KR102138823B1 - Organic optoelectric device and display device - Google Patents

Abstract

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, and The light emitting layer includes a first compound represented by Formula 1 and a second compound represented by a combination of Formula 2 and Formula 3, and the hole transport auxiliary layer comprises an organic optoelectronic device including a third compound represented by Formula 4 and the same. It provides a display device including. Formulas 1 to 4 are as described in the specification.

Description

Organic optoelectronic device and display device {ORGANIC OPTOELECTRIC DEVICE AND DISPLAY DEVICE}

It relates to an organic optoelectronic device and a display device.

Organic optoelectric devices (organic optoelectric diode) is a device that can switch between electrical energy and light energy.

Organic optoelectronic devices can be roughly divided into two types according to the operating principle. One is a photoelectric device that generates electrical energy as excitons formed by optical energy are separated into electrons and holes, and the electrons and holes are transferred to different electrodes, and the other is to supply voltage or current to the electrodes to generate electricity. It is a light emitting element 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 these, organic light emitting diodes (OLEDs) have attracted much attention in recent years due to an increase in demand for flat panel display devices. The organic light emitting device is a device that converts electrical energy into light, and the performance of the organic light emitting device is greatly affected by organic materials positioned between electrodes.

One embodiment provides an organic optoelectronic device capable of lowering a driving voltage and improving power efficiency.

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

According to an embodiment, 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 positioned between the light emitting layer and the hole transport layer It includes a layer, the light emitting layer includes a first compound represented by the following formula (1) and a second compound represented by a combination of the following formula (2) and formula (3), the hole transport auxiliary layer is a third represented by the formula (4) An organic optoelectronic device comprising a compound is provided.

[Formula 1]

In Chemical Formula 1,

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

At least two of Z ¹ to Z ³ are N,

L ¹ is a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted terphenylene group,

R ¹ to R ⁶ are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C12 aryl group, or a cyano group,

R ¹ and R ² are each independently present or combine with each other to form a ring,

R ³ and R ⁴ are each independently present or combine with each other to form a ring,

R ⁵ and R ⁶ are each independently present or combine with each other to form a ring,

R ⁷ , R ⁸ and R ^a are each independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl group, substituted or unsubstituted C6 to C30 aryl group, substituted or unsubstituted C3 to C30 heterocyclic group, substituted Or an unsubstituted silyl group, a substituted or unsubstituted amine group, halogen, cyano group, or a combination thereof,

[Formula 2] [Formula 3]

In Formula 2 or 3,

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

A ¹ and A ² are each independently a substituted or unsubstituted C6 to C30 aryl group,

The two adjacent * in Formula 2 are combined with the two * in Formula 3, and the other two * in Formula 2 are CR ^b and CR ^c , respectively.

R ²⁰ to R ²³ , R ^b and R ^c are each Is 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 C3 to C30 heterocyclic group, or a combination thereof,

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

R ²² and R ²³ are each independently present or combine with each other to form a ring,

[Formula 4]

In Chemical Formula 4,

L ⁴ to L ⁹ 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,

R ⁵⁰ to R ⁵⁵ are each independently hydrogen, deuterium, substituted or unsubstituted C1 to C20 alkyl group, substituted or unsubstituted C6 to C30 aryl group, substituted or unsubstituted C3 to C30 heterocyclic group, substituted or unsubstituted An silyl group, a substituted or unsubstituted amine group, a halogen, a cyano group, or a combination thereof,

R ⁵⁰ and R ⁵¹ are each independently present or combine with each other to form a ring,

R ⁵² and R ⁵³ are each independently present or combine with each other to form a ring,

R ⁵⁴ and R ⁵⁵ are each independently present or combine with each other to form a ring.

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

The driving voltage of the organic optoelectronic device can be lowered and power efficiency can be improved.

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

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

As used herein, unless otherwise defined, at least one hydrogen in a substituent or compound is a deuterium, halogen group, hydroxyl group, amino group, substituted or unsubstituted C1 to C30 amine group, nitro group, 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 with a 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 the substituent or compound is deuterium, C1 to C30 alkyl group, C1 to C10 alkylsilyl group, C6 to C30 arylsilyl group, C3 to C30 cycloalkyl group, C3 to C30 It means substituted with heterocycloalkyl group, C6 to C30 aryl group, 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 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 the substituent or compound is deuterium, C1 to C5 alkyl group, C6 to C18 aryl group, pyridinyl group, quinolinyl group, isoquinolinyl group, di Means substituted with a benzofuranyl group, dibenzothiophenyl group or carbazole group. In addition, in a specific example of the present invention, "substitution" means that at least one hydrogen in the substituent or compound is substituted with a deuterium, C1 to C5 alkyl group, C6 to C18 aryl group, dibenzofuranyl group or dibenzothiophenyl group. it means. In addition, in a specific example of the present invention, "substitution" means that at least one hydrogen in the substituent or compound is deuterium, methyl group, ethyl group, propanyl group, butyl group, phenyl group, biphenyl group, terphenyl group, naphthyl group, triphenyl group, di It means substituted with a benzofuranyl group or a dibenzothiophenyl group.

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

As used herein, the term “aryl group” refers to a group having one or more hydrocarbon aromatic moieties, and all elements of the hydrocarbon aromatic moiety have p-orbitals, and these p-orbitals are conjugated. It forms a form, such as a phenyl group, a naphthyl group, etc., and two or more hydrocarbon aromatic moieties are connected via a sigma bond, such as biphenyl group, terphenyl group, quaterphenyl group, etc., two or more hydrocarbon aromatic moieties These may include non-aromatic fused rings fused directly or indirectly, such as a fluorenyl group and the like.

