KR102495274B1 - Organic optoelectronic 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,
The emission layer includes a composition including a first compound represented by Formula 1 and a second compound represented by Formula 2, and the hole transport auxiliary layer includes an organic optoelectronic device including a third compound represented by Formula 3 below. and a display device.
Details of Chemical Formulas 1 to 3 are as defined in the specification.

Description

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

It relates to organic optoelectronic devices and display devices.

An organic optoelectronic diode is a device capable of converting between electrical energy and light energy.

Organic optoelectronic devices can be largely divided into two types according to their operating principles. One is a photoelectric device that generates electrical energy as excitons formed by light energy are separated into electrons and holes and the electrons and holes are transferred to different electrodes, respectively. It is a light emitting device that generates light energy from

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

Among them, organic light emitting diodes (OLEDs) have recently been attracting great attention due to an increase in demand for flat panel display devices. An 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 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 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. The light emitting layer includes a composition including a first compound represented by Formula 1 and a second compound represented by Formula 2 below, and the hole transport auxiliary layer includes a third compound represented by Formula 3 below. It provides an organic optoelectronic device comprising a.

[Formula 1] [Formula 2]

[Formula 3]

In Formulas 1 to 3,

L ¹ to 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 ¹ to R ¹⁵ 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;

n is an integer from 0 to 2;

Ar ¹ to Ar ⁸ 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;

At least one of Ar ¹ and Ar ² is a substituted or unsubstituted C10 to C30 aryl group or a substituted or unsubstituted C10 to C30 heterocyclic group,

At least one of Ar ⁷ and Ar ⁸ is represented by Formula A1 or Formula A2 below,

[Formula A1] [Formula A2]

In Formulas A1 and A2 above,

* is the connection point,

X is O or S;

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

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

A high-efficiency, long-life organic optoelectronic device can be implemented.

1 is a schematic cross-sectional view of an organic optoelectronic device according to an embodiment.

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

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

In one example of the present invention, "substitution" means that at least one hydrogen in a substituent or compound is deuterium, a C1 to C30 alkyl group, a C1 to C10 alkylsilyl group, a C6 to C30 arylsilyl group, a C3 to C30 cycloalkyl group, a C3 to C30 It means substituted with a heterocycloalkyl group, a C6 to C30 aryl group, or a C2 to C30 heteroaryl group. In addition, in a specific example of the present invention, "substitution" means that at least one hydrogen in a substituent or compound is substituted with deuterium, a C1 to C20 alkyl group, a C6 to C30 aryl group, or a C2 to C30 heteroaryl group. In addition, in a specific example of the present invention, "substitution" means that at least one hydrogen in a substituent or compound is deuterium, a C1 to C5 alkyl group, a C6 to C18 aryl group, a pyridinyl group, a quinolinyl group, an isoquinolinyl group, a di It means substituted with a benzofuranyl group, a dibenzothiophenyl group, or a carbazolyl group. In addition, in a specific example of the present invention, "substitution" refers to a substituent or compound in which at least one hydrogen is substituted with deuterium, a C1 to C5 alkyl group, a C6 to C18 aryl group, a dibenzofuranyl group, or a dibenzothiophenyl group. it means. In addition, in a specific example of the present invention, "substitution" means that at least one hydrogen in a substituent or compound is deuterium, a 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 di It means substituted with a benzofuranyl group or a dibenzothiophenyl group.

In this specification, 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 rest being carbon. .

In the present specification, "aryl group" is a general concept of 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 Forming a form, for example, including a phenyl group, a naphthyl group, etc., including a form in which two or more hydrocarbon aromatic moieties are connected through a sigma bond, for example, a biphenyl group, a terphenyl group, a quaterphenyl group, etc., and two or more hydrocarbon aromatic moieties may include a non-aromatic fused ring in which they are directly or indirectly fused, such as a fluorenyl group and the like.

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

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

For example, "heteroaryl group" means containing at least one heteroatom selected from the group consisting of N, O, S, P, and Si in the aryl group. Two or more heteroaryl groups may be directly connected through a sigma bond, or if 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 hetero atoms.

More specifically, the substituted or unsubstituted C6 to C30 aryl group is 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 naphthyl group, or a substituted or unsubstituted phenanthrenyl group. An 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- A 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 any of these It may be a combination, but is not limited thereto.

More specifically, the substituted or unsubstituted C2 to C30 heterocyclic group is a substituted or unsubstituted furanyl group, a substituted or unsubstituted thiophenyl group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted pyrazolyl group, or a substituted or unsubstituted pyrazolyl group. Or an 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, 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 an 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 isoquinolinyl group, a substituted or unsubstituted Quinazolinyl group, substituted or unsubstituted quinoxalinyl group, substituted or unsubstituted naphthyridinyl group, substituted or unsubstituted benzoxazinyl group, substituted or unsubstituted benzthiazinyl group, substituted or unsubstituted 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 may be a combination thereof, but is not limited thereto.

