KR102787034B1 - Organic optoelectronic device and display device - Google Patents

Abstract

It comprises an anode and a cathode facing each other, a light-emitting layer positioned between the anode and the cathode, a hole transport layer positioned between the anode and the light-emitting layer, and a hole transport auxiliary layer positioned between the light-emitting layer and the hole transport layer.
The present invention relates to an organic optoelectronic device and display device, wherein the light-emitting layer comprises a composition including a first compound represented by chemical formula 1 and a second compound represented by chemical formula 2, and the hole transport auxiliary layer comprises a third compound represented by chemical formula 3.
The details of the above chemical formulas 1 to 3 are as defined in the specification.

Description

ORGANIC OPTOELECTRONIC DEVICE AND DISPLAY DEVICE

It relates to organic optoelectronic devices and display devices.

Organic optoelectronic diodes are devices that can convert electrical energy and light energy into each other.

Organic optoelectronic devices can be broadly divided into two types based on their operating principles. One is a photoelectric device in which excitons formed by light energy are separated into electrons and holes, and the electrons and holes are transferred to different electrodes to generate electrical energy, and the other is a light-emitting device in which light energy is generated from electrical energy by supplying voltage or current to the electrode.

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

Among these, organic light emitting diodes (OLEDs) have recently attracted significant attention due to the increasing demand for flat panel display devices. Organic light emitting diodes are devices that convert electrical energy into light, and the performance of organic light emitting diodes is greatly affected by the organic materials located between the electrodes.

One embodiment provides a high-efficiency and long-life organic optoelectronic device.

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

According to one embodiment, an organic optoelectronic device is provided, including an anode and a cathode facing each other, a light-emitting layer positioned between the anode and the cathode, a hole transport layer positioned between the anode and the light-emitting layer, and a hole transport auxiliary layer positioned between the light-emitting layer and the hole transport layer, wherein the light-emitting layer includes a composition including a first compound represented by the following chemical formula 1 and a second compound represented by the following chemical formula 2, and the hole transport auxiliary layer includes a third compound represented by the following chemical formula 3.

[Chemical Formula 1]

In the above chemical formula 1,

L ¹ to L ⁵ are each independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heterocyclic group, or a combination thereof,

Ar ¹ is a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof,

R ¹ to R ⁴ are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, halogen, a cyano group or a combination thereof,

R ¹ to R ⁴ are each independently present or adjacent groups are connected to form a substituted or unsubstituted aromatic monocyclic or polycyclic ring,

At least one of Ar ¹ and R ¹ to R ⁴ is a group represented by the following chemical formula A,

[Chemical Formula A]

In the above chemical formula A,

Z ¹ to Z ⁵ are each independently N or CL ^a -R ^a ,

At least one of Z ¹ to Z ⁵ is N,

Here, L ^a is each independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heterocyclic group, or a combination thereof,

R ^a is each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, halogen, cyano group or a combination thereof,

R ^a each independently exists or is connected to an adjacent group to form a substituted or unsubstituted aromatic monocyclic or polycyclic ring, or a substituted or unsubstituted aromatic monocyclic or polycyclic heterocycle,

* is the connection point with L ¹ to L ⁵ ;

[Chemical formula 2]

In the above chemical formula 2,

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

L ⁶ and L ⁷ are each independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heterocyclic group, or a combination thereof,

R ⁵ to R ¹⁰ are each independently hydrogen, deuterium, halogen, cyano group, substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C6 to C30 aryl group or a combination thereof,

n is an integer between 0 and 2;

[Chemical Formula 3]

In the above chemical formula 3,

L ⁸ and L ⁹ are each independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heterocyclic group, or a combination thereof,

R ¹¹ to R ¹⁴ are each independently hydrogen, deuterium, halogen, cyano group, substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C6 to C30 aryl group, or a combination thereof,

Ar ⁴ to Ar ⁷ 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.

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

High-efficiency, long-life organic optoelectronic devices can be realized.

FIG. 1 is a cross-sectional view schematically illustrating an organic optoelectronic device according to one embodiment.

Hereinafter, embodiments of the present invention will be described in detail. However, these are presented as examples, and the present invention is not limited thereby, and the present invention is defined only by the scope of the claims described below.

As used herein, unless otherwise defined, the term "substituted" means that at least one hydrogen in a substituent or compound is substituted with 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, a C1 to C30 alkyl group, a C1 to C10 alkylsilyl group, a C6 to C30 arylsilyl group, a C3 to C30 cycloalkyl group, a C3 to C30 heterocycloalkyl group, a C6 to C30 aryl group, a C2 to C30 heteroaryl group, a C1 to C20 alkoxy group, a C1 to C10 trifluoroalkyl group, a cyano group, or a combination thereof.

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

As used herein, unless otherwise defined, "hetero" means containing 1 to 3 heteroatoms selected from the group consisting of N, O, S, P, and Si in one functional group, and the remainder being carbon.

In this specification, "aryl group" is a concept that encompasses a group having one or more hydrocarbon aromatic moieties, and includes a form in which all elements of the hydrocarbon aromatic moieties have p-orbitals and these p-orbitals form conjugation, such as a phenyl group, a naphthyl group, etc., a form in which two or more hydrocarbon aromatic moieties are connected via a sigma bond, such as a biphenyl group, a terphenyl group, a quarterphenyl group, etc., and a non-aromatic fused ring in which two or more hydrocarbon aromatic moieties are directly or indirectly fused, such as a fluorenyl group, etc.