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

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

For example, "heteroaryl (heteroaryl) group" means that the aryl group contains at least one hetero atom selected from the group consisting of N, O, S, P and Si. Two or more heteroaryl groups may be directly connected through a sigma bond, or when the heteroaryl group includes two or more rings, two or more rings may be fused to each other. When the heteroaryl group is a fused ring, each ring may include 1 to 3 heteroatoms.

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

More specifically, a substituted or unsubstituted C6 to C30 aryl group and/or a substituted or unsubstituted C2 to C30 heterocyclic group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthra Senyl group, substituted or unsubstituted phenanthrenyl group, substituted or unsubstituted naphthacenyl group, substituted or unsubstituted pyrenyl group, substituted or unsubstituted biphenyl group, substituted or unsubstituted p-terphenyl group, substituted or unsubstituted A substituted m-terphenyl group, a substituted or unsubstituted o-terphenyl group, a substituted or unsubstituted chrysenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted perenyl group, a substituted or unsubstituted Fluorenyl group, substituted or unsubstituted indenyl group, substituted or unsubstituted furanyl group, substituted or unsubstituted thiophenyl group, substituted or unsubstituted pyrrolyl group, substituted or unsubstituted pyrazolyl group, substituted or unsubstituted Imidazolyl group, substituted or unsubstituted triazoleyl 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 Benzothiophenyl group, a substituted or unsubstituted benzimidazole 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, Substituted or unsubstituted quinoxalinyl group, substituted or unsubstituted naphthyridinyl group, substituted or unsubstituted benzoxazineyl group, substituted or unsubstituted benzthiazinyl group, substituted or unsubstituted acridinyl group, substituted or unsubstituted A substituted phenazineyl group, a substituted or unsubstituted phenothiazineyl group, a substituted or unsubstituted phenoxazinyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group, or a combination thereof It may be a combination, but is not limited thereto.

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

Also, the electronic property refers to a property that can receive electrons when an electric field is applied, and has conductivity characteristics along the LUMO level, injecting electrons formed from the cathode into the light emitting layer, transporting electrons formed from the light emitting layer to the cathode, and in the light emitting layer. It means a property that facilitates movement.

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

The organic optoelectronic device is not particularly limited as long as it is a device capable of mutually converting electrical energy and optical 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, is exemplarily described, but is not limited thereto, and may be applied to other organic optoelectronic devices.

In the drawings, thicknesses are enlarged to clearly represent various layers and regions. The same reference numerals are used for similar parts throughout the specification. When a portion of a layer, film, region, plate, etc. is said to be “above” another portion, this includes not only the case “directly above” the other portion but also another portion in between. Conversely, when one part is "just above" another part, it means that there is no other part in the middle.

1 is a cross-sectional view schematically showing an organic light emitting diode according to an embodiment.

Referring to FIG. 1, the organic light emitting device 300 according to an 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. Including, 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 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 110 may include, for example, metals such as nickel, platinum, vanadium, chromium, copper, zinc, gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); Metal and oxide combinations such as ZnO and Al or SnO ₂ and Sb; Conductive polymers such as poly(3-methylthiophene), poly(3,4-(ethylene-1,2-dioxy)thiophene) (polyehtylenedioxythiophene: PEDOT), polypyrrole and polyaniline, but are not limited thereto. It is not.

The cathode 120 may be made of, for example, a conductor having a low work function to facilitate electron injection, for example, a metal, a metal oxide, and/or a conductive polymer. The cathode 120 may be, for example, metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium, or alloys thereof; Multilayer structure materials such as LiF/Al, LiO ₂ /Al, LiF/Ca, LiF/Al, and BaF ₂ /Ca may be mentioned, but are not limited thereto.

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

As a host, the light emitting layer 130 may include a first compound having a relatively strong electronic property and a second compound having a relatively strong hole property.

The first compound is a compound having relatively strong electronic properties, and may be represented by Formula 1 below.

[Formula 1]

In Chemical Formula 1,

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

At least two of Z ¹ to Z ³ are N,

L ¹ is a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted terphenylene group,

R ¹ to R ⁶ are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C12 aryl group, or a cyano group,

R ¹ and R ² are each independently present or combine with each other to form a ring,

R ³ and R ⁴ are each independently present or combine with each other to form a ring,

R ⁵ and R ⁶ are each independently present or combine with each other to form a ring,

R ⁷ , R ⁸ and R ^a are each independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl group, substituted or unsubstituted C6 to C30 aryl group, substituted or unsubstituted C3 to C30 heterocyclic group, substituted Or an unsubstituted silyl group, a substituted or unsubstituted amine group, halogen, cyano group, or combinations thereof.

The first compound may include a triphenylene moiety and a pyrimidine or triazine moiety to form a bipolar structure, thereby properly balancing holes and electrons, and accordingly, an organic optoelectronic device using the organic compound The efficiency of can be improved.

For example, Z ¹ and Z ² may be nitrogen and Z ³ may be CR ^a .

For example, Z ² and Z ³ may be nitrogen and Z ¹ may be CR ^a .

For example, Z ¹ and Z ³ may be nitrogen and Z ² may be CR ^a .

For example, Z ¹ to Z ³ may each be nitrogen.

For example, L ¹ in Formula 1 is a linking group connecting a triphenylene moiety and a pyrimidine or triazine moiety, and may have a single bond or at least one kink structure. Here, the folding structure refers to a structure in which two connecting parts of a phenylene group, a biphenylene group, or a terphenylene group do not form a straight line structure. For example, in the case of phenylene, allo phenylene (m-phenylene) and meta phenylene (m-phenylene) in which the connecting parts do not form a straight structure have a bent structure, and para-phenylene in which the connecting parts form a straight structure (p-phenylene) ) Does not have a bend structure.

