KR102171073B1 - Compound for organic optoelectronic device, composition for organic optoelectronic device and organic optoelectronic device and display device - Google Patents

Abstract

It relates to a compound for an organic optoelectronic device represented by Formula 1, a composition for an organic optoelectronic device, and an organic optoelectronic device and a display device to which the same is applied.
Details of Chemical Formula 1 are as defined in the specification.

Description

A compound for an organic optoelectronic device, a composition for an organic optoelectronic device, an organic optoelectronic device, and a display device TECHNICAL FIELD

It relates to compounds for organic optoelectronic devices, compositions for organic optoelectronic devices, organic optoelectronic devices, and display devices.

An organic optoelectronic diode is a device capable of converting electrical energy and optical energy to each other.

Organic optoelectronic devices can be largely divided into two types according to the principle of operation. One is a photoelectric device that generates electrical energy by separating excitons formed by light energy into electrons and holes, and the electrons and holes are transferred to different electrodes, and the other is electricity by supplying voltage or current to the electrode. It is a light-emitting device that generates light energy from energy.

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

Among them, organic light emitting diodes (OLEDs) are attracting great attention in recent years due to the increasing demand for flat panel display devices. The organic light-emitting device is a device that converts electrical energy into light by applying a current to an organic light-emitting material, and has a structure in which an organic layer is inserted between an anode and a cathode. Here, the organic layer may include an emission layer and an auxiliary layer optionally, and the auxiliary layer may include, for example, a hole injection layer, a hole transport layer, an electron blocking layer, an electron transport layer, and an electron injection layer to increase the efficiency and stability of the organic light emitting device. And it may include at least one layer selected from the hole blocking layer.

The performance of the organic light emitting device is greatly influenced by the properties of the organic layer, and among them, the organic material included in the organic layer is greatly influenced.

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

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

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

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 the following Formula 1 is provided.

[Formula 1]

In Formula 1,

ET is an N-containing substituted or unsubstituted C2 to C30 heterocyclic group excluding a carbazolyl group,

L is a single bond, a substituted or unsubstituted C6 to C20 arylene group or a substituted or unsubstituted C2 to C30 heteroarylene group,

X is O or S,

R ¹ to R ⁸ are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group or a substituted or unsubstituted C6 to C18 aryl group,

The "substituted" means that at least one hydrogen is substituted with deuterium, a cyano group, a C1 to C20 alkyl group, a C6 to C30 aryl group or a C2 to C30 heteroaryl group.

According to another embodiment, the first compound for an organic optoelectronic device represented by Formula 1; And it provides a composition for an organic optoelectronic device comprising a second compound for an organic optoelectronic device represented by the formula (2) or a combination of the formula (3) and formula (4).

[Formula 2] [Formula 3] [Formula 4]

In Chemical Formulas 2 to 4,

Y ¹ to Y ³ 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,

A ¹ to A 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,

Two adjacent * in Formula 3 are bonded to two * in Formula 4, and the other two * in Formula 3 are each independently CR ^b ,

R ⁹ to R ¹¹ , R ¹⁵ to R ¹⁹ and R ^b 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,

m is one of an integer from 0 to 2;

The "substitution" 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.

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, wherein the organic layer is the 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 device according to an embodiment.

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

Unless otherwise defined, the term "substituted" in the present specification means that at least one hydrogen in a substituent or compound is deuterium, a halogen group, a hydroxyl group, an amino group, a substituted or unsubstituted C1 to C30 amine group, a nitro group, a substituted 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 C1 to C10 trifluoroalkyl group, a cyano group, or a combination thereof.

In an example of the present invention, "substitution" means that at least one hydrogen in a substituent or 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 C3 to C30 It means substituted with a heterocycloalkyl group, a C6 to C30 aryl group, and a C2 to C30 heteroaryl group. In addition, in a specific example of the present invention, "substituted" means that at least one hydrogen in a substituent or 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 addition, in a specific example of the present invention, "substitution" means that at least one hydrogen in a substituent or compound is deuterium, a C1 to C5 alkyl group, a C6 to C18 aryl group, a pyridinyl group, a quinolinyl group, an isoquinolinyl group, a quina It means substituted with a zolinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, or a carbazolyl group. In addition, in a specific example of the present invention, "substitution" means that at least one hydrogen in the substituent or compound is deuterium, a C1 to C5 alkyl group, a C6 to C18 aryl group, a pyridinyl group, a quinazolinyl group, a dibenzofuranyl group, or It means substituted with a dibenzothiophenyl group. In addition, in a specific example of the present invention, "substitution" means that at least one hydrogen in a substituent or compound is deuterium, methyl group, ethyl group, propanyl group, butyl group, phenyl group, biphenyl group, terphenyl group, naphthyl group, triphenyl group, flu It means substituted with an orenyl group, a pyridinyl group, a quinazolinyl group, a carbazolyl group, a dibenzofuranyl group, or a dibenzothiophenyl group.

In the present specification, "hetero" means that one functional group contains 1 to 3 heteroatoms selected from the group consisting of N, O, S, P, and Si, and the rest is carbon, unless otherwise defined. do.

Unless otherwise defined in the chemical formula in the present specification, when a chemical bond is not drawn at a position where a chemical bond is to be drawn, it means that a hydrogen atom is bonded at the position.

In the present specification, "alkyl (alkyl) group" means an aliphatic hydrocarbon group unless otherwise defined. The alkyl group may be a "saturated alkyl group" that does not contain any double bonds or triple bonds.

The alkyl group may be a C1 to C30 alkyl group. 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 1 to 4 carbon atoms are included in the alkyl chain, and methyl, ethyl, propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl and t-butyl It indicates that it is 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, cyclohexyl group. It means practical skills, etc.

