KR102129510B1 - Compound for organic optoelectronic device, composition for organic optoelectronic device and organic optoelectronic device and display device - Google Patents

Abstract

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

Description

Compounds for organic optoelectronic devices, compositions for organic optoelectronic devices, organic optoelectronic devices and display devices 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.

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

Organic optoelectronic devices can be roughly divided into two types according to the operating principle. One is a photoelectric device that generates electrical energy as excitons formed by optical energy are separated into electrons and holes, and the electrons and holes are transferred to different electrodes, and the other is to supply voltage or current to the electrodes to generate electricity. It is a light emitting element that generates light energy from energy.

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

Among these, organic light emitting diodes (OLEDs) have attracted much attention in recent years due to an increase in demand for flat panel display devices. The organic light-emitting device is a device that converts electrical energy into light by applying an electric current to an organic light-emitting material, and is usually made of a structure in which an organic layer is inserted between an anode and a cathode. Here, the organic layer may include a light emitting layer and an optional auxiliary layer, 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 characteristics of the organic layer, and among them, is greatly influenced by the organic material included in the organic layer.

In particular, in order to apply the organic light emitting device to a large-sized flat panel display device, it is necessary to develop an organic material capable of increasing hole and electron mobility and enhancing electrochemical stability.

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

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

Another embodiment provides an organic optoelectronic device comprising the compound.

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

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

[Formula 1]

In Chemical Formula 1,

Z ¹ to Z ⁵ are each independently N or CR ^a ,

At least two of Z ¹ to Z ⁵ are N,

R ^a is each independently hydrogen, deuterium, substituted or unsubstituted C6 to C20 aryl group, substituted or unsubstituted dibenzofuranyl group, substituted or unsubstituted dibenzothiophenyl group, substituted or unsubstituted C1 to C10 Alkyl group or a combination thereof,

At least one of R ^a is a substituted or unsubstituted C6 to C20 aryl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted C1 to C10 alkyl group, or a combination thereof. Is a combination,

R ^a are each independently or adjacent groups connected to each other to form a substituted or unsubstituted aliphatic, aromatic or heteroaromatic monocyclic or polycyclic ring,

R ¹ is a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group,

L ¹ is a single bond, or a substituted or unsubstituted C6 to C30 arylene group,

R ² to R ⁵ are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C20 aryl group,

R ² to R ⁵ are each independently or adjacent groups are connected to each other to form a substituted or unsubstituted aliphatic, aromatic or heteroaromatic monocyclic or polycyclic ring,

The "substitution" means that at least one hydrogen is replaced with a deuterium, C1 to C20 alkyl group, C6 to C30 aryl group, dibenzofuranyl group or dibenzothiophenyl group.

According to another embodiment, the compound for a first organic optoelectronic device described above; And it provides a composition for an organic optoelectronic device comprising a compound for a second organic optoelectronic device represented by the formula (2).

[Formula 2]

In Chemical Formula 2,

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,

A ¹ and A 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 ⁶ to R ¹¹ are each Independently hydrogen, deuterium, substituted or unsubstituted C1 to C20 alkyl group, substituted or unsubstituted C6 to C30 aryl group, substituted or unsubstituted C2 to C30 heterocyclic group, or combinations thereof,

n is an integer from 0 to 2;

The "substitution" means that at least one hydrogen is substituted with deuterium, a C1 to C4 alkyl group, a C6 to C18 aryl group, or a C2 to C30 heteroaryl group.

According to another embodiment, the anode and the cathode facing each other, and includes at least one layer of an organic layer positioned between the anode and the cathode, the organic layer is a compound for an organic optoelectronic device described above, or a composition for an organic optoelectronic device It provides an organic optoelectronic device comprising a.

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

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

1 and 2 are cross-sectional views showing an organic light emitting diode 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 claims to be described later.

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

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

As used herein, "hetero" means that unless otherwise defined, one functional group contains 1 to 3 hetero atoms selected from the group consisting of N, O, S, P and Si, and the rest is carbon. .

