KR102162404B1 - Compound for organic optoelectric device, composition for organic optoelectric device, organic optoelectric device and display device - Google Patents

Abstract

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

Description

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

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

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

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

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

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

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

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

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

According to one embodiment, a compound for an organic optoelectronic device represented by the following Formula 1 is provided.

[Formula 1]

In Formula 1,

X ¹ is O or S,

R ¹ to R ⁸ are each independently hydrogen, deuterium, cyano group, substituted or unsubstituted C1 to C10 alkyl group, substituted or unsubstituted C6 to C20 aryl group, or substituted or unsubstituted C2 to C30 heterocyclic group ,

At least one of R ⁶ and R ⁷ is a substituted or unsubstituted C2 to C30 heterocyclic group containing one or more nitrogen atoms,

At least one of R ⁵ to R ⁸ is represented by Formula 2 below,

[Formula 2]

In Chemical Formula 2,

X ² is O or S,

R ⁹ to R ¹³ are each independently hydrogen, deuterium, cyano group, substituted or unsubstituted C1 to C10 alkyl group, substituted or unsubstituted C6 to C20 aryl group, or substituted or unsubstituted C2 to C30 heterocyclic group .

According to another embodiment, there is provided a composition for an organic optoelectronic device including the compound for an organic optoelectronic device.

According to another embodiment, an anode and a cathode facing each other, and at least one organic layer positioned between the anode and the cathode, wherein the organic layer comprises the aforementioned compound for an organic optoelectronic device or a composition for an organic optoelectronic device. It provides an organic optoelectronic device comprising.

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

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

1 and 2 are cross-sectional views each independently illustrating an organic light emitting device according to an embodiment.

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

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

In an example of the present invention, "substitution" means that at least one hydrogen in a substituent or compound is deuterium, a C1 to C30 alkyl group, a C1 to C10 alkylsilyl group, a C6 to C30 arylsilyl group, a C3 to C30 cycloalkyl group, a C3 to C30 It means substituted with a heterocycloalkyl group, a C6 to C30 aryl group, and a C2 to C30 heteroaryl group. In addition, in a specific example of the present invention, "substituted" means that at least one hydrogen in a substituent or compound is substituted with deuterium, a C1 to C20 alkyl group, a C6 to C30 aryl group, or a C2 to C30 heteroaryl group. In addition, in a specific example of the present invention, "substitution" means that at least one hydrogen in a substituent or compound is substituted with deuterium, a C1 to C5 alkyl group, a C6 to C18 aryl group, a dibenzofuranyl group, or a dibenzothiophenyl group. Means that. In addition, in a specific example of the present invention, "substitution" means that at least one hydrogen in a substituent or compound is deuterium, methyl group, ethyl group, propanyl group, butyl group, phenyl group, biphenyl group, terphenyl group, naphthyl group, triphenyl group, flu It means substituted with an orenyl group, a dibenzofuranyl group, or a dibenzothiophenyl group.

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

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

The alkyl group may be a C1 to C30 alkyl group. More specifically, the alkyl group may be a C1 to C20 alkyl group or a C1 to C10 alkyl group. For example, a C1 to C4 alkyl group means that 1 to 4 carbon atoms are included in the alkyl chain, and methyl, ethyl, propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl and t-butyl It indicates that it is selected from the group consisting of.

Specific examples of the alkyl group include methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, t-butyl group, pentyl group, hexyl group, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group. It means practical skills, etc.

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

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

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

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

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

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

As an example, "heteroaryl group" means containing at least one hetero atom selected from the group consisting of N, O, S, P, and Si in the aryl group. Two or more heteroaryl groups are directly linked through a sigma bond, or when the heteroaryl group includes two or more rings, two or more rings may be fused to each other. When the heteroaryl group is a fused ring, each ring may contain 1 to 3 hetero atoms.

For specific examples, the heterocyclic group may include a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a quinazolinyl group, and the like.

More specifically, a substituted or unsubstituted C6 to C30 aryl group and/or a substituted or unsubstituted C2 to C30 heterocyclic group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthra Senyl group, substituted or unsubstituted phenanthrenyl group, substituted or unsubstituted naphthacenyl group, substituted or unsubstituted pyrenyl group, substituted or unsubstituted biphenyl group, substituted or unsubstituted p-terphenyl group, substituted or unsubstituted A substituted m-terphenyl group, a substituted or unsubstituted o-terphenyl group, a substituted or unsubstituted chrysenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted perylenyl group, a substituted or unsubstituted flu Orenyl group, substituted or unsubstituted indenyl group, substituted or unsubstituted furanyl group, substituted or unsubstituted thiophenyl group, substituted or unsubstituted pyrrolyl group, substituted or unsubstituted pyrazolyl group, substituted or unsubstituted already Dazolyl group, substituted or unsubstituted triazolyl group, substituted or unsubstituted oxazolyl group, substituted or unsubstituted thiazolyl group, substituted or unsubstituted oxadiazolyl group, substituted or unsubstituted thiadiazolyl group, Substituted or unsubstituted pyridyl group, substituted or unsubstituted pyrimidinyl group, substituted or unsubstituted pyrazinyl group, substituted or unsubstituted triazinyl group, substituted or unsubstituted benzofuranyl group, substituted or unsubstituted benzo Thiophenyl 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 an unsubstituted quinoxalinyl group, a substituted or unsubstituted benzoquinolinyl group, a substituted or unsubstituted benzoisoquinolinyl group, a substituted or unsubstituted benzoquinazolinyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or Unsubstituted benzoxazineyl group, substituted or unsubstituted benzthiazinyl group, substituted or unsubstituted acridinyl group, substituted or unsubstituted phenazineyl group, substituted or unsubstituted phenothiazinyl group, substituted or unsubstituted Phenoxazineyl group, substituted or unsubstituted dibenzofuranyl group, or substituted or unsubstituted dibenzothiophenyl group, or It may be a combination of, but is not limited thereto.