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

In this specification, the "heterocyclic group" is a superior concept including a heteroaryl group, and means a group containing at least one heteroatom selected from the group consisting of N, O, S, P, and Si instead of carbon (C) in a ring compound such as an aryl group, a cycloalkyl group, a fused ring thereof, or a combination thereof. When the heterocyclic group is a fused ring, the heterocyclic group as a whole or each ring may contain one or more heteroatoms.

For example, a "heteroaryl group" means an aryl group containing at least one heteroatom selected from the group consisting of N, O, S, P, and Si. Two or more heteroaryl groups may be directly connected via a sigma bond, or, when the heteroaryl group includes two or more rings, the 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 of the heteroatoms.

More specifically, the substituted or unsubstituted C6 to C30 aryl group may be, but is not limited to, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted naphthacenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted p-terphenyl group, a substituted or unsubstituted m-terphenyl group, a substituted or unsubstituted o-terphenyl group, a substituted or unsubstituted chrysenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted perylenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted indenyl group, or a combination thereof.

More specifically, the substituted or unsubstituted C2 to C30 heterocyclic group is selected from the group consisting of a substituted or unsubstituted furanyl group, a substituted or unsubstituted thiophenyl group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted imidazolyl group, a substituted or unsubstituted triazolyl group, a substituted or unsubstituted oxazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted oxadiazolyl group, a substituted or unsubstituted thiadiazolyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted An isoquinolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted benzoxazinyl group, a substituted or unsubstituted benzthiazinyl group, a substituted or unsubstituted acridinyl group, a substituted or unsubstituted phenazinyl group, a substituted or unsubstituted phenothiazinyl group, a substituted or unsubstituted phenoxazinyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group, or a combination thereof, may be, but is not limited thereto.

In this specification, the hole characteristic refers to a characteristic that can form holes by donating electrons when an electric field is applied, and has a conductive characteristic along the HOMO level, which means a characteristic that facilitates the injection of holes formed at the anode into the light-emitting layer, the movement of holes formed in the light-emitting layer to the anode, and the movement in the light-emitting layer.

In addition, electronic properties refer to the property of being able to receive electrons when an electric field is applied, and have conductive properties along the LUMO level, which means the property of facilitating the injection of electrons formed at the cathode into the light-emitting layer, the movement of electrons formed in the light-emitting layer to the cathode, and the movement in the light-emitting layer.

An organic optoelectronic device according to an embodiment of the present invention is described below.

The above organic optoelectronic device is not particularly limited as long as it is a device capable of converting electrical energy and optical energy into each other, and examples thereof include organic photoelectric devices, organic light-emitting devices, organic solar cells, and organic photosensitive drums.

Here, an organic light-emitting device, which is an example of an organic optoelectronic device, is described as an example, but it is not limited thereto and can be equally applied to other organic optoelectronic devices.

In order to clearly express various layers and regions in the drawings, the thickness is enlarged and shown. Similar parts are designated by the same drawing reference numerals throughout the specification. When a part such as a layer, film, region, or plate is said to be "on" another part, this includes not only the case where it is "directly on" the other part, but also the case where there is another part in between. Conversely, when a part is said to be "directly on" another part, it means that there is no other part in between.

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

Referring to FIG. 1, an organic light-emitting device (300) according to one embodiment includes an anode (110) and a cathode (120) facing each other, and an organic layer (105) positioned between the anode (110) and the cathode (120), and the organic layer (105) includes a light-emitting layer (130), a hole transport auxiliary layer (142), and a hole transport layer (141).

The anode (110) can be made of a conductor having a high work function, for example, to facilitate hole injection, and can be made of, for example, a metal, a metal oxide, and/or a conductive polymer. The anode (110) may include, but is not limited to, a metal such as nickel, platinum, vanadium, chromium, copper, zinc, or gold, or an alloy thereof; a metal oxide such as zinc oxide, indium oxide, indium tin oxide (ITO), or indium zinc oxide (IZO); a combination of a metal and an oxide such as ZnO and Al or SnO ₂ and Sb; a conductive polymer such as poly(3-methylthiophene), poly(3,4-(ethylene-1,2-dioxy)thiophene) (polyehtylenedioxythiophene: PEDOT), polypyrrole, and polyaniline.

The cathode (120) can be made of a conductor having a low work function, for example, to facilitate electron injection, and can be made of, for example, a metal, a metal oxide, and/or a conductive polymer. The cathode (120) can 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; a multilayer structure material such as LiF/Al, LiO ₂ /Al, LiF/Ca, LiF/Al, and BaF ₂ /Ca, but is not limited thereto.

The light-emitting layer (130) is located between the anode (110) and the cathode (120) and includes a plurality of hosts and at least one type of dopant.

The light-emitting layer (130) may include a first compound having relatively strong electron properties as a host and a second compound having relatively strong hole properties, and the host may be a composition including the first compound and the second compound.