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

In addition, electronic properties refer to the characteristics of receiving electrons when an electric field is applied, and has conductivity along the LUMO level, so that electrons formed in the cathode are injected into the light emitting layer, electrons formed in the light emitting layer move to the cathode, and in the light emitting layer A property that facilitates movement.

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

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

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

In the drawings, the thickness is shown enlarged to clearly express the various layers and regions. Like reference numerals have been assigned to like parts throughout the specification. When a part such as a layer, film, region, plate, etc. 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.

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

Referring to FIG. 1 , an 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, for example, a conductor having a high work function to smoothly inject holes, and may be made of, for example, metal, metal oxide, and/or conductive polymer. The anode 110 may be, for example, a metal such as nickel, platinum, vanadium, chromium, copper, zinc, gold or an alloy thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO and Al or SnO ₂ and Sb; conductive polymers such as poly(3-methylthiophene), poly(3,4-(ethylene-1,2-dioxy)thiophene) (polyehtylenedioxythiophene: PEDOT), polypyrrole, and polyaniline; It is not.

The cathode 120 may be made of, for example, a conductor having a low work function so as to facilitate electron injection, and may be made of, for example, metal, metal oxide, and/or conductive polymer. The negative electrode 120 may be formed of, for example, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium, or alloys thereof; Multi-layered 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.

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

The hole transport auxiliary layer 142 is located between the light emitting layer 130 and the hole transport layer 141 to be described later, and is located in contact with the light emitting layer 130, so that the mobility of holes at the interface between the light emitting layer 130 and the hole transport layer 141 can be measured in detail. can be controlled The hole transport auxiliary layer 142 may include a third compound and may include a plurality of layers.

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

[Formula 1]

In Formula 1,

L ¹ to L ⁴ 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 ¹ to R ⁵ 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;

Ar ¹ to Ar ³ are each independently a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof;

At least one of Ar ¹ and Ar ² is a substituted or unsubstituted C10 to C30 aryl group or a substituted or unsubstituted C10 to C30 heterocyclic group.

The second compound is a compound having relatively strong hole properties and may be represented by Formula 2 below.

[Formula 2]

In Formula 2,

L ⁵ and L ⁶ 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 ⁶ to R ¹¹ 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;

Ar ⁴ and Ar ⁵ 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;

n is an integer from 0 to 2;

The third compound is a compound included in the hole transport auxiliary layer 142 to precisely control the mobility of holes at the interface between the light emitting layer 130 and the hole transport layer 141, and may be represented by Chemical Formula 3 below.

[Formula 3]

In Formula 3,

L ⁷ to 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 ¹² to R ¹⁵ 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;

Ar ⁶ to Ar ⁸ 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;

At least one of Ar ⁷ and Ar ⁸ is represented by Formula A1 or Formula A2 below,

[Formula A1] [Formula A2]

In Formulas A1 and A2 above,

* is the connection point,

X is O or S;

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

LUMO By expanding the electron cloud, it exhibits smooth electron injection and transfer characteristics, resulting in a balance of holes and electrons in the molecule. In the case of an organic light emitting device to which this is applied, the driving voltage of the device can be lowered, and lifespan characteristics can be improved due to stability due to hole and electron balance.

In addition, the second compound is a compound having excellent hole injection and transport properties, and is used together with the first compound to achieve an appropriate hole and electron charge balance, thereby securing high efficiency, long lifespan, and low voltage driving characteristics of an organic light emitting device to which it is applied. .

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 increase the balance of charges. Therefore, the driving voltage and lifetime characteristics of the organic optoelectronic device can be remarkably improved.

For example, in Formula 1, Ar ¹ to Ar 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 carbazolyl group, or a substituted or unsubstituted phenyl group. Or an unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group,

At least one of Ar ¹ and Ar ² is a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted terphenyl group. It may be a dibenzothiophenyl group.

In addition, Ar ³ is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted terphenyl group. It may be an unsubstituted dibenzothiophenyl group.

In addition, in Formula 1, L ¹ to L ⁴ may each independently be a single bond or a substituted or unsubstituted phenylene group.

Also, in Formula 1, R ¹ to R ⁵ may each independently represent hydrogen or a phenyl group.

As a specific example, any one of R ¹ to R ⁵ may be a phenyl group, or all of R ¹ to R ⁵ may be hydrogen.

For example, all of R ¹ to R ⁵ may be hydrogen, but are not limited thereto.