In the present specification, "aryl group" is a concept encompassing a group having one or more hydrocarbon aromatic moieties,

While all the elements of the hydrocarbon aromatic moiety have p-orbitals, these p-orbitals include a form in which conjugation is formed, such as a phenyl group, a naphthyl group, and the like,

Two or more hydrocarbon aromatic moieties are linked through a sigma bond, including a biphenyl group, a terphenyl group, a quarterphenyl group, and the like,

It may also include non-aromatic fused rings in which two or more hydrocarbon aromatic moieties are directly or indirectly fused. For example, a fluorenyl group etc. are mentioned.

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

In the present specification, "heterocyclic group" is a higher concept including a heteroaryl group, and carbon (C) instead of N, O, in a ring compound such as an aryl group, a cycloalkyl group, a fused ring thereof, or a combination thereof It means containing at least one hetero atom selected from the group consisting of S, P and Si. When the heterocyclic group is a fused ring, one or more heteroatoms may be included in the entire heterocyclic group or each ring.

As an 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 are directly linked 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 contain 1 to 3 hetero atoms.

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, a quinazolinyl 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, 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 triphenylene group, a substituted or unsubstituted perylenyl group, a substituted or unsubstituted flu Orenyl 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 already Dazolyl group, substituted or unsubstituted triazolyl group, substituted or unsubstituted oxazolyl group, substituted or unsubstituted thiazolyl group, substituted or unsubstituted oxadiazolyl group, substituted or unsubstituted thiadiazolyl group, 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 benzo A thiophenyl 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 benzoquinolinyl group, a substituted or unsubstituted benzoisoquinolinyl group, a substituted or unsubstituted benzoquinazolinyl group, a substituted or unsubstituted naphthyridinyl group, A substituted or unsubstituted benzoxazineyl group, a substituted or unsubstituted benzthiazinyl group, a substituted or unsubstituted acridinyl group, a substituted or unsubstituted phenazineyl group, a substituted or unsubstituted phenothiazinyl group, a substituted or Unsubstituted phenoxazineyl group, substituted or unsubstituted dibenzofuranyl group, or substituted or unsubstituted dibenzothiophenyl group, or It may be a combination of these, but is not limited thereto.

In the present specification, the hole property refers to a property capable of donating electrons to form holes when an electric field is applied, and injection of holes formed at the anode into the emission layer by having conduction characteristics according to the HOMO level, and the emission layer It means a property that facilitates the movement of the holes formed in the anode to the anode and in the light emitting layer.

In addition, electronic characteristics refer to the characteristics of receiving electrons when an electric field is applied, and has conduction characteristics according to the LUMO level, so that electrons formed in the cathode are injected into the emission layer, electrons formed in the emission layer move to the cathode, and in the emission layer. It means a property that facilitates movement.

Hereinafter, a compound for an organic optoelectronic device according to an embodiment will be described.

The compound for an organic optoelectronic device according to an embodiment is represented by Formula 1 below.

[Formula 1]

In Formula 1,

ET is an N-containing substituted or unsubstituted C2 to C30 heterocyclic group excluding a carbazolyl group,

L is a single bond, a substituted or unsubstituted C6 to C20 arylene group or a substituted or unsubstituted C2 to C30 heteroarylene group,

X is O or S,

R ¹ to R ⁸ are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group or a substituted or unsubstituted C6 to C18 aryl group,

The "substituted" means that at least one hydrogen is substituted with a deuterium, a cyano group, a C1 to C20 alkyl group, a C6 to C30 aryl group, or a C2 to C30 heteroaryl group.

In one example of the present invention, the "substituted" means that at least one hydrogen is deuterium, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group or a dibenzothiophenyl group. Means substituted.

For example, the ET may be a substituted or unsubstituted C2 to C30 heterocyclic group containing at least two or more N, excluding a carbazolyl group.

For example, the ET is a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted quinolinyl group , Substituted or unsubstituted isoquinolinyl group, substituted or unsubstituted quinazolinyl group, substituted or unsubstituted benzofuranpyridinyl group, substituted or unsubstituted benzofuranpyrimidinyl group, substituted or unsubstituted benzothiophene It may be a pyridinyl group, a substituted or unsubstituted benzothiophenepyrimidinyl group, or a combination thereof. Here, the group to be further substituted in the "substituted or unsubstituted" of ET may be a phenyl group, a biphenyl group, a terphenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a fluorenyl group, or a combination thereof.

In the compound for an organic optoelectronic device according to the present invention, when naphthalene is fused to dibenzofuran or dibenzothiophene, the glass transition temperature (Tg) is increased, and when applied to a device, the stability of the compound during the process can be increased and deterioration can be prevented. The glass transition temperature (Tg) may be related to the thermal stability of the compound and the device to which it is applied. That is, when the compound for an organic optoelectronic device having a high glass transition temperature (Tg) is applied in the form of a thin film to an organic light emitting device, the temperature in a subsequent process, such as an encapsulation process, is performed after depositing the compound for an organic optoelectronic device. It is prevented from being deteriorated by and can secure the life characteristics of the compound and the device.

In addition, since the polarity of nitrogen contained in the ET unit allows interaction with the electrode, it is easy to inject electric charges and high mobility, thereby implementing a low driving voltage.

That is, by applying the compound for an organic optoelectronic device according to the present invention, a device having a long life, low driving and high efficiency can be implemented.

ET of Formula 1 is an N-containing substituted or unsubstituted C2 to C30 heterocyclic group excluding a carbazolyl group, and Formula 1 may be represented by, for example, Formula 1A below.