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

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

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

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

[Formula 1]

In Formula 1,

X ¹ is O or S,

R ¹ to R ⁸ are each independently hydrogen, deuterium, cyano group, substituted or unsubstituted C1 to C10 alkyl group, substituted or unsubstituted C6 to C20 aryl group, or substituted or unsubstituted C2 to C30 heterocyclic group ,

At least one of R ⁶ and R ⁷ is a substituted or unsubstituted C2 to C30 heterocyclic group containing one or more nitrogen atoms,

At least one of R ⁵ to R ⁸ is represented by Formula 2 below,

[Formula 2]

In Chemical Formula 2,

X ² is O or S,

R ⁹ to R ¹³ are each independently hydrogen, deuterium, cyano group, substituted or unsubstituted C1 to C10 alkyl group, substituted or unsubstituted C6 to C20 aryl group, or substituted or unsubstituted C2 to C30 heterocyclic group .

The compound represented by Formula 1 may serve as an electron injection, electron transport, or light-emitting material in an organic optoelectronic device. In particular, when used as a light-emitting material, it is possible to manufacture an organic optoelectronic device with hybrid efficiency while lowering the driving voltage. .

In Chemical Formula 1, at least one of R ⁵ to R ⁸ has a polar group because it is represented by the following Chemical Formula 2, thereby enabling an interaction with an electrode to facilitate electron injection and increase mobility, and ultimately As a result, driving voltage reduction and high efficiency effects can be obtained at the same time. In addition, since the compound represented by Formula 1 has an asymmetric structure, decomposition during deposition can be suppressed.

In an embodiment of the present invention, in Formula 1, at least one of R ⁶ and R ⁷ is a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, It may be a substituted or unsubstituted quinazolinyl group or a substituted or unsubstituted benzothienopyrimidinyl group.

For example, at least one of R ⁶ and R ⁷ may be represented by Formula 3 below.

[Formula 3]

In Chemical Formula 3,

X ³ to X ⁵ are each independently N or CR ^a (R ^a is hydrogen or a C1 to C10 alkyl group),

At least one of X ³ to X ⁵ is N,

R ¹⁴ and R ¹⁵ are each independently hydrogen, deuterium, cyano group, substituted or unsubstituted C1 to C10 alkyl group, substituted or unsubstituted C6 to C20 aryl group, or substituted or unsubstituted C2 to C30 heterocyclic group. .

In Formula 3, at least two or more of X ³ to X ⁵ may be N.

In Formula 3, R ¹⁴ and R ¹⁵ may each independently be any one substituent selected from Group I below.

[Group I]

Formula 2 may be represented by the following Formula 2-1 or Formula 2-2.

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

In Formula 2-1 to Formula 2-2,

Each X ² is independently O or S,

R ⁹ to R ¹³ are each independently hydrogen, deuterium, cyano group, substituted or unsubstituted C1 to C10 alkyl group, substituted or unsubstituted C6 to C20 aryl group, or substituted or unsubstituted C2 to C30 heterocyclic group .

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

[Group 1]

The compound for an organic optoelectronic device described above may be applied to an organic optoelectronic device alone or together with another compound for an organic optoelectronic device. When the above-described compound for an organic optoelectronic device is used alone or in combination with another compound for an organic optoelectronic device, it may be applied in the form of a composition.

The present invention provides a composition for an organic optoelectronic device comprising the compound for an organic optoelectronic device (a first compound for an organic optoelectronic device) represented by Chemical Formula 1 mentioned above.

In addition, the present invention can provide a composition for an organic electronic device comprising the first compound for an organic optoelectronic device and a compound represented by the following formula (4) (a second compound for an organic optoelectronic device).

[Formula 4]

In Chemical Formula 4,

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

Ar ¹ and Ar ² 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 ¹⁶ to R ²¹ are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C50 heterocyclic group, or a combination thereof ego,

m is one of an integer from 0 to 2.

In one embodiment of the present invention, Y ¹ and ^Y2 in Formula 4 may each independently be a single bond or a substituted or unsubstituted C6 to C18 arylene group.

In an embodiment of the present invention, Ar ¹ and Ar ² of Formula 4 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted Naphthyl group, substituted or unsubstituted anthracenyl group, substituted or unsubstituted triphenylenyl group, substituted or unsubstituted pyridinyl group, substituted or unsubstituted pyrimidinyl group, substituted or unsubstituted quinazolyl group, substituted Or an unsubstituted isoquinazolyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted fluorenyl group, or these It may be a combination of.