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 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 the alkyl chain contains 1 to 4 carbon atoms, and is methyl, ethyl, propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl and t-butyl. It is selected from the group consisting of.

The alkyl group is, for example, 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 It means practical skill.

As used herein, "aryl (aryl) group" is a concept that collectively refers to a group having one or more hydrocarbon aromatic moieties,

While all elements of the hydrocarbon aromatic moiety have p-orbitals, these p-orbitals include forms that form conjugates, such as phenyl groups, naphthyl groups, and the like.

Forms in which two or more hydrocarbon aromatic moieties are linked through a sigma bond, such as biphenyl group, terphenyl group, quarterphenyl group, and the like,

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

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

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

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

The heterocyclic group may include, for example, a pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, 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 perenyl 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 A polyzolyl group, a substituted or unsubstituted triazole group, a substituted or unsubstituted oxazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted oxadiazolyl group, a substituted or unsubstituted thiadiazolyl group, Substituted or unsubstituted pyridyl group, substituted or unsubstituted pyrimidinyl group, substituted or unsubstituted pyrazinyl group, substituted or unsubstituted triazinyl group, substituted or unsubstituted benzofuranyl group, substituted or unsubstituted benzo Thiophenyl group, substituted or unsubstituted benzimidazole 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 benzoxazine group, substituted or unsubstituted benzthiazinyl group, substituted or unsubstituted acridinyl group, substituted or unsubstituted phenazineyl group, substituted or unsubstituted phenothiazineyl group, substituted or unsubstituted Phenoxanil 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 that can form a hole by donating electrons when an electric field is applied, and has conductivity characteristics along the HOMO level, and injection of the hole formed at the anode into the light emitting layer, the light emitting layer It means a property that facilitates the movement of the holes formed in the anode to the anode and the light emitting layer.

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

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

Compound for an organic optoelectronic device according to an embodiment is represented by the following formula (1).

[Formula 1]

In Chemical Formula 1,

Z ¹ to Z ⁵ are each independently N or CR ^a ,

At least two of Z ¹ to Z ⁵ are N,

R ^a is each independently hydrogen, deuterium, substituted or unsubstituted C6 to C20 aryl group, substituted or unsubstituted dibenzofuranyl group, substituted or unsubstituted dibenzothiophenyl group, substituted or unsubstituted C1 to C10 Alkyl group or a combination thereof,

At least one of R ^a is a substituted or unsubstituted C6 to C20 aryl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted C1 to C10 alkyl group, or a combination thereof. Is a combination,

R ^a are each independently or adjacent groups connected to each other to form a substituted or unsubstituted aliphatic, aromatic or heteroaromatic monocyclic or polycyclic ring,

R ¹ is a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group,

L ¹ is a single bond, or a substituted or unsubstituted C6 to C30 arylene group,

R ² to R ⁵ are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C20 aryl group,

R ² to R ⁵ are each independently or adjacent groups are connected to each other to form a substituted or unsubstituted aliphatic, aromatic or heteroaromatic monocyclic or polycyclic ring,

The "substitution" means that at least one hydrogen is replaced with a deuterium, C1 to C20 alkyl group, C6 to C30 aryl group, dibenzofuranyl group or dibenzothiophenyl group.

In one example of the present invention, the "substitution" means that at least one hydrogen is substituted with a deuterium, phenyl group, biphenyl group, terphenyl group, naphthyl group, or fluorenyl group.

The compound for an organic optoelectronic device according to the present invention is a structure in which the N-containing hexagonal ring capable of improving electron transport in the N-position of the benzimidazole moiety having electronic properties is directly substituted without a linking group. Since this structure breaks the conjugation between the benzimidazole moiety and the N-containing hexagonal ring, LUMO is independently distributed within the N-containing hexagonal ring, which is an electron transporting substituent, thereby enabling efficient transfer of electrons, thereby driving voltage. At the same time as lowering, it is possible to realize a device having a long life and high efficiency.