The hole transport auxiliary layer (142) is positioned between the light-emitting layer (130) and the hole transport layer (141) described below and is positioned in contact with the light-emitting layer (130), thereby enabling fine control of hole mobility at the interface between the light-emitting layer (130) and the hole transport layer (141). The hole transport auxiliary layer (142) may include a third compound and may also include multiple layers.

The first compound is a compound with relatively strong electronic properties and can be expressed by the following chemical formula 1.

[Chemical Formula 1]

In the above chemical formula 1,

L ¹ to L ⁵ are each independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heterocyclic group, or a combination thereof,

Ar ¹ is a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof,

R ¹ to R ⁴ are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, halogen, a cyano group or a combination thereof,

R ¹ to R ⁴ are each independently present or adjacent groups are connected to form a substituted or unsubstituted aromatic monocyclic or polycyclic ring,

At least one of Ar ¹ and R ¹ to R ⁴ is a group represented by the following chemical formula A,

[Chemical Formula A]

In the above chemical formula A,

Z ¹ to Z ⁵ are each independently N or CL ^a -R ^a ,

At least one of Z ¹ to Z ⁵ is N,

Here, L ^a is each independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heterocyclic group, or a combination thereof,

R ^a is each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, halogen, cyano group or a combination thereof,

R ^a each independently exists or is connected to an adjacent group to form a substituted or unsubstituted aromatic monocyclic or polycyclic ring, or a substituted or unsubstituted aromatic monocyclic or polycyclic heterocycle,

* is the connection point with L ¹ to L ⁵ .

The second compound is a compound with relatively strong hole properties and can be expressed by the following chemical formula 2.

[Chemical formula 2]

In the above chemical formula 2,

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

L ⁶ and L ⁷ are each independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heterocyclic group, or a combination thereof,

R ⁵ to R ¹⁰ are each independently hydrogen, deuterium, halogen, cyano group, substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C6 to C30 aryl group or a combination thereof,

n is an integer between 0 and 2.

The third compound is a compound that is included in the hole transport auxiliary layer (142) and precisely controls the mobility of holes at the interface between the light-emitting layer (130) and the hole transport layer (141), and can be expressed by the following chemical formula 3.

[Chemical Formula 3]

In the above chemical formula 3,

L ⁸ and L ⁹ are each independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heterocyclic group, or a combination thereof,

R ¹¹ to R ¹⁴ are each independently hydrogen, deuterium, halogen, cyano group, substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C6 to C30 aryl group, or a combination thereof,

Ar ⁴ to Ar ⁷ 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.

The first compound is a compound having a property of accepting both holes and electrons when an electric field is applied, that is, a bipolar property. Specifically, since a nitrogen-containing ring, such as pyrimidine or triazine, is substituted in the carbazole core, the glass transition temperature is improved relative to the molecular weight, so that heat resistance can be secured. In addition, by combining a bicarbazole compound as the second host, the first host material having fast and stable electron transfer properties and the second host material having fast and stable hole transfer properties can be used to balance holes and electrons in the device.

In addition, by applying a compound such as the third compound to the hole transport auxiliary layer, it is possible to prevent holes or electrons from accumulating at the interface between the hole transport layer and the light-emitting layer and to improve charge balance. Accordingly, the driving voltage and life characteristics of the organic optoelectronic device can be significantly improved.

For example, in the chemical formula 1, L ¹ to L ⁵ can each independently be a single bond, a substituted or unsubstituted C6 to C20 arylene group, or a substituted or unsubstituted C2 to C20 heterocyclic group.

For example, L ¹ to L ⁵ can each independently be a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

For example, L ¹ to L ⁵ can each independently be a single bond, a substituted or unsubstituted m-phenylene group, a substituted or unsubstituted p-phenylene group, a substituted or unsubstituted o-phenylene group, or a substituted or unsubstituted biphenylene group. Here, the substitution may be, for example, but is not limited to, substitution of at least one hydrogen with deuterium, a C1 to C20 alkyl group, a C6 to C20 aryl group, a C2 to C20 heterocyclic group, halogen, a cyano group, or a combination thereof.

For example, Ar ¹ may be 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, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted fluorenyl group, a group represented by the above chemical formula A, or a combination thereof.

For example, Ar ¹ may be, but is not limited to, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, or a group represented by the above chemical formula A.

For example, R ¹ to R ⁴ can each independently be hydrogen, deuterium, a cyano group, 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, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a group represented by the above chemical formula A, or a combination thereof.

For example, R ¹ to R ⁴ may each independently be hydrogen, deuterium, a cyano group, 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 dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a group represented by the above chemical formula A, but is not limited thereto.

For example, the first compound can be expressed by any one of the following chemical formulas 1A to 1L, depending on the bonding position of the group represented by the chemical formula A.

[Chemical Formula 1A] [Chemical Formula 1B] [Chemical Formula 1C]

[Formula 1D] [Formula 1E] [Formula 1F]

[Chemical Formula 1G] [Chemical Formula 1H] [Chemical Formula 1I]

[Chemical Formula 1J] [Chemical Formula 1K] [Chemical Formula 1L]

In the chemical formulas 1A to 1L above, L ¹ to L ⁵ , Ar ¹ and R ¹ to R ⁴ , Z ¹ to Z ⁵ are as described above,

R ^c , R ^d , R ^e , R ^f , R ^g and R ^h are as defined for R ¹ to R ⁴ described above,

Z ^1a to Z ^5a are as defined for Z ¹ to Z ⁵ described above,

Z ^1b to Z ^5b are also defined as Z ¹ to Z ⁵ described above.

