KR20210033792A - Organic optoelectronic device and display device - Google Patents

Abstract

The present invention relates to an organic optoelectronic element of high efficiency and long life, and a display device. The organic optoelectronic element comprises: an anode and a cathode facing each other; a light emitting layer positioned between the anode and the cathode; a hole transport layer positioned between the anode and the light emitting layer; and a hole transport auxiliary layer positioned between the light emitting layer and the hole transport layer, wherein the light emitting layer includes a first compound represented by a combination of chemical formula 1 and chemical formula 2 and a second compound represented by chemical formula 3, and the hole transport auxiliary layer includes a third compound represented by chemical formula 4. Details of chemical formula 1 to 4 are as defined in the specification.

Description

Organic optoelectronic device and display device TECHNICAL FIELD

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

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

Organic optoelectronic devices can be roughly divided into two types according to the principle of operation. One is a photoelectric device that generates electrical energy by separating the excitons formed by light energy into electrons and holes, and the electrons and holes are transferred to different electrodes, and the other is electrical energy by supplying voltage or current to the electrode. 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) are attracting great 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 influenced by an organic material 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 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. A layer, wherein the emission layer includes a first compound represented by a combination of the following Formula 1 and the following Formula 2, and a second compound represented by the following Formula 3, and the hole transport auxiliary layer is a first compound represented by the following Formula 4 It provides an organic optoelectronic device comprising the 3 compound.

[Formula 1] [Formula 2]

In Formula 1 and Formula 2,

Two adjacent ones of a ₁ * to a ₄ * of Formula 1 are each connected to _{b 1} * and b _{2 * of Formula 2,}

of a ₁ * to a ₄ * b ₁ * and b ₂ * and the rest not connected to each independently CL ^a -R ^a ,

L ^a and Y ¹ and Y ² are each independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heterocyclic group, or a combination thereof,

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

R ^a and R ¹ to R ⁷ are each independently hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C12 aryl group;

[Formula 3]

In Chemical Formula 3,

Z ¹ to Z ⁶ are each independently N or CL ^b -R ^b ,

At least two of Z ¹ to Z ^{6 are N,}

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

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

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

[Formula 4]

In Chemical Formula 4,

X ¹ is O or S,

L ¹ to 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 ⁸ to R ¹¹ are each independently a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof,

R ¹² and R ¹³ are each independently hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C12 aryl group.

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

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

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

In one example of the present invention, "substituted" means that at least one hydrogen in a substituent or compound is deuterium, a C1 to C30 alkyl group, a C1 to C10 alkylsilyl group, a C6 to C30 arylsilyl group, a C3 to C30 cycloalkyl group, a C3 to C30 It means substituted with a heterocycloalkyl group, a C6 to C30 aryl group, and a C2 to C30 heteroaryl group. In addition, in a specific example of the present invention, "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" means that at least one hydrogen in a substituent or compound 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, 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.

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

In the present specification, "aryl group" is a concept that encompasses a group having one or more hydrocarbon aromatic moieties, and while all elements of the hydrocarbon aromatic moiety have p-orbitals, these p-orbitals are conjugated. Forms forming, for example, a phenyl group, a naphthyl group, etc., and two or more hydrocarbon aromatic moieties are linked through a sigma bond, including a biphenyl group, a terphenyl group, a quaterphenyl group, etc., and two or more hydrocarbon aromatic moieties They may contain directly or indirectly fused non-aromatic fused rings such as fluorenyl groups and the like.

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

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

For example, "heteroaryl group" means containing at least one hetero atom selected from the group consisting of N, O, S, P, and Si in the aryl group. Two or more heteroaryl groups are 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 contain 1 to 3 heteroatoms.

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

More specifically, a substituted or unsubstituted C2 to C30 heterocyclic group, a substituted or unsubstituted furanyl group, a substituted or unsubstituted thiophenyl group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted pyrazolyl group, a substituted Or unsubstituted imidazolyl group, substituted or unsubstituted triazolyl group, substituted or unsubstituted oxazolyl group, substituted or unsubstituted thiazolyl group, substituted or unsubstituted oxadiazolyl group, substituted or unsubstituted Thiadiazolyl group, substituted or unsubstituted pyridyl group, substituted or unsubstituted pyrimidinyl group, substituted or unsubstituted pyrazinyl group, substituted or unsubstituted triazinyl group, substituted or unsubstituted benzofuranyl group, substituted Or unsubstituted benzothiophenyl group, substituted or unsubstituted benzimidazolyl group, substituted or unsubstituted indolyl group, substituted or unsubstituted quinolinyl group, substituted or unsubstituted isoquinolinyl group, substituted or unsubstituted Quinazolinyl group, substituted or unsubstituted quinoxalinyl group, substituted or unsubstituted naphthyridinyl group, substituted or unsubstituted benzoxazineyl group, substituted or unsubstituted benzthiazinyl group, substituted or unsubstituted acridinyl group , A substituted or unsubstituted phenazineyl group, a substituted or unsubstituted phenothiazinyl group, a substituted or unsubstituted phenoxazineyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group , Or a combination thereof, but is not limited thereto.

In the present specification, "adjacent groups are connected to each other to form a substituted or unsubstituted aromatic monocyclic or polycyclic ring, or a substituted or unsubstituted aromatic monocyclic or polycyclic heterocycle" means an aromatic ring or an aromatic heterocycle It means that when any two substituents directly substituted on are adjacent to each other, they are connected to each other to form an additional ring.

For example, adjacent groups are connected to each other to form a substituted or unsubstituted aromatic monocyclic or polycyclic ring; Alternatively, an aromatic polycyclic heterocycle may be formed, and as a specific example, a substituted or unsubstituted aromatic monocyclic ring or a substituted or unsubstituted aromatic polycyclic heterocycle may be formed.

For example, any two substituents directly substituted on the pyrimidine ring are linked to each other to form an additional ring, so that a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted benzofuranpyrimidine, or a substituted or non-substituted with the pyrimidine ring. Ringed benzothiophenepyrimidines can be formed.

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

In addition, electronic properties refer to the property of receiving electrons when an electric field is applied, and has conduction properties according to the LUMO level, so that electrons formed at the cathode are injected into the emission layer, electrons formed at the emission layer move to the cathode, and in the emission layer It refers to 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 light energy, and examples thereof include an organic photoelectric device, an organic light emitting device, an organic solar cell, and an organic photoreceptor drum.

Herein, 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 thicknesses are enlarged in order to clearly express various layers and regions. Like reference numerals are attached to similar 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 the other part is "directly above" but also the case where there is another part in the middle. Conversely, when one part is "directly above" another part, it means that there is no other part in the middle.

1 is a schematic cross-sectional view of an organic light-emitting device according to an 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 disposed between the anode 110 and the cathode 120. And, the organic layer 105 includes a light emitting layer 130, a hole transport auxiliary layer 142, and a hole transport layer 141.

