenyl group, 4-biphenyl group, o-terphenyl group, m-terphenyl group or p-terphenyl group.

Specifically, Ar ¹ in the formula (1) is a substituted or unsubstituted C6 to C30 aryl ring, preferably a substituted or unsubstituted C6 to C18 aryl group, more preferably, a substituted or unsubstituted C6 to C12 It is preferably an aryl group. For example, Ar ¹ according to one embodiment is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted p-terphenyl group, a substituted or unsubstituted m-terphenyl group, a substituted or unsubstituted o-terphenyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted triphenylenyl group, An orenyl group, for example, a phenyl group, a naphthyl group, a biphenyl group, and a terphenyl group.

More specifically, in one embodiment of the present invention, the Ar ¹ may be a phenyl group, a p-biphenyl group, an m-biphenyl group, a p-terphenylene group, a m-terphenylene group, It is not.

Here, the "substitution" in the substituted aryl group of Ar ¹ means that at least one hydrogen is substituted with a deuterium, a C1 to C20 alkyl group, or a C6 to C30 aryl group. For example, the "substitution" means that at least one hydrogen is replaced by a substituent selected from the group consisting of deuterium, C1 to C10 alkyl groups, or C6 to C18 aryl groups such as at least one hydrogen, deuterium, C1 to C4 alkyl groups, C12 < / RTI > aryl group.

L ¹ and L ² in the above formula (1) are each independently a single bond or a substituted or unsubstituted C6 to C30 arylene group, preferably a single bond or a substituted or unsubstituted C6 to C18 aryl It is preferable that R < 1 > For example, the linking groups L ¹ and L ² according to an embodiment are each independently a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted naphthylene group, a substituted Or an unsubstituted or substituted p-terphenylene group, a substituted or unsubstituted m-terphenylene group, a substituted or unsubstituted o-terphenylene group, a substituted or unsubstituted anthracenylene group, a substituted or unsubstituted phenanthrenylene group , A substituted or unsubstituted triphenylenylene group, or a substituted or unsubstituted fluorenylene group.

More specifically, in one embodiment of the present invention, each of L ¹ and L ² may independently be a single bond, a phenyl group, a p-biphenyl group, an m-biphenyl group, or the like, but is not limited thereto.

In one embodiment of the present invention, Ar ¹ in the formula (1) is a phenyl group, a naphthaligly group, a biphenyl group, a terphenyl group, or a fluorenyl group, L ¹ and L ² each independently represent a single bond, a phenyl group or a biphenyl group , For example, the following formulas (1-a) to (1-d).

[Chemical Formula 1-a]

[Chemical Formula 1-b]

[Chemical Formula 1-c]

[Chemical formula 1-d]

In formulas (1-a) to (1-d)

X ¹ to X ³ are each independently N or CR ^a ,

At least one of X ¹ to X ³ is N,

Y is O or S,

n1, n2, m, and k are each independently an integer of 0 to 2,

R ^a and R ¹ to R ¹⁴ are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C18 aryl group, or a combination thereof,

R ¹³ and R ¹⁴ are connected to each other to form a substituted or unsubstituted aromatic monocyclic or polycyclic ring.

In one example, R ¹³ and R ¹⁴ in the above-mentioned 1-a and 1-b may be adjacent to each other and may be a naphthyl group, an anthracenyl group, a phenanthryl group, a triphenylene group or a fluorenyl group.

In one example, m in formula (1-b) and formula (1-d) may be 1 and k may be 0.

In one example, m in formula (1-b) and formula (1-d) may be 2, and k may be 0.

In one example, n1 and n2 in the above general formulas (1-a) to (1-d) may each independently be 0 or 1.

In one example, n1 and n2 in the general formulas (1-a) to (1-d) may all be 0. R ¹ to R ¹² in Formula 1 may each independently be hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a combination thereof, Is preferably hydrogen, deuterium, an unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C18 aryl group, or a combination thereof, more preferably hydrogen, deuterium, substituted or unsubstituted C1 to C4 An alkyl group, a substituted or unsubstituted C6 to C12 aryl group, or a combination thereof.