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

[Group 1]

[A-1] [A-2] [A-3] [A-4]

[A-5] [A-6] [A-7] [A-8] [A-9]

[A-10] [A-11] [A-12] [A-13] [A-14]

[A-15] [A-16] [A-17] [A-18]

[A-19] [A-20] [A-21] [A-22]

[A-23] [A-24] [A-25] [A-26]

[A-27] [A-28] [A-29] [A-30]

[A-31]

[A-32] [A-33] [A-34] [A-35]

[A-36] [A-37] [A-38]

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

For example, in Formula 2, Ar ⁴ and Ar ⁵ 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 quaterphenyl group, a substituted or unsubstituted quarterphenyl group, or a substituted or unsubstituted biphenyl group. Unsubstituted naphthyl group, substituted or unsubstituted anthracenyl group, substituted or unsubstituted triphenylene group, substituted or unsubstituted pyridinyl group, substituted or unsubstituted pyrimidinyl group, substituted or unsubstituted dibenzofuran It may be a dibenzothiophenyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted fluorenyl group.

As a specific example, Chemical Formula 2 may be represented by Chemical Formula 2-1 below.

[Formula 2-1]

In Formula 2-1, Ar ⁴ , Ar ⁵ , L ⁵ , L ⁶ , and R ⁶ to R ¹¹ are defined as described above.

In one embodiment, the second compound may be represented by Formula 2-1, wherein R ⁶ to R ¹¹ in Formula 2-1 are all hydrogen, *-L ⁵ -Ar ⁴ and *-L ⁶ -Ar ⁵ may each independently be one of the substituents listed in Group I below.

[Group I]

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

For example, Ar ⁴ and Ar ⁵ may each independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group.

In addition, L ⁵ and L ⁶ may each independently be a single bond or a substituted or unsubstituted phenylene group.

In addition, R ⁶ to R ¹¹ may each independently be hydrogen or a C6 aryl group.

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

[Group 2]

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

[B-136] [B-137] [B-138] [B-139]

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 within the above range, efficiency and lifespan can be improved by implementing bipolar characteristics by setting an appropriate weight ratio using the electron transport capability of the first compound and the hole transport capability of the second compound. Within the above range, for example, about 10:90 to 90:10, about 20:80 to 80:20, about 20:80 to 70:30, it may be included in a weight ratio of about 20:80 to 60:40. For example, it may be included in a weight ratio of 30:70 to 50:50, for example, it may be included in a weight ratio of 30:70.

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

The light emitting layer may further include a dopant. The dopant may be, for example, a phosphorescent dopant, for example, a red, green or blue phosphorescent dopant, and may be, for example, a red phosphorescent dopant.

The dopant is a material that emits light by being mixed with the above-mentioned host in a small amount, and a material such as a metal complex that emits light by multiple excitation that is excited in a triplet state or higher may be used. The dopant may be, for example, an inorganic, organic, or organic-inorganic compound, and may include one type or two or more types.

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

[Formula Z]

L ¹⁰ MX ^'

In Formula Z, M is a metal, L ¹⁰ and X' are the same as or different from each other and are ligands that form a complex with M.

M may be, for example, Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or combinations thereof, and L ¹⁰ and X' may be, for example, bi It may be a dentate ligand.

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

The third compound is a compound having a high HOMO energy level and may have good hole injection characteristics. 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, the third compound may include a third compound represented by any one of Chemical Formulas 3-1 to 3-3 below.

[Formula 3-1] [Formula 3-2]

[Formula 3-3]

In Chemical Formulas 3-1 to 3-3, X, R ^a to R ^g , R ¹² to R ¹⁵ , L ⁷ to L ⁹ , Ar ⁶ and Ar ⁷ are as described above.

As a specific example, Ar ⁶ in Formulas 3-1 to 3-3 is a substituted or unsubstituted phenyl group or a substituted or unsubstituted biphenyl group, and Ar ⁷ is a substituted or unsubstituted phenyl group or 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 triphenylene group, a substituted or unsubstituted flu Orenyl group, substituted or unsubstituted pyrenyl group, substituted or unsubstituted furanyl group, substituted or unsubstituted thiophenyl group, substituted or unsubstituted dibenzofuranyl group, substituted or unsubstituted dibenzothiophenyl group, or It may be a substituted or unsubstituted carbazolyl group.

As a more specific example, Ar ⁷ in Formulas 3-1 to 3-3 may be any one selected from the substituents listed in Group II below.

[Group II]

In Group II above, * is a connection point.

In one embodiment, the third compound may be represented by Chemical Formula 3-1, in which case Ar ⁶ is a phenyl group, Ar ⁷ is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group, R ¹² to R ¹⁵ may each independently be hydrogen or a C6 to C12 aryl group, R ^a to R ^g may be hydrogen, and X may be O or S.