The first compound has a bent structure between the triphenylene moiety and the pyrimidine or triazine moiety, and thus the triphenylene moiety susceptible to holes in the bipolar structured compound described above and the pyrimidine or tree susceptible to electrons By properly localizing the azine moiety and controlling the flow of the conjugate system, it is possible to exhibit excellent bipolar properties. Accordingly, the life of the organic optoelectronic device can be improved.

For example, L ¹ in Formula 1 may be a single bond or one of the linking groups listed in Group 1 below.

[Group 1]

In group 1, * is a connection point.

The linking group listed in Group 1 may be a substituted or unsubstituted linking group.

Here, the substituted linking group is at least one hydrogen deuterium, substituted or unsubstituted C1 to C20 alkyl group, substituted or unsubstituted C6 to C30 aryl group, substituted or unsubstituted C3 to C30 heterocyclic group, substituted or unsubstituted It may be substituted with a silyl group, a substituted or unsubstituted amine group, halogen, cyano group, or a combination thereof.

For example, R ¹ and R ⁶ of Formula 1 are each independently hydrogen, deuterium, substituted or unsubstituted C1 to C4 alkyl group, substituted or unsubstituted phenyl group, substituted or unsubstituted biphenyl group, substituted or unsubstituted naphth It may be a teal group or a cyano group. Here, the substitution may be, for example, at least one hydrogen substituted with deuterium, a C1 to C10 alkyl group, a phenyl group, a biphenyl group, a naphthyl group, or a cyano group.

For example, R ¹ and R ⁶ in Formula 1 may be each independently hydrogen, deuterium, methyl group, ethyl group, phenyl group, biphenyl group, naphthyl group, or cyano group.

For example, R ⁷ and R ⁸ in Formula 1 may each independently be hydrogen, deuterium, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C3 to C30 heterocyclic group, or a combination thereof.

For example, R ⁷ and R ⁸ in Formula 1 are each independently hydrogen, deuterium, substituted or unsubstituted phenyl group, substituted or unsubstituted biphenyl group, substituted or unsubstituted terphenyl group, substituted or unsubstituted naphthyl group, Substituted or unsubstituted anthracenyl group, substituted or unsubstituted phenanthrenyl group, substituted or unsubstituted triphenylenyl group, substituted or unsubstituted pyridinyl group, substituted or unsubstituted pyrimidinyl group, substituted or unsubstituted Triazinyl group, substituted or unsubstituted dibenzothiophenyl group, substituted or unsubstituted dibenzofuranyl group, substituted or unsubstituted carbazolyl group, substituted or unsubstituted fluorenyl group, substituted or unsubstituted qui It may be a monolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinoxalinyl group, or a combination thereof.

For example, R ⁷ and R ⁸ in Formula 1 are each independently substituted or unsubstituted phenyl group, substituted or unsubstituted biphenyl group, substituted or unsubstituted terphenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted Anthracenyl group, substituted or unsubstituted phenanthrenyl group, substituted or unsubstituted pyridinyl group, substituted or unsubstituted pyrimidinyl group, substituted or unsubstituted triazinyl group, substituted or unsubstituted dibenzothiophene It may be a diary, a substituted or unsubstituted dibenzofuranyl group, or a combination thereof.

For example, R ⁷ and R ⁸ in Formula 1 may each independently be one of the functional groups listed in Group 2 below.

[Group 2]

In group 2, * is a connection point.

The functional groups listed in Group 2 may be substituted or unsubstituted functional groups.

The substituted functional group here is at least one hydrogen deuterium, substituted or unsubstituted C1 to C20 alkyl group, substituted or unsubstituted C6 to C30 aryl group, substituted or unsubstituted C3 to C30 heterocyclic group, substituted or unsubstituted It may be substituted with a silyl group, a substituted or unsubstituted amine group, halogen, cyano group, or a combination thereof.

The first compound may be represented by, for example, the following Chemical Formula 1-I or 1-II depending on the binding position of the triphenylene moiety.

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

In Formula 1-I or 1-II, Z ¹ to Z ³ , L ¹ and R ¹ to R ⁸ are as described above.

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

[Group 3]

The second compound is a compound having relatively strong hole characteristics, and may be represented by a combination of the following Chemical Formulas 2 and 3.

[Formula 2] [Formula 3]

In Formula 2 or 3,

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

A ¹ and A ² are each independently a substituted or unsubstituted C6 to C30 aryl group,

The two adjacent * in Formula 2 are combined with the two * in Formula 3, and the other two * in Formula 2 are CR ^b and CR ^c , respectively.

R ²⁰ to R ²³ , R ^b and R ^c are each Is 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 C3 to C30 heterocyclic group, or a combination thereof,

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

R ²² and R ²³ are each independently present or combine with each other to form a ring.

The second compound is an aryl-substituted indolocarbazole compound, and may have excellent hole characteristics. The second compound may be included together with the first compound described above to increase the balance of electrons and holes in the light emitting layer 130, thereby realizing a long-life organic optoelectronic device.

For example, Y ¹ and Y ² are each independently 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, It may be a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenylene group, or a substituted or unsubstituted fluorenylene group.

For example, Y ¹ and Y ² may be each independently a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted naphthylene group.

For example, Y ¹ and Y ² are each independently a single bond, a substituted or unsubstituted m-phenylene group, a substituted or unsubstituted p-phenylene group, a substituted or unsubstituted m-biphenylene group, a substituted or unsubstituted P-biphenylene group or a substituted or unsubstituted naphthylene group. Here, the substitution may be that at least one hydrogen is substituted with deuterium, a C1 to C20 alkyl group, a C6 to C12 aryl group, or a cyano group.