The anode 110 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 be a metal such as nickel, platinum, vanadium, chromium, copper, zinc, or gold, or an alloy thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO and Al or SnO _{2 and Sb;} Poly(3-methylthiophene), poly(3,4-(ethylene-1,2-dioxy)thiophene) (polyehtylenedioxythiophene: PEDOT), conductive polymers such as polypyrrole and polyaniline, but are 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, and may be made of, for example, a metal, a metal oxide, and/or a conductive polymer. The negative electrode 120 may be a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium, or an alloy thereof; A multilayered material such as LiF/Al, LiO ₂ /Al, LiF/Ca, LiF/Al, and BaF ₂ /Ca may be mentioned, but is not limited thereto.

The emission 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 emission layer 130 may include a first compound having relatively strong hole characteristics and a second compound having relatively strong electronic characteristics as a host.

The first compound is a compound having relatively strong hole properties, and may be represented by a combination of the following Chemical Formulas 1 and 2.

[Formula 1] [Formula 2]

In Formula 1 and Formula 2,

Two adjacent ones of a ₁ * to a ₄ * of Formula 1 are each connected with _{b 1} * and b _{2 * of Formula 2,}

of a ₁ * to a ₄ * b ₁ * and b ₂ * and the rest not connected to each independently CL ^a -R ^a ,

L ^a and Y ¹ and Y ² are each independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heterocyclic group, or a combination thereof,

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

R ^a and R ¹ to R ⁷ are each independently hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C12 aryl group.

The first compound has at least one naphthyl group at the N position of the indolocarbazole group, and thus has high HOMO energy as the HOMO electron cloud expands from the indolocarbazole to the naphthyl group, and thus has excellent hole injection and transfer properties.

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

In addition, by applying a fused ring-containing compound such as the third compound to the hole transport auxiliary layer, it is possible to increase hole mobility and glass transition temperature at the same time, and accordingly, the accumulation of lattice is improved due to the increase of the dipole moment, resulting in a high glass transition temperature as well as molecular weight. Since the deposition process temperature is lower than that, it is possible to implement excellent life characteristics by ensuring device stability and driving stability in the device manufacturing process.

For example, the first compound may be represented by any one of the following Formulas 1A to 1F, depending on the fusion position.

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

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

In Formulas 1A to 1F, Y ¹ , Y ² , Ar ¹ and R ¹ to R ⁷ are as described above,

L ^a1 to L ^a4 are the same as the definition ^{of L a described above, and R a1} to R ^a4 are the same as the definition ^{of R a above.}

Specifically, the first compound may be represented by Formula 1C.

For example, the first compound may be represented by the following Formula 1C-1 or 1C-2.

[Formula 1C-1] [Formula 1C-2]

In Formula 1C-1 and Formula 1C-2, Y ¹ , Y ² , Ar ¹ , R ¹ to R ⁷ , L ^a1 , L ^a2 , R ^a1 and R ^a2 are as described above.

In one embodiment, the first compound may be represented by Formula 1C-1.

For example, in Formula 1C-1, Y ¹ and Y ² are each independently a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group, and Ar ¹ is a substituted or unsubstituted phenyl group, It may be a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, or a substituted or unsubstituted naphthyl group.

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

[Group 1]

[HA-1] [HA-2] [HA-3] [HA-4]

[HA-5] [HA-6] [HA-7] [HA-8]

[HA-9] [HA-10] [HA-11] [HA-12]

[HA-13] [HA-14] [HA-15] [HA-16]

[HA-17] [HA-18] [HA-19] [HA-20]

[HA-21] [HA-22] [HA-23] [HA-24]

[HB-1][HB-2][HB-3][HB-4]

[HB-5][HB-6][HB-7][HB-8]

[HB-9][HB-10][HB-11][HB-12]

[HB-13][HB-14][HB-15][HB-16]

[HB-17][HB-18][HB-19][HB-20]

[HB-21][HB-22][HB-23][HB-24]

[HB-25][HB-26][HB-27][HB-28]

[HB-29][HB-30][HB-31][HB-32]

[HB-33][HB-34][HB-35][HB-36]

[HB-37][HB-38][HB-39][HB-40]

[HC-1][HC-2][HC-3][HC-4]

[HC-5][HC-6][HC-7][HC-8]

[HC-9][HC-10][HC-11][HC-12]

[HC-13][HC-14][HC-15][HC-16]

[HC-17][HC-18][HC-19][HC-20]

[HC-21][HC-22][HC-23][HC-24]

[HC-25][HC-26][HC-27][HC-28]

[HC-29][HC-30][HC-31][HC-32]

[HC-33][HC-34][HC-35][HC-36]

[HC-37][HC-38][HC-39][HC-40]

[HD-1] [HD-2] [HD-3] [HD-4]

[HD-5] [HD-6] [HD-7] [HD-8]

[HD-9] [HD-10] [HD-11] [HD-12]

[HD-13] [HD-14] [HD-15] [HD-16]

[HD-17] [HD-18] [HD-19] [HD-20]

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

[HE-1][HE-2][HE-3][HE-4]

[HE-5][HE-6][HE-7][HE-8]

[HE-9][HE-10][HE-11][HE-12]

[HE-13][HE-14][HE-15][HE-16]

[HE-17][HE-18][HE-19][HE-20]

[HE-21][HE-22][HE-23][HE-24]

[HE-25][HE-26][HE-27][HE-28]

[HE-29][HE-30][HE-31][HE-32]

[HE-33][HE-34][HE-35][HE-36]

[HE-37][HE-38][HE-39][HE-40]

[HF-1][HF-2][HF-3][HF-4]

[HF-5][HF-6][HF-7][HF-8]

[HF-9][HF-10][HF-11][HF-12]

[HF-13][HF-14][HF-15][HF-16]

[HF-17][HF-18][HF-19][HF-20]

[HF-21][HF-22][HF-23][HF-24]

[HF-25][HF-26][HF-27][HF-28]

[HF-29][HF-30][HF-31][HF-32]

[HF-33][HF-34][HF-35][HF-36]

The second compound is a compound having relatively strong electronic properties and may be represented by Formula 3 below.

[Formula 3]

In Chemical Formula 3,

Z ¹ to Z ⁶ are each independently N or CL ^b -R ^b ,

At least two of Z ¹ to Z ^{6 are N,}

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

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

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

Since the second compound effectively expands the LUMO energy band by including the nitrogen-containing hexagonal ring moiety, it is included together with the above-described first compound to increase the balance between holes and electrons, thereby greatly improving the lifespan characteristics of the device to which it is applied. .

For example, ^{two of Z 1} to Z ⁶ may be nitrogen (N) and the rest may be CL ^b -R ^b .

For example, Z ¹ and Z ³ are nitrogen, Z ² is N or CL ^b -R ^b , Z ⁴ is N or CL ^b -R ^b , Z ⁵ is N or CL ^b -R ^b , and Z ⁶ is N or It may be ^{CL b} -R ^b.