Specifically, each of R ⁹ to R ¹² in Formula 1 may be independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C18 aryl group, or a combination thereof , Preferably hydrogen, deuterium, a substituted or unsubstituted C1 to C4 alkyl group, a substituted or unsubstituted C6 to C12 aryl group, or a combination thereof. For example, each of R ⁹ to R ¹² according to one embodiment is independently selected from the group consisting of hydrogen, deuterium, methyl, ethyl, propyl, n-butyl, sec-butyl, Or a combination thereof.

Specifically, R ¹ to R ⁴ in Formula 1 may each independently be hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C18 aryl group, or a combination thereof , Preferably hydrogen, deuterium, a substituted or unsubstituted C1 to C4 alkyl group, a substituted or unsubstituted C6 to C12 aryl group, or a combination thereof. For example, R ¹ to R ⁴ according to one embodiment may each independently be hydrogen, deuterium, a methyl group, a phenyl group, or a combination thereof.

Specifically, R ⁵ to R ⁸ in the above formula (1) may each independently be hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C18 aryl group, or a combination thereof , Preferably hydrogen, deuterium, a substituted or unsubstituted C1 to C4 alkyl group, a substituted or unsubstituted C6 to C12 aryl group, or a combination thereof. For example, R ⁵ to R ⁸ according to one embodiment may each independently be hydrogen, deuterium, methyl, phenyl or combinations thereof.

In one embodiment of the present invention, R ¹ to R ¹² in Formula 1 may each independently be hydrogen.

The compound for organic optoelectronic devices represented by Formula 1 may be selected from compounds listed in the following Group 1, but is not limited thereto.

[Group 1]

The compound for a first organic optoelectronic device described above can be applied to an organic optoelectronic device and can be applied to an organic optoelectronic device either alone or in combination with another compound for an organic optoelectronic device. When the above-mentioned compound for an organic optoelectronic device is used together with another compound for an organic optoelectronic device, it can be applied in the form of a composition.

Hereinafter, an example of the composition for an organic optoelectronic device including the aforementioned compound for a first organic optoelectronic device will be described.

The composition for an organic optoelectronic device according to another embodiment of the present invention includes the compound for the first organic optoelectronic device and the compound for the second organic optoelectronic device represented by the following formula (2).

(2)

In Formula 2,

L ³ and L ⁴ are each independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, or a combination thereof,

Ar ² and Ar ³ are each independently a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof,

R ²¹ to R ²⁶ are each Independently, hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or combinations thereof,

l is one of integers from 0 to 2,

Means that at least one hydrogen is substituted by deuterium, a C1 to C4 alkyl group, a C6 to C18 aryl group, or a C2 to C30 heteroaryl group.

In one embodiment of the present invention, L ² and L ³ in Formula 2 may each independently be a single bond, or a substituted or unsubstituted C6 to C18 arylene group.

In one embodiment of the present invention, Ar ² and Ar ³ in Formula 2 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted A naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted quinazolyl group, a substituted Substituted or unsubstituted quinolinyl groups, substituted or unsubstituted dibenzothiophenyl groups, substituted or unsubstituted dibenzofuranyl groups, substituted or unsubstituted quinolinyl groups, substituted or unsubstituted quinolinyl groups, substituted or unsubstituted quinolinyl groups, An unsubstituted isoquinolinyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted fluorenyl group, or a combination thereof.

In one embodiment of the present invention, Ar ² and Ar ³ in Formula 2 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted Naphthyl group, substituted or unsubstituted anthracenyl group, substituted or unsubstituted triphenylenyl group, substituted or unsubstituted pyridinyl group, substituted or unsubstituted quinazolyl group, substituted or unsubstituted isoquinazolyl group, A substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, Or an unsubstituted fluorenyl group, or a combination thereof.

In one embodiment of the present invention, Ar ² and Ar ³ in Formula 2 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted A naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted fluorenyl group, or a combination thereof.

In one example, each of R ²¹ to R ²⁶ in Formula 2 may be independently hydrogen, deuterium, or a substituted or unsubstituted C6 to C12 aryl group. For example, R ²¹ to R ²⁶ in Formula 2 may be Independently hydrogen or deuterium.