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

[Group 3]

[C-1] 　　　　　　　　　　　　　[C-2]　　　　　　　　　　　　　　[C-3]　　　　　　　　　[C-3]

[C-5]　　　　　　　　　　　　[C-6]　　　　　　　　　　　　　[C-7]　　　　　　　　　　[C-8]

[C-9]　　　　　　　　　　　[C-10]　　　　　　　　　　　　　[C-11]　　　　　　　　　　[C-1　　

[C-13]　　　　　　　　　　　　[C-14]　　　　　　　　　　　　　[C-15]　　　　　　　　　[　　　6]

[C-17]　　　　　　　　　　　[C-18]　　　　　　　　　　　　　[C-19]　　　　　　　　　[C-2　]

[C-21]　　　　　　　　　　　　[C-22]　　　　　　　　　　　　[C-23]　　　　　　　　　[C-23]

[C-25]　　　　　　　　　　　　[C-26]　　　　　　　　　　　　　　[C-27]　　　　　　　　[C-27]

[C-29]　　　　　　　　　　　　[C-30]　　　　　　　　　　　　　　[C-31]　　　　　　　　　[C-31]

[C33]

[C-37] [C-38]

[C-41]　　　　　　　　　　　　[C-42]　　　　　　　　　　　　　　[C-43]　　　　　　　　　[C-43]

[C-45]　　　　　　　　　　　　[C-46]　　　　　　　　　　　　　　[C-47]　　　　　　　　　[C-48]

[C-50]

[C-53]:

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

[C-61]　　　　　　　　　　　　　　[C-62]　　　　　　　　　　　　　[C-63]　　　　　　　　[C-63]

[C-65]　　　　　　　　　　　　　　[C-66]　　　　　　　　　　　　　[C-67]　　　　　　　　[C-67]　　　　　　　　

[C-70]

[C-73]　　　　　　　　　　　　　　[C-74]　　　　　　　　　　　　　[C-75]　　　　　　　　[C-75]

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

[C-81]　　　　　　　　　　　　　　[C-82]　　　　　　　　　　　　　[C-83]　　　　　　　　[C-83]

[C-85]　　　　　　　　　　　　　[C-86]　　　　　　　　　　　　[C-87]　　　　　　　　　　　　　　　　　　　　　　　　　　　　　　

[C-90]

[C-93]:

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

[C-101]　　　　　　　　　　　　　[C-102]　　　　　　　　　　[C-103]　　　　　　　　　[　　　]

[C-105]　　　　　　　　　　　　　[C-106]　　　　　　　　　　　　[C-107]　　　　　　　　　[C-108]

[C-109] [C-110]

[C-113]　　　　　　　　　　　　　[C-114]

[C-117]　　　　　　　　　　[C-118]　　　　　　　　　[C-119]

[C-121] [C-122] [C-122]

[C-125] [C-126] [C-126]

[C-129]　　　　　　　　　　　[C-130]　　　　　　　　　　　　[C-131]

[C-133]　　　　　　　　　　[C-134]　　　　　　　　　　　[C-135]

[C-137] [C-138] [C-138]

[C-141] [C-142] [C-142]

[C-145]　　　　　　　　　　 [C-146]　　　　　　　　　　　　　　[C-147]

[C-149]　　　　　　　　　　[C-150]　　　　　　　　　　　　　　[C-151]

[C-153] [C-154] [C-154]

[C-157] [C-158] [C-158] [C-159]

[C-161] [C-162] [C-162] [C-163] [C-163]

[C-165] [C-166] [C-166] [C-167] [C-167]

[C-169] [C-170] [C-170]

[C-173] [C-174] [C-174] [C-175] [C-175]

[C-177]:

[C-181]　　　　　　　　　　[C-182]　　　　　　　　　　　[C-183]　　　　　　　　　　　　[　　4]

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

In this case, Ar ¹ to Ar ³ in Formula 1 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 dibenzofuranyl group, or a substituted or an unsubstituted dibenzothiophenyl group, and at least one of Ar ¹ and Ar ² is a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group. It may be a cyclic dibenzothiophenyl group.

L ⁵ and L ⁶ in Formula 2-1 are each independently a single bond or a substituted or unsubstituted C6 to C12 arylene group;

Ar ⁴ and Ar ⁵ are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group,

R ⁶ to R ¹¹ may each independently represent hydrogen or a phenyl group.

In Formula 3-1, Ar ⁶ is a phenyl group, Ar ⁷ is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group, and L ⁷ and L ⁹ are each independently a phenylene group; And, R ¹² to R ¹⁵ are each independently hydrogen or a C6 to C12 aryl group, R ^a to R ^g are hydrogen, and X may be O or S.

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 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 Chemical Formula 4 below, but is not limited thereto.

[Formula 4]

In Formula 4,

R ¹⁶ to R ²² 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 ¹⁶ and R ¹⁷ are each independently present or bonded to each other to form a ring;

R ¹⁸ and R ¹⁹ are each independently present or bonded to each other to form a ring;

R ²⁰ to R ²² 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 substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof.