[Formula 1A]

In Formula 1A,

Z ¹ to Z ⁵ are each independently N or CR ^a , at least one of Z ¹ to Z ⁵ is N, and R ^a is each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, substituted or unsubstituted A cyclic C6 to C18 aryl group or a substituted or unsubstituted C2 to C20 heterocyclic group, and R ^a is each independently present or connected to adjacent groups to each other to form a substituted or unsubstituted aliphatic, aromatic or heteroaromatic monocyclic or poly Cyclic rings can be formed.

In an example of the present invention, two or three of Z ¹ to Z ⁵ of Formula 1A may be N, and when Z ¹ to Z ⁵ are CR ^a , R ^a is each independently hydrogen, deuterium, phenyl group, naph It may be selected from a yl group, a terphenyl group, a biphenyl group, a triphenylene group, a fluorenyl group, a dibenzofuranyl group, and a dibenzothiophenyl group.

L, X and R ¹ to R ⁸ are as described above.

Formula 1 may be represented by any one of Formulas 1A-I to 1A-IV, for example.

[Formula 1A-I] [Formula 1A-II]

[Formula 1A-III] [Formula 1A-IV]

In Formula 1A-I to Formula 1A-IV,

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

At least two or more of Z ¹ to Z ⁵ are N,

L is a single bond or a substituted or unsubstituted C6 to C20 arylene group,

X is O or S,

R ¹ to R ⁸ are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group or a substituted or unsubstituted C6 to C18 aryl group,

R ^a is each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C18 aryl group, or a substituted or unsubstituted C2 to C20 heterocyclic group,

Each of R ^a is independently present or linked to adjacent groups to form a substituted or unsubstituted aliphatic, aromatic or heteroaromatic monocyclic or polycyclic ring.

In an embodiment of the present invention, when each of R ^a is independently present, the ET is a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted pyrazinyl group or a substituted or It may be an unsubstituted pyridazinyl group.

When R ^a is connected to adjacent groups to form a substituted or unsubstituted aliphatic, aromatic or heteroaromatic monocyclic or polycyclic ring, ET is a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoqui Nolinyl group, substituted or unsubstituted quinazolinyl group, substituted or unsubstituted benzofuranpyridinyl group, substituted or unsubstituted benzofuranpyrimidinyl group, substituted or unsubstituted benzothiophenepyridinyl group or substituted or unsubstituted It may be a benzothiophenepyrimidinyl group, and in an embodiment of the present invention, ET may be selected from the substituents listed in Group I below.

[Group I]

In the group I, * is a point connected to "L" in Formula 1.

In a specific embodiment of the present invention, the ET group may be a substituted or unsubstituted pyrimidinyl group or a substituted or unsubstituted triazinyl group.

In one embodiment of the present invention, L may be a single bond or a substituted or unsubstituted C6 to C20 arylene group, and in a specific embodiment of the present invention, a single bond, a substituted or unsubstituted phenylene group or a substituted or It may be an unsubstituted biphenylene group.

In one embodiment of the present invention, the R ¹ to R ⁸ may each independently be hydrogen, deuterium, a substituted or unsubstituted C1 to C5 alkyl group or a substituted or unsubstituted C6 to C12 aryl group, and in a specific embodiment , Hydrogen, deuterium, a substituted or unsubstituted C1 to C5 alkyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted naphthyl group, and in the most specific embodiment, all hydrogen I can.

In one embodiment of the present invention, R ^a is each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C5 alkyl group, a substituted or unsubstituted C6 to C12 aryl group, or a substituted or unsubstituted C2 to C20 hetero It may be a cyclic group, and in a specific embodiment, a substituted or unsubstituted C6 to C12 aryl group, or a substituted or unsubstituted C2 to C20 heterocyclic group, and in the most specific embodiment, a substituted or unsubstituted phenyl group, It may be a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

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

[Group 1]

In addition, the compound for an organic optoelectronic device represented by Formula 1 may be applied to an organic optoelectronic device, and may be applied to an organic optoelectronic device alone or together with other compounds for an organic optoelectronic device. When the compound for an organic optoelectronic device is used together with other compounds for an organic optoelectronic device, it may be applied in the form of a composition.

Hereinafter, an example of a composition for an organic optoelectronic device including the compound for an organic optoelectronic device represented by Formula 1 will be described.

A composition for an organic optoelectronic device according to another embodiment of the present invention includes a first compound for an organic optoelectronic device represented by Formula 1; And a second compound for an organic optoelectronic device represented by the following Chemical Formula 2 or a combination of the following Chemical Formulas 3 and 4.

[Formula 2] [Formula 3] [Formula 4]

In Chemical Formulas 2 to 4,

Y ¹ to Y ³ 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,

A ¹ to A 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,

Two adjacent * in Formula 3 are bonded to two * in Formula 4, and the other two * in Formula 3 are each independently CR ^b ,

R ⁹ to R ¹¹ , R ¹⁵ to R ¹⁹ and R ^b 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,

m is one of an integer from 0 to 2,

The "substitution" 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 a specific embodiment of the present invention, the "substituted" means that at least one hydrogen is deuterium, phenyl group, ortho-biphenyl group, meta-biphenyl group, para-biphenyl group, terphenyl group, naphthyl group, fluorenyl group, tri It means substituted with a phenylene group, a pyridinyl group, a carbazolyl group, a dibenzofuranyl group, or a dibenzothiophenyl group.

In an embodiment of the present invention, Y ¹ to Y ³ in Formulas 2 to 4 may each independently be a single bond or a substituted or unsubstituted C6 to C18 arylene group. Specifically, it may be a single bond, a meta-phenylene group, or a para-phenylene group.

In an embodiment of the present invention, A ¹ to A ³ in Formulas 2 to 4 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 quarterphenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted anthracenyl group, substituted or unsubstituted triphenylene group, substituted or unsubstituted pyridinyl group, substituted or unsubstituted dibenzofuranyl group , A substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted fluorenyl group, or a combination thereof. Specifically, 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 triphenylene group, a substituted or unsubstituted fluorine It may be a nil group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted dibenzofuranyl group.