For example, each of the above L ^a is independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heterocyclic group, or a combination thereof,

For example, L ^a can each independently be a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted dibenzofuranylene group, or a substituted or unsubstituted dibenzothiophenylene group.

For example, L ^a can each independently be a single bond, a substituted or unsubstituted m-phenylene group, or a substituted or unsubstituted p-phenylene group, but is not limited thereto.

For example, R ^a is each independently hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, a substituted or unsubstituted C2 to C20 heterocyclic group, or a combination thereof,

For example, R ^a can each independently be hydrogen, deuterium, a cyano group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrene group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

For example, R ^a may each independently be hydrogen, deuterium, a cyano group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted m-biphenyl group, a substituted or unsubstituted p-biphenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group, but is not limited thereto.

R ^a may exist independently, or adjacent groups may be linked to each other to form a substituted or unsubstituted aromatic monocyclic or polycyclic ring, or a substituted or unsubstituted aromatic monocyclic or polycyclic heterocycle.

For example, in the group represented by the chemical formula A, at least two of Z ¹ to Z ⁵ are N, and each R ^a can exist independently.

For example, the group represented by the chemical formula A may be a substituted or unsubstituted pyrimidinyl group or a substituted or unsubstituted triazinyl group.

For example, Z ¹ and Z ³ may be N, and Z ² , Z ⁴ , and Z ⁵ may each independently be CL ^a -R ^a ; Z ³ and Z ⁵ may be N, and Z ¹ , Z ² , and Z ⁴ may each independently be CL ^a -R ^a ; or Z ² and Z ⁴ may be N, and Z ¹ , Z ³ , and Z ⁵ may each independently be CL ^a -R ^a . In this case, L ^a and R ^a are as described above.

For example, Z ¹ , Z ³ and Z ⁵ can be N, and Z ² and Z ⁴ can be independently CL ^a -R ^a . In this case, L ^a and R ^a are as described above.

For example, in a group represented by chemical formula A, at least one of Z ¹ to Z ⁵ is N, and adjacent R ^a can be connected to each other to form a substituted or unsubstituted aromatic monocyclic ring, or a substituted or unsubstituted aromatic monocyclic heterocycle.

In this case, the group represented by chemical formula A may be a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted quinazolinyl group, or a substituted or unsubstituted naphthyridinyl group.

For example, Z ³ and Z ⁴ are each CR ^a , adjacent R ^a are connected to each other to form a benzene ring, and any one of Z ¹ , Z ² , and Z ⁵ can be N.

For example, Z ³ and Z ⁴ are CR ^a and adjacent R ^a are connected to each other to form a benzene ring, and any two of Z ¹ , Z ² , and Z ⁵ can be N.

For example, Z ³ and Z ⁴ may be CR ^a , adjacent R ^a may be connected to each other to form a benzene ring, and Z ¹ , Z ² , and Z ⁵ may each be N.

For example, the chemical formula A may be expressed by any one of the following chemical formulas A-1 to A-7, but is not limited thereto.

[Chemical Formula A-1] [Chemical Formula A-2] [Chemical Formula A-3]

[Chemical Formula A-4] [Chemical Formula A-5] [Chemical Formula A-6] [Chemical Formula A-7]

In the above chemical formulas A-1 to A-7,

L ^a1 to L ^a5 , and L ^b1 and L ^b2 are as defined for L ^a above,

R ^a1 to R ^a5 , R ^b1 and R ^b2 are as defined for R ^a above.

As a specific example, the group represented by the chemical formula A may be a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted quinazolinyl group, or a substituted or unsubstituted naphthyridinyl group.

As a more specific example, the chemical formula A can be expressed by any one of the groups listed in Group I below.

[Group I]

For example, the chemical formula 1A can be expressed as any one of the following chemical formulas 1A-1 to 1A-4 depending on the specific bonding position of the group expressed by the chemical formula A.

[Chemical Formula 1A-1] [Chemical Formula 1A-2]

[Chemical Formula 1A-3] [Chemical Formula 1A-4]

In the above chemical formulas 1A-1 to 1A-4, L ¹ to L ⁵ , Ar ¹ , R ² to R ⁴ and Z ¹ to Z ⁵ are as described above.

For example, chemical formula 1A can be expressed as chemical formula 1A-2 or chemical formula 1A-4.

For example, the chemical formula 1C above can be expressed by any one of the following chemical formulas 1C-1 to 1C-4 depending on the specific bonding position of the group represented by the chemical formula A.

[Chemical Formula 1C-1] [Chemical Formula 1C-2] [Chemical Formula 1C-3] [Chemical Formula 1C-4]

In the chemical formulas 1C-1 to 1C-4, L ¹ to L ⁵ , R ² to R ⁴ , Z ¹ to Z ⁵ , Z ^1a to Z ^5a , and Z ^1b to Z ^5b are as described above.