For example, R ²⁰ may be a substituted or unsubstituted C6 to C30 aryl group, and for example, R ²⁰ may be a substituted or unsubstituted phenyl group or a substituted or unsubstituted biphenyl group.

For example, R ²¹ and R ²² are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted bisfluorene group, or a substituted or unsubstituted biphenyl 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 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 is 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 light emitting layer 130, the hole transport auxiliary layer 142, and the hole transport layer 141 described above. ) may be further included.

In the organic light emitting device 300, after forming an anode or a cathode on a substrate, an organic layer is formed by a dry film method such as evaporation, sputtering, plasma plating, or ion plating, or a solution process, and the like. It can be prepared by forming a cathode or an anode thereon.

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

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

(Synthesis of Third Compound)

synthesis example 1: Synthesis of Compound C-1

Compound C-1 was synthesized by referring to a method known in KR10-1931250B1.

LC Mass M+H ⁺ = 636.26

synthesis example 2: Synthesis of Compound C-2

Compound C-2 was synthesized by referring to a method known in KR10-1931250B1.

LC Mass M+H ⁺ = 744.26

(Synthesis of First Compound)

synthesis example 3: Synthesis of Intermediate M-1

[Scheme 1]

11,12-dihydroindolo[2,3-a]carbazole (78.35 g, 305.69 mmol), bromobenzene (26.8 mL, 254.74 mmol), NaOt-Bu (26.93 g, 280.22 mmol) and Pd ₂ (dba) ₃ (7 g, 7.64mmol) was suspended in 1400ml of toluene, and then P(t-Bu) ₃ (3.64ml, 15.28mmol) was added and stirred under reflux for 12 hours. Distilled water was added to the reaction mixture and the mixture was separated. The product thus obtained was purified with a silica gel column to obtain intermediate M-1 (55.8 g, 55%). LC Mass M+H ⁺ = 333.13

synthesis example 4: synthesis of intermediate M-2

[Scheme 2]

Intermediate M-2 (68.7 g, 68.7 g, 305.69 mmol) and 3-bromobiphenyl (59.38 g, 254.74 mmol) were used in the same manner as in Synthesis Example 3. 57%) was obtained. LC Mass M+H ⁺ = 409.16

synthesis example 5: Synthesis of Intermediate M-3

[Scheme 3]

2,4-dichloro-6-phenyl-1,3,5-triazine (74.50 g, 331.13 mmol) and 4-biphenylboronic acid (55.47 g, 281.46 mmol) were mixed with tetrahydrofuran (THF) and distilled water (3:1) 0.7 After dissolving in L, Pd(PPh ₃ ) ₄ (11.48g, 9.93mmol) and K ₂ CO ₃ (68.65g, 496.69mmol) were added and stirred under reflux for 12 hours. After cooling the reaction solution and separating the layers, the organic layer was collected and concentrated. The concentrated residue was purified by a silica gel column to obtain intermediate M-3 (75.9 g, 67%). LC Mass M+H ⁺ = 344.09

synthesis example 6: Synthesis of Intermediate M-4

[Scheme 4]

Intermediate M- 4 (87.1 g, 74%) was obtained.

LC Mass M+H ⁺ = 358.07

synthesis example 7: synthesis of intermediate M-5

[Scheme 5]

Intermediate M- 5 (71.6 g, 69%) was obtained.

LC Mass M+H ⁺ = 420.12

synthesis example 8: Synthesis of Compound A-1

[Scheme 6]

Compound A-1 (62.4 g, 70%) was obtained by using Intermediate M-1 (46.3 g, 139.40 mmol) and Intermediate M-3 (47.8 g, 139.99 mmol) in the same manner as in Synthesis Example 3. LC Mass M+H ⁺ = 640.24

Comparative Synthesis Example 1: Synthesis of Compound R-5

[Scheme 7]

Step 1: Synthesis of Intermediate M-7

In the same manner as in Synthesis Example 3, using 5,12-dihydroindolo[3,2-a]carbazole (63 g, 246 mmol) and 3-bromobiphenyl (45.66 g, 196.81 mmol), intermediate M-7 (58.2 g) , 58%) was obtained.

LC Mass M+H ⁺ = 409.16

Step 2: Synthesis of Compound R-5

In the same manner as in Synthesis Example 3, compound R-5 (48.1 g, 72%) was obtained using intermediate M-7 (43 g, 105.35 mmol) and 2-bromotriphenylene (32.24 g, 105.35 mmol).

LC Mass M+H ⁺ = 635.24

synthesis example 9 to 11 and Comparative Synthesis Example 2: Synthesis of Compound A-21, Compound A-32, Compound A-3 and Compound R-3

Synthesis Example 8 except that starting material 1 and starting material 2 in the table below were used instead of M-1 (corresponding to starting material 1 in the table below) and M-3 (corresponding to starting material 2 in the table below) of Synthesis Example 8. Each compound was prepared in the same way.