In one example, l in formula 2 may be 0 or 1, for example, l may be 0.

In one specific embodiment of the present invention, * -L ³ -Ar ² and * -L ⁴ -Ar ³ are one of the substituents listed in the following Group II, and Formula 2 is a Is a compound to which the substituents listed in Group II are bonded.

[Group I]

[Group II]

In Groups I and II above, * is the connection point.

The second organic optoelectronic device compound represented by Formula 2 may be selected from the compounds listed in the following Group 2, for example.

[Group 2]

The first host compound and the second host compound described above can be prepared in various compositions in various combinations.

The composition according to an embodiment of the present invention comprises a compound represented by Formula 1-1 or Formula 1-2 as a first host, wherein L ² and L ³ are each independently a single bond, A substituted or unsubstituted C6 to C30 arylene group; Ar ² and Ar ³ are each independently a substituted or unsubstituted C6 to C30 aryl group; R ²¹ to R ²⁶ are each Independently, hydrogen, deuterium, substituted or unsubstituted C1 to C20 alkyl groups, substituted or unsubstituted C6 to C30 aryl groups; and l is 0 as a second host.

The composition according to one embodiment of the present invention comprises the compound represented by Formula 1-1 or Formula 1-2 as a first host and the compound represented by Formula E-31, E-99, E-129, And E-140 as a second host.

The compound for the second organic optoelectronic device may be used in the light emitting layer together with the compound for the first organic optoelectronic device to increase the mobility of the charge and increase the stability, thereby improving the luminous efficiency and lifetime. Also, the charge mobility can be controlled by controlling the ratio of the compound for the second organic optoelectronic device and the compound for the first organic optoelectronic device.

Such as from about 1: 9 to about 9: 1, and more specifically from 2: 8 to 8: 2, from 3: 7 to 7: 3, from 4: 6 to 6: 4, and from 5: 5 For example, the compound for the first organic optoelectronic device and the compound for the second organic optoelectronic device can be included in the range of 3: 7. The compound for a first organic optoelectronic device and the compound for a second organic optoelectronic device may be in a weight ratio of 1: 1 to 1: 4 and a weight ratio of 1: 1 to 1: 3, a weight ratio of 1: 1 to 4: Lt; / RTI >

 By including it in the above range, the efficiency and the life can be improved at the same time.

The composition may further include at least one organic compound in addition to the compound for a first organic optoelectronic device and the compound for a second organic optoelectronic device.

The compound for an organic optoelectronic device may further include a dopant. The dopant may be a red, green or blue dopant.

The dopant may be a material that emits light by mixing a small amount of light, and may be a material such as a metal complex that emits light by multiple excitation that excites it to a triplet state. The dopant may be, for example, an inorganic, organic, or organic compound, and may include one or more species.

Examples of the phosphorescent dopant include Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd or combinations thereof And the like. The phosphorescent dopant may be, for example, a compound represented by the following formula (Z), but is not limited thereto.

(Z)

L ₂ MX

In the above formula (Z), M is a metal, L and X are the same or different from each other and are ligands that complex with M.

M may be, for example, Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd or combinations thereof, For example, it may be a bidentate ligand.

Hereinafter, the compound for an organic optoelectronic device or the organic optoelectronic device to which the composition for an organic optoelectronic device is applied will be described.

The organic optoelectronic device according to another embodiment includes 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 is a compound for the organic optoelectronic device, And a composition for a device.

For example, the organic layer includes a light emitting layer, and the light emitting layer may include a compound for an organic optoelectronic device of the present invention, or a composition for an organic optoelectronic device.

Specifically, the compound for an organic optoelectronic device or the composition for an organic optoelectronic device may be included as a host of the light emitting layer, for example, a green host.

The organic layer may include at least one auxiliary layer selected from a light emitting layer and a hole injecting layer, a hole transporting layer, an electron blocking layer, an electron transporting layer, an electron injecting layer and a hole blocking layer, , Or compositions for organic optoelectronic devices.