In one embodiment of the present invention, R ¹⁶ to R ²¹ in Formula 4 may each independently be hydrogen, deuterium, or a substituted or unsubstituted C6 to C12 aryl group.

In an embodiment of the present invention, m in Formula 4 may be 0 or 1.

In a specific embodiment of the present invention, Formula 4 is one of the structures listed in Group II below, and *-Y ¹ -Ar ¹ , and *-Y ² -Ar ² are one of the substituents listed in Group III below. I can.

[Group Ⅱ]

[Group Ⅲ]

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

Specifically, Formula 4 is represented by C-8 of Group II, and *-Y ¹ -Ar ¹ , and *-Y ² -Ar ² are any one of B-1 to B-4 of Group III. Can be expressed.

More specifically, the *-Y ¹ -Ar ¹ , and *-Y ² -Ar ² may be selected from B-2, B-3 of the group III, and combinations thereof.

The second compound for an organic optoelectronic device represented by Formula 4 may be, for example, a compound listed in Group 2 below, but is not limited thereto.

[Group 2]

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

[C-136] [C-137] [C-138] [C-139]

In addition, the present invention is an organic optoelectronic device comprising the first compound for an organic optoelectronic device and a compound consisting of a combination of a moiety represented by the following formula (5) and a moiety represented by the following formula (6) A composition for a device can be provided.

[Formula 5] [Formula 6]

In Formulas 5 and 6,

Y ³ and Y ⁴ are each independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, or a combination thereof,

Ar ³ and Ar ^{4 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 ²² to R ²⁵ are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C50 aryl group, a substituted or unsubstituted C2 to C50 heterocyclic group, or a combination thereof. ,

Two adjacent * in Formula 5 are combined with two * in Formula 6 to form a fused ring, and * not forming a fused ring in Formula 5 are each independently CR ^b ,

R ^b is hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C12 aryl group, a substituted or unsubstituted C2 to C12 heterocyclic group, or a combination thereof.

For example, Ar ³ and Ar ⁴ may each independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, or a combination thereof.

For example, at least one of Ar ³ and Ar ⁴ may include a substituted or unsubstituted carbazole group.

The second organic compound consisting of a combination of the moiety represented by Formula 5 and the moiety represented by Formula 6 may be represented by, for example, any one of the following Formulas 7-1 to 7-5, depending on the bonding position.

[Chemical Formula 7-1] [Chemical Formula 7-2]

[Chemical Formula 7-3] [Chemical Formula 7-4]

[Formula 7-5]

In Formula 7-1 to Formula 7-5,

Y ³ and Y ⁴ are each independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, or a combination thereof,

Ar ³ and Ar ⁴ 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 ²² to R ²⁵ are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C50 aryl group, a substituted or unsubstituted C2 to C50 heterocyclic group, or a combination thereof. .

For example, at least one of Ar ³ and Ar ⁴ in Formulas 7-1 to 7-5 may be a substituent having hole characteristics, and may include, for example, a substituted or unsubstituted carbazole group. The second compound for an organic optoelectronic device comprising a combination of the moiety represented by Formula 5 and the moiety represented by Formula 6 may be, for example, a compound listed in Group II, but is not limited thereto. [Group IV] (In the specific compound described in [Group IV] below, all heteroatoms are "N".)

[Group IV]

The composition according to an embodiment may be applied to an organic layer of an organic optoelectronic device, for example, may be applied to a light emitting layer of an organic optoelectronic device, and the first organic optoelectronic device compound and the second organic optoelectronic device compound are a host Can play a role as In this case, the first compound for an organic optoelectronic device may be a compound having a bipolar property having relatively strong electronic properties, and the second compound for an organic optoelectronic device is a compound having a bipolar property having a relatively strong hole property, and the first It is used together with the compound for an organic optoelectronic device to improve the mobility and stability of electric charges, thereby further improving luminous efficiency and lifetime characteristics.

In a device in which a material having electron or hole properties biased to one side is introduced into the light emitting layer, carrier recombination occurs at the interface between the light emitting layer and the electron or hole transport layer, resulting in relatively large amounts of excitons. As a result, due to the interaction between the molecular excitons in the emission layer and the charge at the transport layer interface, a roll-off phenomenon in which the efficiency is rapidly decreased occurs, and the emission lifetime characteristics are also rapidly decreased. In order to solve this problem, the first organic optoelectronic device compound and the second organic optoelectronic device compound are simultaneously introduced into the light emitting layer as host compounds to balance the carriers in the light emitting layer so that the light emitting region is not biased toward either the electron or hole transport layer. By fabricating a device capable of improving the roll-off, it is also possible to significantly improve the service life characteristics.

Various compositions may be prepared by various combinations of the first compound for an organic optoelectronic device and the compound for a second organic optoelectronic device described above.

As described above, the second compound for an organic optoelectronic device is used in an emission layer together with the compound for a first organic optoelectronic device to increase charge mobility and stability, thereby improving driving voltage, luminous efficiency, and lifetime characteristics. .