For example, ^{three of Z 1} to Z ⁶ may be nitrogen (N) and the rest may be CL ^b -R ^b .

For example, Z ¹ , Z ³ and Z ⁵ may be nitrogen, Z ² may be N or CL ^b -R ^b , Z ⁴ may be N or CL ^b -R ^b , and Z ⁶ may be N or CL ^b -R ^b .

As a specific example, ^{when each of R b} is independently present, the second compound may be represented by the following Chemical Formula 3-1.

[Chemical Formula 3-1]

In Formula 3-1, Z ¹ , Z ³ and Z ⁵ are each independently N or CL ^b -R ^b , ^{and at least two of Z 1} , Z ³ and Z ⁵ are N, and L ^b2 , L ^b4 and L ^b6 is the ^{same as L b} and R ^b2 , R ^b4 and R ^b6 are the same ^{as R b.}

As a more specific example, Chemical Formula 3-1 may be represented by Chemical Formula 3-1a or Chemical Formula 3-1b.

[Formula 3-1a] [Formula 3-1b]

In Formulas 3-1a and 3-1b, L ^b2 , L ^b4 and L ^b6 , and R ^b2 , R ^b4 and R ^b6 are as described above.

For example, ^{adjacent groups of R b may be} linked to form a substituted or unsubstituted aliphatic, aromatic or heteroaromatic monocyclic or polycyclic ring.

In the present specification, "adjacent groups are linked to form a substituted or unsubstituted aliphatic, aromatic or heteroaromatic monocyclic or polycyclic ring" means that any two adjacent substituents are fused to each other to form a ring do. For example, adjacent R ^b in Formula 3 may be linked to each other to form a heteroaromatic polycyclic ring together with a nitrogen-containing hexagonal ring moiety in which they are substituted. Examples of the heteroaromatic polycyclic ring formed at this time include a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted benzofuranpyrimidinyl group, a substituted or unsubstituted benzothiophenepyrimidine Diary, etc. may be mentioned, and for example, it may be represented by the following Chemical Formula 3-2 or Chemical Formula 3-3.

[Chemical Formula 3-2] [Chemical Formula 3-3]

In Formula 3-2 and Formula 3-3, Z ¹ , Z ⁴ , Z ⁵ , Z ⁶ , L ¹⁰ , R ¹² are as described above, X ² is O or S, and R ^c , R ^d , R ^e and R ^f are each independently hydrogen, deuterium, a halogen group, a cyano group, a C1 to C20 alkyl group, a C6 to C30 aryl group, a C2 to C30 heteroaryl group, or a combination thereof.

For example, Z ¹ and Z ⁵ in Formula 3-2 may be N.

For example, Z ¹ and Z ⁴ in Formula 3-2 may be N.

For example, Chemical Formula 3-2 may be represented by Chemical Formula 3-2a or Chemical Formula 3-2b.

[Formula 3-2a] [Formula 3-2b]

In Formulas 3-2a and 3-2b, L ^b4 to L ^b6 , R ^b4 to R ^b6 , R ^c and R ^d are as described above.

For example, Z ¹ and Z ⁵ in Chemical Formula 3-3 may be N.

For example, Z ⁴ and Z ⁶ in Formula 3-3 may be N.

For example, Chemical Formula 3-3 may be represented by Chemical Formula 3-3a or Chemical Formula 3-3b.

[Chemical Formula 3-3a] [Chemical Formula 3-3b]

In Formulas 3-3a and 3-3b, X ² , L ^b1 , L ^b4 , L ^b5 , L ^b6 , R ^b1 , R ^b4 , R ^b5 , R ^b6 , R ^e and R ^f are as described above.

For example, R ^b in Formula 3 may each independently be hydrogen, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group.

Each of R ^b is independently hydrogen, 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, a substituted or Unsubstituted anthracenyl group, substituted or unsubstituted phenanthrenyl group, substituted or unsubstituted triphenylene group, substituted or unsubstituted dibenzofuranyl group, substituted or unsubstituted dibenzothiophenyl group, substituted or unsubstituted Substituted carbazolyl group, substituted or unsubstituted benzocarbazolyl group, substituted or unsubstituted dibenzocarbazolyl group, substituted or unsubstituted pyrimidinyl group, substituted or unsubstituted triazinyl group, substituted or unsubstituted benzo A furanpyrimidinyl group, or a substituted or unsubstituted benzothiophenepyrimidinyl group,

Here, "substitution" may be one in which at least one hydrogen is substituted with at least one of a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a dibenzofuranyl group, and a dibenzothiophenyl group.

As a specific example, each of R ^b may be independently selected from the substituents listed in Group I below.

[Group I]

In the above group I,

X ⁵ and X ¹⁰¹ are O or S,

R ¹⁰¹ to R ¹⁸⁴ are each independently hydrogen, deuterium, a halogen group, a cyano group, a C1 to C20 alkyl group, a C6 to C30 aryl group, a C2 to C30 heteroaryl group, or a combination thereof,

* Is the connection point.

In a specific embodiment, Chemical Formula 3 may be represented by Chemical Formula 3-1a or Chemical Formula 3-3a.

In a more specific embodiment, Formula 3 may be represented by Formula 3-1a.

For example, in Formula 3-1a, L ^b2 , L ^b4 and L ^b6 are each independently a single bond or a phenylene group unsubstituted or substituted with a C6 to C12 aryl group, and R ^b2 , R ^b4 and R ^b6 are each independently 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 triphenylene group, a substituted or unsubstituted dibenzo Furanyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted carbazolyl group, ^{and at least one of R 8} , R ¹⁰ and R ¹² is a substituted or unsubstituted triphenylene group, a substituted or unsubstituted It may be a carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

For example, in Formula 3-3a, X ² is O or S, L ^b1 and L ^b5 are each independently a single bond or a phenylene group, and R ^b1 and R ^b5 are each independently a substituted or unsubstituted phenyl group, a substituted Or an unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzoti It may be an ofenyl group or a substituted or unsubstituted carbazolyl group.

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

[Group 2]

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

^{For example, Y 1} and Y ² of Formula 1C-1 are each independently a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group, and Ar ¹ is a substituted or unsubstituted phenyl group, a substituted Or it may be an unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, or a substituted or unsubstituted naphthyl group.

^{L a1} and L ^a2 of Formula 1C-1 are each a single bond, and R ^a1 , R ^a2 , R ¹ to R ⁷ are each independently hydrogen, deuterium, cyano group, substituted or unsubstituted C1 to C10 alkyl group or substituted Or it may be an unsubstituted C6 to C12 aryl group.

^{L b2} , L ^b4 and L ^b6 of Formula 3-1a are each independently a single bond or a phenylene group unsubstituted or substituted with a C6 to C12 aryl group,

R ^b2 , R ^b4 and R ^b6 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 It may be a triphenylene group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted carbazolyl group.