The auxiliary layer may further include an electron transporting auxiliary layer adjacent to the light emitting layer, and the electron transporting auxiliary layer may include a compound for the organic optoelectronic device or a composition for an organic optoelectronic device.

In one embodiment of the present invention, the compound for organic optoelectronic devices included in the electron transporting layer may be represented by the formula 1-I, the formula 1-a, or the formula 1-c .

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

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

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

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

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

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

The organic layer 105 includes the light emitting layer 130 including the compound for the organic optoelectronic device described above.

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

Referring to FIG. 2, the organic light emitting diode 200 further includes a hole-assist layer 140 in addition to the light-emitting layer 130. The hole auxiliary layer 140 can further enhance hole injection and / or hole mobility between the anode 120 and the light emitting layer 130 and block electrons. The hole-assist layer 140 may be, for example, a hole transport layer, a hole injection layer, and / or an electron blocking layer, and may include at least one layer.

1 or 2 may further include an electron injection layer, an electron transport layer, an electron transporting auxiliary layer, a hole transporting layer, a hole transporting auxiliary layer, a hole injecting layer, or a combination layer thereof have. The compound for organic optoelectronic devices of the present invention can be included in these organic layers. The organic light emitting devices 100 and 200 may be formed by forming an anode or a cathode on a substrate and then performing a dry deposition method such as evaporation, sputtering, plasma plating, and ion plating; Or a wet film formation method such as spin coating, dipping or flow coating, and then forming a cathode or anode on the organic layer.

The 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.

Hereinafter, the starting materials and the reaction materials used in Examples and Synthesis Examples were purchased from Sigma-Aldrich, Apichemical or TCI, or synthesized by known methods, unless otherwise specified.

(Preparation of compound for organic optoelectronic device)

The compounds shown as more specific examples of the compounds of the present invention were synthesized by the following steps.

(Compound for first organic optoelectronic device)

Synthetic example  1: Synthesis of compound [1]

[Reaction Scheme 1]

Step 1  : Synthesis of intermediate A

Dichloro-6-phenyl-1,3,5-triazine (50.55 g, 223.59 mmol) and dibenzofuran-3-ylboronic acid (40.3 g, 190.06 mmol) were added to a 2 L round bottom flask in a nitrogen atmosphere. ) Was dissolved in 900 mL of tetrahydrofuran, and tetrakis (triphenylphosphine) palladium (12.9 g, 11.18 mmol) was added thereto and stirred. Saturated potassium carbonate (61.8 g, 447.19 mmol) was added, and the mixture was heated at 80 占 폚 for 12 hours to reflux. After completion of the reaction, the organic layer was separated, and water was removed with anhydrous MgSO ₄ , followed by filtration and concentration under reduced pressure. The thus-obtained residue was crystallized using dichloromethane and hexane to obtain 35.3 g (44%) of intermediate A.

Step 2  : Synthesis of intermediate B

3-Bromocarbazole (7.4 g, 29.96 mmol) was added to 240 mL of N, N-dimethylformamide (DMF) and stirred with a sodium hydride (60% g, 59.92 mmol) is slowly added. After 30 minutes, the intermediate A (12.6 g, 35.25 mmol) was slowly added and stirred for 12 hours. Pour the reaction into water and filter the resulting solid. The residue thus obtained was solidified using dichlorobenzene and methanol to obtain 17 g (85%) of intermediate B.

Step 3  : Compound [ 1]  synthesis

50 ml of xylene was dissolved in the intermediate B (16.5 g, 29.06 mmol), carbazole (5.8 g, 34.88 mmol) and tertiary butoxy sodium (5.6 g, 58.13 mmol), palladium (dibenzylideneacetone) g, 1.45 mmol) and tert-butylphosphine (1.41 g, 2.91 mmol, 50% toluene mixture). The reaction solution was heated at 120 캜 for 12 hours under a nitrogen stream and stirred. After the completion of the reaction, methanol was poured into the reaction product to filter out the resulting solid, and the solid substance was dissolved again in dichlorobenzene. Activated carbon and anhydrous magnesium sulfate were added thereto, stirred, filtered and then recrystallized from dichlorobenzene and methanol to obtain 16 g %).

