KR102064298B1 - 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, a composition for an organic optoelectronic device, an organic optoelectronic device, and a display device to which the same is represented.
Details of Chemical Formula 1 are as defined in the specification.

Description

COMPOUND FOR ORGANIC OPTOELECTRONIC DEVICE, COMPOSITION FOR ORGANIC OPTOELECTRONIC DEVICE AND ORGANIC OPTOELECTRONIC DEVICE AND DISPLAY DEVICE}

A compound for organic optoelectronic devices, a composition for organic optoelectronic devices, an organic optoelectronic device, and a display device.

Organic optoelectronic diodes are devices that can switch electrical energy and light energy.

Organic optoelectronic devices can be divided into two types according to the principle of operation. One is an optoelectronic device in which excitons formed by light energy are separated into electrons and holes, and the electrons and holes are transferred to other electrodes, respectively, to generate electrical energy. It is a light emitting device that generates light energy from energy.

Examples of the organic optoelectronic device may be an organic photoelectric device, an organic light emitting device, an organic solar cell and an organic photo conductor drum.

Among these, organic light emitting diodes (OLEDs) have recently attracted much attention as demand for flat panel displays increases. The organic light emitting device converts electrical energy into light by applying an electric current to the organic light emitting material. The organic light emitting device has a structure in which an organic layer is inserted between an anode and a cathode. The organic layer may include an emission layer and an auxiliary layer, and the auxiliary layer may include, for example, 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 to increase efficiency and stability of the organic light emitting device. It may include at least one layer selected from the layer.

The performance of the organic light emitting device is greatly influenced by the characteristics of the organic layer, and in particular, is affected by the organic material included in the organic layer.

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

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

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

Yet another embodiment provides an organic optoelectronic device including the compound.

Another embodiment provides a display device including the organic optoelectronic device.

According to one embodiment, a compound for an organic optoelectronic device represented by Chemical Formula 1 is provided.

[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, or a combination thereof,

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, an anode and a cathode facing each other, and at least one organic layer positioned between the anode and the cathode, the organic layer is a compound for an organic optoelectronic device, or a composition for an organic optoelectronic device It provides an organic optoelectronic device comprising a.

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

High efficiency long life organic optoelectronic devices can be implemented.

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

Hereinafter, embodiments of the present invention will be described in detail. However, this is presented as an example, by which the present invention is not limited and the present invention is defined only by the scope of the claims to be described later.

As used herein, unless otherwise defined, "substituted" means that at least one hydrogen in a substituent or compound is a deuterium, a halogen group, a hydroxyl group, an amino group, a substituted or unsubstituted C1 to C30 amine group, a nitro group, a substitution or Unsubstituted C1 to C40 silyl group, C1 to C30 alkyl group, C1 to C10 alkylsilyl group, C6 to C30 arylsilyl group, C3 to C30 cycloalkyl group, C3 to C30 heterocycloalkyl group, C6 to C30 aryl group, C2 to C30 It means substituted by a heteroaryl group, a C1 to C20 alkoxy group, a fluoro group, a C1 to C10 trifluoroalkyl group, a cyano group, or a combination thereof.

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

As used herein, "hetero" means one to three heteroatoms selected from the group consisting of N, O, S, P, and Si in one functional group, and the remainder is carbon unless otherwise defined. .

As used herein, unless otherwise defined, an "alkyl group" means an aliphatic hydrocarbon group. The alkyl group may be a "saturated alkyl group" that 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, a C1 to C4 alkyl group means that the alkyl chain contains 1 to 4 carbon atoms, with methyl, ethyl, propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl and t-butyl Selected from the group consisting of:

Specific examples of the alkyl group include 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 cyclohex It means a practical skill.

As used herein, the term "aryl group" refers to a group of groups having at least one hydrocarbon aromatic moiety, wherein all of the elements of the hydrocarbon aromatic moiety have a p-orbital, and these p-orbitals are conjugated. Forms such as a phenyl group, naphthyl group, and the like, two or more hydrocarbon aromatic moieties are connected via a sigma bond, such as biphenyl group, terphenyl group, quarterphenyl group and the like, two or more hydrocarbon aromatic moiety Non-aromatic fused rings to which they are fused either directly or indirectly. For example, a fluorenyl group may be mentioned.

Aryl groups include monocyclic, polycyclic or fused ring polycyclic (ie, rings that divide adjacent pairs of carbon atoms) functional groups.

As used herein, a "heterocyclic group" is a higher concept that includes a heteroaryl group, and instead of carbon (C) in a ring compound such as an aryl group, a cycloalkyl group, a fused ring thereof, or a combination thereof, N, O, It means containing at least one hetero atom selected from the group consisting of S, P and Si. In the case where the heterocyclic group is a fused ring, the heterocyclic group may include one or more heteroatoms for all or each ring.