The first compound and the second compound may be included in a weight ratio of, for example, 1:99 to 99:1. By being included in the above range, it is possible to improve efficiency and lifespan by implementing bipolar characteristics by adjusting an appropriate weight ratio using the hole transport capacity of the first compound and the electron transport capacity of the second compound. Within the above range, for example, it may be included in a weight ratio of 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. have. For example, it may be included in a weight ratio of 50:50 to 60:40, for example, it may be included in a weight ratio of 60:40.

In an embodiment of the present invention, the first compound and the second compound may each be included as a host of an emission layer, for example, a phosphorescent host.

In addition to the above-described host, the emission layer may further include one or more compounds.

The emission layer may further include a dopant. The dopant may be, for example, a phosphorescent dopant, such as 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 mixing in a small amount with the above-described host, and in general, a material such as a metal complex that emits light through multiple excitation excitation in a triplet state or more may be used. The dopant may be, for example, an inorganic, organic, or organic-inorganic compound, and may include one or two or more.

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

[Formula Z]

L ⁷ MX ⁴

In Formula Z, M is a metal, L ⁷ and X ⁴ are the same as or different from each other, and are ligands forming a complex compound with M.

The M may be, for example, Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or a combination thereof, and L ⁸ and X ⁴ may be, for example, bi It may be a dentate ligand.

The hole transport auxiliary layer 142 may be positioned between the light emitting layer 130 and the hole transport layer 141 to be described later, and in particular, may be positioned in contact with the light emitting layer 130. Since the hole transport auxiliary layer 142 is positioned in contact with the light emitting layer 130, the mobility of holes at the interface between the light emitting layer 130 and the hole transport layer 141 can be precisely controlled. 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 Chemical Formula 4 below.

[Formula 4]

In Chemical Formula 4,

X ¹ is O or S,

L ¹ to 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 ⁸ to R ¹¹ are each independently a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof,

R ¹² and R ¹³ are each independently hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C12 aryl group.

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 the mobility of holes 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 be represented by any one of the following Formulas 4-1 to 4-4, depending on the specific substitution position of the amine group.

[Formula 4-1] [Formula 4-2]

[Chemical Formula 4-3] [Chemical Formula 4-4]

In Formulas 4-1 to 4-4, X ¹ , L ¹ to L ⁶ , and R ⁸ to R ¹³ are as described above.

As a specific example, the third compound may be represented by Formula 4-2 or Formula 4-3.

Formula 4-2 may be represented by, for example, one of the following Formula 4-2a, Formula 4-2b, Formula 4-2c, and Formula 4-2d.

[Formula 4-2a] [Formula 4-2b]

[Formula 4-2c] [Formula 4-2d]

In Formulas 4-2a to 4-2d, X ¹ , L ¹ to L ⁶ , and R ⁸ to R ¹³ are as described above.

Formula 4-3 may be represented by any one of Formula 4-3a, Formula 4-3b, and Formula 4-3c, for example.

[Formula 4-3a] [Formula 4-3b]

[Formula 4-3c]

In Formulas 4-3a to 4-3c, X ¹ , L ¹ to L ⁶ , and R ⁸ to R ¹³ are as described above.

In an example of the present invention, the third compound may be represented by Formula 4-2b.

For example, L ¹ and L ⁴ may each independently be a single bond, and L ² , L ³ , L ⁵ and L ⁶ may each independently be a single bond, a substituted or unsubstituted phenylene group.

For example, the R ⁸ to R ¹¹ 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 Senyl group, substituted or unsubstituted phenanthrenyl group, substituted or unsubstituted triphenylene group, substituted or unsubstituted fluorenyl group, substituted or unsubstituted dibenzofuranyl group, substituted or unsubstituted dibenzothiophenyl group , It may be a substituted or unsubstituted fused dibenzofuranyl group or a substituted or unsubstituted fused dibenzothiophenyl group.

In a specific example, R ⁸ to R ¹¹ are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group. I can.

For example, ^{at least one of R 8} to R ¹¹ may be a substituted or unsubstituted dibenzofuranyl group or a substituted or unsubstituted dibenzothiophenyl group.

For example, R ¹² and R ¹³ may each independently be hydrogen or a C1 to C5 alkyl group.

As a specific example, each of R ¹² and R ¹³ may be hydrogen.

In a specific embodiment, the first compound may be represented by Formula 1C-1, the second compound may be represented by Formula 3-1a, and the third compound may be represented by Formula 4-2b.

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

[Group 3]

The hole transport layer 141 is positioned between the anode 110 and the emission layer 130, and may facilitate hole transport from the anode 110 to the emission 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 the 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 ¹⁴ to R ¹⁸ 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 ¹⁴ and R ¹⁵ are each independently present or bonded to each other to form a ring,

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

R ¹⁸ to R ²⁰ are each independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,

L ⁷ to L ¹⁰ 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 ¹⁸ may be a substituted or unsubstituted C6 to C30 aryl group. For example, R ¹⁸ may be a substituted or unsubstituted phenyl group or a substituted or unsubstituted biphenyl group.

For example, R ¹⁹ and R ²⁰ 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, a 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 a combination thereof. .

The compound represented by Formula 5 may be, for example, one of the compounds listed in Group 4, 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.

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

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

The above-described implementation examples 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 the rights.

(Preparation of the first compound)

Synthesis example 1: Synthesis of compound HC-28

[Scheme 1]

a) Synthesis of intermediate HC-28-1

Intermediate A (30g, 121.9mmol), 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 acetate 2 equivalents and 1,1'-bis (diphenylphosphino) ferrocene-palladium (II) dichloride 0.03 equivalent, tricyclohexylphosphine 0.2 equivalent N,N-dimethylformamide After putting it in 300mL, it stirred at 130 degreeC for 12 hours. After completion of the reaction, the reaction solution was extracted with water and EA to remove moisture from the organic layer obtained using magnesium sulfate, concentrated, and purified by column chromatography to obtain an intermediate HC-28-1 as a white solid (29.66 g, 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 The equivalent was added to 200 mL of 1,4-dioxane and 100 mL of water, followed by heating at 90° C. for 16 hours under a nitrogen stream. After removing the reaction solvent, it was dissolved in dichloromethane, filtered through silica gel/celite, and an appropriate amount of the organic solvent was removed, and then recrystallized with methanol to obtain an 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) was added to 150 mL of xylene and heated under a nitrogen stream for 12 hours. And refluxed. After xylene was removed, 200 mL of methanol was added to the mixture obtained therefrom to filter the crystallized solid, dissolved in dichloromethane, filtered through silica gel/celite, and after removing an appropriate amount of organic solvent, recrystallized from acetone to obtain intermediate HC- 28-3 (9.83 g, 77% yield) was obtained.

d) Synthesis of intermediate HC-28-4

In a 1000 ml flask, the synthesized intermediate HC-28-3 (211.37 g, 0.51 mol) and triethyl phosphite (528 ml, 3.08 mol) were added, followed by nitrogen substitution and stirred at 160° C. for 12 hours. After completion of the reaction, 3L of MeOH was added, stirred, filtered, and the filtrate was volatilized. Purified by column chromatography (Hexane) to obtain an intermediate HC-28-4 (152.14 g, 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 1 using the synthesized intermediate HC-28-4 and intermediate HC-28-B.