LC Mass (theory: 653.73 g / mol, measured: M + H ⁺ = 654.22 g / mol)

Synthetic example  2: Synthesis of compound [40]

[Reaction Scheme 2]

Step 1  : Synthesis of intermediate C

(36.3 g, 159.15 mmol) was reacted with 2,4-dichloro-6-phenyl-1,3,5-triazine (42.3 g, 30 g (43%) of intermediate C was obtained using the same method as the synthesis method.

Step 2  : Synthesis of intermediate D

16 g (80%) of Intermediate D was obtained using the same synthetic method as Intermediate B using 3-bromocarbazole (7.17 g, 29.13 mmol) and Intermediate C (12.8 g, 34.28 mmol).

Step 3  : Compound [ 40] of  synthesis

13 g (76%) of compound [40] was obtained by using the intermediate D (14.8 g, 25.38 mmol) and carbazole (5.1 g, 30.46 mmol) using the same synthetic method as that for the compound [ .

LC Mass (theory: 669.79 g / mol, measured: M + H ⁺ = 670.20 g / mol)

Synthetic example  3: Compound [ 2]  synthesis

[Reaction Scheme 3]

Step 1  : Synthesis of intermediate E

17 g (85%) of Intermediate E was obtained using the same synthetic method as Intermediate B using 2-bromocarbazole (7.4 g, 29.96 mmol) and Intermediate A (12.61 g, 35.25 mmol).

Step 2  : Compound [ 2]  synthesis

14 g (82%) of compound [2] was obtained using the intermediate E (14.756 g, 26 mmol) and carbazole (5.22 g, 31.21 mmol) using the same synthetic method as that for the compound [ .

LC Mass (theory: 653.73 g / mol, measured: M + H ⁺ = 654.22 g / mol)

Synthetic example  4: Compound [ 41]  synthesis

[Reaction Scheme 4]

Step 1  : Synthesis of Intermediate F

16 g (80%) of Intermediate Compound F was obtained using the same synthetic method as Intermediate B using 2-bromocarbazole (7.2 g, 29.13 mmol) and Intermediate C (12.81 g, 34.28 mmol).

Step 2  : Compound [ 41]  synthesis

13 g (81%) of the compound [41] was obtained by using the intermediate F (13.9 g, 23.9 mmol) and carbazole (4.8 g, 28.67 mmol) .

LC Mass (theory: 669.79 g / mol, measured: M + H ⁺ = 670.20 g / mol)

compare Synthetic example  1: Synthesis of Comparative Compound 1

[Reaction Scheme 5]

The comparative compound 1 was synthesized using the same method as the method for synthesizing the compound [1].

LC Mass (calculated: 563.65 g / mol, measured: M + H ⁺ = 564.21 g / mol)

(Fabrication of organic light emitting device: The light-  Device 1)

Example  One

An organic light emitting device was fabricated using the compound [1] obtained in Synthesis Example 1 as a host and Ir (PPy) ₃ as a dopant.

As the anode, ITO was used in a thickness of 1000 angstroms, and as a cathode, aluminum (Al) was used in a thickness of 1,000 angstroms. 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 with 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, N4'-diphenylbiphenyl-4,4'-diamine (NPB) 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 / (80 nm) was deposited thereon to form a 800 Å hole transporting layer. Subsequently, using the compound [1] obtained in Synthesis Example 1 under the same vacuum deposition condition, a light emitting layer having a thickness of 300 Å was formed. Ir (PPy) 3, which is a phosphorescent dopant, was simultaneously deposited thereon. 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, Alq3 was deposited under the same vacuum deposition conditions to form an electron transport layer having a thickness of 200 ANGSTROM. LiF and Al were sequentially deposited as an anode on the electron transport layer to prepare an organic photoelectric device.

The structure of the organic photoelectric device was ITO / NPB (80 nm) / EML (compound [1] (93 wt%) + Ir (PPy) ₃ (7 wt%), 30 nm) / Balq 20 nm) / LiF (1 nm) / Al (100 nm).