For example, "heteroaryl group" means containing at least one hetero atom 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 to each other. When the heteroaryl group is a fused ring, each ring may include 1 to 3 heteroatoms.

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, a substituted or unsubstituted C6 to C30 aryl group and / or a substituted or unsubstituted C2 to C30 heterocyclic group is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthra Senyl group, substituted or unsubstituted phenanthrenyl group, substituted or unsubstituted naphthacenyl group, substituted or unsubstituted pyrenyl group, substituted or unsubstituted biphenyl group, substituted or unsubstituted p-terphenyl group, substituted or unsubstituted 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 Fluorenyl group, substituted or unsubstituted indenyl group, substituted or unsubstituted furanyl group, substituted or unsubstituted thiophenyl group, substituted or unsubstituted pyrrolyl group, substituted or unsubstituted pyrazolyl group, substituted or unsubstituted A substituted imidazolyl group, a substituted or unsubstituted triazolyl group, a substituted or unsubstituted oxazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted oxadiazoleyl group, a substituted or unsubstituted thiadiazole Diary, substituted or unsubstituted pyridyl group, substituted or unsubstituted pyrimidinyl group, substituted or unsubstituted pyrazinyl group, substituted or unsubstituted triazinyl group, substituted or unsubstituted benzofuranyl group, substituted or unsubstituted Benzothiophenyl group, substituted or unsubstituted benzimidazolyl group, substituted or unsubstituted indolyl group, substituted or unsubstituted quinolinyl group, substituted or unsubstituted isoquinolinyl group, substituted or unsubstituted quinazolinyl group , Substituted or unsubstituted quinoxalinyl group, substituted or unsubstituted naphthyridinyl group, substituted or unsubstituted benzoxazinyl group, substituted or unsubstituted benzthiazinyl group, substituted or unsubstituted sub A crydinyl group, a substituted or unsubstituted phenazineyl group, a substituted or unsubstituted phenothiazineyl group, a substituted or unsubstituted phenoxazineyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzo Thiophenyl group, or a combination thereof, but is not limited thereto.

In the present specification, a single bond means a bond directly connected without passing through carbon or a hetero atom other than carbon, for example, L means a single bond means that a substituent linked to L is directly connected to the central 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 characteristic refers to a characteristic capable of forming holes by donating electrons when an electric field is applied, and injecting holes formed at the anode into the light emitting layer having conductive properties along the HOMO level, and emitting layer. It refers to a property that facilitates the movement of the hole formed in the anode and movement in the light emitting layer.

In addition, the electron characteristic refers to a characteristic that can receive electrons when an electric field is applied, and has a conductivity characteristic along the LUMO level, and injects electrons formed in the cathode into the light emitting layer, moves electrons formed in the light emitting layer to the cathode, and It means a property that facilitates movement.

Hereinafter, a compound for an organic optoelectronic device according to one embodiment is described.

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

[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, or a combination thereof,

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

The compound for an organic optoelectronic device represented by Chemical Formula 1 according to one embodiment includes a carbazole substituted with a carbazole group, and a heterocyclic group containing at least one nitrogen dibenzofuran or dibenzo It includes a structure that is bonded at position 3 of thiophene (dibenzothiophen) as a basic skeleton.

The heterocyclic group containing nitrogen according to one embodiment includes a substituent in which dibenzofuran or dibenzothiophene is directly connected without a linking group, so that the heterocyclic group containing nitrogen and the third position of dibenzofuran are Alternatively, the position 3 of the dibenzothiophene is combined to extend the orbit of the LUMO on the structure, so that the structure can easily receive electrons when the electric field is applied. Accordingly, the driving voltage of the organic optoelectronic device to which the compound for organic optoelectronic devices is applied may be lowered.

In addition, the compound for an organic optoelectronic device according to an embodiment binds to a nitrogen-containing heterocyclic ring substituted with a 3-position of dibenzofuran or dibenzothiophene having a large triplet energy and being electrochemically stable, and including carbazole. The organic optoelectronics to which the organic compound is applied have both the electron withdrawing group (EWG) and the electron donating group (EDG), so that the whole molecule exhibits bipolar characteristics and has high bonding strength between holes and electrons. In addition to being advantageous as a host in the light emitting layer of the device, it can be applied to a hole transport layer and a hole injection layer.

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

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

Compound for an organic optoelectronic device according to an embodiment may be represented by the formula 1-1 to formula 1-3:

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

In Chemical 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, or a combination thereof,

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 1-3.

In one example, X ¹ to X ³ of Formulas 1-1 to 1-3 may all be N.

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

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

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

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

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

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

In one embodiment, Ar ¹ of 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 of Formulas 1-1 to 1-3 may be a single bond.

In one example, L ¹ of Formulas 1-1 to 1-3 may be a single bond, L ² may be a phenylene group, or L ² may be a single bond, and L ¹ may be a phenylene group.