In addition, the first organic optoelectronic device compound and the second organic optoelectronic device compound are, for example, about 1:9 to 9:1, 2:8 to 8:2, 3:7 to 7:3, 4:6 to 6 :4, and may be included in a weight ratio of 5:5, specifically 1:9 to 8:2, 1:9 to 7:3, 1:9 to 6:4, 1:9 to 5:5 weight ratio It may be included, and more specifically, may be included in a weight ratio of 2:8 to 7:3, 2:8 to 6:4, and 2:8 to 5:5. In addition, it may be included in a weight ratio of 3:7 to 6:4, and 3:7 to 5:5, and most specifically, it may be included in a weight ratio of 3:7 to 4:6 or 5:5.

The composition for an organic optoelectronic device may be used as a host of a green or red organic light emitting device.

The compound or composition for an organic optoelectronic device may further include one or more organic compounds in addition to other compounds for an organic optoelectronic device.

The composition including the first compound for an organic optoelectronic device and the compound for a second organic optoelectronic device may further include a dopant.

The dopant may be a red, green, or blue dopant, for example, a red or green phosphorescent dopant.

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

Examples of the phosphorescent dopant include an organometallic compound including Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or a combination thereof, For example, a compound represented by the following formula Z may be used, but is not limited thereto.

[Formula Z]

L ₂ MX

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

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

More specifically, the phosphorescent dopant is an organometallic compound including one of Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or a combination thereof. In a specific embodiment, the phosphorescent dopant may be an organometallic compound represented by Formula 401 below.

<Formula 401>

In Formula 401, M is selected from Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb and Tm; X401 to X404 are each independently nitrogen or carbon; A401 and A402 rings are independently of each other, substituted or unsubstituted benzene, substituted or unsubstituted naphthalene, substituted or unsubstituted fluorene, substituted or unsubstituted spiro-fluorene, substituted or unsubstituted indene, substituted Or unsubstituted pyrrole, substituted or unsubstituted thiophene, substituted or unsubstituted furan, substituted or unsubstituted imidazole, substituted or unsubstituted pyrazole, substituted or unsubstituted thiazole, substituted or Unsubstituted isothiazole, substituted or unsubstituted oxazole, substituted or unsubstituted isoxazole, substituted or unsubstituted pyridine, substituted or unsubstituted pyrazine, substituted or unsubstituted pyrimidine, substituted or Unsubstituted pyridazine, substituted or unsubstituted quinoline, substituted or unsubstituted isoquinoline, substituted or unsubstituted benzoquinoline, substituted or unsubstituted quinoxaline, substituted or unsubstituted quinazoline, substituted or unsubstituted Carbazole, substituted or unsubstituted benzoimidazole, substituted or unsubstituted benzofuran, substituted or unsubstituted benzothiophene, substituted or unsubstituted isobenzothiophene, substituted or unsubstituted benzoxazole , Substituted or unsubstituted isobenzoxazole, substituted or unsubstituted triazole, substituted or unsubstituted oxadiazole, substituted or unsubstituted triazine, substituted or unsubstituted dibenzofuran and substituted or Selected from unsubstituted dibenzothiophenes; Herein, "substituted" means that at least one hydrogen in a substituent or compound is deuterium, a halogen group, a hydroxyl group, a cyano 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 heterocyclic group, C1 to It means substituted with a C20 alkoxy group, a C1 to C10 trifluoroalkyl group, or a combination thereof; L401 is an organic ligand; xc1 is 1, 2 or 3; xc2 is 0, 1, 2 or 3.

The L401 may be any monovalent, divalent or trivalent organic ligand. For example, L401 is a halogen ligand (e.g. Cl, F), a diketone ligand (e.g., acetylacetonate, 1,3-diphenyl-1,3-propanedionate, 2,2,6 ,6-tetramethyl-3,5-heptanedionate, hexafluoroacetonate), carboxylic acid ligands (e.g. picolinate, dimethyl-3-pyrazolecarboxylate, benzoate), carbon mono It may be selected from an oxide ligand, an isonitrile ligand, a cyano ligand and a phosphorus ligand (eg, phosphine, phosphite), but is not limited thereto.

The Q401 to Q407, Q411 to Q417, and Q421 to Q427 are independently selected from hydrogen, a C1 to C60 alkyl group, a C2 to C60 alkenyl group, a C6 to C60 aryl group, and a C2 to C60 heteroaryl group.

When A401 in Formula 401 has two or more substituents, two or more substituents of A401 may be bonded to each other to form a saturated or unsaturated ring.

When A402 in Formula 401 has two or more substituents, two or more substituents of A402 may be bonded to each other to form a saturated or unsaturated ring.