Example  2 and 3

The same procedure as in Example 1 was carried out except that the compound [40] of Synthesis Example 2 and the compound [2] of Synthesis Example 3 were used in place of the compound [1] of Synthesis Example 1, Thereby preparing a light emitting device.

Comparative Example  1 and 2

Comparative Compound 1 of Comparative Synthesis Example 1, CBP (4,4'-bis (N-carbazolyl) -1,1'-biphenyl, CAS No. 58328-31-7) was used instead of Compound [1] The organic light emitting devices of Comparative Example 1 and Comparative Example 2 were fabricated in the same manner as in Example 1. [

Evaluation 1: Characteristic evaluation of organic light emitting device

The current density change, the luminance change, and the luminous efficiency according to the voltages of the organic light emitting devices according to Examples 1 to 3 and Comparative Examples 1 and 2 were measured and the results are shown in Table 1 below.

The specific measurement method is as follows. (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).

compound The driving voltage (V) The luminous efficiency (cd / A) Example 1 The compound [1] 3.77 61.5 Example 2 The compound [40] 3.91 59.6 Example 3 The compound [2] 3.97 62.2 Comparative Example 1 Comparative compound 1 4.23 52.1 Comparative Example 2 CBP 4.8 31.4

Referring to Table 1, it can be seen that the organic electroluminescent devices according to Examples 1 to 3 have improved driving voltage and luminous efficiency as compared with the organic electroluminescent devices according to Comparative Example 1 and Comparative Example 2. This means that, in the compounds according to Examples 1 to 3, not only the carbazole group contains substituted carbazole, but also the carbazole group in which N is substituted for dibenzofuran or dibenzothiophene directly connected without triazine, It is thought that the cloud expands and the driving voltage becomes lower.

(Fabrication of organic light emitting device: The light-  Device 2)

The compounds for the second organic optoelectronic device, E-31, E-99, E-129 and E-140 were synthesized by a known method.

[E-31] [E-99] [E-129] [E-140]

Example  4

The glass substrate coated with ITO (Indium tin oxide) thin film with a thickness of 1,500 Å was washed with distilled water ultrasonic wave. After the distilled water was washed, the substrate was ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, or methanol, dried, and transferred to a plasma cleaner. Then, the substrate was cleaned using oxygen plasma for 10 minutes, and then the substrate was transferred to a vacuum evaporator. Compound A was vacuum deposited on the ITO substrate using the ITO transparent electrode thus prepared as an anode to form a hole injection layer having a thickness of 700 A and a compound B was deposited to a thickness of 50 A on the injection layer. To form a hole transporting layer. (2-phenylpyridine) iridium (III) [Ir (ppy) ₃ ] was doped in an amount of 10 wt% by using the compound [1] and the compound E-31 of Synthesis Example 1 as a host simultaneously on the hole transport layer And a 400 Å thick light emitting layer was formed by vacuum deposition. Here, the compound [1] and the compound E-31 were used in a weight ratio of 5: 5, and the ratios were separately described in the following examples.

Subsequently, Compound D and Liq were simultaneously vacuum deposited on the light emitting layer at a ratio of 1: 1 to form an electron transport layer having a thickness of 300 Å. Liq 15 Å and Al 1,200 Å were successively vacuum deposited on the electron transport layer to form a cathode, The device was fabricated.

The organic light emitting device has a structure having five organic thin film layers. Specifically, the organic light emitting device has the following structure.

E-31: Ir (ppy) ₃ = 27 wt%: 63 wt%: 10 wt%] (400 Å) / Compound D: Liq (300 Å) / Liq (15 Å) / Al (1,200 Å).

Compound A: N4, N4'-diphenyl-N4, N4'-bis (9-phenyl-9H-carbazol-3-yl) biphenyl-

Compound B: 1,4,5,8,9,11-hexaazatriphenylene-hexacarbonitrile (HAT-CN),

Compound C: N- (biphenyl-4-yl) -9,9-dimethyl- N- (4- (9-phenyl-9H-carbazol-

Compound D: 8- (4- (4,6-di (naphthalen-2-yl) -1,3,5-triazin- 2- yl) phenyl) quinoline

Example  5 - Example  14, and Comparative Example  3 to Comparative Example  6

Organic light-emitting devices of Examples 5 to 14 and Comparative Examples 3 to 6 were fabricated in the same manner as in Example 4, using the host as shown in Table 2 below.