For example, chemical formula 1C can be expressed as chemical formula 1C-2 or chemical formula 1C-4.

The first compound may be, for example, but is not limited to, one selected from the compounds listed in Group 1 below.

[Group 1]

By including the second compound together with the first compound, the balance between holes and electrons can be increased, thereby significantly improving the driving or life characteristics of a device to which it is applied.

For example, the chemical formula 2 can be expressed as the following chemical formula 2-1.

[Chemical Formula 2-1]

In the above chemical formula 2-1, the definitions of Ar ² , Ar ³ , L ⁶ , L ⁷ , R ⁵ to R ¹⁰ are as described above.

In one embodiment, the second compound can be represented by the chemical formula 2-1, wherein R ⁵ to R ¹⁰ of the chemical formula 2-1 are all hydrogen, and *-L ⁶ -Ar ² and *-L ⁷ -Ar ³ can each independently be one of the substituents listed in Group II below.

[Group II]

In the above group II, * is a connection point.

For example, Ar ² and Ar ³ can each independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group.

Additionally, L ⁶ and L ⁷ can each independently be a single bond or a substituted or unsubstituted phenylene group.

Additionally, R ⁵ to R ¹⁰ can each independently be hydrogen or a C6 aryl group.

The second compound may be, for example, but is not limited to, one selected from the compounds listed in Group 2 below.

[Group 2]

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

[C-111] [C-112] [C-113]

The first compound and the second compound may be included in a weight ratio of, for example, 1:99 to 99:1. By being included in the above range, the electron transport ability of the first compound and the hole transport ability of the second compound can be used to achieve an appropriate weight ratio to implement bipolar characteristics, thereby improving efficiency and lifespan. Within the above range, the weight ratio may be, for example, about 10:90 to 90:10, about 20:80 to 80:20, about 20:80 to 70:30, about 20:80 to 60:40. For example, the weight ratio may be 30:70 to 50:50, and for example, the weight ratio may be 30:70.

The emitting layer may further include one or more compounds in addition to the aforementioned host.

The emissive layer may further comprise a dopant. The dopant may be, for example, a phosphorescent dopant, for example, a red, green or blue phosphorescent dopant, for example, a red phosphorescent dopant.

A dopant is a substance that causes light emission when mixed in a small amount with the aforementioned host. Generally, a substance such as a metal complex that causes light emission by multiple excitation that excites to a triplet state or higher can be used. The dopant can be, for example, an inorganic, organic, or organic-inorganic compound, and can be included in one or more types.

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

[chemical formula Z]

L ¹⁰ MX

In the above chemical formula Z, M is a metal, L ¹⁰ and X are the same or different and are ligands that form a complex with M.

The above M can be, for example, Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd or a combination thereof, and the above L ¹⁰ and X can be, for example, a bidentate ligand.

The positive hole transport auxiliary layer (142) may include a third compound.

The third compound is a compound having a high HOMO energy level and can have good hole injection properties. Accordingly, the third compound can be applied to the hole transport auxiliary layer (142) to effectively improve the mobility of holes at the interface between the light-emitting layer (130) and the hole transport layer (141), thereby effectively lowering the operating voltage of the organic optoelectronic device.

For example, Ar ⁴ to Ar ⁷ in the chemical formula 3 may each independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a combination thereof.

For example, the third compound can be expressed by the following chemical formula 3-1.

[Chemical Formula 3-1]

In the chemical formula 3-1 above, L ⁸ , L ⁹ , R ¹¹ to R ¹⁴ , and Ar ⁴ to Ar ⁶ are as described above,

X is O, S, or CR ⁱ R ^j ,

R ⁱ , R ^j and R ¹⁵ to R ¹⁷ are each independently hydrogen, deuterium, halogen, cyano group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a combination thereof.

As a more specific example, L ⁸ and L ⁹ in the chemical formula 3-1 are each independently a meta-phenylene group or a para-phenylene group,

Ar ⁴ is a phenyl group,

Ar ⁵ and Ar ⁶ are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group,

R ¹¹ to R ¹⁷ can each independently be hydrogen or a phenyl group.

The third compound may be, for example, one selected from the compounds listed in Group 3 below, but is not limited thereto.

[Group 3]

[D-1] [D-2] [D-2]　　　　　　　[D-3]　　　　　　　　　　　　[D-4]

[D-5] [D-6] [D-6]　　　　　　　[D-7]　　　　　　　　　　　[D-8]

[D-9] [D-10] [D-10] [D-10]　　　　　　[D-11]　　　　　　　　　　　[D-12]

[D-13]　　　　　　　　　　　　[D-14]　　　　　[D-15] [D-15] [D-16]

[D-17]　　　　　　　　　　　[D-18]　　　　　　　[D-19] [D-19] [D-20]

[D-21]　　　　　　　　　　　　[D-22]　　　　[D-23] [D-24]

[D-25] [D-26] [D-26] [D-27] [D-28]

[D-29] [D-30] [D-30] [D-31] [D-31] [D-32]

[D-33] [D-34] [D-34] [D-34] [D-35] [D-35] [D-36]

[D-37] [D-38] [D-38] [D-38] [D-39] [D-39] [D-40]

[D-41]　　　　　　　　　　　　[D-42]　　　　　[D-43] [D-44]

[D-45] [D-46] [D-46] [D-46] [D-47] [D-48]

[D-49] [D-50] [D-50] [D-51] [D-51] [D-52]

[D-53] [D-54] [D-54] [D-55] [D-56]

[D-57]　　　　　　　　　　　　　　　　[D-58]　　　　[D-59] [D-60]

[D-61]　　　　　　　　　　　　　　　　[D-62]　　　　[D-63] [D-64]

[D-65]　　　　　　　　　　　　　　　　[D-66]　　　　[D-67] [D-68]

In a more specific embodiment, the first compound may be represented by the chemical formula 1B, the second compound may be represented by the chemical formula 2-1, and the third compound may be represented by the chemical formula 3-1 below.