In one example, L ¹ and L ² of Formulas 1-1 to 1-3 may be phenylene groups.

When the nitrogen-containing heterocyclic group includes a substituent directly connected without a linking group at position 3 of the dibenzofuranyl group or the dibenzothiophenyl group as shown in Chemical Formulas 1-1 to 1-3, the electron cloud of LUMO is located on one plane Since the expansion effect can be maximized, an optimum effect can be obtained in terms of driving reduction and life extension when the compound is applied to the organic light emitting diode. If a nitrogen-containing heterocyclic group and dibenzofuran or dibenzothiophene are linked to a position other than No. 3, or a compound containing an arylene linker or the like is contained between the nitrogen-containing heterocyclic group and dibenzofuran or dibenzothiophene; When applied to the organic light emitting device, the effect of driving reduction through the expansion of the LUMO electron cloud is reduced.

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

As the substituted or unsubstituted C6 to C30 aryl group in the formula (1), for example, substituted or unsubstituted phenyl group, substituted or unsubstituted naphthal group, substituted or unsubstituted anthracenyl group, substituted or unsubstituted Phenanthryl groups, substituted or unsubstituted naphthacenyl groups, substituted or unsubstituted pyrenyl groups, substituted or unsubstituted biphenyl groups, substituted or unsubstituted terphenyl groups, substituted or unsubstituted quarterphenyl groups, substituted or unsubstituted A crysenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted perylenyl group, and a substituted or unsubstituted fluorenyl group, etc. are mentioned, For example, a phenyl group, 1-naphthyl group, 2 -Naphthyl group, 2-biphenylyl group, 3-biphenylyl group, 4-biphenylyl group, o-terphenyl group, m-terphenyl group, 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 preferable that it is an aryl group. For example, Ar ¹ according to one embodiment is substituted or unsubstituted phenyl group, substituted or unsubstituted biphenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted p-terphenyl group, substituted or unsubstituted m-terphenyl group, substituted or unsubstituted o-terphenyl group, substituted or unsubstituted anthracenyl group, substituted or unsubstituted phenanthrenyl group, substituted or unsubstituted triphenylenyl group, or substituted or unsubstituted flu Orenyl group, for example, a phenyl group, a naphthyl group, a biphenyl group, a terphenyl group.

More specifically, in one embodiment of the present invention, Ar ¹ may be a phenyl group, p-biphenyl group, m-biphenyl group, p-terphenylene group, m-terphenylene group, o-terphenylene group and the like, but is not limited thereto. It doesn't happen.

At this time, "substituted" in the substituted aryl group of Ar ¹ means that at least one hydrogen is substituted with deuterium, C1 to C20 alkyl group, or C6 to C30 aryl group. For example, the "substituted" means that at least one hydrogen is deuterium, C1 to C10 alkyl group, or C6 to C18 aryl group, for example, at least one hydrogen is deuterium, C1 to C4 alkyl group, or C6 to Mean substituted by C12 aryl group.

L ¹ and L ² in Chemical Formula 1 are each independently a linkage group, 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 it is a len group. For example, the linking groups L ¹ and L ² according to one 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 substitution Or an 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 triphenylenylene group, or a substituted or unsubstituted fluorenylene group.

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

In one embodiment of the present invention, Ar ¹ of Formula 1 is a phenyl group, naphthal group, biphenyl group, terphenyl group, or fluorenyl group, L ¹ and L ² are each independently a single bond, a phenyl group or a biphenyl group For example, it may be represented by the following Chemical Formula 1-a to Chemical Formula 1-d.

[Formula 1-a]

[Formula 1-b]

[Formula 1-c]

[Formula 1-d]

In Formula 1-a to Formula 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 adjacent groups to form a monocyclic or polycyclic ring of substituted or unsubstituted aromatic.

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

In one example, m of Formula 1-b and Formula 1-d may be 1, k is 0.

In one example, m of Formula 1-b and Formula 1-d may be 2, k is 0.

In one example, n1 and n2 of Formula 1-a to Formula 1-d may be each independently 0 or 1.

In one example, n1 and n2 of Formula 1-a to Formula 1-d may be all 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, preferably Is hydrogen, deuterium, unsubstituted C1 to C10 alkyl group, substituted or unsubstituted C6 to C18 aryl group, or a combination thereof, and more preferably hydrogen, deuterium, substituted or unsubstituted C1 to C4 It is preferably an alkyl group, a substituted or unsubstituted C6 to C12 aryl group, or a combination thereof.

Specifically, R ⁹ to R ¹² 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 ⁹ to R ¹² according to an embodiment are each independently hydrogen, deuterium, methyl group, ethyl group, propyl group, n-butyl group, sec-butyl group, tert-butyl group, isobutyl group, phenyl group or Combinations 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, methyl group, phenyl group, or a combination thereof.