Evaluation 2: Evaluation of characteristics of organic light emitting device

The luminous efficiency and lifetime characteristics of the organic light emitting devices according to Examples 4 to 14 and Comparative Examples 3 to 6 were evaluated, and the results are shown in Table 2 below.

The specific measurement method is as follows.

(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).

(4) Life measurement

The time at which the luminance (cd / m ² ) was maintained at 6,000 cd / m ² and the current efficiency (cd / A) decreased to 97% was measured and the results were obtained.

The first host Second host The first host and the second host
ratio Driving voltage
(V) Luminous efficiency
(cd / A) life span
(T97, h) Example 4 The compound [1] E-31 1: 1 4.82 59.4 74 Example 5 The compound [1] E-31 4: 6 4.93 63.3 83 Example 6 The compound [1] E-99 1: 1 4.95 63.2 88 Example 7 The compound [40] E-140 1: 1 4.84 56.7 58 Example 8 The compound [2] E-31 1: 1 4.83 59.2 93 Example 9 The compound [2] E-99 1: 1 4.63 58.7 105 Example 10 The compound [2] E-99 4: 6 4.82 65.5 127 Example 11 The compound [2] E-140 1: 1 4.60 58.1 94 Example 12 The compound [2] E-140 4: 6 4.90 65.7 114 Example 13 The compound [41] E-129 5: 5 4.78 57.4 60 Example 14 The compound [41] E-99 1: 1 5.02 61.1 73 Comparative Example 3 CBP - - 7.5 33.0 One Comparative Example 4 - E-31 - 7.8 10 One Comparative Example 5 - E-99 - 7.6 19 One Comparative Example 6 Comparative compound
One E-31 1: 1 5.23 53.0 20

Referring to Table 2, it can be seen that the organic light emitting devices according to Examples 4 to 14 have significantly improved luminous efficiency and lifetime characteristics as compared with the organic light emitting devices according to Comparative Examples 3 to 6. As described above, since the nitrogen-containing heterocyclic group and the 3-position of dibenzofuran or dibenzothiophene contain substituents directly connected to each other without a linking group, the LUMO electron cloud expands and becomes a structure that is easy to receive electrons when an electric field is applied. This is an effect as the voltage is lowered.

Specifically, Comparative Example 3 using the CBP compound as the first host compound and Comparative Examples 4 and 5 using only the second host compound were superior to the organic light emitting device according to the embodiment of the present invention, Efficiency and life span. Further, in the case of using the first host and the second host according to the embodiment of the present invention, the same second host was used, but the comparison compound 1 without diphenofuran or dibenzothiophene directly substituted in the nitrogen- As compared with Comparative Example 6 used as the first host, it can be confirmed that the lifetime of the organic light emitting device according to Examples 4 to 14 is increased by at least four times.

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

Claims (14)

A compound for an organic optoelectronic device represented by the following Formula 1:
[Chemical Formula 1]

In formula (1)
X ¹ to X ³ are each independently N or CR ^a ,
At least one of X ¹ to X ³ is N,
Y is O or S,
Ar ¹ is a substituted or unsubstituted C6 to C30 aryl group,
R ^a and R ¹ to R ¹² are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group,
L ¹ and L ² are each independently a single bond or a substituted or unsubstituted C6 to C30 arylene group,
a and b are each independently an integer of 1 to 3; The method according to claim 1,
The compound for organic optoelectronic device represented by the following formulas 1-1 to 1-3:
[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

In Formulas 1-1 to 1-3,
X ¹ to X ³ are each independently N or CR ^a ,
At least one of X ¹ to X ³ is N,
Ar ¹ is a substituted or unsubstituted C6 to C30 aryl group,
Y is O or S,
R ^a and R ¹ to R ¹² are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group,
L ¹ and L ² are each independently a single bond or a substituted or unsubstituted C6 to C18 arylene group,
a and b are each independently an integer of 1 to 3; The method according to claim 1,
A compound for an organic optoelectronic device represented by the following formula (1-a) or (1-b):
[Chemical Formula 1-a]