In addition, the efficiency and driving voltage of the device can be further improved by simultaneously including a substituent capable of improving hole transportability in the C position in the second position of the benzimidazole moiety.

The Chemical Formula 1 may be represented by any one of the following Chemical Formulas 1A to 1D according to the specific type of R ¹ .

[Formula 1A] [Formula 1B]

[Formula 1C] [Formula 1D]

In Formulas 1A to 1D, Z ¹ to Z ⁵ , R ^a , L ¹ , and R ² to R ⁵ are as described above,

R ^b , R ^c , R ^d , R ^e , and R ^f may each independently be hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C20 aryl group.

Formula 1 may be more specifically represented by any one of Formula 1B-I, Formula 1B-II, Formula 1C-I, Formula 1C-II, Formula 1D-I, and Formula 1D-II according to the substitution position of R ¹ Can.

[Formula 1B-Ⅰ] [Formula 1B-Ⅱ] [Formula 1C-Ⅰ]

[Formula 1C-Ⅱ] [Formula 1D-Ⅰ] [Formula 1D-Ⅱ]

In Formula 1B-I, Formula 1B-II, Formula 1C-I, Formula 1C-II, Formula 1D-I, and Formula 1D-II, Z ¹ to Z ⁵ , R ^a , L ¹ , R ² to R ⁵ , R ^d , R ^e , and R ^f are as described above.

In one embodiment of the present invention, when R ^a are each independently present, at least one of R ^a is a substituted or unsubstituted C6 to C20 aryl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted It may be a dibenzothiophenyl group, a substituted or unsubstituted C1 to C10 alkyl group, or a combination thereof, and in a specific embodiment, at least two of R ^a are substituted or unsubstituted C6 to C20 aryl groups, substituted or It may be an unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted C1 to C10 alkyl group, or a combination thereof. In this case, R ^a is specifically substituted or unsubstituted phenyl group, substituted or unsubstituted biphenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted terphenyl group, substituted or unsubstituted fluorenyl group, substituted Or it may be an unsubstituted fused fluorenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group. More specifically, R ^a is each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted fluorenyl group, It may be a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group, for example, R ^a is each independently a phenyl group, biphenyl group, terphenyl group, dibenzofuranyl group, or dibenzothi It may be an offense diary.

Further substituents of R ^a may be C6 to C12 aryl groups.

Meanwhile, when each of R ^a is independently present, the hexagonal ring containing Z ¹ to Z ⁵ is a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted tria It may be a genyl group, a substituted or unsubstituted pyrazinyl group, or a substituted or unsubstituted pyridazinyl group, specifically a substituted or unsubstituted pyrimidinyl group, or a substituted or unsubstituted triazinyl group,

In addition, when adjacent R ^{a is} connected to each other to form a substituted or unsubstituted aliphatic, aromatic or heteroaromatic monocyclic or polycyclic ring, the hexagonal ring containing Z ¹ to Z ⁵ is a substituted or unsubstituted quina It may be a zolinyl group, a substituted or unsubstituted benzofuranpyrimidinyl group, or a substituted or unsubstituted benzothiophenpyrimidinyl group, and specifically a substituted or unsubstituted quinazolinyl group.

More specifically, the formula 1 may be represented by any one of the following formulas 1-1 to 1-5 according to the type of the hexagonal ring containing Z ¹ to Z ⁵ .

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

In Formula 1-1 to Formula 1-5,

R ^a2 to R ^a5 are as defined for R ^a above, and R ¹ , L ¹ , and R ² to R ⁵ are as defined above.

In addition, R ^a6 and R ^a7 may each independently be hydrogen, deuterium, C6 to C20 aryl group, C1 to C10 alkyl group, or a combination thereof, specifically, hydrogen, deuterium, C6 to C12 aryl group, C1 to C6 It may be an alkyl group, for example, all hydrogen.

The hexagonal ring containing Z ¹ to Z ⁵ may be selected from, for example, the substituents listed in Group I below.

[Group Ⅰ]

In group I above,

* Is the point of connection.