는 서로 동일하거나 상이할 수 있다. 상기 화학식 401 중 xc1이 2 이상일 경우, A401 및 A402는 각각 이웃하는 다른 리간드의 A401 및 A402와 각각 직접(directly) 또는 연결기(예를 들면, C1 내지C5 알킬렌기, -N(R')-(여기서, R'은 C1 내지 C10 알킬기 또는 C6 내지 C20 아릴기임) 또는 -C(=O)-)를 사이에 두고 연결될 수 있다.When xc1 in Formula 401 is 2 or more, a plurality of ligands in Formula 401

May be the same or different from each other. When xc1 in Formula 401 is 2 or more, A401 and A402 are each directly or a linking group (e.g., C1 to C5 alkylene group, -N(R')-( Here, R'may be a C1 to C10 alkyl group or a C6 to C20 aryl group) or -C(=O)-).

For example, the phosphorescent dopant may be a red or green phosphorescent dopant, and may be selected from the following compounds PD1 to PD75, but is not limited thereto.

In addition, by controlling the ratio of the second organic optoelectronic device compound and the first organic optoelectronic device compound, it is possible to control the mobility of electric charges. When the composition of the present invention is used as a host, the combination ratio thereof may vary depending on the type of dopant used or the propensity of the dopant, and the first organic optoelectronic device compound and the second organic optoelectronic device compound are For example, it may be included in a weight ratio of 1:10 to 10:1. Specifically, it may be 2:8 to 8:2, 9:1 to 5:5, 8:2 to 5:5, 7:3 to 5:5, and as the most specific example, the first organic optoelectronic device compound and agent 2 The mixing weight ratio of the compound for an organic optoelectronic device may be 5:5.

By being included in the weight ratio range, bipolar characteristics are more effectively implemented, and efficiency and lifespan can be improved at the same time.

The composition may be formed by a dry film formation method such as chemical vapor deposition or a solution process.

Hereinafter, an organic optoelectronic device to which the composition for an organic optoelectronic device is applied will be described.

An organic optoelectronic device according to another embodiment may include an anode and a cathode facing each other, and at least one organic layer disposed between the anode and the cathode, and the organic layer may include the composition for an organic optoelectronic device described above. .

For example, the organic layer may include an emission layer, and the emission layer may include the composition for an organic optoelectronic device of the present invention.

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

In addition, the organic layer includes a light emitting layer, and at least one auxiliary layer selected from a hole injection layer, a hole transport layer, an electron blocking layer, an electron transport layer, an electron injection layer and a hole blocking layer, and the auxiliary layer is the composition for an organic optoelectronic device It may include.

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

Here, an organic light emitting device, which is an example of an organic optoelectronic device, will be described with reference to the drawings.

1 and 2 are cross-sectional views illustrating an organic light-emitting device according to an embodiment.

Referring to FIG. 1, an organic light emitting diode 100 according to an embodiment includes an anode 120 and a cathode 110 facing each other, and an organic layer 105 positioned between the anode 120 and the cathode 110. Include.

The anode 120 may be made of a conductor having a high work function to facilitate hole injection, for example, and may be made of a metal, a metal oxide, and/or a conductive polymer. The anode 120 may be a metal such as nickel, platinum, vanadium, chromium, copper, zinc, or gold, or an alloy thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO and Al or SnO2 and Sb; Poly(3-methylthiophene), poly(3,4-(ethylene-1,2-dioxy)thiophene) (polyehtylenedioxythiophene: PEDT), conductive polymers such as polypyrrole and polyaniline, but are limited thereto. It is not.

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

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

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

Referring to FIG. 2, the organic light-emitting device 200 further includes a hole auxiliary layer 140 in addition to the emission layer 130. The hole auxiliary layer 140 may further increase hole injection and/or hole mobility between the anode 120 and the light emitting layer 130 and block electrons. The hole auxiliary layer 140 may be, for example, a hole transport layer, a hole injection layer, and/or an electron blocking layer, and may include at least one layer.

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

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

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

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

(Preparation of compound for organic optoelectronic device)

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

(First organic optoelectronic device compound)

Synthesis example 1: synthesis of compound 2

[Reaction Scheme]

(1) 4-bromo-2-chloro-Dibenzofuran 15 g (53.58 mmol), 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-Dibenzofurane in a round bottom flask 15.76 g (53.58 mmol), tetrakis (triphenylphosphine) palladium [Pd(PPh3)4] 1.858 g (1.61 mmol), potassium carbonate 7.406 g (53.58 mmol) were added to 200 mL of THF and 100 mL of distilled water, and added for 12 hours. During heating to reflux. Upon completion of the reaction, the mixture was cooled to room temperature, and THF and distilled water were separated, and then the separated THF was added dropwise to 100 mL of methanol to crystallize, and the resulting solid was filtered and washed with water and methanol. The obtained solid was dried in a vacuum oven to obtain compound 2-A (13 g, 66% yield).

MS (m/z, [M]+): 368.81

(2) In a round bottom flask, intermediate compound 2-A 13 g (35.32 mmol), Pd(dppf)Cl2 1.442 g (1.77 mmol), Tricyclohexylphosphine 1.981 g (7.06 mmol), Potassium Acetate 10.4 g (105.96 mmol), Bis( 10.76 g (42.76 mmol) of pinacolato)diboron was suspended in 100 ml of DMF and stirred under reflux for 48 hours. After completion of the reaction, the resulting solid was added to 300 ml of distilled water and stirred for 1 hour, followed by filtering with silica gel to obtain compound 2-B (10 g, 62% yield) as the target compound.