Synthesis example 2: Synthesis of compound HC-18

[Scheme 3]

a) Synthesis of intermediate HC-18-1

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

b) Synthesis of intermediate HC-18-2

In the same manner as d) of Synthesis Example 1, intermediate HC-18-2 was synthesized.

c) Synthesis of intermediate HC-18-3

[Scheme 4]

Intermediate HC-18-3 was synthesized in the same manner as in Synthesis Example 1 b) using the intermediate HC-18-A and the intermediate HC-18-B.

d) Synthesis of compound HC-18

[Scheme 5]

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

Synthesis example 3: Synthesis of compound HC-6

[Scheme 6]

a) Synthesis of intermediate HC-6-1

In the same manner as in c) of Synthesis Example 1, intermediate HC-6-1 was synthesized using an iodobenzene intermediate instead of 2-bromonaphthalene.

b) Synthesis of intermediate HC-6-2

In the same manner as d) of Synthesis Example 1, intermediate HC-6-2 was synthesized.

c) Synthesis of compound HC-6

[Scheme 7]

Compound HC-6 was synthesized using the synthesized intermediate HC-6-2 and intermediate HC-18-3 in the same manner as in Synthesis Example 1 e).

Synthesis example 4: Synthesis of compound HC-37

[Scheme 8]

Compound HC-37 was synthesized using the synthesized intermediate HC-28-4 and intermediate HC-18-3 in the same manner as in Synthesis Example 1 e).

(Preparation of the second compound)

Synthesis example 5: Synthesis of compound B-135

[Scheme 9]

a) Synthesis of Intermediate B-135-1

Intermediate B-135-1 was synthesized in the same manner as in b) of Synthesis Example 1, using 1.0 equivalents of 1-Bromo-4-chloro-benzene and 2-naphthalene boronic acid, respectively.

b) Synthesis of Intermediate B-135-2

In a 500 mL round-bottom flask, 1 equivalent of the intermediate B-135-1 was added to 250 mL of DMF, 0.05 equivalents of dichlorodiphenylphosphinoferrocene palladium, 1.2 equivalents of bispina colado diborone, 2 equivalents of potassium acetate, and 18 hours under nitrogen atmosphere. While heated to reflux. The reaction solution was cooled, and the solid was collected by dropping it in 1 L of water. The obtained solid is dissolved in boiling toluene, treated with activated carbon, filtered through silica gel, and the filtrate is concentrated. After stirring the concentrated solid with a small amount of hexane, the solid was filtered to synthesize intermediate B-135-2.

c) Synthesis of Intermediate B-17-1

[Scheme 10]

In a 500 mL round-bottom flask, 22.6 g (100 mmol) of 2,4-dichloro-6-phenyltriazine was added to 100 mL of tetrahydrofuran, 100 mL of toluene, and 100 mL of distilled water, and dibenzofuran-3-boronic acid (CAS No.: 395087). -89-5) 0.9 equivalents, 0.03 equivalents of tetrakistriphenylphosphine palladium, and 2 equivalents of potassium carbonate are added and heated to reflux under a nitrogen atmosphere. After 6 hours, the reaction solution was cooled, the water layer was removed, and the organic layer was dried under reduced pressure. After washing the obtained solid with water and hexane, the solid was recrystallized from 200 mL of toluene to obtain 21.4 g (60% yield) of intermediate B-17-1.

d) Synthesis of compound B-135

Compound B-135 was synthesized in the same manner as in a) of Synthesis Example 5, using 1.0 equivalent of each of Intermediate B-135-2 and Intermediate B-17-1.

LC/MS measurement (C37H23N3O, theoretical value: 525.18 g/mol, measured value: M= 525.22 g/mol)

Synthesis example 6: Synthesis of compound A-1

[Scheme 11]

a) Synthesis of Intermediate A-1-1

In a round bottom flask, 2,4-Dichloro-6-phenyl-1,3,5-triazine (21.0 g, 93.12 mmol), intermediate B-135-2 (20.5 g, 62.08 mmol), tetrakis (triphenylphosphine) palladium (2.1 g, 1.86 mmol) and potassium carbonate (17.1 g, 124.16 mmol) are dissolved in 200 mL of tetrahydrofuran and 100 mL of distilled water, and heated to reflux under a nitrogen atmosphere. After 6 hours, the reaction solution was cooled, the water layer was removed, and the organic layer was dried under reduced pressure. After washing the obtained solid with water and methanol, the solid was recrystallized from 400 mL of toluene to obtain 18.0 g (74% yield) of Intermediate A-1-1.

b) Synthesis of Compound A-1

Intermediate A-1-1 (22.5 g 57.2 mmol) and carbazole (7.9 g, 47.6 mmol) were dissolved in 200 mL of DMF, and NaH was added. After stirring at room temperature for 4 hours, a reaction solution was added to 500 mL of water to form a precipitate. The formed solid was filtered and washed with water and methanol. The obtained solid was recrystallized in 500 mL of clorobenzene to obtain 22.8 g (91%) of compound A-1.

LC/MS calculated for: C37H24N4 Exact Mass: 524.20 found for 524.25 [M+H]

Synthesis example 7: Synthesis of compound B-17

[Scheme 12]

In a 500 mL round-bottom flask, 200 mL of tetrahydrofuran and 100 mL of distilled water were added to the intermediate B-17-1 (56.9 mmol), followed by 1.1 equivalents of 3,5-diphenylbenzeneboronic acid (CAS No.: 128388-54-5). , Tetrakistriphenylphosphine palladium 0.03 equivalents, potassium carbonate 2 equivalents, and heated to reflux under a nitrogen atmosphere. After 18 hours, the reaction solution was cooled, the precipitated solid was filtered, and washed with 500 mL of water. The solid was recrystallized with 500 mL of monochlorobenzene to obtain compound B-17.

LC/MS calculated for: C39H25N3O Exact Mass: 555.1998 found for 556.21 [M+H]

Synthesis example 8: Synthesis of Compound B-20

[Scheme 13]

Intermediate B-17-1 and 1.1 equivalents of (5'-phenyl[1,1':3',1"-terphenyl]-4-yl)-boronic acid (CAS No.: 491612-72-7) were used. Thus, compound B-20 was synthesized in the same manner as in Synthesis Example 7.