In a specific embodiment of the present invention, L ¹ may be a single bond, or a substituted or unsubstituted C6 to C20 arylene group, specifically, a single bond, a substituted or unsubstituted C6 to C12 arylene group, For example, it may be a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group.

In a specific embodiment of the present invention, R ^b , R ^c , R ^d , R ^e , R ^f , and R ² to R ⁵ are each independently hydrogen, deuterium, substituted or unsubstituted C1 to C4 alkyl group, or It may be a substituted or unsubstituted C6 to C12 aryl group.

In a more specific embodiment of the present invention, R ^b , R ^c , R ^d , R ^e , R ^f , and R ² to R ⁵ are each independently hydrogen, deuterium, substituted or unsubstituted C1 to C4 alkyl group, It may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted naphthyl group, such as hydrogen or a phenyl group.

On the other hand, R ² to R ⁵ are each independently or adjacent groups are connected to each other to form a substituted or unsubstituted aliphatic, aromatic or heteroaromatic monocyclic or polycyclic ring.

When R ² to R ⁵ are each independently present, for example, they may be represented by the following formula a or formula b,

[Formula a] [Formula b]

When adjacent groups of R ² to R ⁵ are connected to each other to form a substituted or unsubstituted aliphatic, aromatic or heteroaromatic monocyclic or polycyclic ring, it may be represented by the following formula (c).

[Formula c]

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

[Group 1]

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

Hereinafter, an example of the composition for an organic optoelectronic device comprising the above-described compound for an organic optoelectronic device will be described.

The composition for an organic optoelectronic device according to another embodiment of the present invention includes the first organic optoelectronic device compound; And a compound for a second organic optoelectronic device represented by Formula 2 below.

[Formula 2]

In Chemical Formula 2,

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,

A ¹ and A 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 ⁶ to R ¹¹ are each Independently hydrogen, deuterium, substituted or unsubstituted C1 to C20 alkyl group, substituted or unsubstituted C6 to C30 aryl group, substituted or unsubstituted C2 to C30 heterocyclic group, or combinations thereof,

n is an integer from 0 to 2;

The "substitution" means that at least one hydrogen is substituted with deuterium, a C1 to C4 alkyl group, a C6 to C18 aryl group, or a C2 to C30 heteroaryl group. In a specific embodiment of the present invention, the "substitution" means that at least one hydrogen is deuterium, phenyl group, ortho-biphenyl group, meta-biphenyl group, para-biphenyl group, terphenyl group, naphthyl group, fluorenyl group, tri It means substituted with a phenylene group, a pyridinyl group, a carbazolyl group, a dibenzofuranyl group, or a dibenzothiophenyl group.

In one embodiment of the present invention, Y ¹ and Y ² in Formula 2 may be each independently a single bond, or a substituted or unsubstituted C6 to C18 arylene group. Specifically, it may be a single bond, a meta-phenylene group, or a para-phenylene group.

In one embodiment of the present invention, A ¹ and A ² of Formula 2 are each independently, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted Quarterphenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted anthracenyl group, substituted or unsubstituted triphenylene group, substituted or unsubstituted pyridinyl group, substituted or unsubstituted dibenzofuranyl group, substituted or It may be an unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted fluorenyl group, or a combination thereof. Specifically, 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 fluoride It may be a nil group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted dibenzofuranyl group.

In one embodiment of the present invention, R ⁶ to R ¹¹ in Formula 2 may be each independently hydrogen, deuterium, or a substituted or unsubstituted C6 to C12 aryl group. Specifically, it may be hydrogen or a phenyl group, for example, one of R ⁶ to R ¹¹ may be a phenyl group, and the other may be hydrogen.

In one embodiment of the present invention, n in Formula 2 may be 0 or 1.

In one specific embodiment of the present invention, Formula 2 is one of the structures listed in Group II below, and *-Y ¹ -A ¹ and *-Y ² -A ² may be one of the substituents listed in Group III below. have.