No. starting material 1 starting material 2 product transference number(%)
LC-Mass (M+H ⁺ ) Synthesis Example 9 M-2 M-2 A-21 73%716.27 Synthesis Example 10 M-1 M-4 A-32 77%654.22 Synthesis Example 11 M-1 M-5 A-3 81%
716.27 Comparative Synthesis Example 2 M-1 M-6 R-3 69%564.21

Comparative Synthesis Example 3: Synthesis of Compound R-1

Compound R-1 was synthesized according to the method known in KR10-1618683B1.

Comparative Synthesis Example 4: Synthesis of Compound R-2

[Scheme 8]

Step 1: Synthesis of Intermediate M-6

In the same manner as in Synthesis Example 5, 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)carbazole (33.57g, 114.53mmol) and 2-bromodibenzothiophene (30g, 114.53mmol) was used to obtain intermediate M-6 (27.6 g, 69%).

LC Mass M+H ⁺ = 350.09

Step 2: Synthesis of Compound R-2

Using M-6 (25g, 71.61mmol) and 2-(3-Bromophenyl)-4,6-diphenyl-1,3,5-triazine (27.72g, 71.61mmol) in the same manner as in Synthesis Example 3, the compound R-2 (39.47 g, 84%) was obtained. LC Mass M+H ⁺ = 657.20

Comparative Synthesis Example 5: Synthesis of Compound R-4

Compound R-4 was synthesized by referring to a method known in KR10-1857632B1.

LC Mass M+H+ = 658.19

(Synthesis of Second Compound)

synthesis example 12: Synthesis of compound B-99

Compound B-99 was synthesized by referring to a method known in KR10-1773363B1.

LC Mass M+H+ = 561.23

Synthesis Example 13: Synthesis of Compound B-136

Compound B-136 was synthesized by referring to a method known in KR10-1773363B1.

LC Mass M+H+ = 561.23

Synthesis Example 14: Synthesis of Compound B-139

Compound B-139 was synthesized by referring to a method known in KR10-1773363B1.

LC Mass M+H+ = 637.26

(Manufacture of organic light emitting device)

Example 1

A glass substrate coated with ITO (Indium tin oxide) to a thickness of 1,500 Å was washed with distilled water. After the distilled water cleaning was completed, the substrate was ultrasonically washed with solvents such as isopropyl alcohol, acetone, and methanol, dried, transferred to a plasma cleaner, cleaned by using oxygen plasma for 10 minutes, and then transferred to a vacuum layerer. Using the prepared ITO transparent electrode as an anode, N4,N4'-diphenyl-N4,N4'-bis(9-phenyl-9H-carbazol-3-yl)biphenyl-4,4'diamine was deposited on the ITO substrate. (N4,N4'-diphenyl-N4,N4'-bis(9-phenyl-9H-carbazol-3-yl)biphenyl-4,4'-diamine) (Compound A) was vacuum-deposited to form a 700 Å-thick hole injection layer. And forming 1,4,5,8,9,11-hexaazatriphenylene-hexacarbonitrile (1,4,5,8,9,11-hexaazatriphenylene-hexacarbonitrile, HATCN) on the hole injection layer ( After depositing compound B) to a thickness of 50 Å, N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl) -9H-fluoren-2-amine (N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9Hfluoren-2 -amine) (compound C) was deposited to a thickness of 700 Å to form a hole transport layer. A hole transport auxiliary layer having a thickness of 320 Å was formed on the hole transport layer by vacuum deposition of Compound C-1 obtained in Synthesis Example 1. Subsequently, Compound A-1 obtained in Synthesis Example 8 and Compound B-99 obtained in Synthesis Example 12 were simultaneously used as a host on the top of the hole transport auxiliary layer, and tris(4-methyl-2,5-diphenylpyridine) iridium as a dopant. (III) (Compound D) was doped with 10wt% to form a 400Å thick light emitting layer by vacuum deposition. Here, compound A-1 and compound B-99 were used in a weight ratio of 3:7. Then, 8-(4-(4-(naphthalen-2-yl)-6-(naphthalen-3-yl)-1,3,5-triazin-2-yl)phenyl)quinoline was applied on the light emitting layer. (8-(4-(4-(naphthalen-2-yl)-6-(naphthalen-3-yl)-1,3,5-triazin-2-yl)phenyl)quinoline) (Compound E) and Liq At the same time, a 300 Å thick electron transport layer was formed by vacuum deposition at a ratio of 1:1, and an organic light emitting device was fabricated by sequentially vacuum depositing 15 Å of Liq and 1,200 Å of Al on the electron transport layer to form a cathode.