In one embodiment of the present invention, R ⁹ to R ¹¹ , R ¹⁵ to R ^19, and R ^b of Formulas 2 to 4 may each independently be hydrogen, deuterium, or a substituted or unsubstituted C6 to C12 aryl group. Specifically, it may be hydrogen or a phenyl group, for example, one of R ⁹ to R ¹¹ may be a phenyl group, and the rest may be hydrogen.

In an embodiment of the present invention, m in Formula 2 may be 0 or 1.

In a specific embodiment of the present invention, Formula 2 is one of the structures listed in Group II below, and *-Y ¹ -A ¹ and *-Y ² -A ² may be one of the substituents listed in Group III below. have.

[Group II]

[Group Ⅲ]

In groups II and III above, * is a connection point.

In an embodiment of the present invention, Formula 2 is represented by Formula C-8 or Formula C-17 of Group II,

The *-Y ¹ -A ¹ and *-Y ² -A ² may be selected from B-1, B-2, and B-3 of the group III.

For example, the second compound for an organic optoelectronic device represented by Formula 2 may be represented by Formula 2-I.

[Formula 2-I]

In Formula 2-I,

Y ¹ and Y ² are each independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, a divalent substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof,

A ¹ and A 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, a substituted Or unsubstituted phenanthrenyl group, substituted or unsubstituted triphenylene group, substituted or unsubstituted pyridinyl group, substituted or unsubstituted dibenzothiophenyl group, substituted or unsubstituted dibenzofuranyl group, substituted or unsubstituted A cyclic carbazolyl group, a substituted or unsubstituted fluorenyl group, or a combination thereof,

R ⁹ to R ¹¹ and R ¹⁵ to R ¹⁷ 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.

In an embodiment of the present invention, R ⁹ to R ¹¹ and R ¹⁵ to R ¹⁷ are each Independently, it may be hydrogen, deuterium, a C1 to C5 alkyl group, a phenyl group, a naphthyl group, a biphenyl group or a pyridinyl group, and more specifically hydrogen, a methyl group, a phenyl group, a naphthyl group or a biphenyl group. In addition, R ⁹ to R ¹¹ and R ¹⁵ to R ¹⁷ are each It may independently be hydrogen or a phenyl group.

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

[Group 2]

[E-1] [E-2] [E-3] [E-4] [E-5]

[E-6] [E-7] [E-8] [E-9] [E-10]

[E-11] [E-12] [E-13] [E-14] [E-15]

[E-16] [E-17] [E-18] [E-19] [E-20]

[E-21] [E-22] [E-23] [E-24] [E-25]

[E-26] [E-27] [E-28] [E-29] [E-30]

[E-31] [E-32] [E-33] [E-34] [E-35]

[E-36] [E-37] [E-38] [E-39] [E-40]

[E-41] [E-42] [E-43] [E-44] [E-45]

[E-46] [E-47] [E-48] [E-49] [E-50]

[E-51] [E-52] [E-53] [E-54] [E-55]

[E-56] [E-57] [E-58] [E-59] [E-60]

[E-61] [E-62] [E-63] [E-64] [E-65]

[E-66] [E-67] [E-68] [E-69] [E-70]

[E-71] [E-72] [E-73] [E-74] [E-75]

[E-76] [E-77] [E-78] [E-79] [E-80]

[E-81] [E-82] [E-83] [E-84] [E-85]

[E-86] [E-87] [E-88] [E-89] [E-90]

[E-91] [E-92] [E-93] [E-94] [E-95]

[E-96] [E-97] [E-98] [E-99] [E-100]

[E-101] [E-102] [E-103] [E-104] [E-105]

[E-106] [E-107] [E-108] [E-109] [E-110]

[E-111] [E-112] [E-113] [E-114] [E-115]

[E-116] [E-117] [E-118] [E-119] [E-120]

[E-121] [E-122] [E-123] [E-124] [E-125]

[E-126] [E-127] [E-128] [E-129] [E-130]

[E-131] [E-132] [E-133] [E-134] [E-135]

[E-136] [E-137] [E-138] [E-139]

.

.

In an embodiment of the present invention, the second compound for an organic optoelectronic device consisting of a combination of a moiety represented by Formula 3 and a moiety represented by Formula 4 may be represented by at least one of Formulas 3-I to 3-V I can.

[Chemical Formula 3-Ⅰ] [Chemical Formula 3-Ⅱ] [Chemical Formula 3-Ⅲ]

[Chemical Formula 3-Ⅳ] [Chemical Formula 3-Ⅴ]

In Formulas 3-I to 3-V,

Y ¹ and Y ³ are each independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, a divalent substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof,

A ¹ and A ³ 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, a substituted Or unsubstituted phenanthrenyl group, substituted or unsubstituted triphenylene group, substituted or unsubstituted pyridinyl group, substituted or unsubstituted dibenzothiophenyl group, substituted or unsubstituted dibenzofuranyl group, substituted or unsubstituted A cyclic carbazolyl group, a substituted or unsubstituted fluorenyl group, or a combination thereof,

R ⁹ to R ¹¹ , R ¹⁸ and R ¹⁹ 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.

In an embodiment of the present invention, R ⁹ to R ¹¹ , R ¹⁸ and R ¹⁹ are each Independently, it may be hydrogen, deuterium, a C1 to C5 alkyl group, a phenyl group, a naphthyl group, a biphenyl group or a pyridinyl group, and more specifically hydrogen, a methyl group, a phenyl group, a naphthyl group or a biphenyl group. In addition, R ⁹ to R ¹¹ , R ¹⁸ and R ¹⁹ are each It may independently be hydrogen or a phenyl group.