[Group Ⅱ]

[Group Ⅲ]

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

In one embodiment of the present invention, Formula 2 is represented by Formula C-8 or Formula C-17 of Group II,

The *-Y ¹ -A ¹ and *-Y ² -A ² may be selected from B-1, B-2, and B-3 of Group III.

The compound for a second organic optoelectronic device represented by Formula 2 may be selected from compounds listed in Group 2 below.

[Group 2]

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

[E-136] [E-137] [E-138]

The first host compound and the second host compound described above can prepare various compositions by various combinations.

The composition according to an embodiment of the present invention may include a compound represented by Formula 1A or Formula 1B as a first host, and a compound represented by C-8 of Group II as a second host, and specifically In the above formula 1B may be represented by formula 1B-I or formula 1B-II.

R ^a of Formula 1A and Formula 1B is, for example, hydrogen, deuterium, substituted or unsubstituted phenyl group, substituted or unsubstituted biphenyl group, substituted or unsubstituted terphenyl group, substituted or unsubstituted dibenzofuranyl group, or substituted Or an unsubstituted dibenzothiophenyl group, at least one of R ^a is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted dibenzofuranyl group, Or it may be a substituted or unsubstituted dibenzothiophenyl group.

In addition, in the composition according to an embodiment of the present invention, the first host may be represented by Formula 1-1 or Formula 1-5, and includes a compound represented by C-8 of Group II as a second host. can do.

R ^a2 and R ^a4 of Formula 1-1 and Formula 1-5 are each independently hydrogen, deuterium, substituted or unsubstituted phenyl group, substituted or unsubstituted biphenyl group, substituted or unsubstituted terphenyl group, substituted or unsubstituted A substituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group, and at least one of R ^a2 and R ^a4 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted ter A phenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group,

R ^a6 and R ^a7 may each independently be hydrogen, deuterium, a C6 to C20 aryl group, a C1 to C10 alkyl group, or a combination thereof.

For example, *-Y ¹ -A ¹ and *-Y ² -A ² of Formula 2 may be selected from B-1 to B-3 of Group III.

The compound for the second organic optoelectronic device can be used in the light emitting layer together with the compound for the first organic optoelectronic device to improve the luminous efficiency and lifetime characteristics by increasing the mobility of the charge and increasing the stability. In addition, the mobility of charges can be controlled by adjusting the ratio of the compound for the second organic optoelectronic device and the compound for the first organic optoelectronic device. When the composition of the present invention is used as a host, the combination ratio of these may vary depending on the type of dopant used or the tendency of the dopant, or when the composition of the present invention is used in an electron transport auxiliary layer, used in an OLED device The combination ratio of the compounds in the composition of the present invention may vary according to the type of host and dopant of the EML layer. For example, the compound for a first organic optoelectronic device and the compound for a second organic optoelectronic device of the present invention may be included in a weight ratio of about 1:9 to 9:1, specifically 1:9 to 8:2, 1:9 to 7 :3, 1:9 to 6:4, 1:9 to 5:5, and may be included in the range of 2:8 to 8:2, 2:8 to 7:3, 2:8 to 6:4, 2 :8 to 5:5.

In addition, when the composition of the present invention is used as a host, the compound for the first organic optoelectronic device and the compound for the second organic optoelectronic device are 1:9 to 5:5, 2:8 to 5:5, 3:7 to 5 :5 may be included in a weight ratio range. For example, the compound for the first organic optoelectronic device and the compound for the second organic optoelectronic device may be included in the range of 5:5 or 4:6. By being included in the above range, it is possible to simultaneously improve efficiency and life.

The composition may further include at least one organic compound in addition to the compound for the first organic optoelectronic device and the compound for the second organic optoelectronic device described above.

The compound for an organic optoelectronic device may further include a dopant. The dopant may be a red, green, or blue dopant.

The dopant is a material mixed with a small amount to cause luminescence, and a material such as a metal complex that emits light by multiple excitations that excite more than a triplet state may be used. The dopant may be, for example, an inorganic, organic, or organic compound, and may be included in 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 combinations thereof. And an organometallic compound containing. The phosphorescent dopant may be, for example, a compound represented by Formula Z below, but is not limited thereto.