Specifically, R ⁵ to R ⁸ 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 ⁵ to R ⁸ according to an embodiment may be each independently hydrogen, deuterium, methyl group, phenyl group or a combination thereof.

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

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

[Group 1]

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

Hereinafter, an example of the composition for organic optoelectronic devices including the above-described first compound for organic optoelectronic devices will be described.

The composition for an organic optoelectronic device according to another embodiment of the present invention includes the compound for a first organic optoelectronic device described above and a compound for a second organic optoelectronic device represented by Formula 2 below.

[Formula 2]

In Chemical 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 a combination thereof,

l is one of integers from 0 to 2,

"Substituted" means that at least one hydrogen is substituted with 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 of 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 of 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 pyrimidinyl group, substituted or unsubstituted quinazolyl group, substituted Or an unsubstituted isoquinazolyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted triazineyl group, a substituted or unsubstituted quinolinyl group, a substituted or Unsubstituted isoquinolinyl group, substituted or unsubstituted carbazolyl group, substituted or unsubstituted fluorenyl group, or a combination thereof.

In one embodiment of the present invention, Ar ² and Ar ³ of 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, Substituted or unsubstituted dibenzothiophenyl group, substituted or unsubstituted dibenzofuranyl group, substituted or unsubstituted quinolinyl group, substituted or unsubstituted isoquinolinyl group, substituted or unsubstituted carbazolyl group, substituted Or an unsubstituted fluorenyl group, or a combination thereof.

In one embodiment of the present invention, Ar ² and Ar ³ of 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 fluorenyl group, or a combination thereof.

In one example, R ²¹ to R ²⁶ of Formula 2 may each independently represent hydrogen, deuterium, or a substituted or unsubstituted C6 to C12 aryl group, for example, R ²¹ to R ²⁶ of Formula 2 may each 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 is one of the substituents listed in the following Group II, wherein the formula 2 is one of the structures listed in the following Group I The substituents listed in group II are attached.

[Group I]

[Group II]

In groups I and II above, * is the point of attachment.

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

[Group 2]

The first host compound and the second host compound described above may prepare various compositions by various combinations.

The composition according to an embodiment of the present invention includes a compound represented by Chemical Formula 1-1, or Chemical Formula 1-2 as a first host, and in Chemical Formula 2, 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, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group; l may comprise a compound of 0 as the second host.

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

The second organic optoelectronic device compound may be used in the light emitting layer together with the first organic optoelectronic device compound to improve light emission efficiency and lifespan by increasing charge mobility and stability. In addition, the mobility of the charge may be controlled by adjusting the ratio of the second organic optoelectronic device compound and the first organic optoelectronic device compound.

For example, in a weight ratio of about 1: 9 to 9: 1, specifically, in a weight ratio of 2: 8 to 8: 2, 3: 7 to 7: 3, 4: 6 to 6: 4, and 5: 5. For example, the compound for the first organic optoelectronic device and the compound for the second organic optoelectronic device may be included in the range of 3: 7. In addition, the compound for the first organic optoelectronic device and the compound for the second organic optoelectronic device may be a weight ratio of 1: 1 to 1: 4, the weight ratio of 1: 1 to 1: 3, the weight ratio of 1: 1 to 4: 6. Can be.

 By being included in the above range it is possible to improve efficiency and life at the same time.

The composition may further include at least one organic compound in addition to the above-mentioned compound for the first organic optoelectronic device and the compound for the 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 is a substance mixed with a small amount to emit light, and a material such as a metal complex that emits light by multiple excitation which excites above a triplet state may be used. The dopant may be, for example, an inorganic, organic, or inorganic compound, and may be included in one kind or two or more kinds.

An example of the dopant may be a phosphorescent dopant, and an example of the phosphorescent dopant may be Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or a combination thereof. An organometallic compound containing these can be mentioned. The phosphorescent dopant may be, for example, a compound represented by Chemical Formula Z, but is not limited thereto.

[Formula 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 a ligand to form a complex with M.

M may be, for example, Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or a combination thereof, wherein L and X are examples For example, it may be a bidentate ligand.

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

An 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, the organic layer is the above-described compound for organic optoelectronic devices, or organic optoelectronic It may include a composition for the device.

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

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

The organic layer may include a light emitting layer and 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, and the auxiliary layer may be a compound for the organic optoelectronic device. Or an organic optoelectronic device composition.

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

In an embodiment of the present invention, the compound for an organic optoelectronic device included in the electron transport auxiliary layer may be represented by Chemical Formula 1-I, Chemical Formula 1-a, or Chemical Formula 1-c. .

The organic optoelectronic device is not particularly limited as long as the device can switch electrical energy and light energy. Examples thereof include organic photoelectric devices, organic light emitting devices, organic solar cells, and organic photosensitive drums.