In an embodiment of the present invention, Y ¹ and Y ³ in Formulas 3-I to 3-V may each independently be a single bond, a phenylene group, a biphenylene group, a pyridylene group, or a pyrimidinylene group.

In an embodiment of the present invention, A ¹ and A ³ in Formulas 3-I to 3-V are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted pyridyl group, and a substituted Or it may be an unsubstituted pyrimidinyl group, or a substituted or unsubstituted triazinyl group.

In an embodiment of the present invention, R ⁹ to R ¹¹ , R ¹⁸ and R ¹⁹ of Formulas 3-I to 3-V are each It may independently be hydrogen.

The second compound for an organic optoelectronic device composed of a combination of the moiety represented by Formula 3 and the moiety represented by Formula 4 may be represented by, for example, Formula 3-III.

The second compound for an organic optoelectronic device consisting of a combination of the moiety represented by Formula 3 and the moiety represented by Formula 4 may be, for example, a compound listed in Group 3, but is not limited thereto.

[Group 3]

[F-1] [F-2] [F-3] [F-4] [F-5]

[F-6] [F-7] [F-8] [F-9] [F-10]

[F-11] [F-12] [F-13] [F-14] [F-15]

[F-16] [F-17] [F-18] [F-19] [F-20]

[F-21] [F-22] [F-23] [F-24] [F-25]

[F-26] [F-27] [F-28] [F-29] [F-30]

[F-31] [F-32] [F-33] [F-34] [F-35]

[F-36] [F-37] [F-38] [F-39] [F-40]

The above-described first organic optoelectronic device compound (first host compound) and second organic optoelectronic device compound (second host compound) may be prepared in various compositions by various combinations.

The composition according to an embodiment of the present invention comprises a compound represented by any one of Formulas 1A-I to 1A-III as a first host, and a compound represented by C-8 of Group II as a second host can do.

For example, *-Y ¹ -A ¹ and *-Y ² -A ² of Formula 2 may be selected from B-1 to B-3 of Group III.

The second compound for an organic optoelectronic device may be used in a light emitting layer together with the compound for an organic optoelectronic device to improve charge mobility and stability, thereby improving luminous efficiency and lifetime characteristics. In addition, by controlling the ratio of the second organic optoelectronic device compound and the first organic optoelectronic device compound, it is possible to control the mobility of electric charges. When the composition of the present invention is used as a host, the combination ratio thereof may vary depending on the type of dopant used or the propensity of the dopant, or when the composition of the present invention is used for the electron transport auxiliary layer, it is used for OLED devices. The combination ratio of the compound in the composition of the present invention may vary depending on the type of the host and the dopant of the EML layer. For example, it may be included in a weight ratio of about 1:9 to 9:1, specifically 1:9 to 8:2, 1:9 to 7:3, 1:9 to 6:4, 1:9 to 5:5 It may be included in a range, and may be included in the range of 2:8 to 8:2, 2:8 to 7:3, 2:8 to 6:4, and 2:8 to 5:5.

In addition, when the composition of the present invention is used as a host, the first compound for an organic optoelectronic device and the second compound for an organic optoelectronic device are 1:9 to 5:5, 2:8 to 5:5, 3:7 to 5 It can be included in a weight ratio range of :5. For example, a first compound for an organic optoelectronic device and a compound for a second organic optoelectronic device may be included in the range of 5:5 or 3:7. By being included in the above range, it is possible to improve efficiency and life at the same time.

The composition may further include one or more organic compounds in addition to the above-described first organic optoelectronic device compound and second organic optoelectronic device compound.

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 material that emits light by mixing in a small amount, and in general, a material such as a metal complex that emits light by multiple excitation excitation in a triplet state or more may be used. The dopant may be, for example, an inorganic, organic, or organic-inorganic compound, and may include one or two or more.

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

[Formula Z]

L ₂ MX

In Formula Z, M is a metal, L and X are the same as or different from each other, and are ligands that form a complex compound with M.

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

In an embodiment of the present invention, the phosphorescent dopant may be a green phosphorescent dopant, and an Ir complex compound such as Ir(ppy) ₃ may be used. In this case, the wavelength range of the green phosphorescent dopant may be 500 nm to 550 nm.

Hereinafter, an organic optoelectronic device to which the compound for an organic optoelectronic device or 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, wherein the organic layer is the compound for an organic optoelectronic device or organic optoelectronic It may include a device composition.

For example, the organic layer may include an emission layer, and the emission layer may include the 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 a composition for an organic optoelectronic device may be included as a host of the emission layer, such as a green host.

The maximum emission wavelength of the organic optoelectronic device according to an embodiment of the present invention may be 500 nm to 550 nm.

In addition, as an example of the present invention, 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, such as a red host. The maximum emission wavelength of the organic optoelectronic device according to an embodiment of the present invention may be 600 nm to 650 nm.

In addition, the organic layer includes 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 is the compound for an organic optoelectronic device Or, it may include a composition for an organic optoelectronic device.

The organic optoelectronic device is not particularly limited as long as it is a device capable of mutually converting electrical energy and light energy, and examples thereof include an organic photoelectric device, an organic light emitting device, an organic solar cell, and an organic photoreceptor drum.

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.

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 disposed between the anode 120 and the cathode 110. Include.

The anode 120 may be made of a conductor having a high work function to facilitate hole injection, for example, and may be made of a metal, a metal oxide, and/or a conductive polymer. The anode 120 may be a metal such as nickel, platinum, vanadium, chromium, copper, zinc, or 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 metals and oxides such as ZnO and Al or SnO ₂ and Sb; Poly(3-methylthiophene), poly(3,4-(ethylene-1,2-dioxy)thiophene) (polyehtylenedioxythiophene: PEDT), conductive polymers such as polypyrrole and polyaniline, but are limited thereto. It is not.