LC/MS calculated for: C45H29N3O Exact Mass: 627.2311 found for 628.24 [M+H]

Synthesis example 9: Synthesis of compound B-23

[Scheme 14]

a) Synthesis of Intermediate B-23-1

In a 500 mL round bottom flask, 15 g (81.34 mmol) cyanuric chloride was dissolved in 200 mL of anhydrous tetrahydrofuran, and 1 equivalent of 4-biphenyl magnesium bromide solution (0.5M tetrahydrofuran) was added dropwise at 0°C under a nitrogen atmosphere, and then gradually cooled to room temperature. Raise. After stirring at room temperature for 1 hour, the reaction solution was added to 500 mL of ice water and the layers were separated. The organic layer was separated, treated with anhydrous magnesium sulfate, and concentrated. The concentrated residue was recrystallized from tetrahydrofuran and methanol to obtain 17.2 g of Intermediate B-23-1.

b) Synthesis of Intermediate B-23-2

Using Intermediate B-23-1, Intermediate B-23-2 was synthesized in the same manner as c) in Synthesis Example 5 above.

c) Synthesis of Compound B-23

Compound B-23 was synthesized in the same manner as in Synthesis Example 7 using Intermediate B-23-2 and 1.1 equivalents of 3,5-diphenylbenzeneboronic acid.

LC/MS calculated for: C45H29N3O Exact Mass: 627.2311 found for 628.24 [M+H]

Synthesis example 10: Synthesis of compound B-24

[Scheme 15]

Compound B-24 was synthesized in the same manner as in Synthesis Example 7 using Intermediate B-23-2 and 1.1 equivalents of B-[1,1':4',1''-Terphenyl]-3-yl boronic acid. I did.

LC/MS calculated for: C45H29N3O Exact Mass: 627.2311 found for 628.24 [M+H]

Synthesis example 11: Synthesis of compound B-71

[Scheme 16]

a) Synthesis of Intermediate B-71-1

In a 500 mL round-bottom flask, 14.06 g (56.90 mmol) of 3-bromo-dibenzofuran, 200 mL of tetrahydrofuran, and 100 mL of distilled water were added, and 1 equivalent of 3'-chloro-phenylboronic acid, tetrakistriphenylphosphine palladium 0.03 Equivalents and 2 equivalents of potassium carbonate are added and heated to reflux under nitrogen atmosphere. After 18 hours, the reaction solution was cooled, the precipitated solid was filtered, and washed with 500 mL of water. The solid was recrystallized from 500 mL of monochlorobenzene to obtain 12.05 g of intermediate B-71-1. (Yield 76%)

b) Synthesis of Intermediate B-71-2

In a 500 mL round-bottom flask, 24.53 g (88.02 mmol) of the synthesized intermediate B-71-1 was added to 250 mL of DMF, and 0.05 equivalents of dichlorodiphenylphosphinoferrocene palladium, 1.2 equivalents of bispinacola diborone, and 2 equivalents of potassium acetate were added. The mixture was heated to reflux for 18 hours under a nitrogen atmosphere. The reaction solution was cooled, and the solid was collected by dropping it in 1 L of water. The obtained solid is dissolved in boiling toluene, treated with activated carbon, filtered through silica gel, and the filtrate is concentrated. After stirring the concentrated solid with a small amount of hexane, the solid was filtered to obtain 22.81 g of intermediate B-71-2. (Yield 70%)

c) Synthesis of Compound B-71

Intermediate B-71-2 and 2,4-Bis([1,1'-biphenyl]-4-yl)-6-chloro-1,3,5-triazine were used in 1.0 equivalents, respectively, as in Synthesis Example 7 Compound B-71 was synthesized in the same way.

LC/MS calculated for: C45H29N3O Exact Mass: 627.2311 found for 628.25 [M+H]

Synthesis example 12: Synthesis of compound B-124

[Scheme 17]

a) Synthesis of Intermediate B-124-1

Intermediate B-124-1 was synthesized in the same manner as in c) of Synthesis Example 5, using 1.1 equivalents of 1-bromo-3-chloro-5-phenylbenzene and biphenyl-4-boronic acid. At this time, the product was purified through a flash column using hexane instead of recrystallization.

b) Synthesis of Intermediate B-124-2

In a 500 mL round-bottom flask, 30 g (88.02 mmol) of the synthesized intermediate B-124-1 was added to 250 mL of DMF, 0.05 equivalents of dichlorodiphenylphosphinoferrocene palladium, 1.2 equivalents of bispinacola diborone, and 2 equivalents of potassium acetate were added. It was heated to reflux for 18 hours under a nitrogen atmosphere. The reaction solution was cooled, and the solid was collected by dropping it in 1 L of water. The obtained solid is dissolved in boiling toluene, treated with activated carbon, filtered through silica gel, and the filtrate is concentrated. After stirring the concentrated solid with a small amount of hexane, the solid was filtered to obtain 28.5 g (70% yield) of intermediate B-124-2.

c) Synthesis of compound B-124

Compound B-124 was synthesized in the same manner as in Synthesis Example 7 using 1.0 equivalent of each of Intermediate B-124-2 and Intermediate B-17-1.

LC/MS calculated for: C45H29N3O Exact Mass: 627.2311 found for 628.22 [M+H]

Synthesis example 13: Synthesis of compound B-129

[Scheme 18]

a) Synthesis of Intermediate B-129-1

Intermediate B-129-1 was synthesized in the same manner as a) of Synthesis Example 11, using 1.0 equivalents of 1-Bromo-4-chloro-benzene and 3-dibenzofuranylboronic acid, respectively.

b) Synthesis of Intermediate B-129-2

Intermediate B-129-2 was synthesized in the same manner as in Synthesis Example 11 b) using an equivalent ratio of Intermediate B-129-1 and Diboron 1:1.2.

c) Synthesis of Compound B-129

Compound B-129 in the same manner as in Synthesis Example 7 using 1.0 equivalent of each of the intermediates B-129-2 and 2-chloro-4-(biphenyl-4-yl)6-phenyl-1,3,5-triazine Was synthesized.

LC/MS calculated for: C39H25N3O Exact Mass: 551.20 found for 551.24 [M+H]

Synthesis example 14: Synthesis of compound D-35

[Scheme 19]

Compound D-35 was synthesized using Intermediate D-35-1 and Intermediate D-35-2 with reference to the synthesis method disclosed in Korean Patent Laid-Open No. 10-2019-0079348.