For example, 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, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted fluorenyl group, or a combination thereof.

For example, A ¹ and A ² may each independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted naphthyl group.

The second compound may be represented by any one of the following Chemical Formulas 2-A to 2-E depending on the bonding position of Chemical Formulas 2 and 3.

[Formula 2-A] [Formula 2-B] [Formula 2-C]

[Formula 2-D] [Formula 2-E]

In the above formulas 2-A to 2-E, Y ¹ , Y ² , A ¹ , A ² , R ²⁰ to R ²³ , R ^b and R ^c are as described above.

The second compound may be, for example, one of the compounds listed in Group 4 below, but is not limited thereto.

[Group 4]

The first compound and the second compound may be included in a weight ratio of about 1:99 to 99:1, such as about 10:90 to 90:10, about 20:80 to 80:20, about 30:70 to 70:30 , About 40:60 to 60:40 or about 50:50.

The host may further include at least one compound in addition to the first compound and the second compound.

The emission layer 130 may further include a dopant. The dopant can be a red, green or blue dopant.

The dopant is a substance mixed with a small amount of the above-mentioned host to cause light emission, and is generally an organic compound or a metal complex such as Al that exhibits fluorescence emitted by singlet excitons or a metal complex or a floor that is excited by a triplet state or more. Materials such as metal complexes that emit light by multiple excitations can be used. The dopant may be, for example, an inorganic, organic, or organic compound, and may be included in one or two or more.

Examples of dopants include organic metal compounds including Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or combinations thereof. The dopant may be, for example, a compound represented by Formula Z below, but is not limited thereto.

[Formula Z]

L ₂ MX

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

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

The hole transport auxiliary layer 142 may be located between the light emitting layer 130 and the hole transport layer 141 to be described later, and may be located in contact with the light emitting layer 130. The hole transport auxiliary layer 142 may be positioned in contact with the light emitting layer 130 to precisely control 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 plurality of layers.

The hole transport auxiliary layer 142 may include, for example, a third compound represented by Formula 4 below.

[Formula 4]

In Chemical Formula 4,

L ⁴ to L ⁹ 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,

R ⁵⁰ to R ⁵⁵ are each independently hydrogen, deuterium, substituted or unsubstituted C1 to C20 alkyl group, substituted or unsubstituted C6 to C30 aryl group, substituted or unsubstituted C3 to C30 heterocyclic group, substituted or unsubstituted An silyl group, a substituted or unsubstituted amine group, a halogen, a cyano group, or a combination thereof,

R ⁵⁰ and R ⁵¹ are each independently present or combine with each other to form a ring,

R ⁵² and R ⁵³ are each independently present or combine with each other to form a ring,

R ⁵⁴ and R ⁵⁵ are each independently present or combine with each other to form a ring.

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

For example, L ⁴ to L ⁹ are each independently 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, Substituted or unsubstituted anthracenyl group, substituted or unsubstituted phenanthrenylene group, substituted or unsubstituted dibenzothiophenylene group, substituted or unsubstituted dibenzofuranylene group, substituted or unsubstituted carbazolylene group Or it may be a substituted or unsubstituted fluorenylene group. For example, L ⁴ to L ⁹ is a single bond, a substituted or unsubstituted m-phenylene group, a substituted or unsubstituted p-phenylene group, a substituted or unsubstituted m-biphenylene group, a substituted or unsubstituted p-biphenyl It may be a alkylene group or a substituted or unsubstituted naphthylene group. Here, the substitution may be that at least one hydrogen is substituted with deuterium, a C1 to C20 alkyl group, a C6 to C12 aryl group, or a cyano group.

For example, R ⁵⁰ to R ⁵⁵ may each independently be hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C3 to C30 heterocyclic group. .

For example, R ⁵⁰ to R ⁵⁵ are each independently hydrogen, deuterium, substituted or unsubstituted phenyl group, substituted or unsubstituted biphenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted dibenzofuranyl group, substituted Or it may be an unsubstituted dibenzothiophenyl group or a substituted or unsubstituted fluorenyl group.

For example, R ⁵⁰ to R ⁵⁵ may be each independently substituted or unsubstituted C6 to C30 aryl group, for example, each independently substituted or unsubstituted phenyl group, substituted or unsubstituted biphenyl group, substituted or unsubstituted ter It may be a phenyl 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, or a combination thereof.

For example, at least one of R ⁵⁰ to R ⁵⁵ may be a substituted or unsubstituted C3 to C30 heterocyclic group.

For example, at least one of R ⁵⁰ to R ⁵⁵ may be a group represented by Formula A below.

[Formula A]

In the above formula A,

X ³ is O or S,

R ⁶⁰ to R ⁶⁷ are each independently hydrogen, deuterium, substituted or unsubstituted C1 to C20 alkyl group, substituted or unsubstituted C6 to C30 aryl group, substituted or unsubstituted C3 to C30 heterocyclic group, substituted or unsubstituted A silyl group, a substituted or unsubstituted amine group, a halogen, a cyano group, or a combination thereof, or a linking group with any one of L ⁴ to L ⁹ in Formula 4,

R ⁶⁰ to R ⁶⁷ are each independently present or two adjacent R ⁶⁰ to R ⁶⁷ combine to form a ring.

For example, R ⁵⁰ to any one of the R ⁵⁵ may be an expressed by the general formula A, the other of R ⁵⁰ to R ⁵⁵ may each independently represent a date a substituted or unsubstituted C6 to C30 aryl.