Herein, an organic light emitting diode as 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 diode according to an embodiment.

Referring to FIG. 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 positioned between the anode 120 and the cathode 110. Include.

The anode 120 may be made of a high work function conductor, for example, to facilitate hole injection, and may be made of metal, metal oxide, and / or conductive polymer, for example. The anode 120 is, for example, 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), indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO and Al or SnO ₂ and Sb; Conductive polymers such as poly (3-methylthiophene), poly (3,4- (ethylene-1,2-dioxy) thiophene) (polyehtylenedioxythiophene: PEDT), polypyrrole and polyaniline, and the like. It is not.

The cathode 110 may be made of a low work function conductor, for example, to facilitate electron injection, and may be made of a metal, a metal oxide, and / or a conductive polymer, for example. The cathode 110 may be, for example, a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium, or an alloy thereof; Multilayer structure materials such as LiF / Al, LiO ₂ / Al, LiF / Ca, LiF / Al, and BaF ₂ / Ca, but are not limited thereto.

The organic layer 105 includes a light emitting layer 130 including the compound for an 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 auxiliary layer 140 in addition to the light emitting layer 130. The hole auxiliary layer 140 may further increase hole injection and / or hole mobility between the anode 120 and the emission layer 130 and block electrons. The hole auxiliary 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.

Although not shown, the organic layer 105 of FIG. 1 or 2 may further include an electron injection layer, an electron transport layer, an electron transport auxiliary layer, a hole transport layer, a hole transport auxiliary layer, a hole injection layer, or a combination thereof. have. The compound for an organic optoelectronic device of the present invention may be included in these organic layers. The organic light emitting diodes 100 and 200 may include a dry film method such as an anode or a cathode formed on a substrate and then vacuum evaporation, sputtering, plasma plating and ion plating; Alternatively, the organic layer may be formed by a wet film method such as spin coating, dipping, flow coating, or the like, followed by forming a cathode or an anode thereon.

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

The following presents specific embodiments of the present invention. However, the examples described below are merely for illustrating or explaining the present invention in detail, and thus the present invention is not limited thereto.

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

(Production of Compound for Organic Optoelectronic Devices)

Compounds given as more specific examples of the compounds of the present invention were synthesized through the following steps.

(Compound for First Organic Optoelectronic Device)

Synthesis Example  1: Synthesis of Compound [1]

Scheme 1

First step  : Synthesis of Intermediate A

2,4-dichloro-6-phenyl-1,3,5-triazine (50.55 g, 223.59 mmol) and dibenzofuran-3-ylboronic acid (40.3 g, 190.06 mmol) in a 2 L round-bottom flask in a nitrogen environment ) Was dissolved in 900 mL of tetrahydrofuran, and tetrakis (triphenylphosphine) palladium (12.9 g, 11.18 mmol) was added thereto and stirred. Potassium carbonate saturated in water (61.8 g, 447.19 mmol) was added thereto, and the mixture was heated and refluxed at 80 ° C. for 12 hours. After completion of the reaction, the organic layer was separated and then water was removed with anhydrous MgSO ₄ , filtered and concentrated under reduced pressure. The obtained residue was crystallized using dichloromethane and hexane to give 35.3 g (44%) of intermediate A.

2nd step  : Synthesis of Intermediate B

In a 1 L round bottom flask, 3-bromocarbazole (7.4 g, 29.96 mmol) was added to 240 mL of N, N-dimethylformamide (DMF) and stirred, followed by sodium hydride (60%, mineral oil) (2.4 g, 59.92 mmol) is added slowly. After 30 minutes, Intermediate A (12.6 g, 35.25 mmol) was slowly added and stirred for 12 hours. The reactant is poured into water to filter out the solids. The obtained residue was solidified with dichlorobenzene and methanol to obtain 17 g (85%) of intermediate B.

3rd step  : Compound [ Of 1  synthesis

The intermediate B (16.5 g, 29.06 mmol), carbazole (5.8 g, 34.88 mmol), and tertiary butoxysodium (5.6 g, 58.13 mmol) were dissolved in 50 ml of xylene, followed by palladium (dibenzylideneacetone) (0.836 g, 1.45 mmol) and tertiarybutylphosphine (1.41 g, 2.91 mmol, 50% toluene mixture) are added dropwise. The reaction solution was stirred by heating to 120 ° C. for 12 hours under a stream of nitrogen. After completion of the reaction, the solids produced by pouring methanol into the reaction product were filtered. Then, the solids were dissolved in dichlorobenzene again, activated carbon and anhydrous magnesium sulfate were added, stirred, filtered, and recrystallized using dichlorobenzene and methanol. Compound [1] 16 g (84 %) Was obtained.