(Preparation of the third compound)

Synthesis example 15: Synthesis of compound E-13

[Scheme 20]

a) Synthesis of Intermediate E-13-1

In a 3L round bottom flask, add 150g (498.5 mmol) of 4-bromo-2-fluoro-1-iodobenzene to 1.5L of N, N-dimethylformamide and set the internal temperature to 0℃. Sodium thiomethoxide (CAS No.: 5188-07-8) 35.44g (498.52mmol), potassium carbonate 103.19g (747.98mmol) is gradually added. At this time, maintain the internal temperature of 0℃. Heat to 80° C. under a nitrogen atmosphere. After 6 hours, the reaction solution was cooled, ethyl acetate and an aqueous layer were added and stirred, and then the organic layer was decompressed and 106.61 g (65% yield) of Intermediate E-13-1 was obtained by column chromatography.

b) Synthesis of Intermediate E-13-2

Intermediate E-13-1 (106g 322mmol) was dissolved in tetrahydrofuran (THF) 1.0L, and 4-Chlorophenylboronic acid (57.66g, 322mmol) and tetrakis (triphenylphosphine) palladium (11.2g, 9.7mmol) were added thereto and stirred. . Then, saturated potassium carbonate (111.32g, 805mmol) was added to water and heated at 80° C. for 12 hours to reflux. After completion of the reaction, water was added to the reaction solution, extracted with dichloromethane (DCM), and then water was removed with magnesium sulfate anhydrous, filtered and concentrated under reduced pressure. The obtained residue was separated and purified through flash column chromatography, obtaining 63.66 g (63%) of an intermediate E-13-2.

c) Synthesis of Intermediate E-13-3

Add 63g (200.87 mmol) of Intermediate E-13-2 to 600 mL of acetic acid and set the internal temperature to 0℃. Slowly add 20.4ml of hydrogen peroxide. At this time, maintain the internal temperature of 0℃. After stirring at room temperature for 6 hours, the reaction solution was put in ice water, extracted with dichloromethane (DCM), and then water was removed with magnesium sulfate anhydrous, filtered and concentrated under reduced pressure to obtain 61 g (92% yield) of intermediate E-13-3. .

d) Synthesis of Intermediate E-13-4

Intermediate E-13-3 60g (182.12mmol) was added to 400 mL of sulfuric acid and stirred at room temperature for 6 hours, then the reaction solution was added to ice water and the pH was adjusted to 9 using NaOH aqueous solution. Then, after extraction with dichloromethane (DCM), water was removed with magnesium sulfate anhydrous, filtered and concentrated under reduced pressure to obtain 38 g (70% yield) of intermediate E-13-4.

e) Synthesis of Intermediate E-13-5

Intermediate E-13-4 5.0 g (16.82 mmol), diphenylamine 2.85 g (16.82 mmol), sodium t-butoxide 4.04 g (42.04 mmol), tri-tert-butylphosphine 0.7 g (1.69 mmol) in xylene 100 ml And then Pd(dba) ₂ 0.77g (0.84mmol) was added and stirred at 100°C for 12 hours under a nitrogen atmosphere. After completion of the reaction, extraction was performed with xylene and distilled water, and the organic layer was dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The product was purified by silica gel column chromatography with normal hexane/dichloromethane (2: 1 volume ratio) to give 4.7 g (72% yield) as a white solid of intermediate E-13-5.

f) Synthesis of compound E-13

Intermediate E-13-5 4.5g (11.68mmol) and 3-Dibenzothiophene-Phenylamine 3.3g (11.68mmol), sodium t-butoxide 2.81g (29.21mmol), Tri-tert-butylphosphine 1.2g (1.17mmol) Was dissolved in 50ml of xylene, _{0.54g (0.58mmol) of Pd(dba) 2} was added, and the mixture was stirred under reflux for 12 hours under a nitrogen atmosphere. After completion of the reaction, extraction was performed with xylene and distilled water, and the organic layer was dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The product was purified by silica gel column chromatography with normal hexane/dichloromethane (2: 1 volume ratio) to obtain 5.5 g (75% yield) as a white solid of compound E-13.

Calc: C, 80.74; H, 4.52; N, 4.48; S, 10.26

Analytical value: C, 80.74; H, 4.52; N, 4.48; S, 10.26

Synthesis example 16: Synthesis of compound E-65

[Scheme 21]

Using 2-Dibenzothiophene-Phenylamine instead of 3-Dibenzothiophene-Phenylamine, 3.9 g (yield 66%) of a white solid of Compound E-65 was obtained by the same synthesis method as f) of Synthesis Example 15 above.

Calc: C, 80.74; H, 4.52; N, 4.48; S, 10.26

Analytical value: C, 80.74; H, 4.52; N, 4.48; S, 10.26

Comparative Synthesis Example 1: Synthesis of Comparative Compound 1

Comparative Compound 1 was synthesized by referring to the synthesis method disclosed in Korean Patent Publication No. 10-2016-0051133.

Comparative Synthesis Example 2: Synthesis of Comparative Compound 2

Comparative compound 2 was synthesized in the same manner as known in US2017-0317293A1.

(Production of organic light emitting device)

Example 1

Indium tin oxide (ITO) was washed with distilled water on a glass substrate coated with a thin film of 1,500Å thickness. After washing with distilled water, ultrasonic cleaning was performed with a solvent such as isopropyl alcohol, acetone, methanol, etc., dried, transferred to a plasma cleaner, and cleaned for 10 minutes using oxygen plasma, and then transferred to a vacuum evaporator. Using the prepared ITO transparent electrode as an anode, Compound A was vacuum deposited on the ITO substrate to form a hole injection layer having a thickness of 700 Å, and Compound B was deposited on the injection layer to a thickness of 50 Å, and then Compound C was deposited with a thickness of 700 Å. It was deposited to a thickness to form a hole transport layer. Compound E-13 was deposited to a thickness of 700Å on the hole transport layer to form a hole transport auxiliary layer. Compounds HC-28 and D-35 were simultaneously used as hosts on the hole transport auxiliary layer and _{doped with [Ir(piq) 2} acac] 2wt% as a dopant to form a light emitting layer having a thickness of 400Å by vacuum evaporation. Here, compound HC-28 and compound D-35 were used in a weight ratio of 6:4. Then, compound D and Liq were simultaneously vacuum deposited on the emission layer in a 1:1 ratio to form an electron transport layer having a thickness of 300 Å, and then Liq 15 Å and Al 1,200 Å were sequentially vacuum-deposited on the electron transport layer to form a cathode to form a cathode. The device was fabricated.

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

ITO / Compound A (700Å) / Compound B (50Å) / Compound C (700Å) / compound E-13 (700Å) / EML [ compound HC-28: D-35: [Ir (piq) 2 acac] (2wt% )] (400Å) / Compound D: Liq (300Å) / Liq (15Å) / Al (1,200Å) was prepared in the structure.

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

Compound B: 1,4,5,8,9,11-hexaazatriphenylene-hexacarbonitrile (HAT-CN)

Compound C: N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine

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

Examples 2 to 6

An organic light-emitting device was manufactured in the same manner as in Example 1, except that the composition was changed to the composition shown in Table 1.

Comparative Examples 1 to 5

An organic light-emitting device was manufactured in the same manner as in Example 1, except that the composition was changed to the composition shown in Table 1.

evaluation

The driving voltages of the organic light emitting devices according to Examples 1 to 6 and Comparative Examples 1 to 5 were measured by the following method, and the results are shown in Table 1.

Measurement of driving voltage: The driving voltage of each device was measured using a current-voltmeter (Keithley 2400).