For example, two of R ⁵⁰ to R ⁵⁵ may be groups represented by Formula A, and the rest of R ⁵⁰ to R ⁵⁵ may be independently substituted or unsubstituted C6 to C30 aryl groups.

For example, three of R ⁵⁰ to R ⁵⁵ may be groups represented by Formula A, and the rest of R ⁵⁰ to R ⁵⁵ may be independently substituted or unsubstituted C6 to C30 aryl groups.

The third compound may be, for example, one of the compounds listed in Group 5 below, but is not limited thereto.

[Group 5]

The hole transport layer 141 is positioned between the anode 110 and the light emitting layer 130, and may 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 a work function of a conductor constituting the anode 110 and a HOMO energy level of a material constituting 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 Formula 5 below, but is not limited thereto.

[Formula 5]

In Chemical Formula 5,

R ¹¹⁸ to R ¹²¹ 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 ¹¹⁸ and R ¹¹⁹ are each independently present or combine with each other to form a ring,

R ¹²⁰ and R ¹²¹ are each independently present or combine with each other to form a ring,

Ar ¹⁰ to Ar ¹² are each independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,

L ¹⁰ to L ¹³ 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.

For example, Ar ¹⁰ may be a substituted or unsubstituted C6 to C30 aryl group, for example, Ar ¹⁰ may be a substituted or unsubstituted phenyl group or a substituted or unsubstituted biphenyl group.

For example, Ar ¹¹ and Ar ¹² are each independently substituted or unsubstituted phenyl group, substituted or unsubstituted biphenyl group, substituted or unsubstituted fluorenyl group, substituted or unsubstituted bisfluorene group, substituted or unsubstituted Triphenylenyl group, substituted or unsubstituted anthracenyl group, substituted or unsubstituted terphenyl group, substituted or unsubstituted dibenzofuranyl group, substituted or unsubstituted dibenzothiophenyl group, or a combination thereof. .

The compound represented by Chemical Formula 5 may be, for example, one of the compounds listed in Group 6 below, but is not limited thereto.

[Group 6]

The organic layer 105 includes 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 above-described light emitting layer 130, the hole transport auxiliary layer 142, and the hole transport layer 141 ) May be further included.

The organic light emitting device 300 forms an anode or a cathode on a substrate, and then forms an organic layer by a dry film deposition method such as evaporation, sputtering, plasma plating, and ion plating, or a solution process, and then It can be manufactured by forming a cathode or an anode on the top.

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.

Hereinafter, the above-described embodiment will be described in more detail through examples. However, the following examples are for illustrative purposes only and are not intended to limit the scope of rights.

(Synthesis of the first compound)

Synthetic example 1, 2

Compounds A-35 and A-33 were synthesized using starting materials 1 and 2 of Table 1 with reference to the synthesis method disclosed in Korean Patent Publication No. 10-2014-0135524.

Synthetic example Starting material 1 Starting material 2 product yield
(%) One

A-35 81% 2

A-33 79%

(Synthesis of second compound)

Synthetic example 3: Synthesis of Compound HC-28

[Scheme 1]

a) Synthesis of Intermediate HC-28-1

Intermediate A (30 g, 121.9 mmol), 4,4,4',4', 5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxabo) in a 500 mL flask Loran) 1 equivalent, potassium equivalent 2, 1,1'-bis(diphenylphosphino) ferrocene-palladium(II)dichloride 0.03 equivalent, tricyclohexylphosphine 0.2 equivalent N,N-dimethylformamide After putting in 300 mL, the mixture was stirred at 130° C. for 12 hours. After completion of the reaction, the reaction solution was extracted with water and EA to remove moisture using magnesium sulfate and concentrated, purified by column chromatography to give intermediate HC-28-1 as a white solid (29.66g, 83). % Yield).

b) Synthesis of Intermediate HC-28-2

In a 500 mL flask, 29.66 g (0.4 mol) of intermediate HC-28-1, 2 equivalents of intermediate B (1-bromo-2-nitrobenzene), 2 equivalents of potassium carbonate, tetrakis(triphenylphosphine) palladium (0) 0.02 After adding the equivalent to 200 mL of 1,4-dioxane and 100 mL of water, the mixture was heated to 90° C. for 16 hours under a nitrogen stream. After removing the reaction solvent, dissolved in dichloromethane, filtered with silica gel/celite, and after removing the appropriate amount of the organic solvent, recrystallized with methanol to obtain the intermediate HC-28-2 as a solid (16.92 g, 58% yield).

c) Synthesis of Intermediate HC-28-3

In a 500 mL flask, the synthesized intermediate HC-28-2 8.7 g (30.2 mmol), intermediate C (2-bromonaphthalene) 7.5 g (36.2 mmol), sodium t-butoxide (NaO t Bu) 4.3 g (45.3 mmol), Pd(dba) ₂ 1.0 g (1.8 mmol), tri t-butylphosphine (P( t Bu) ₃ ) 2.2 g (50% in toluene) into 150 mL of xylene and heated for 12 hours under a nitrogen stream And refluxed. After removing the xylene, 200 mL of methanol was added to the mixture obtained therefrom, and the solid crystallized was filtered, dissolved in dichloromethane, filtered with silica gel/celite, and after removing an appropriate amount of the organic solvent, recrystallized with acetone to obtain the intermediate HC- 28-3 (9.83 g, 77% yield) was obtained.

d) Synthesis of Intermediate HC-28-4

The synthesized intermediate HC-28-3 (211.37 g, 0.51 mol) and triethyl phosphite were synthesized in a 1000 ml flask. (528ml, 3.08mol) was added and nitrogen was replaced and stirred at 160°C for 12 hours. After completion of the reaction, 3 L of MeOH was added, stirred, filtered, and the filtrate was volatilized. Purified by column chromatography (Hexane) to give the intermediate HC-28-4 (152.14g, 78% yield).

e) Synthesis of Compound HC-28

[Scheme 2]

Compound HC-28 was synthesized in the same manner as in c) of Synthesis Example 3 using the synthesized intermediate HC-28-4 and intermediate HC-28-B.