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

The organic layer 105 includes the emission layer 130 including the compound for an organic optoelectronic device described above.

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

Referring to FIG. 2, the organic light-emitting device 200 further includes a hole auxiliary layer 140 in addition to the emission layer 130. The hole auxiliary layer 140 may further increase hole injection and/or hole mobility between the anode 120 and the light emitting 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.

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

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

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

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

(Preparation of compound for organic optoelectronic device)

The compounds presented as more specific examples of the compounds of the present invention were synthesized through the following steps.

(First organic optoelectronic device compound)

Intermediate synthesis

Synthesis example 1: Synthesis of Intermediate K-1

In a round bottom flask, 53.15 g (250.61 mmol) of 4-dibenzofuranboronic acid, 50 g (227.83 mmol) of 2-bromo-5-chloro-benzaldehyde, 62.98 g (455.66 mmol) of potassium carbonate and tetrakistriphenylphosphine After adding 7.89 g (6.84 mmol) of palladium, the mixture was suspended in 1000 ml of toluene and 500 ml of distilled water, and then stirred under reflux for 12 hours under a nitrogen atmosphere. After completion of the reaction, the extract was extracted with toluene, dried over magnesium sulfate, filtered with silica gel, and the filtrate was concentrated under reduced pressure. The resulting solid was stirred for 1 hour by adding 300 ml of methanol to the concentrate, followed by filtering to obtain 64.64 g of compound K-1 (yield 93%).

LC-Mass (Theoretical: 306.74 g/mol, Found: M+ = 306.79 g/mol)

Synthesis example 2: Synthesis of Intermediate K-2

In a round-bottom flask, 64.64g (210.73 mmol) of the compound K-1 and 79.46g (231.80 mmol) of (methoxymethyl)triphenylphosphonium chloride were suspended in 600 ml of tetrahydrofuran and maintained at 0°C. Subsequently, 28.38g (252.87 mmol) of potassium t-butoxide was slowly added under 0°C, followed by stirring at room temperature for 12 hours. After completion of the reaction, 600 ml of distilled water was added for extraction, the extract was concentrated, suspended in 500 ml of methylene chloride, dried over magnesium sulfate, filtered with silica gel, and concentrated again. After dissolving the concentrated reaction solution in 400 ml of methylene chloride, 20 g of methanesulfonic acid was slowly added, followed by stirring at room temperature for 12 hours. After the reaction was completed, the resulting solid was filtered, washed with 200 ml of distilled water and 200 ml of methanol, and dried to obtain 48.4 g of compound K-2 (yield 76%).

LC-Mass (Theoretical: 302.75 g/mol, Found: M+ = 303.84 g/mol)

Synthesis example 3: Intermediate K-2- 1 of synthesis

In a round bottom flask, compound K-2 11 g (36.3336 mmol) synthesized above and Pd(dba) ₂ 1.25 g (2.1800 mmol), KOAc 10.7 g (109.0008 mmol), P(Cy) ₃ 2.45 g (8.7200 mmol) , Bis(pinacolato)diboron 11.07 g (43.6003 mmol) was suspended in 150 ml of DMF and stirred under reflux for 12 hours. After completion of the reaction, the mixture was cooled to room temperature, and 300 ml of distilled water was added, followed by stirring for 1 hour. The solid produced during stirring was filtered, washed with methanol, heated and dissolved in 300 ml of toluene, filtered with silica gel, and the filtrate was concentrated and recrystallized with toluene to obtain the target compound, Compound K-2-1 9.05 g (Yield = 63%). I did.

Synthesis example 4: Synthesis of the compound represented by compound 1

In a round bottom flask, compound K-2-1 5.3 g (13.4426 mmol) synthesized above and Pd(PPh ₃ ) ₄ 0.47 g (0.4033 mmol), K ₂ CO ₃ 3.72 g (26.8852 mmol), intermediate K-3 5.08 g (13.7868 mmol) was suspended in 80 ml of THF/40 ml of distilled water and stirred under reflux for 12 hours. After the reaction was completed, the resulting solid was filtered, washed with distilled water, methyl alcohol, and acetone, and then heated and dissolved in 250 ml of dichlorobenzene. The solution was filtered with Silicagel, concentrated, and recrystallized in dichlorobenzene to obtain 4.9 g (63% yield) of the target compound, Compound 1.

LC-Mass (Theoretical value: 575.66 g/mol, found: M+ = 576.19 g/mol)

Synthesis example 5: synthesis of the compound represented by compound 2

In a round bottom flask, compound K-2-1 4 g (10.1453 mmol) synthesized above and Pd(PPh ₃ ) ₄ 0.35 g (0.3044 mmol), K ₂ CO ₃ 2.80 g (20.2906 mmol), intermediate K-4 4.53 After suspending g (13.1889 mmol) in 75 ml of THF/30 ml of distilled water, the mixture was stirred under reflux for 12 hours. After the reaction was completed, the generated solid was filtered, washed with distilled water, methyl alcohol, and acetone, and then heated and dissolved in 200 ml of dichlorobenzene. The solution was filtered through Silicagel, concentrated, and recrystallized in Monochlorobenzene to obtain 4.1 g (70% yield) of Compound 1 as the target compound.