LC Mass (Theoretical value: 653.73 g / mol, Measured value: M + H ⁺ = 654.22 g / mol)

Synthesis Example  2: synthesis of compound [40]

Scheme 2

First step  : Synthesis of Intermediate C

Of intermediate A using 2,4-dichloro-6-phenyl-1,3,5-triazine (42.3 g, 187.24 mmol) and benzothiophen-3-ylboronic acid (36.3 g, 159.15 mmol) Using the same method as the synthesis method, intermediate C 30 g (43%) was obtained.

2nd step  : Synthesis of Intermediate D

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

3rd step  : Compound [ Of 40  synthesis

Using Intermediate D (14.8 g, 25.38 mmol) and Carbazole (5.1 g, 30.46 mmol), 13 g (76%) of Compound [40] was obtained using the same synthesis method as the synthesis of Compound [1]. .

LC Mass (Theoretical value: 669.79 g / mol, Measured value: M + H ⁺ = 670.20 g / mol)

Synthesis Example  3: compound [ 2]  synthesis

Scheme 3

First step  : Synthesis of Intermediate E

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

2nd step  : Compound [ 2]  synthesis

Using Intermediate E (14.756 g, 26 mmol) and carbazole (5.22 g, 31.21 mmol), 14 g (82%) of Compound [2] was obtained using the same synthesis method as the synthesis of Compound [1]. .

LC Mass (Theoretical value: 653.73 g / mol, Measured value: M + H ⁺ = 654.22 g / mol)

Synthesis Example  4: compound [ Of 41  synthesis

Scheme 4

First step  : Synthesis of Intermediate F

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

2nd step  : Compound [ Of 41  synthesis

Using Intermediate F (13.9 g, 23.9 mmol) and Carbazole (4.8 g, 28.67 mmol), 13 g (81%) of Compound [41] was obtained using the same synthesis method as the synthesis of Compound [1]. .

LC Mass (Theoretical value: 669.79 g / mol, Measured value: M + H ⁺ = 670.20 g / mol)

compare Synthesis Example  1: Synthesis of Comparative Compound 1

Scheme 5

Comparative Compound 1 was synthesized using the same method as the synthesis method of Compound [1].

LC Mass (Theoretical value: 563.65 g / mol, Measured value: M + H ⁺ = 564.21 g / mol)

(Production of organic light emitting device: Light emitting layer  Element 1)

Example  One

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

ITO was used as the cathode at a thickness of 1000 kPa, and aluminum (Al) was used as the cathode at a thickness of 1,000 kPa. Specifically, the method of manufacturing the organic light emitting device, the anode is cut into ITO glass substrate having a sheet resistance value of 15 Ω / ㎠ to 50mm X 50 mm X 0.7 mm in acetone, isopropyl alcohol and pure water Ultrasonic cleaning for each 15 minutes was followed by UV ozone cleaning for 30 minutes.

N4, N4'-di (naphthalen-1-yl) -N4, N4'-diphenylbiphenyl-4,4'-diamine (NPB) under conditions of vacuum of 650X10-7Pa and deposition rate of 0.1 to 0.3 nm / s on the substrate (80 nm) was deposited to form a hole transport layer of 800 kPa. Subsequently, using the compound [1] obtained in Synthesis Example 1 under the same vacuum deposition conditions, a light emitting layer having a film thickness of 300 kPa was formed, and Ir (PPy) 3, which is a phosphorescent dopant, was simultaneously deposited. At this time, by adjusting the deposition rate of the phosphorescent dopant, when the total amount of the light emitting layer is 100% by weight, the deposition rate of the phosphorescent dopant was deposited so as to be 7% by weight.

Bis (2-methyl-8-quinolinolate) -4- (phenylphenolato) aluminum (BAlq) was deposited on the emission layer to form a hole blocking layer having a thickness of 50 Å. Subsequently, Alq3 was deposited under the same vacuum deposition conditions to form an electron transport layer having a film thickness of 200 GPa. An organic photoelectric device was manufactured by sequentially depositing LiF and Al as a cathode on the electron transport layer.

The structure of the organic photoelectric device is ITO / NPB (80 nm) / EML (Compound [1] (93 wt%) + Ir (PPy) ₃ (7 wt%), 30 nm) / Balq (5 nm) / Alq3 ( 20 nm) / LiF (1 nm) / Al (100 nm).

Example  2 and 3

The organic compounds of Examples 2 and 3 were prepared in the same manner as in Example 1, except that Compound [40] of Synthesis Example 2 and Compound [2] of Synthesis Example 3 were used instead of Compound [1] of Synthesis Example 1. A light emitting device was prepared.

Comparative example  1 and 2

Instead of Compound [1] of Synthesis Example 1, Comparative Compound 1 of Comparative Synthesis Example 1, CBP (4,4'-bis (N-carbazolyl) -1,1'-biphenyl, CAS No.58328-31-7), respectively Except for using the organic light emitting device of Comparative Example 1 and Comparative Example 2 were prepared in the same manner as in Example 1.