The organic light emitting device has a structure having 6 organic thin film layers, specifically ITO / A (700Å) / B (50Å) / C (700Å) / hole transport auxiliary layer [C-1 (320Å)] / EML [A-1: B-99: D = 3: 7: 10%] (400 Å) / E: Liq (300 Å) / Liq (15 Å) / Al (1,200 Å) structure was produced.

Example 2

An organic light emitting device was manufactured in the same manner as in Example 1, except that Compound C-2 obtained in Synthesis Example 2 was used instead of Compound C-1 in the hole transport auxiliary layer.

Example 3

An organic light emitting device was manufactured in the same manner as in Example 1, except that Compound B-136 obtained in Synthesis Example 13 was used instead of Compound B-99 in the light emitting layer.

Example 4

An organic light-emitting device was prepared in the same manner as in Example 1, except that Compound A-21 obtained in Synthesis Example 9 was used instead of Compound A-1 and Compound B-136 obtained in Synthesis Example 13 was used instead of Compound B-99 in the light emitting layer. was produced.

Example 5

An organic light emitting device was manufactured in the same manner as in Example 1, except that Compound A-32 obtained in Synthesis Example 10 was used instead of Compound A-1 in the light emitting layer.

Example 6

An organic light emitting device was manufactured in the same manner as in Example 1, except that Compound A-21 obtained in Synthesis Example 9 was used instead of Compound A-1 in the light emitting layer.

Comparative Example 1

An organic light emitting device was manufactured in the same manner as in Example 1, except that Compound R-1 obtained in Comparative Synthesis Example 3 was used instead of Compound A-1 in the light emitting layer.

Comparative Example 2

Organic light emitting in the same manner as in Example 1, except that Compound R-2 obtained in Comparative Synthesis Example 4 was used instead of Compound A-1 in the light emitting layer, and Compound B-136 obtained in Synthesis Example 13 was used instead of Compound B-99. device was made.

Comparative Example 3

An organic light emitting device was manufactured in the same manner as in Example 1, except that Compound R-4 obtained in Comparative Synthesis Example 5 was used instead of Compound A-1 in the light emitting layer.

Comparative Example 4

An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound R-5 obtained in Comparative Synthesis Example 1 was used instead of Compound C-1 for the hole transport auxiliary layer.

Example 7 and Comparative Example 5

As shown in Table 4 below, organic light-emitting devices of Example 7 and Comparative Example 5 were manufactured in the same manner as in Example 1, except that the host was changed and the dopant ratio was changed.

Evaluation: Confirmation of driving voltage improvement and lifetime increase effect

Driving voltage and lifetime characteristics of the organic light emitting devices according to Examples 1 to 7 and Comparative Examples 1 to 5 were evaluated. The specific measurement method is as follows, and the results are shown in Tables 2 to 4.

(1) Life measurement

For the manufactured organic light emitting device, the initial luminance (cd/m ² ) of the devices of Examples 1 to 5 and Example 7, and Comparative Examples 1, 2 and Comparative Example 5 using the Polaronics lifetime measurement system was measured at 24,000 cd/m. m ² Light was emitted and the decrease in luminance over time was measured, and the time point when the luminance decreased to 90% compared to the initial luminance was measured as T90 life.

(2) T90 lifetime ratio (%) calculation

In Table 2 or Table 4, relative comparison values of T90 (h) of the remaining examples and comparative examples are shown based on the T90 lives of Examples 1 and 7, respectively.

T90 lifetime ratio (%) = {T90 (h) of (Comparative Example and other Examples) / T90 (h) of (Example 1 or Example 7)} X 100

(3) Driving voltage measurement

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

(4) Calculation of driving voltage ratio (%)

Table 3 shows the relative comparison values of the driving voltages of Comparative Examples 3 and 4 based on the driving voltage values of Example 6.

Drive voltage ratio (%) = {Drive voltage (V) of (Comparative Examples 3 and 4) / Drive voltage (V) of (Example 6)} X 100

hole transport
auxiliary layer 1st host 2nd host First Host:
2nd host
(wt%:wt%) dopant ratio
(wt%) T90 Life Rate (%) Example 1 C-1 A-1 B-99 3:7 10 100% Example 2 C-2 A-1 B-99 3:7 10 107% Example 3 C-1 A-1 B-136 3:7 10 92% Example 4 C-1 A-21 B-136 3:7 10 104% Example 5 C-1 A-32 B-99 3:7 10 92% Comparative Example 1 C-1 R-1 B-99 3:7 10 71% Comparative Example 2 C-1 R-2 B-136 3:7 10 40%

hole transport
auxiliary layer 1st host 2nd host First Host:
2nd host
(wt%:wt%) dopant
ratio
(wt%) Driving
Voltage ratio (%) Example 6 C-1 A-21 B-99 3:7 10 100% Comparative Example 3 C-1 R-4 B-99 3:7 10 111% Comparative Example 4 R-5 A-1 B-99 3:7 10 114%

hole transport
auxiliary layer 1st host 2nd host First Host:
2nd host
(wt%:wt%) dopant
ratio
(wt%) T90 Life Rate (%) Example 7 C-1 A-3 B-139 3:7 7 100% Comparative Example 5 C-1 R-3 B-139 3:7 7 71%

Referring to Tables 2 to 4, it can be seen that the compound for an organic optoelectronic device according to the present invention has lower driving voltage and improved lifespan compared to the compound for an organic optoelectronic device according to 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 of those skilled in the art using the basic concept of the present invention defined in the following claims are also present. belong to the scope of the invention.