Host 1 2nd host Hole transport auxiliary layer Driving voltage Example 1 HC-28 D-35 E-13 4.17 Example 2 HC-10 B-135 E-65 4.16 Example 3 HC-37 B-129 E-65 4.12 Example 4 HC-10 D-35 E-65 4.29 Example 5 HC-28 B-23 E-13 3.99 Example 6 HC-10 A-1 E-13 4.11 Comparative Example 1 HC-18 B-71 Comparative compound 1 4.51 Comparative Example 2 HC-28 B-23 Comparative compound 1 4.55 Comparative Example 3 HC-37 B-20 Comparative compound 1 4.70 Comparative Example 4 HC-10 A-1 Comparative compound 1 4.43 Comparative Example 5 Comparative compound 2 D-35 Comparative compound 1 4.77

Referring to Table 1, it can be seen that the driving voltage of the organic light emitting devices according to Examples 1 to 6 is significantly lower than that of the organic light emitting devices according to Comparative Examples 1 to 5.

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

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

Claims (14)

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

In Formula 1 and Formula 2,
Two adjacent ones of a ₁ * to a ₄ * of Formula 1 are each connected with _{b 1} * and b _{2 * of Formula 2,}
of a ₁ * to a ₄ * b ₁ * and b ₂ * and the rest not connected to each independently CL ^a -R ^a ,
L ^a and Y ¹ and Y ² are each independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heterocyclic group, or a combination thereof,
Ar ¹ is a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof,
R ^a and R ¹ to R ⁷ are each independently hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C12 aryl group;
[Formula 3]

In Chemical Formula 3,
Z ¹ to Z ⁶ are each independently N or CL ^b -R ^b ,
At least two of Z ¹ to Z ^{6 are N,}
L ^b is each independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heterocyclic group, or a combination thereof,
R ^b is each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, a substituted or unsubstituted silyl group , A substituted or unsubstituted amine group, a halogen, a cyano group, or a combination thereof,
Each R ^b is independently present or adjacent groups are linked to form a substituted or unsubstituted aliphatic, aromatic or heteroaromatic monocyclic or polycyclic ring;
[Formula 4]

In Chemical Formula 4,
X ¹ is O or S,
L ¹ to 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 ⁸ to R ¹¹ are each independently a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof,
R ¹² and R ¹³ are each independently hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C12 aryl group. In claim 1,
The first compound is an organic optoelectronic device represented by any one of the following Formulas 1A to 1F:
[Formula 1A] [Formula 1B] [Formula 1C]

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

In Formula 1A to Formula 1F,
Y ¹ and Y ² , Ar ¹ and R ¹ to R ⁷ are as defined in claim 1,
L ^a1 to L ^a4 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 ^a1 to R ^a4 are each independently a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof. In paragraph 2,
The first compound is an organic optoelectronic device represented by Formula 1C. In claim 1,
The Y ¹ and Y ² are each independently a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group,
The Ar ¹ is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, or a substituted or unsubstituted naphthyl group. The method of claim 1,
The second compound is an organic optoelectronic device represented by any one of the following Formulas 3-1 to 3-3:
[Chemical Formula 3-1] [Chemical Formula 3-2] [Chemical Formula 3-3]

In Formulas 3-1 to 3-3,
In Formula 3-1, Z ¹ , Z ³ and Z ⁵ are N or CL ^b -R ^b , and at least two of ^{Z 1} , Z ³ and Z ^{5 are N,}
In Formula 3-2, Z ¹ , Z ⁴ and Z ⁵ are N or CL ^b -R ^b , and at least two of ^{Z 1} , Z ⁴ and Z ^{5 are N,}
In Formula 3-3, Z ¹ , Z ⁴ , Z ⁵ and Z ⁶ are N or CL ^b -R ^b , and at least two of ^{Z 1} , Z ⁴ , Z ⁵ and Z ^{6 are N,}
L ^b , L ^b2 , L ^b4 and L ^b6 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 ^b , R ^b2 , R ^b4 and R ^b6 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocycle A group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a halogen, a cyano group, or a combination thereof,
R ^c , R ^d , R ^e and R ^f are each independently hydrogen, deuterium, a halogen group, a cyano group, a C1 to C20 alkyl group, a C6 to C30 aryl group, a C2 to C30 heteroaryl group, or a combination thereof, organic Optoelectronic devices. The method of claim 1,
The second compound is an organic optoelectronic device represented by the following Formula 3-1a:
[Formula 3-1a]

In Formula 3-1a,
L ^b2 , L ^b4 and L ^b6 are each independently a single bond or a phenylene group unsubstituted or substituted with a C6 to C12 aryl group,
R ^b2 , R ^b4 and R ^b6 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 A substituted triphenylene group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted carbazolyl group. The method of claim 6,
The first compound is an organic optoelectronic device represented by the following Formula 1C-1:
[Formula 1C-1]

In Formula 1C-1,
Y ¹ and Y ² , Ar ¹ , R ¹ to R ⁷ , L ^a1 , L ^a2 , R ^a1 and R ^a2 are as defined in claim 4. The method of claim 1,
The third compound is an organic optoelectronic device represented by any one of the following Formulas 4-1 to 4-4:
[Formula 4-1] [Formula 4-2]

[Chemical Formula 4-3] [Chemical Formula 4-4]

In Formula 4-1 to Formula 4-4,
X ¹ , L ¹ to L ⁶ , R ⁸ to R ¹¹ , R ¹² and R ¹³ are as defined in claim 1. The method of claim 1,
The third compound is an organic optoelectronic device represented by the following Formula 4-2b:
[Formula 4-2b]

In Formula 4-2b,
X ¹ , L ¹ to L ⁶ , R ⁸ to R ¹¹ , R ¹² and R ¹³ are as defined in claim 1. The method of claim 1,
At least one of R ⁸ to R ¹¹ is a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group. The method of claim 9,
The first compound is represented by the following formula 1C-1,
The second compound is an organic optoelectronic device represented by the following Formula 3-1a:
[Formula 1C-1]

In Formula 1C-1,
Y ¹ and Y ² are each independently a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group,
Ar ¹ is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, or a substituted or unsubstituted naphthyl group,
L ^a1 and L ^a2 are each a single bond,
R ^a1 , R ^a2 , R ¹ to R ⁷ are each independently hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C12 aryl group;
[Formula 3-1a]

In Formula 3-1a,
L ^b2 , L ^b4 and L ^b6 are each independently a single bond or a phenylene group unsubstituted or substituted with a C6 to C12 aryl group,
R ^b2 , R ^b4 and R ^b6 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 A substituted triphenylene group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted carbazolyl group,
At least one of R ^b2 , R ^b4 and R ^b6 is a substituted or unsubstituted triphenylene group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophene It's a diary. The method of claim 1,
Each of the first compound and the second compound is included as a phosphorescent host of the emission layer. The method of claim 1,
The light emitting layer is an organic optoelectronic device further comprising a dopant. A display device comprising the organic optoelectronic device according to any one of claims 1 to 13.

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