MS (m/z, [M]+): 460.33

(3) In a round bottom flask, 2-B 10 g (22.47 mmol), 2-chloro-4,6-diphenyl-1,3,5-Triazine 6 g (22.47 mmol), tetrakis (triphenylphosphine) palladium [Pd(PPh3)4] 1.298 g (1.12 mmol) and 9.315 g (67.4 mmol) of potassium carbonate were added to 100 mL of THF and 30 mL of distilled water, and heated to reflux for 12 hours. Upon completion of the reaction, the mixture was cooled to room temperature, and THF and distilled water were separated, and then the separated THF was added dropwise to 100 mL of methanol to crystallize, and the resulting solid was filtered and washed with water and methanol. The obtained solid was dried in a vacuum oven to obtain compound 2 (9 g, 71% yield).

MS (m/z, [M]+): 565.62

Synthesis example 2: synthesis of compound 3

[Reaction Scheme]

(1) 4-bromo-2-chloro-Dibenzofuran 20 g (71.45 mmol), 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-Dibenzofurane in a round bottom flask 21 g (71.45 mmol), tetrakis (triphenylphosphine) palladium [Pd(PPh3)4] 2.477 g (2.14 mmol), potassium carbonate 9.875 g (71.45 mmol) were added to 300 mL of THF and 150 mL of distilled water, and added for 12 hours. During heating to reflux. Upon completion of the reaction, the mixture was cooled to room temperature, and THF and distilled water were separated, and then the separated THF was added dropwise to 100 mL of methanol to crystallize, and the resulting solid was filtered and washed with water and methanol. The obtained solid was dried in a vacuum oven to obtain compound 3-A (20 g, 76% yield).

MS (m/z, [M]+): 368.81

(2) In a round bottom flask, intermediate compound 3-A 20 g (54.34 mmol), Pd(dppf)Cl2 2.2 g (2.72 mmol), Tricyclohexylphosphine 3 g (10.87 mmol), Potassium Acetate 16 g (163 mmol), Bis( Pinacolato)diboron 16.55 g (65.21 mmol) was suspended in 135 ml of DMF and stirred under reflux for 48 hours. After completion of the reaction, the resulting solid was added to 300 ml of distilled water, and the resulting solid was stirred for 1 hour, filtered, and then filtered with silica gel to obtain the target compound, Compound 3-B (16 g, 64% yield).

MS (m/z, [M]+): 460.33

(3) In a round bottom flask, 3-B 15.5 g (33.7 mmol), 2-chloro-4,6-diphenyl-1,3,5-Triazine 9 g (33.7 mmol), tetrakis (triphenylphosphine) palladium [Pd(PPh3)4] 1.947 g (1.69 mmol) and 13.973 g (101.1 mmol) of potassium carbonate were added to 170 mL of THF and 50 mL of distilled water, and heated to reflux for 12 hours. Upon completion of the reaction, the mixture was cooled to room temperature, and THF and distilled water were separated, and then the separated THF was added dropwise to 100 mL of methanol to crystallize, and the resulting solid was filtered and washed with water and methanol. The obtained solid was dried in a vacuum oven to obtain compound 3 (12 g, 63% yield).

MS (m/z, [M]+): 565.62

Synthesis example 3: Synthesis of compound 7

[Reaction Scheme]

In a round bottom flask, 3-B 12 g (26.23 mmol), 2-[1,1'-biphenyl]-4-yl-4-chloro-6-phenyl-1,3,5-Triazine 9 g (26.23 mmol) , Tetrakis (triphenylphosphine) palladium [Pd(PPh3)4] 1.513 g (1.31 mmol), potassium carbonate 10.877 g (78.70 mmol) were added to 130 mL of THF and 40 mL of distilled water, and heated to reflux for 12 hours. Upon completion of the reaction, the mixture was cooled to room temperature, and THF and distilled water were separated, and then the separated THF was added dropwise to 100 mL of methanol to crystallize, and the resulting solid was filtered and washed with water and methanol. The obtained solid was dried in a vacuum oven to give compound 7 (12 g, 71% yield).

MS (m/z, [M]+): 641.71

Comparative Synthesis Example 1: synthesis of compound c

[Reaction Scheme]

(1) In a round bottom flask, intermediate C-1 (PharmaBlock, cas: 1472062-94-4) 12 g (34.98 mmol), 3-chlorophenyl boronic acid 5.457 g (34.98 mmol), potassium carbonate 14.5 g (104.93 mmol), Pd(PPh3)4 (Tetrakis- (triphenylphosphine) palladium(0)) 2.021 g (1.75 mmol) was added to 150 mL of tetrahydrofuran and 75 mL of water, followed by heating at 70° C. for 12 hours under a nitrogen stream. The resulting mixture was added to 500 mL of methanol, the crystallized solid was filtered, dissolved in dichlorobenzene, filtered through silica gel/celite, and an appropriate amount of the organic solvent was removed, and then recrystallized with methanol to obtain compound C-2 (12 g , 82% yield) was obtained.