Evaluation 1: Characterization of Organic Light Emitting Diode

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

The specific measuring method is as follows. (1) Measurement of change of current density according to voltage change

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

(2) Measurement of luminance change according to voltage change

The resulting organic light emitting device was measured using a luminance meter (Minolta Cs-1000A) while increasing the voltage from 0V to 10V to obtain a result.

(3) Measurement of luminous efficiency

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

compound Driving voltage (V) Luminous Efficiency (cd / A) Example 1 Compound [1] 3.77 61.5 Example 2 Compound [40] 3.91 59.6 Example 3 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 light emitting diodes according to Examples 1 to 3 have improved driving voltage and luminous efficiency compared to the organic light emitting diodes according to Comparative Example 1 and Comparative Example 2. In the compounds according to Examples 1 to 3, not only include carbazoles with substituted carbazole groups, but also the triazines in which dibenzofuran or dibenzothiophene is directly connected to N of the carbazole group are replaced with LUMO electrons. It is thought that the cloud expands and the driving voltage is lower.

(Production of organic light emitting device: Light emitting layer  Element 2)

Compounds for the second organic optoelectronic device, E-31, E-99, E-129, and E-140, were synthesized by known methods.

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

Example  4

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

Subsequently, the compound D and Liq are vacuum-deposited on the emission layer at a ratio of 1: 1 at the same time to form an electron transport layer having a thickness of 300Å, and the Liq 15Å and the Al 1,200Å are sequentially vacuum-deposited on the electron transport layer to form a cathode. The device was produced.

The organic light emitting device has a structure having five organic thin film layers, specifically as follows.

ITO / Compound A (700Å) / Compound B (50Å) / Compound C (1,020Å) / EML [Compound [1]: E-31: Ir (ppy) ₃ = 27wt%: 63wt%: 10wt%] (400Å) / Compound D: Liq (300 Pa) / Liq (15 Pa) / Al (1,200 Pa) was produced in the structure.

Compound A: N4, N4'-diphenyl-N4, N4'-bis (9-phenyl-9H-carbazol-3-yl) biphenyl-4,4'-diamine

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-3-yl) phenyl) -9H-fluoren-2-amine

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

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

As shown in Table 2, the organic light emitting device of Examples 5 to 14 and Comparative Examples 3 to 6 was manufactured in the same manner as in Example 4 using a host.

Evaluation 2: Characterization of Organic Light Emitting Diode

The light emitting efficiency and lifespan characteristics of the organic light emitting diodes 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 measuring method is as follows.

(1) Measurement of change of current density according to voltage change

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

(2) Measurement of luminance change according to voltage change

The resulting organic light emitting device was measured using a luminance meter (Minolta Cs-1000A) while increasing the voltage from 0V to 10V to obtain a result.

(3) Measurement of luminous efficiency

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

(4) life measurement

The results were obtained by measuring 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%.

First host 2nd host First host and second host
ratio Driving voltage
(V) Luminous efficiency
(cd / A) life span
(T97, h) Example 4 Compound [1] E-31 1: 1 4.82 59.4 74 Example 5 Compound [1] E-31 4: 6 4.93 63.3 83 Example 6 Compound [1] E-99 1: 1 4.95 63.2 88 Example 7 Compound [40] E-140 1: 1 4.84 56.7 58 Example 8 Compound [2] E-31 1: 1 4.83 59.2 93 Example 9 Compound [2] E-99 1: 1 4.63 58.7 105 Example 10 Compound [2] E-99 4: 6 4.82 65.5 127 Example 11 Compound [2] E-140 1: 1 4.60 58.1 94 Example 12 Compound [2] E-140 4: 6 4.90 65.7 114 Example 13 Compound [41] E-129 5: 5 4.78 57.4 60 Example 14 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 device according to Examples 4 to 14 is significantly improved in the luminous efficiency and life characteristics compared to the organic light emitting device according to Comparative Examples 3 to 6. As described above, since the heterocyclic ring containing nitrogen and the 3 position of dibenzofuran or dibenzothiophene include a substituent directly connected without a linking group, the LUMO electron cloud is expanded, and thus the structure is susceptible to electrons upon application of an electric field. The effect is that 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, compared with the organic light emitting device according to an embodiment of the present invention, high driving voltage and significantly lower light emission Efficiency and lifetime. In addition, in the case of using the first host and the second host according to an embodiment of the present invention, Comparative Compound 1 without diphenzofuran or dibenzothiophene directly substituted with a nitrogen-containing heterocycle was used. Compared with Comparative Example 6 used as the first host, it can be seen that the organic light emitting device according to Examples 4 to 14 has an effect of increasing the life by up to four times or more.