In this case, in the chemical formula 1B above,

Z ¹ , Z ³ and Z ⁵ are each N,

Z ² and Z ⁴ are each independently CL ^a -R ^a ,

L ^a and L ¹ to L ⁴ are each a single bond,

L ⁵ is a phenylene group or a biphenylene group,

R ^a is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted terphenyl group, or a substituted or unsubstituted triphenylene group,

R ¹ to R ⁴ can each independently be hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C12 aryl group.

In this case, in the chemical formula 2-1 above,

*-L ⁶ -Ar ² and *-L ⁷ -Ar ³ are each independently any one of the substituents B-1 to B-4 listed in the above Group II,

R ⁵ to R ¹⁰ can each independently be hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C12 aryl group.

In this case, in the chemical formula 3-1 above,

L ⁸ and L ⁹ are each independently a meta-phenylene group or a para-phenylene group,

Ar ⁴ is a phenyl group,

Ar ⁵ and Ar ⁶ are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group,

R ¹¹ to R ¹⁷ can each independently be hydrogen or a phenyl group.

The hole transport layer (141) is positioned between the anode (110) and the light-emitting layer (130) and can facilitate hole transport from the anode (110) to the light-emitting layer (130). For example, the hole transport layer (141) may include a material having a HOMO energy level between the work function of a conductor forming the anode (110) and the HOMO energy level of a material forming the light-emitting layer (130).

The hole transport layer (141) may include, for example, an amine derivative.

The hole transport layer (141) may include, for example, a compound represented by the following chemical formula 4, but is not limited thereto.

[Chemical Formula 4]

In the above chemical formula 4,

R ¹⁸ to R ²¹ are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof,

R ¹⁸ and R ¹⁹ exist independently or combine with each other to form a ring,

R ²⁰ and R ²¹ exist independently or combine with each other to form a ring,

R ²² to R ²⁴ are each independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,

L ¹¹ to L ¹⁴ are each independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof.

For example, R ²² can be a substituted or unsubstituted C6 to C30 aryl group, for example, R ²² can be a substituted or unsubstituted phenyl group or a substituted or unsubstituted biphenyl group.

For example, R ²³ and R ²⁴ can each independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted bisfluorene group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a combination thereof.

The compound represented by the above chemical formula 4 may be, for example, one of the compounds listed in Group 4 below, but is not limited thereto.

[Group 4]

The organic layer (105) may further include a hole injection layer, an electron blocking layer, an electron transport layer, an electron injection layer, and/or a hole blocking layer (not shown) in addition to the aforementioned light-emitting layer (130), hole transport auxiliary layer (142), and hole transport layer (141).

The organic light-emitting device (300) can be manufactured by forming an anode or cathode on a substrate, forming an organic layer using a dry film method such as evaporation, sputtering, plasma plating, and ion plating, or a solution process, and then forming a cathode or anode thereon.

The above-described organic optoelectronic device can be applied to a display device. For example, the organic light-emitting device can be applied to an organic light-emitting display device.

The above-described implementation examples are described in more detail through the following examples. However, the following examples are for the purpose of explanation only and do not limit the scope of rights.

(Synthesis of the first compound)

Synthetic example 1: Synthesis of compound A-27

[Reaction Formula 1]

Compound A-27 was synthesized by referring to the method disclosed in KR10-1947747B1.

Synthetic example 2: Synthesis of compound A-13

[Reaction Formula 2]

Compound A-13 was synthesized by referring to the method disclosed in KR10-2019-0090204A.

(Synthesis of the second compound)

Synthetic example 3: Synthesis of compound C-74

Compound C-74 was synthesized by referring to the method disclosed in KR10-1773363B1.

LC Mass M ⁺ H ⁺ = 637.33

(Synthesis of the third compound)

Synthetic example 4: Synthesis of compound D-53

[Reaction Formula 3]

Compound D-53 was synthesized by referring to the method disclosed in KR10-2019-0038303A.

Synthetic example 5: Synthesis of compound D-55

[Reaction Formula 4]

Compound D-55 was synthesized by referring to the method disclosed in KR10-2019-0038303A.

(Comparative compound synthesis)

Reference synthesis example 1: Synthesis of compound R-1

Compound R-1 was synthesized by referring to the method disclosed in KR10-2019-0038303A.