MS (m/z, [M]+): 419.12

(2) Intermediate C-2 12 g (28.63 mmol), B-3-dibenzofuranyl-Boronic acid, 6.072 g (28.63 mmol), potassium carbonate 11.871 g (85.89 mmol), Pd(PPh3)4 (Tetrakis) in a round bottom flask -(triphenylphosphine) palladium(0)) 1.654 g (1.43 mmol) was added to 130 mL of tetrahydrofuran and 40 mL of water, followed by heating at 70° C. for 12 hours under a nitrogen stream. The resulting mixture was added to 500 mL of methanol, the crystallized solid was filtered, dissolved in dichlorobenzene, filtered through silica gel/celite, and an appropriate amount of the organic solvent was removed, and then recrystallized with methanol to obtain compound C (10 g, 63 % Yield) was obtained.

MS (m/z, [M]+): 551.20

(2nd organic optoelectronic device compound)

Synthesis example 4: Synthesis of Compound C-99

In a 500 mL round-bottom flask equipped with a stirrer under a nitrogen atmosphere, 3-bromo-N-biphenylcarbazole 15.00 g (37.66 mmol), 3-boronicester-N-biphenyl carbazole 16.77 g (37.66 mmol) and After mixing 200 mL of tetrahydrofuran:toluene (1:1) and 100 mL of a 2M-potassium carbonate aqueous solution, 2.18 g (1.88 mmol) of tetrakistriphenylphosphine palladium (0) was added, and heated to reflux for 12 hours under a nitrogen stream. I did. After completion of the reaction, the reactant was poured into methanol to filter the solid, and then the solid obtained therefrom was sufficiently washed with water and methanol and dried. The resultant product obtained from this was dissolved in 500 mL of a solid in chlorobenzene, and the solution was filtered with silica gel to completely remove the solvent, dissolved by heating in 400 mL of toluene, and then recrystallized to give 16.54 g (yield: 69%) of compound C-99. .

[Chemical Formula C-99]

(Production of organic light emitting device)

Example One:

The glass substrate coated with ITO (Indium tin oxide) to a thickness of 1500Å was washed with distilled water and ultrasonic waves. After washing with distilled water, ultrasonic cleaning was performed with a solvent such as isopropyl alcohol, acetone, methanol, etc., dried, transferred to a plasma cleaner, and then cleaned for 10 minutes using oxygen plasma, and then transferred to a vacuum evaporator. Using the prepared ITO transparent electrode as an anode, Compound A was vacuum deposited on the ITO substrate to form a hole injection layer having a thickness of 700 Å, and Compound B was deposited on the injection layer to a thickness of 50 Å, and then Compound C was deposited with a thickness of 1020 Å. It was deposited to a thickness to form a hole transport layer. Compound C-99 and Compound 2 were simultaneously used as a host on the hole transport layer, and Ir(ppy) ₃ was doped with 7 wt% as a dopant to form a 400 Å-thick light emitting layer by vacuum deposition. Here, Compound C-99 and Compound 2 were used in a weight ratio of 6:4, and the ratio was separately described for the following examples. Then, compound D and Liq were simultaneously vacuum-deposited at a 1:1 ratio on the emission layer to form an electron transport layer having a thickness of 300 Å, and Liq 15 Å and Al 1200 Å were sequentially vacuum-deposited on the electron transport layer to form a cathode, thereby forming an organic light-emitting device. Was produced.

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

ITO/Compound A(700Å)/Compound B(50Å)/Compound C(1020Å)/EML[Compound C-99:Compound 2:Ir(ppy) ₃ (7wt%)](400Å)/Compound D:Liq(300Å )/Liq(15Å?)/Al(1200Å).

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

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

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

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

Example 2, Example 3 and Comparative example One

As described in Table 1 below, organic light emitting devices of Examples 2, 3, and 1 were manufactured in the same manner as in Example 1 using a first host and a second host.

evaluation

The effects of the organic light emitting diodes according to Examples 1 to 3 and Comparative Example 1 were evaluated as follows. The specific measurement method is as follows.

(1) Measurement of driving voltage

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

(2) Measurement of change in current density due to voltage change

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

(3) Measurement of luminance change according to voltage change

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

(4) Measurement of luminous efficiency

The current efficiency (cd/A) of the same current density (10 mA/cm ² ) was calculated using the luminance, current density, and voltage measured from (2) and (3).

(5) External quantum efficiency (EQE)

For the fabricated organic light emitting device, all devices were evaluated by encapsulating them with a desiccant, and the EQE at the required luminance (9000 cd/m ² ) was measured using an IPCE measurement system.

division First host 2nd host Host 1:
2nd host
(Weight ratio) Driving voltage
(V) Luminous efficiency
(cd/A) EQE Example 1 Compound 2 C-99 4:6 3.90 67.3 19.6 Example 2 Compound 3 C-99 4:6 3.86 70.1 19.4 Example 3 Compound 7 C-99 4:6 3.88 72.9 20.1 Comparative Example 1 Compound c C-99 4:6 4.01 69.9 19.4

Referring to Table 1, when the first host according to the embodiment is used alone or in combination with the second host, it is confirmed that the driving voltage of the organic light emitting device to which it is applied is lowered and the lifespan is significantly improved compared to the comparative example. I can.