Synthetic example 4: Synthesis of Compound HC-18

[Scheme 3]

a) Synthesis of Intermediate HC-18-1

In the same manner as in c) of Synthesis Example 3, the intermediate HC-18-1 was synthesized using 4-bromobiphenyl intermediate instead of 2-bromonaphthalene.

b) Synthesis of Intermediate HC-18-2

In the same manner as in d) of Synthesis Example 3, intermediate HC-18-2 was synthesized.

c) Synthesis of Intermediate HC-18-3

[Scheme 4]

Intermediates HC-18-3 were synthesized in the same manner as in b) of Synthesis Example 3 using intermediates HC-18-A and HC-18-B.

d) Synthesis of Compound HC-18

[Scheme 5]

In the same manner as in e) of Synthesis Example 3, the compound HC-18 was synthesized using the synthesized intermediates HC-18-2 and HC-18-3.

Synthetic example 5: Synthesis of Compound HC-20

a) Synthesis of Intermediate HC-20-1

[Scheme 6]

Intermediate HC-20-1 was synthesized in the same manner as in b) of Synthesis Example 3 using intermediates HC-20-A and HC-20-B.

b) Synthesis of Compound HC-20

[Scheme 7]

In the same manner as in e) of Synthesis Example 3, the compound HC-20 was synthesized using the synthesized intermediates HC-18-2 and HC-20-1.

Synthetic example 6: Synthesis of Compound HC-37

[Scheme 8]

In the same manner as in e) of Synthesis Example 3, the compound HC-37 was synthesized using the synthesized intermediates HC-28-4 and HC-18-3.

Synthetic example 7: Synthesis of Compound C-14

[Scheme 9]

In a round-bottom flask, intermediate I-1 8 g (31.2 mmol), 4-iodobiphenyl 20.5 g (73.32 mmol), CuI 1.19 g (6.24 mmol), 1,10-phenanthoroline 1.12 g (6.24 mmol), K ₂ CO ₃ 12.9 g (93.6 mmol) was added and 50 ml of DMF was added, followed by stirring under reflux for 24 hours under a nitrogen atmosphere. After completion of the reaction, distilled water was added to precipitate crystals and filtered. The solid was dissolved in 250 ml of xylene, filtered through silica gel, and precipitated as a white solid to obtain 16.2 g of compound C-14 (yield 93%).

(Synthesis of third compound)

Synthetic example 8: Synthesis of Compound F-148

Compound F-148 was synthesized with reference to the contents disclosed in Korean Patent Registration No. 10-1627746.

[F-148]

Comparative Synthesis Example One

With reference to the contents disclosed in Korean Patent Publication No. 10-2016-0149527, the following compound Ref. 1 was synthesized.

Comparative Synthesis Example 2

The following compound Ref.2 was synthesized with reference to US Patent Publication No. 2017-0104167 .

Preparation of organic light emitting device

Example One

The glass substrate coated with ITO (Indium tin oxide) with a thickness of 1500Å was washed with distilled water ultrasonically. After washing with distilled water, ultrasonic cleaning was performed with a solvent such as isopropyl alcohol, acetone, methanol, or the like, dried, and then transferred to a plasma cleaner, followed by cleaning the substrate with oxygen plasma for 10 minutes and then transferred to a vacuum evaporator. Using the prepared ITO transparent electrode as an anode, vacuum deposition of Compound A on the top of the ITO substrate forms a hole injection layer having a thickness of 700Å, and depositing Compound B on the top of the injection layer to a thickness of 50Å, followed by the deposition of Compound C of 700Å It was deposited to a thickness to form a hole transport layer. Compound F-148 synthesized in Synthesis Example 8 was deposited on the hole transport layer to a thickness of 400 Pa to form a hole transport auxiliary layer. Compound A-35 synthesized in Synthesis Example 1 and compound HC-28 synthesized in Synthesis Example 3 were simultaneously used as a host on the hole transport auxiliary layer and doped with [Ir(piq) ₂ acac] 2wt% with a dopant to vacuum deposition. As a result, a 400 mm thick light emitting layer was formed. Here, Compound A-35 and Compound HC-28 were used in a 3:7 weight ratio. Subsequently, an electron transport layer having a thickness of 300 증착 is formed by vacuum-depositing Compound D and Liq on the light emitting layer at a ratio of 1:1 at the same time, and Liq 15 Å and Al 1200 에 are 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 six layers of organic thin films, and is specifically as follows.

ITO/Compound A(700Å)/Compound B(50Å)/Compound C(700Å)/Compound F-148(400Å)/EML [Compound B-24: HC-28: [Ir(piq) ₂ acac] (2wt %)] (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)quinoline

Example Lessons 2 to 7 Comparative example 1-1 to 7-3

An organic light-emitting device in the same manner as in Example 1, except that the compound shown in Table 1 was used instead of Compound A-35 and HC-28 as the host of the light-emitting layer, and the compound shown in Table 1 was used instead of F-148 of the hole transport auxiliary layer. Was prepared.

evaluation

The driving voltage and power efficiency of the organic light emitting devices according to Examples 1 to 7 and Comparative Examples 1-1 to 7-3 were evaluated.