[Chemical Formula 1-b]

[Chemical Formula 1-c]

[Chemical formula 1-d]

In formulas (1-a) to (1-d)
X ¹ to X ³ are each independently N or CR ^a ,
At least one of X ¹ to X ³ is N,
Y is O or S,
n1, n2, m, and k are each independently an integer of 0 to 2,
R ^a and R ¹ to R ¹⁴ are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C18 aryl group, or a combination thereof,
R ¹³ and R ¹⁴ are each independently present or linked to form a substituted or unsubstituted aromatic monocyclic or polycyclic ring. The method according to claim 1,
Ar ¹ represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted p-terphenyl group, a substituted or unsubstituted m-terphenyl group, A substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted triphenylenyl group, or a substituted or unsubstituted fluorenyl group, which is a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted anthraphenyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, . The method according to claim 1,
L ¹ and L ² each independently represent a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted p-terphenylene group , A substituted or unsubstituted m-terphenylene group, a substituted or unsubstituted o-terphenylene group, a substituted or unsubstituted anthracenylene group, a substituted or unsubstituted phenanthrenylene group, a substituted or unsubstituted triphenylenyl group Or a substituted or unsubstituted fluorenylene group. The method according to claim 1,
Which is one selected from the compounds listed in the following Group 1:
[Group 1]

. A compound for a first organic optoelectronic device according to claim 1; And
1. A composition for an organic optoelectronic device comprising a compound for a second organic optoelectronic device represented by the following Formula 2:
(2)

In Formula 2,
L³ And L⁴Are each independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, or a combination thereof,
Ar² And Ar³Are each independently a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof,
R²¹ To R²⁶Respectively A substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof,
l is an integer from 0 to 2;
Means that at least one hydrogen is substituted by deuterium, a C1 to C4 alkyl group, a C6 to C18 aryl group, or a C2 to C30 heteroaryl group. 8. The method of claim 7,
Ar ² and Ar ³ in Formula 2 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted Substituted or unsubstituted pyridinyl groups, substituted or unsubstituted pyrimidinyl groups, substituted or unsubstituted triazinyl groups, substituted or unsubstituted quinolinyl groups, substituted or unsubstituted quinolinyl groups, substituted or unsubstituted quinolinyl groups, substituted or unsubstituted quinolinyl groups, A substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenylene group, a substituted or unsubstituted dibenzofuranyl group, A substituted or unsubstituted carbazolyl group, a substituted or unsubstituted fluorenyl group, or a combination thereof. 8. The method of claim 7,
* -L ³ -Ar ² and * -L ⁴ -Ar ³ in the general formula (2) are each one of the substituents listed in the following Group II,
Wherein the compound for a second organic optoelectronic device is a compound having a substituent group bonded to one of the structures listed in Group I below in the following Group II:
[Group I]

[Group II]

In Groups I and II above, * is the connection point. Positive and negative facing each other, and
And at least one organic layer positioned between the anode and the cathode,
Wherein the organic layer is the compound for an organic optoelectronic device according to any one of claims 1 to 6; or
An organic optoelectronic device comprising the composition for an organic optoelectronic device according to any one of claims 7 to 9. 11. The method of claim 10,
Wherein the organic layer includes a light emitting layer,
Wherein the light emitting layer comprises the compound for the organic optoelectronic device or the composition for the organic optoelectronic device. 12. The method of claim 11,
Wherein the compound for an organic optoelectronic device or the composition for the organic optoelectronic device is included as a host of the light emitting layer. 12. The method of claim 11,
Wherein the organic layer further comprises at least one auxiliary layer selected from a hole injection layer, a hole transport layer, an electron blocking layer, an electron transport layer, an electron injection layer and a hole blocking layer,
Wherein the auxiliary layer further comprises an electron transporting layer adjacent to the light emitting layer,
Wherein the electron transporting auxiliary layer comprises the compound for an organic optoelectronic device; Or a composition for the organic optoelectronic device. A display device comprising the organic opto-electronic device according to claim 10.

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