LC-Mass (Theoretical value: 575.66 g/mol, found: M+ = 576.19 g/mol)

Comparison of the compound and the compound of the present invention In simulation T1 value compare

T1(simulation) = 2.4 eV compound 1 T1(simulation) = 2.53 eV

(Production of organic light emitting device)

Example 1: Green light emitting device

The glass substrate coated with ITO (Indium tin oxide) to a thickness of 1500Å was washed with distilled water and ultrasonic waves. After washing with distilled water, ultrasonic cleaning was performed with a solvent such as isopropyl alcohol, acetone, methanol, etc., dried, transferred to a plasma cleaner, and cleaned for 10 minutes using oxygen plasma, and then transferred to a vacuum evaporator. Using the prepared ITO transparent electrode as an anode, Compound A was vacuum deposited on the ITO substrate to form a hole injection layer having a thickness of 700 Å, and Compound B was deposited on the injection layer to a thickness of 50 Å, and then Compound C was deposited with a thickness of 1020 Å. It was deposited to a thickness to form a hole transport layer. Using Compound 1 and Compound E-99 as hosts on the hole transport layer and doping with 10 wt% of Tris(2-phenylpyridine)iridium(III) [Ir(ppy) ₃ ] as a dopant, a 400Å-thick light-emitting layer was formed by vacuum deposition. I did. Here, compound 1 and compound E-99 were used in a weight ratio of 3:7, and the ratio was separately described for the following examples. Then, compound D and Liq were simultaneously vacuum-deposited at a 1:1 ratio on the emission layer to form an electron transport layer having a thickness of 300 Å, and Liq 15 Å and Al 1200 Å were sequentially vacuum-deposited on the electron transport layer to form a cathode to form an organic light-emitting device. Was produced.

The organic light-emitting device has a structure having a five-layer organic thin film layer, and is specifically as follows.

ITO/Compound A(700Å)/Compound B(50Å)/Compound C(1020Å)/EML[Compound 1: Compound E-99: Ir(ppy) ₃ ](400Å) / Compound D: Liq(300Å) / Liq( 15Å) / Al (1200Å).

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)quinolone

Example 2

An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 2 was used instead of Compound 1 for the compound of the emission layer.

Comparative example One

An organic light-emitting device was manufactured in the same manner as in Example 1, except that CBP was used instead of Compound 1 for the compound of the emission layer.

Example 3

Example 3: Red light emitting device

The glass substrate coated with ITO (Indium tin oxide) to a thickness of 1500Å was washed with distilled water and ultrasonic waves. After washing with distilled water, ultrasonic cleaning was performed with a solvent such as isopropyl alcohol, acetone, methanol, etc., dried, transferred to a plasma cleaner, and cleaned for 10 minutes using oxygen plasma, and then transferred to a vacuum evaporator. Using the prepared ITO transparent electrode as an anode, Compound A was vacuum deposited on the ITO substrate to form a hole injection layer having a thickness of 700 Å, and Compound B was deposited on the injection layer to a thickness of 50 Å, and then Compound C was deposited with a thickness of 1020 Å. It was deposited to a thickness to form a hole transport layer. Compound 1 and compound F-46 were used as hosts on the hole transport layer, and [Ir(piq) ₂ acac] was doped with 5 wt% as a dopant to form a light emitting layer having a thickness of 400 Å by vacuum deposition. Compound 1 and Compound E-99 were used in a weight ratio of 3:7, and then Compound D and Liq were simultaneously vacuum-deposited at a ratio of 1:1 on the emission layer to form an electron transport layer having a thickness of 300 Å, and Liq 15 Å and 15 Å on the electron transport layer. An organic light-emitting device was manufactured by sequentially vacuum-depositing 1200Å Al to form a cathode.

The organic light-emitting device has a structure having a five-layer organic thin film layer, and is specifically as follows.

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)quinolone

Compound E:

Example 4

An organic light-emitting device was manufactured in the same manner as in Example 3, except that Compound 2 was used instead of Compound 1 for the compound of the emission layer.

Comparative example 2

An organic light-emitting device was manufactured in the same manner as in Example 3, except that Compound E was used as the compound of the emission layer.

evaluation

The luminous efficiency and lifespan characteristics of the organic light emitting diodes according to Examples 1 to 4 and Comparative Examples 1 and 2 were evaluated. Specific measurement methods are as follows, and the results are shown in Tables 1 and 2.

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

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

(2) Measurement of luminance change according to voltage change

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

(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).

(4) Life measurement

Reduction of the brightness corresponding to the polar Optronics life measured using the measurement system Examples 1 to 6 and the comparative device Initial luminance (cd / m ²⁾ for 5000cd / m and time emits light at a ^second of Example 1 for the manufacture of organic light emitting devices The time when the luminance decreased to 97% compared to the initial luminance was measured as T97 life.

(5) Measurement of driving voltage

The driving voltage of each device was measured at 15 mA/cm ² using a current-voltmeter (Keithley 2400).

Green element division First host Second host Efficiency (Cd/A) Life (T97, h) Driving voltage (V) Example 1 Compound 1 Compound E-99 67.6 20 3.92 Example 2 Compound 2 Compound E-99 65.6 42 3.78 Comparative Example 1 CBP - 40.2 5 5.24

Referring to Table 1, it can be seen that the organic light emitting device according to Examples 1 and 2 improved both luminous efficiency and lifetime characteristics at the same time compared to the organic light emitting device according to Comparative Example 1, and in particular, improved in terms of life and efficiency. .

Red element division First host Second host Efficiency (Cd/A) Driving voltage (V) Example 3 Compound 1 Compound F-46 22.3 3.83 Example 4 Compound 2 Compound F-46 22.4 3.98 Comparative Example 2 Compound E - 21.1 4.52

Referring to Table 2, it can be seen that the luminous efficiency and driving characteristics of the organic light-emitting devices according to Examples 3 and 4 are simultaneously improved compared to the organic light-emitting devices according to Comparative Example 2.

The present invention is not limited to the above embodiments, but may be manufactured in a variety of different forms, and a person of ordinary skill in the art to which the present invention pertains to other specific forms without changing the technical spirit or essential features of the present invention. It will be appreciated that it can be implemented with. Therefore, it should be understood that the embodiments described above are illustrative in all respects and not limiting.