Specific measurement methods are as follows, and the results are shown in Table 2.

(1) Driving voltage measurement

The driving voltage of each device was measured using a current-voltmeter (Keithley 2400) to obtain results.

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

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

(3) Measurement of luminance change according to voltage change

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

(4) Power efficiency measurement

Power efficiency (lm/w) was calculated using the luminance, current density, and voltage measured from (2) and (3) above.

First compound Second compound Third compound Driving voltage (V) Power efficiency (lm/w) Example 1 A-35 HC-28 F-148 3.77 18.6 Comparative Example 1-1 A-35 HC-28 Ref. One 4.18 15.0 Comparative Example 1-2 A-35 HC-28 Ref. 2 4.58 14.5 Comparative Example 1-3 A-35 - F-148 4.22 11.0 Example 2 A-35 C-14 F-148 3.79 16.3 Comparative Example 2-1 A-35 C-14 Ref. One 4.19 13.4 Comparative Example 2-2 A-35 C-14 Ref. 2 4.59 12.9 Example 3 A-35 HC-37 F-148 3.73 18.6 Comparative Example 3-1 A-35 HC-37 Ref. One 4.12 14.9 Comparative Example 3-2 A-35 HC-37 Ref. 2 4.52 14.3 Example 4 A-35 HC-20 F-148 3.66 17.9 Comparative Example 4-1 A-35 HC-20 Ref. One 4.06 14.9 Comparative Example 4-2 A-35 HC-20 Ref. 2 4.46 13.8 Example 5 A-35 HC-18 F-148 3.66 18.4 Comparative Example 5-1 A-35 HC-18 Ref. One 4.05 15.3 Comparative Example 5-2 A-35 HC-18 Ref. 2 4.45 14.5 Example 6 A-36 C-14 F-148 3.79 16.5 Comparative Example 6-1 A-36 C-14 Ref. One 4.17 13.7 Comparative Example 6-2 A-36 C-14 Ref. 2 4.53 13.0 Example 7 A-33 HC-28 F-148 3.87 16.5 Comparative Example 7-1 A-33 HC-28 Ref. One 4.29 13.5 Comparative Example 7-2 A-33 HC-28 Ref. 2 4.73 13.0 Comparative Example 7-3 A-33 - F-148 4.64 9.9

Referring to Table 2, it can be seen that the organic light emitting devices according to Examples 1 to 7 have significantly lower driving voltages and improved power efficiency compared to the organic light emitting devices according to Comparative Examples 1-1 to 7-3.

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 of those skilled in the art using the basic concept of the present invention defined in the following claims are also provided. It belongs to the scope of the invention.

300: organic light emitting device
110: anode
120: cathode
130: emitting layer
141: hole transport layer
142: hole transport auxiliary layer

Claims (13)

Anode and 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
Including,
The light emitting layer includes a first compound represented by the following Chemical Formula 1 and a second compound represented by a combination of the following Chemical Formula 2 and Chemical Formula 3,
The hole transport auxiliary layer is an organic optoelectronic device comprising a third compound represented by the following formula (4):
[Formula 1]

In Chemical Formula 1,
Z ¹ to Z ³ are each independently N or CR ^a ,
At least two of Z ¹ to Z ³ are N,
L ¹ is a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted terphenylene group,
R ¹ to R ⁶ are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C12 aryl group, or a cyano group,
R ¹ and R ² are each independently present or combine with each other to form a ring,
R ³ and R ⁴ are each independently present or combine with each other to form a ring,
R ⁵ and R ⁶ are each independently present or combine with each other to form a ring,
R ⁷ , R ⁸ and R ^a are each independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl group, substituted or unsubstituted C6 to C30 aryl group, substituted or unsubstituted C3 to C30 heterocyclic group, substituted Or an unsubstituted silyl group, a substituted or unsubstituted amine group, halogen, cyano group, or a combination thereof,
[Formula 2] [Formula 3]

In Formula 2 or 3,
Y ¹ and Y ² are each independently a single bond or a substituted or unsubstituted C6 to C30 arylene group,
A ¹ and A ² are each independently a substituted or unsubstituted C6 to C30 aryl group,
The two adjacent * in Formula 2 are combined with the two * in Formula 3, and the other two * in Formula 2 are each CR ^b And CR ^c ,
R ²⁰ to R ²³ , R ^b and R ^c are each Is 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 C3 to C30 heterocyclic group, or a combination thereof,
R ²⁰ and R ²¹ are each independently present or combine with each other to form a ring,
R ²² and R ²³ are each independently present or combine with each other to form a ring,
[Formula 4]

In Chemical Formula 4,
L ⁴ to L ⁹ 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,
R ⁵⁰ to R ⁵⁵ are each independently hydrogen, deuterium, substituted or unsubstituted C1 to C20 alkyl group, substituted or unsubstituted C6 to C30 aryl group, substituted or unsubstituted C3 to C30 heterocyclic group, substituted or unsubstituted An silyl group, a substituted or unsubstituted amine group, a halogen, a cyano group, or a combination thereof,
R ⁵⁰ and R ⁵¹ are each independently present or combine with each other to form a ring,
R ⁵² and R ⁵³ are each independently present or combine with each other to form a ring,
R ⁵⁴ and R ⁵⁵ are each independently present or combine with each other to form a ring.
In claim 1,
L ¹ of Formula 1 is a single bond or an organic optoelectronic device which is one of the linkers listed in Group 1 below:
[Group 1]