The present invention is not limited to the above embodiments, but may be manufactured in a variety of different forms, and a person of ordinary skill in the art to which the present invention pertains may not change the technical spirit or essential features of the present invention, It will be appreciated that it can be implemented with. Therefore, it should be understood that the embodiments described above are illustrative in all respects and not limiting.

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

Claims (16)

A compound for a first host of an emission layer in an organic optoelectronic device represented by Formula 1 below; And
The second host compound of the emission layer in the organic optoelectronic device represented by the following formula (4) or the second host compound of the emission layer in the organic optoelectronic device consisting of a combination of a moiety represented by the following formula (5) and a moiety represented by the following formula (6) ;
Composition for an organic optoelectronic device comprising:
[Formula 1]

In Formula 1,
X ¹ is O or S,
R ¹ to R ⁸ are each independently hydrogen, deuterium, cyano group, substituted or unsubstituted C1 to C10 alkyl group, substituted or unsubstituted C6 to C20 aryl group, or substituted or unsubstituted C2 to C30 heterocyclic group ,
At least one of R ⁶ and R ⁷ is represented by the following Formula 3,
[Formula 3]

In Chemical Formula 3,
X ³ to X ⁵ are each independently N or CR ^a (R ^a is hydrogen or a C1 to C10 alkyl group),
At least one of X ³ to X ⁵ is N,
R ¹⁴ and R ¹⁵ are each independently any one substituent selected from the following group I,
[Group I]

At least one of R ⁵ to R ⁸ is represented by the following formula 2-2,
[Formula 2-2]

In Formula 2-2,
X ² is O or S,
R ⁹ to R ¹³ are each independently hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group. ,
[Formula 4]

In Chemical Formula 4,
Y ¹ and Y ² are each independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, or a combination thereof,
Ar ¹ and Ar ² 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 ¹⁶ to R ²¹ are each Independently, hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C50 heterocyclic group, or a combination thereof,
m is one of an integer from 0 to 2,
[Formula 5] [Formula 6]

In Formulas 5 and 6,
Y ³ and Y ⁴ are each independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, or a combination thereof,
Ar ³ and Ar ⁴ 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 ²² to R ²⁵ are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C50 aryl group, a substituted or unsubstituted C2 to C50 heterocyclic group, or a combination thereof. ,
Two adjacent * in Formula 5 are combined with two * in Formula 6 to form a fused ring, and * not forming a fused ring in Formula 5 are each independently CR ^b ,
R ^b is hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C12 aryl group, a substituted or unsubstituted C2 to C12 heterocyclic group, or a combination thereof.
delete delete The method of claim 1,
At least two or more of the X ³ to X ⁵ is N. Compound for an organic optoelectronic device.
delete delete delete delete The method of claim 1,
Ar ¹ and Ar ² of Formula 4 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthra Senyl group, substituted or unsubstituted triphenylenyl group, substituted or unsubstituted pyridinyl group, substituted or unsubstituted pyrimidinyl group, substituted or unsubstituted quinazolyl group, substituted or unsubstituted isoquinazolyl group, A composition for an organic optoelectronic device which is a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted fluorenyl group, or a combination thereof.
The method of claim 1,
Formula 4 is one of the structures listed in the following Group II, the *-Y ¹ -Ar ¹ , and *-Y ² -Ar ² is one of the substituents listed in the following Group III composition for an organic optoelectronic device:
[Group Ⅱ]

[Group Ⅲ]

In groups II and III above, * is a connection point.
The method of claim 10,
Formula 4 is represented by C-8 of Group II, and *-Y ¹ -Ar ¹ and *-Y ² -Ar ² are each independently represented by any one of B-1 to B-4 of Group III. Composition for organic optoelectronic devices.
The method of claim 1,
The compound consisting of a combination of the moiety represented by Formula 5 and the moiety represented by Formula 6 is a composition for an organic optoelectronic device represented by at least one of the following Formulas 7-1 to 7-5:
[Chemical Formula 7-1] [Chemical Formula 7-2]

[Chemical Formula 7-3] [Chemical Formula 7-4]

[Formula 7-5]

In Formulas 7-1 to 7-5,
Y ³ and Y ⁴ are each independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, or a combination thereof,
Ar ³ and Ar ⁴ 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 ²² to R ²⁵ are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C50 aryl group, a substituted or unsubstituted C2 to C50 heterocyclic group, or a combination thereof. .
The method of claim 1,
The composition for an organic optoelectronic device comprising the compound for an organic optoelectronic device represented by Formula 1 and the compound for an organic optoelectronic device represented by Formula 4 in a weight ratio of 3:7 to 6:4.
The anode and cathode facing each other, and
Including at least one layer of an organic layer positioned between the anode and the cathode,
The organic layer is an organic optoelectronic device comprising the composition for an organic optoelectronic device according to any one of claims 1, 4 and 9 to 13.
The method of claim 14,
The organic layer includes a light emitting layer,
The composition for an organic optoelectronic device is an organic optoelectronic device included as a host of the emission layer.
A display device including the organic optoelectronic device according to claim 14.

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