Reference synthesis example 2: Synthesis of compound R-2

[Reaction Formula 5]

In a round-bottomed flask were added 7.6 g (23.6 mmol) of bis (4-biphenyl-yl) amine, 9.4 g (23.6 mmol) of intermediate M-2, and 3.4 g (35.4 mmol) of sodium t-butoxide, and 240 ml of toluene was added to dissolve. To this, 0.14 g (0.24 mmol) of Pd (dba) ₂ and 0.12 g (0.60 mmol) of tri-tert-butylphosphine were sequentially added, and the mixture was refluxed and stirred for 4 hours under a nitrogen atmosphere. After completion of the reaction, the mixture was extracted with toluene and distilled water, and the organic layer was dried over magnesium sulfate and filtered, and the filtrate was concentrated under reduced pressure. The product was purified by silica gel column chromatography with n-hexane/dichloromethane (7:3 by volume) to obtain 13.5 g (yield 90%) of compound R-2.

(Fabrication of organic light-emitting devices)

Example 1

A glass substrate coated with a 1,500Å thick ITO (Indium Tin Oxide) film was washed with distilled water. After washing with distilled water, the substrate was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, or methanol, dried, and then transferred to a plasma cleaner. The substrate was then cleaned for 10 minutes using oxygen plasma and then transferred to a vacuum layer depositor. Using the ITO transparent electrode prepared in this way as an anode, N4,N4'-diphenyl-N4,N4'-bis(9-phenyl-9H-carbazol-3-yl)biphenyl-4,4'-diamine (Compound A) was vacuum-deposited on the ITO substrate to form a hole injection layer with a thickness of 700 Å, and 1,4,5,8,9,11-hexaazatriphenylene-hexacarbonitrile (HATCN) (Compound B) was deposited on the hole injection layer with a thickness of 50 Å. A hole transport layer was formed by depositing N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine (Compound C) to a thickness of 700 Å. A hole transport auxiliary layer was formed on the hole transport layer by vacuum deposition of Compound D-53 obtained in Synthesis Example 4 to a thickness of 320 Å. Next, compound A-27 obtained in Synthesis Example 1 and compound C-74 obtained in Synthesis Example 3 were simultaneously used as hosts on the hole transport auxiliary layer, and tris(4-methyl-2,5-diphenylpyridine)iridium(III) (compound D) was doped at 10 wt% as a dopant to form a 400 Å thick light-emitting layer by vacuum deposition. Here, compound A-27 and compound C-74 were used at a weight ratio of 3:7. Next, 8-(4-(4-(naphthalen-2-yl)-6-(naphthalen-3-yl)-1,3,5-[0677] triazin-2-yl)phenyl)quinoline (8-(4-(4-(naphthalen-2-yl)-6-(naphthalen-3-yl)-1,3,5-triazin-2-yl)phenyl)quinoline) (Compound E) and Liq were simultaneously vacuum-deposited at a 1:1 ratio on the light-emitting layer to form a 300Å thick electron transport layer, and 15Å of Liq and 1,200Å of Al were sequentially vacuum-deposited on the electron transport layer to form a cathode, thereby fabricating an organic light-emitting device.

The above organic light-emitting device has a structure with six organic thin film layers, and is specifically manufactured with a structure of ITO/A(700Å)/B(50Å)/C(700Å)/hole transport auxiliary layer[D-53(320Å)]/EML[A-27:C-74:D=3:7:10%](400Å)/E:Liq(300Å)/Liq(15Å)/Al(1,200Å).

Example 2, Comparative example 1 and Comparative example 2

An organic light-emitting device was manufactured using the same method as Example 1 by applying each compound to the hole transport auxiliary layer and the light-emitting layer as described in Tables 1 and 2.

Evaluation: Improvement of driving voltage or life characteristics Rising effect check

The driving voltage and life characteristics of the organic light-emitting devices according to Examples 1 and 2 and Comparative Examples 1 and 2 were evaluated. The specific measurement methods are as follows, and the results are as shown in Tables 1 and 2.

(1) Life span measurement

Using a polaronics life measurement system for the manufactured organic light-emitting devices, the devices of Examples 1 and 2, and Comparative Examples 1 and 2 were made to emit light at an initial luminance (cd/m ² ) of 24,000 cd/m ² , and the decrease in luminance over time was measured. The point in time when the luminance decreased by 90% compared to the initial luminance was measured as the T90 lifespan.

(2) Driving voltage measurement

The results were obtained by measuring the driving voltage of each device at 15 mA/cm ² using a current-voltage meter (Keithley 2400).

(3) Calculation of T90 life ratio (%)

The evaluation was conducted based on the T90 life of Comparative Example 1 in Table 1.

(4) Calculation of driving voltage ratio (%)

The evaluation was conducted based on the driving voltage value of Comparative Example 2 in Table 2.

Public transport
Auxiliary layer 1st host 2nd host 1st host:
2nd host
(wt%:wt%) Dopant ratio
(wt%) T90 life ratio (%) Example 1 D-53 A-27 C-74 3:7 10 120 Comparative Example 1 D-53 R-1 C-74 3:7 10 100

Public transport
Auxiliary layer 1st host 2nd host 1st host:
2nd host
(wt%:wt%) Dopant
ratio
(wt%) Driving voltage ratio (%) Example 2 D-55 A-13 C-74 3:7 10 95 Comparative Example 2 R-2 A-13 C-74 3:7 10 100

Referring to Tables 1 and 2, it can be confirmed that the compound for an organic optoelectronic device according to the present invention has a lower operating voltage and improved life characteristics compared to the compound for an organic optoelectronic device according to a comparative example.