The linking group listed in Group 1 above is a substituted or unsubstituted linking group,
The substituted linking group is at least one hydrogen is deuterium, substituted or unsubstituted C1 to C20 alkyl group, substituted or unsubstituted C6 to C30 aryl group, substituted or unsubstituted C3 to C30 heterocyclic group, substituted or unsubstituted A silyl group, a substituted or unsubstituted amine group, a halogen, a cyano group, or a combination thereof,
* Is the connection point.
In claim 1,
R ⁷ and R ⁸ in Formula 1 are each independently hydrogen, deuterium, substituted or unsubstituted phenyl group, substituted or unsubstituted biphenyl group, substituted or unsubstituted terphenyl group, substituted or unsubstituted naphthyl group, substituted or Unsubstituted anthracenyl group, substituted or unsubstituted phenanthrenyl group, substituted or unsubstituted triphenylenyl group, substituted or unsubstituted pyridinyl group, substituted or unsubstituted pyrimidinyl group, substituted or unsubstituted tria Genyl group, substituted or unsubstituted dibenzothiophenyl group, substituted or unsubstituted dibenzofuranyl group, substituted or unsubstituted carbazolyl group, substituted or unsubstituted fluorenyl group, substituted or unsubstituted quinolinyl group , A substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinoxalinyl group, or a combination thereof.
In claim 1,
R ⁷ and R ⁸ of Formula 1 are each independently an organic optoelectronic device that is one of the functional groups listed in Group 2:
[Group 2]

The functional groups listed in Group 2 above are substituted or unsubstituted functional groups,
The substituted functional group is at least one hydrogen deuterium, substituted or unsubstituted C1 to C20 alkyl group, substituted or unsubstituted C6 to C30 aryl group, substituted or unsubstituted C3 to C30 heterocyclic group, substituted or unsubstituted A silyl group, a substituted or unsubstituted amine group, a halogen, a cyano group, or a combination thereof,
* Is the connection point.
In claim 1,
The second compound is an organic optoelectronic device represented by any one of the following formulas 2-A to 2-E:
[Formula 2-A] [Formula 2-B] [Formula 2-C]

[Formula 2-D] [Formula 2-E]

In the above formulas 2-A to 2-E,
Y ¹ and Y ² are each independently a single bond or a substituted or unsubstituted C6 to C30 arylene group,
A ¹ and A ² are each independently a substituted or unsubstituted C6 to C30 aryl group,
R ²⁰ to R ²³ , R ^b and R ^c are each Is 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 C3 to C30 heterocyclic group, or a combination thereof,
R ²⁰ and R ²¹ are each independently present or combine with each other to form a ring,
R ²² and R ²³ are each independently present or combine with each other to form a ring.
In claim 1,
Y ¹ and Y ² are each independently a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted naphthylene group,
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, An organic optoelectronic device which is a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted fluorenyl group, or a combination thereof.
In claim 1,
R ⁵⁰ to R ⁵⁵ in Formula 4 are each independently hydrogen, deuterium, substituted or unsubstituted phenyl group, substituted or unsubstituted biphenyl group, substituted or unsubstituted terphenyl group, substituted or unsubstituted naphthyl group, substituted or Unsubstituted anthracenyl group, substituted or unsubstituted phenanthrenyl group, substituted or unsubstituted triphenylenyl group, substituted or unsubstituted dibenzothiophenyl group, substituted or unsubstituted dibenzofuranyl group, substituted or unsubstituted An organic optoelectronic device which is a substituted carbazolyl group, a substituted or unsubstituted fluorenyl group, or a combination thereof.
In claim 1,
R ⁵⁰ to R ⁵⁵ of Formula 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 naphthyl group, a substituted or unsubstituted anthra. An organic optoelectronic device having a senyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted triphenylenyl group, or a combination thereof.
In claim 1,
At least one of R ⁵⁰ to R ⁵⁵ in Formula 4 is an organic optoelectronic device represented by the following Formula A:
[Formula A]

In the above formula A,
X ³ is O or S,
R ⁶⁰ to R ⁶⁷ are each independently hydrogen, deuterium, substituted or unsubstituted C1 to C20 alkyl group, substituted or unsubstituted C6 to C30 aryl group, substituted or unsubstituted C3 to C30 heterocyclic group, substituted or unsubstituted A silyl group, a substituted or unsubstituted amine group, a halogen, a cyano group, or a combination thereof, or a linking group with any one of L ⁴ to L ⁹ in Formula 4,
R ⁶⁰ to R ⁶⁷ are each independently present or two adjacent R ⁶⁰ to R ⁶⁷ combine to form a ring.
In claim 1,
The hole transport auxiliary layer is an organic optoelectronic device in contact with the light emitting layer.
In claim 1,
The hole transport layer is an organic optoelectronic device comprising a compound represented by the formula (5):
[Formula 5]

In Chemical Formula 5,
R ¹¹⁸ to R ¹²¹ 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 ¹¹⁸ and R ¹¹⁹ are each independently present or combine with each other to form a ring,
R ¹²⁰ and R ¹²¹ are each independently present or combine with each other to form a ring,
Ar ¹⁰ to Ar ¹² are each independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,
L ¹⁰ to L ¹³ 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.
In claim 11,
Ar ¹⁰ in Formula 5 is a substituted or unsubstituted phenyl group or a substituted or unsubstituted biphenyl group,
Ar ¹¹ and Ar ¹² in Chemical Formula 5 are each independently substituted or unsubstituted phenyl group, substituted or unsubstituted biphenyl group, substituted or unsubstituted fluorenyl group, substituted or unsubstituted bisfluorene group, substituted or unsubstituted A substituted 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 an organic combination thereof Optoelectronic device.
A display device comprising the organic optoelectronic device according to any one of claims 1 to 12.

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