100, 200: organic light emitting device
105: organic layer
110: cathode
120: anode
130: light-emitting layer
140: hole auxiliary layer

Claims (16)

Compound for an organic optoelectronic device represented by the following Formula 1:
[Formula 1]

In Formula 1,
ET is a triazinyl group unsubstituted or substituted with "phenyl group, bipheny group, terphenyl group, dibenzofuranyl group, dibenzothiophenyl group, fluorenyl group, or a combination thereof",
L is a single bond,
X is O or S,
R ¹ to R ⁸ are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group or a substituted or unsubstituted C6 to C18 aryl group,
The "substituted" means that at least one hydrogen is substituted with deuterium, a cyano group, a C1 to C20 alkyl group, a C6 to C30 aryl group, or a C2 to C30 heteroaryl group. The method of claim 1,
Compound for an organic optoelectronic device represented by the following formula 1A:
[Formula 1A]

In Formula 1A,
Z ¹ , Z ³ and Z ⁵ are each independently N,
Z ² and Z ⁴ are each independently CR ^a ,
L is a single bond,
X is O or S,
R ¹ to R ⁸ are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group or a substituted or unsubstituted C6 to C18 aryl group,
Wherein R ^a is hydrogen, a substituted or unsubstituted C6 to C18 aryl group or a substituted or unsubstituted C2 to C20 heterocyclic group,
The "substituted" means that at least one hydrogen is substituted with deuterium, a cyano group, a C1 to C20 alkyl group, a C6 to C30 aryl group, or a C2 to C30 heteroaryl group. The method of claim 2,
Compounds for organic optoelectronic devices represented by any one of the following Formulas 1A-I to 1A-IV:
[Formula 1A-I] [Formula 1A-II]

[Formula 1A-III] [Formula 1A-IV]

In Formula 1A-I to Formula 1A-IV,
Z ¹ , Z ³ and Z ⁵ are each independently N,
Z ² and Z ⁴ are each independently CR ^a ,
L is a single bond,
X is O or S,
R ¹ to R ⁸ are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group or a substituted or unsubstituted C6 to C18 aryl group,
R ^a is hydrogen, a substituted or unsubstituted C6 to C18 aryl group or a substituted or unsubstituted C2 to C20 heterocyclic group,
The "substituted" means that at least one hydrogen is substituted with a deuterium, a cyano group, a C1 to C20 alkyl group, a C6 to C30 aryl group or a C2 to C30 heteroaryl group. delete delete The method of claim 1,
The ET is a compound for an organic optoelectronic device selected from the substituents listed in the following group I:
[Group I]

In group I above,
* Is a point connected to "L" in Formula 1. The method of claim 1,
Compounds for organic optoelectronic devices selected from the compounds listed in the following Group 1:
[Group 1]

. The first compound for an organic optoelectronic device according to claim 1; And
A composition for an organic optoelectronic device comprising a compound for a second organic optoelectronic device represented by the following Formula 2 or a combination of Formulas 3 and 4:
[Formula 2] [Formula 3] [Formula 4]

In Chemical Formulas 2 to 4,
Y ¹ to Y ³ 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,
A ¹ to A 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,
Two adjacent * in Formula 3 are bonded to two * in Formula 4, and the remaining two * in Formula 3 are each independently CR ^b ,
R ⁹ to R ¹¹ , R ¹⁵ to R ¹⁹ and R ^b 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,
m is one of an integer from 0 to 2,
The "substitution" 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 8,
A ¹ to A ³ of Formulas 2 to 4 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 quarter phenyl group, a substituted or Unsubstituted naphthyl group, substituted or unsubstituted anthracenyl group, substituted or unsubstituted triphenylene group, substituted or unsubstituted pyridinyl group, substituted or unsubstituted dibenzofuranyl group, substituted or unsubstituted dibenzo A composition for an organic optoelectronic device, which is a thiophenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted fluorenyl group, or a combination thereof. The method of claim 8,
Formula 2 is one of the structures listed in Group II below,
The *-Y ¹ -A ¹ and *-Y ² -A ² is one of the substituents listed in the following group III composition for an organic optoelectronic device:
[Group II]

[Group III]

In groups II and III above, * is a connection point. The method of claim 10,
Formula 2 is represented by Formula C-8 or Formula C-17 of Group II,
The *-Y ¹ -A ¹ and *-Y ² -A ² is a composition for an organic optoelectronic device selected from B-1, B-2, and B-3 of the group III. The method of claim 8,
The second compound for an organic optoelectronic device is a composition for an organic optoelectronic device represented by the following Formula 2-I or Formula 3-III:
[Formula 2-I] [Formula 3-III]

In Formula 2-I and Formula 3-III,
Y ¹ to Y ³ are each independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, a divalent substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof,
A ¹ to A ³ 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, a substituted Or unsubstituted phenanthrenyl group, substituted or unsubstituted triphenylene group, substituted or unsubstituted pyridinyl group, substituted or unsubstituted dibenzothiophenyl group, substituted or unsubstituted dibenzofuranyl group, substituted or unsubstituted A cyclic carbazolyl group, a substituted or unsubstituted fluorenyl group, or a combination thereof,
R ⁹ to R ¹¹ and R ¹⁵ to R ¹⁹ 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. The anode and cathode facing each other, and
Including at least one layer of an 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, 6 and 7; or
An organic optoelectronic device comprising the composition for an organic optoelectronic device according to any one of claims 8 to 12. The method of claim 13,
The organic layer includes a light emitting layer,
The organic optoelectronic device compound or the organic optoelectronic device composition is included as a host of the emission layer. The method of claim 13,
An organic optoelectronic device having a maximum emission wavelength of 500 nm to 550 nm. A display device comprising the organic optoelectronic device according to claim 13.

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