[Formula Z]

L ₂ MX

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

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

In one embodiment of the present invention, the phosphorescent dopant may be a green phosphorescent dopant, for example, an Ir complex compound such as Ir(ppy) ₃ may be used. At this time, the wavelength range of the green phosphorescent dopant may be 500 nm to 550 nm.

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

The organic optoelectronic device according to another embodiment includes 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 is a compound for an organic optoelectronic device described above, or an organic optoelectronic device It may include a composition for a device.

For example, the organic layer may include a light emitting layer, and the light emitting layer may include a compound for an organic optoelectronic device of the present invention or a composition for an organic optoelectronic device.

Specifically, the compound for an organic optoelectronic device, or a composition for an organic optoelectronic device may be included as a host of the light emitting layer, for example, a green host and a red 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 a compound for the organic optoelectronic device Or, it may include a composition for an organic optoelectronic device.

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

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

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

Referring to FIG. 1, the organic optoelectronic device 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. Includes.

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 includes, for example, a metal such as nickel, platinum, vanadium, chromium, copper, zinc, gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); Metal and oxide combinations such as ZnO and Al or SnO ₂ and Sb; Conductive polymers such as poly(3-methylthiophene), poly(3,4-(ethylene-1,2-dioxy)thiophene) (polyehtylenedioxythiophene: PEDT), polypyrrole and polyaniline, but are not 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, for example, a metal, a metal oxide, and/or a conductive polymer. The negative electrode 110 may include, for example, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium, or alloys thereof; Multilayer structure materials such as LiF/Al, LiO ₂ /Al, LiF/Ca, LiF/Al and BaF ₂ /Ca may be mentioned, but are not limited thereto.

The organic layer 105 includes a light emitting layer 130 that includes the compound for an organic optoelectronic device described above.

2 is a cross-sectional view showing an organic light emitting diode 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 light emitting 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 illustrated, 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 can be included in these organic layers. The organic light emitting devices 100 and 200 include an anode or a cathode formed on a substrate, and then dry deposition methods such as evaporation, sputtering, plasma plating, and ion plating; Alternatively, an organic layer may be formed by a wet coating method such as spin coating, dipping, or flow coating, and then formed by forming a cathode or an anode thereon.

The aforementioned organic light emitting device 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 only for specifically illustrating or describing the present invention, and the present invention is not limited thereto.

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

(Production of compounds for organic optoelectronic devices)

The compound presented as a more specific example of the compound of the present invention was synthesized through the following steps.

(Compound for the first organic optoelectronic device)

Synthetic example 1: Synthesis of Compound 1

Step 1: 9H-Carbazole 1eq (30.8g), 4-Bromo-Aldehyde 1eq (34.1g), sodium-t-butoxide 2eq (35.4g), Pd ₂ (dba) ₃ 0.05eq (5.3g) toluene ( 750 ml) and stirred under reflux for 0.1 hour under a triturate butylphosphine 0.15 eq nitrogen stream. After completion of the reaction, extraction was performed with toluene and distilled water, and the organic layer was dried over magnesium sulfate (MgSO ₄ ), filtered, and the filtrate was concentrated under reduced pressure. The organic solution was removed and silica gel column was used with hexane:dichloromethane=7:3 (v/v) to recrystallize the product solid with dichloromethane and acetone to obtain intermediate a-1 (36.5g, Y=73%).

Step 2: Dissolve the intermediate a-1 1 eq (36.5 g) and 1,2-diaminobenzene 1 eq (15.3 g) in 300 ml of dimethylformamide (DMF), and then add sodium meth bisulfate 1.2eq (30.7 g) to 300 ml of distilled water. After melting, it is slowly dropped at room temperature under a stream of nitrogen. When the reaction was completed, the organic layer was dissolved in dichloromethane and recrystallized with acetone to obtain intermediate a-2 (22.3 g, Y=46%).