Although the preferred embodiments of the present invention have been described in detail above, the scope of the present invention is not limited thereto, and various modifications and improvements made by those skilled in the art using the basic concept of the present invention defined in the following claims also fall within the scope of the present invention.

300: Organic light emitting diode
110: Bipolar
120: Negative
130: Emissive layer
141: Hole transport layer
142: Auxiliary layer for positive transport
105: Organic layer

Claims (8)

Positive and negative poles facing each other,
A light-emitting layer positioned between the anode and the cathode,
A hole transport layer positioned between the anode and the light-emitting layer, and
A hole transport auxiliary layer located between the above light-emitting layer and the above hole transport layer
Including,
The above-mentioned light-emitting layer comprises a composition including a first compound represented by any one of the following chemical formulas 1A to 1C and a second compound represented by the following chemical formula 2,
The above-mentioned hole transport auxiliary layer is an organic optoelectronic device including a third compound represented by the following chemical formula 3:
[Chemical Formula 1A] [Chemical Formula 1B] [Chemical Formula 1C]

In the above chemical formulas 1A to 1C,
L ¹ to L ⁵ are each independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, or a combination thereof,
Ar ¹ is a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof,
R ¹ to R ⁴ are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted amine group, halogen, cyano group or a combination thereof,
L ^a2 and L ^a4 are each single bonds,
R ^a2 is a substituted or unsubstituted para-biphenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group,
R ^a4 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrene group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluorenyl group, or a substituted or unsubstituted carbazolyl group;
[Chemical formula 2]

In the above chemical formula 2,
Ar ² and Ar ³ are each independently a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or a combination thereof,
L ⁶ and L ⁷ are each independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heterocyclic group, or a combination thereof,
R ⁵ to R ¹⁰ are each independently hydrogen, deuterium, halogen, cyano group, substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C6 to C30 aryl group or a combination thereof,
n is an integer between 0 and 2;
[Chemical Formula 3]

In the above chemical formula 3,
L ⁸ and L ⁹ are each independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heterocyclic group, or a combination thereof,
R ¹¹ to R ¹⁴ are each independently hydrogen, deuterium, halogen, cyano group, substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C6 to C30 aryl group, or a combination thereof,
Ar ⁴ to Ar ⁷ 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. In the first paragraph,
The above first compound is an organic optoelectronic device represented by the above chemical formula 1B. In the first paragraph,
The above chemical formula 2 is an organic optoelectronic device represented by the following chemical formula 2-1:
[Chemical Formula 2-1]

In the above chemical formula 2-1,
R ⁵ to R ¹⁰ are as defined in paragraph 1,
*-L ⁶ -Ar ² and *-L ⁷ -Ar ³ are each independently one of the substituents listed in Group II below,
[Group II]

In the above group II, * is a connection point. In paragraph 1,
An organic optoelectronic device, wherein Ar ⁵ to Ar ⁷ in the chemical formula 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 fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a combination thereof. In paragraph 1,
The above chemical formula 3 is an organic optoelectronic device represented by the following chemical formula 3-1:
[Chemical Formula 3-1]

In the above chemical formula 3-1,
L ⁸ , L ⁹ , R ¹¹ to R ¹⁴ , and Ar ⁴ to Ar ⁶ are as defined in paragraph 1,
X is O, S, or CR ⁱ R ^j ,
R ⁱ , R ^j and R ¹⁵ to R ¹⁷ are each independently hydrogen, deuterium, halogen, cyano group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a combination thereof. In the first paragraph,
The above first compound is represented by the following chemical formula 1B,
The above second compound is represented by the following chemical formula 2-1,
The third compound is an organic optoelectronic device represented by the following chemical formula 3-1:
[Chemical Formula 1B] [Chemical Formula 2-1] [Chemical Formula 3-1]

In the above chemical formula 1B,
L ^a2 , L ^a4 and L ¹ to L ⁴ are each a single bond,
L ⁵ is a phenylene group or a biphenylene group,
R ^a2 is a substituted or unsubstituted para-biphenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group,
R ^a4 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrene group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluorenyl group, or a substituted or unsubstituted carbazolyl group,
R ¹ to R ⁴ are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C12 aryl group;
In the above chemical formula 2-1,
*-L ⁶ -Ar ² and *-L ⁷ -Ar ³ are each independently any one of the substituents B-1 to B-4 listed in Group II-1 below,
[Group II-1]

R ⁵ to R ¹⁰ are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C12 aryl group;
In the above chemical formula 3-1,
L ⁸ and L ⁹ are each independently a meta-phenylene group or a para-phenylene group,
Ar ⁴ is a phenyl group,
Ar ⁵ and Ar ⁶ are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group,
R ¹¹ to R ¹⁷ are each independently hydrogen, deuterium, or a phenyl group. In the first paragraph,
An organic optoelectronic device wherein the light-emitting layer further comprises a dopant. A display device comprising an organic optoelectronic device according to any one of claims 1 to 7.