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

Claims (10)

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 composition including a first compound represented by Formula 1 and a second compound represented by Formula 2 below,
The hole transport auxiliary layer is an organic optoelectronic device including a third compound represented by Chemical Formula 3:
[Formula 1] [Formula 2]

[Formula 3]

In Formulas 1 to 3,
L ¹ to 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 ¹ to R ¹⁵ are each independently hydrogen, deuterium, a substituted or unsubstituted C6 to C12 aryl group, or a combination thereof;
n is an integer from 0 to 2;
Ar ¹ to Ar ⁸ 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;
At least one of Ar ¹ and Ar ² is a substituted or unsubstituted C10 to C30 aryl group or a substituted or unsubstituted C10 to C30 heterocyclic group,
At least one of Ar ⁷ and Ar ⁸ is represented by Formula A1 or Formula A2 below,
[Formula A1] [Formula A2]

In Formulas A1 and A2 above,
* is the connection point,
X is O or S;
R ^a to R ^g are each independently hydrogen, deuterium, a substituted or unsubstituted C6 to C12 aryl group, or a combination thereof. In paragraph 1,
Ar ¹ to Ar 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 carbazolyl group, or a substituted or unsubstituted dibenzofuran a dibenzothiophenyl group, or a substituted or unsubstituted dibenzothiophenyl group;
At least one of Ar ¹ and Ar ² is a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted terphenyl group. A dibenzothiophenyl group, an organic optoelectronic device. In paragraph 1,
Ar ⁴ and Ar ⁵ 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 quaterphenyl group, a substituted or unsubstituted naphthyl group, or a substituted Or an unsubstituted anthracenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted A dibenzothiophenyl group, a substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted fluorenyl group, an organic optoelectronic device. In paragraph 1,
Chemical Formula 2 is an organic optoelectronic device represented by Chemical Formula 2-1:
[Formula 2-1]

In Formula 2-1,
R ⁶ to R ¹¹ are as defined in claim 1,
*-L ⁵ -Ar ⁴ and *-L ⁶ -Ar ⁵ are each independently one of the substituents listed in Group I below;
[Group I]

In the above group I, * is a connection point. In paragraph 1,
The third compound is an organic optoelectronic device represented by any one of Formulas 3-1 to 3-3:
[Formula 3-1] [Formula 3-2]

[Formula 3-3]

In Formulas 3-1 to 3-3,
X, R ^a to R ^g and R ¹² to R ¹⁵ are as defined in claim 1,
Ar ⁶ is a substituted or unsubstituted phenyl group or a substituted or unsubstituted biphenyl group;
Ar ⁷ is 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, or a substituted or unsubstituted phenanthre A substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted furanyl group, a substituted or unsubstituted thiophenyl group, a substituted or unsubstituted A dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted carbazolyl group. According to claim 5,
Wherein Ar ⁷ is any one selected from the substituents listed in the following Group II organic optoelectronic device:
[Group II]

In Group II above, * is a connection point. In paragraph 1,
The second compound is represented by Formula 2-1 below,
The third compound is an organic optoelectronic device represented by Chemical Formula 3-1:
[Formula 2-1]

In Formula 2-1,
L ⁵ and L ⁶ are each independently a single bond or a substituted or unsubstituted C6 to C12 arylene group;
Ar ⁴ and Ar ⁵ are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group;
R ⁶ to R ¹¹ are each independently hydrogen, deuterium or a phenyl group;
[Formula 3-1]

In Formula 3-1,
Ar ⁶ is a phenyl group;
Ar ⁷ is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group;
L ⁷ and L ⁹ are each independently a phenylene group;
R ¹² to R ¹⁵ are each independently hydrogen, deuterium or a C6 to C12 aryl group;
R ^a to R ^g are hydrogen or deuterium,
X is O or S. In paragraph 7,
Ar ¹ to Ar ³ in Formula 1 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 dibenzofuranyl group, or a substituted or unsubstituted dibenzofuranyl group. A cyclic dibenzothiophenyl group,
At least one of Ar ¹ and Ar ² is a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group. device. According to claim 1,
The organic optoelectronic device further comprises a dopant. A display device comprising the organic optoelectronic device according to any one of claims 1 to 9.

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