 The present invention is not limited to the above embodiments, but may be manufactured in various forms, and a person skilled in the art to which the present invention pertains has another specific form without changing the technical spirit or essential features of the present invention. It will be appreciated that the present invention may be practiced as. Therefore, it should be understood that the embodiments described above are exemplary in all respects and not restrictive.

100 and 200: organic light emitting element
105: organic layer 110: cathode
120: anode 130: light emitting layer
140: hole auxiliary layer

Claims (14)

Compound for an organic optoelectronic device represented by the general formula (1):
[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 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, substituted or unsubstituted anthracenyl group, substituted or unsubstituted phenanthrenyl group, substituted or unsubstituted triphenylenyl group, or substituted or unsubstituted fluorenyl group,
R ^a , and R ¹ to R ¹² are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C4 alkyl group, a substituted or unsubstituted C6 to C12 aryl group, or a combination thereof,
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 1-3. The method of claim 1,
Compounds for organic optoelectronic devices represented by Formula 1-1 to Formula 1-3:
[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

In Chemical 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 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, substituted or unsubstituted anthracenyl group, substituted or unsubstituted phenanthrenyl group, substituted or unsubstituted triphenylenyl group, or substituted or unsubstituted fluorenyl 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 C4 alkyl group, a substituted or unsubstituted C6 to C12 aryl group, or a combination thereof,
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 1-3. The method of claim 1,
Compound for an organic optoelectronic device represented by the general formula 1-a or 1-b:
[Formula 1-a]

[Formula 1-b]

[Formula 1-c]

[Formula 1-d]

In Formula 1-a to Formula 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 C4 alkyl group, a substituted or unsubstituted C6 to C12 aryl group, or a combination thereof,
R ¹³ and R ¹⁴ are each independently present or linked to each other to form a substituted or unsubstituted aromatic monocyclic or polycyclic ring. delete The method of claim 1,
L ¹ and L ² 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 unsubstituted p-terphenylene group , Substituted or unsubstituted m-terphenylene group, substituted or unsubstituted o-terphenylene group, substituted or unsubstituted anthracenylene group, substituted or unsubstituted phenanthrenylene group, substituted or unsubstituted triphenylenyl The compound for organic optoelectronic devices which is a len group or a substituted or unsubstituted fluorenylene group. The method of claim 1,
Compound for an organic optoelectronic device, which is one selected from compounds listed in Group 1 below:
[Group 1]

. Compound for a first organic optoelectronic device according to claim 1; And
An organic optoelectronic device composition comprising a compound for a second organic optoelectronic device represented by the formula (2):
[Formula 2]

In Chemical 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 a combination thereof,
l is an integer from 0 to 2;
"Substituted" means that at least one hydrogen is substituted with deuterium, a C1 to C4 alkyl group, a C6 to C18 aryl group, or a C2 to C30 heteroaryl group. The method of claim 7, wherein
Ar ² and Ar ³ of 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 Anthracenyl group, substituted or unsubstituted triphenylenyl group, substituted or unsubstituted pyridinyl group, substituted or unsubstituted pyrimidinyl group, substituted or unsubstituted triazinyl group, substituted or unsubstituted quinolinyl group, Substituted or unsubstituted isoquinolinyl group, substituted or unsubstituted quinazolyl group, substituted or unsubstituted isoquinazolyl group, substituted or unsubstituted dibenzothiophenyl group, substituted or unsubstituted dibenzofuranyl group, A composition for organic optoelectronic devices, which is a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted fluorenyl group, or a combination thereof. The method of claim 7, wherein
* -L ³ -Ar ² and * -L ⁴ -Ar ³ of Formula 2 are each one of the substituents listed in the following Group II,
The second compound for an organic optoelectronic device is a compound for organic optoelectronic devices is a compound in which the substituents listed in the following group II is bonded to one of the structures listed in Group I:
[Group I]

[Group II]

In groups I and II above, * is the point of attachment. The anode and cathode facing each other, and
At least one organic layer positioned between the anode and the cathode,
The organic layer is a compound for an organic optoelectronic device according to any one of claims 1 to 3, 5 and 6. or
An organic optoelectronic device comprising the composition for an organic optoelectronic device according to any one of claims 7 to 9. The method of claim 10,
The organic layer includes a light emitting layer,
The light emitting layer is an organic optoelectronic device comprising the compound for an organic optoelectronic device or the composition for an organic optoelectronic device. The method of claim 11,
The compound for an organic optoelectronic device or the composition for an organic optoelectronic device is included as a host of the light emitting layer. The method of claim 11,
The organic layer further includes 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,
The auxiliary layer further includes an electron transport auxiliary layer adjacent to the light emitting layer,
The electron transport auxiliary layer is a compound for the organic optoelectronic device; Or an organic optoelectronic device comprising the composition for an organic optoelectronic device. A display device comprising the organic optoelectronic device of claim 10.

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