Step 3: Intermediate a-2 1eq (22.3g) and 2-[1,1'-biphenyl]-4-yl-4-chloro-6-phenyl-1,3,5-Triazine 1.2eq (25.7g) After dissolving in dimethylformamide, add 1.5 eq (3.7 g) of sodium hydride (in natural oil, 60%) and reflux and stir for 6 hours. When the reaction is complete, drop the reactant in distilled water to solidify, filter the solid After extraction, it is dissolved in dichloromethane. Then, the organic layer was dried over magnesium sulfate (MgSO ₄ ), filtered, and the filtrate was concentrated under reduced pressure. The organic solution was removed and the product solid obtained by column chromatography on silica gel with hexane:dichloromethane =7:3 (v/v) was recrystallized with monochlorobenzene to obtain compound 1 (10.7g, Y=26%).

LC-Mass measurement (theoretical value: 666.77 g/mol, measured value: M+ = 667 g/mol)

Synthetic example 2: Synthesis of Compound 2

Step 1: 9H-Carbazole 1eq (41.2g), Bromobenzene 1eq (50.3.g), sodium-t-butoxide 2eq (47.4g), Pd ₂ (dba) ₃ 0.05eq (7.1g) to toluene (800ml) After suspension, tri-tert-butylphosphine was stirred at reflux for 18 hours under 0.15 eq (7.48 g) nitrogen stream. After completion of the reaction, extraction was performed with toluene and distilled water, and the organic layer was dried over magnesium sulfate (MgSO ₄ ), filtered, and the filtrate was concentrated under reduced pressure. The organic solution was removed and silica gel column was used with hexane:dichloromethane=7:3 (v/v) to recrystallize the product solid with dichloromethane and acetone to obtain intermediate b-1 (42.0g, Y=70%).

Step 2: Dissolve the intermediate b-1 1eq (42.0g) in DMF, anhydrous 10eq (126g), lower the reactor temperature to 0°C, and slowly add phosphoric chloride 1.2eq (31.7g). When the injection is completed, the reaction is completed by heating at 90° C. for 8 hours under nitrogen reflux. When the reaction was completed, dichloromethane and distilled water were added to extract the organic layer, dried over magnesium sulfate (MgSO ₄ ), filtered and the filtrate was concentrated under reduced pressure. The organic solution was removed and silica gel column was used with hexane:dichloromethane=7:3 (v/v) to recrystallize the product solid with dichloromethane and nucleic acid to obtain intermediate b-2 (37.9g, Y=81%).

Step 3: Intermediate b-2 1eq (37.9g) and 1,2-diaminobenzene 1eq (15.9g) dissolved in 300ml of dimethylformamide (DMF) in a flask of sodium meta bisulfate 1.2eq (31.9g) in distilled water 300ml And then slowly drop it under a stream of nitrogen at room temperature. When the reaction was completed, the organic layer was dissolved in dichloromethane, and then recrystallized with acetone to obtain intermediate b-3 (29.5 g, Y=59%).

Step 4: Intermediate b-3 1eq (29.5g) and 2-[1,1'-biphenyl]-4-yl-4-chloro-6-phenyl-1,3,5-Triazine 1.2eq (33.9g) After dissolving in dimethylformamide, add 1.5 eq (4.9 g) of sodium hydride (in natural oil, 60%) and reflux and stir for 6 hours. After completion of the reaction, extraction is performed with dichloromethane and distilled water, and then the organic layer is magnesium sulfate ( It was dried over MgSO ₄ ), filtered and the filtrate was concentrated under reduced pressure. The organic solution was removed and the product solid obtained by column chromatography on silica gel with hexane:dichloromethane =7:3 (v/v) was recrystallized from monochlorobenzene to obtain compound 2 (10.7g, Y=26%).

LC-Mass measurement (theoretical value: 666.77 g/mol, measured value: M+ = 667 g/mol)

Synthetic example 3: Synthesis of Compound 6

Step 1: Intermediate a-2 1eq (20.0g) and 2,4-bis([1,1'-biphenyl]-4-yl)-6- obtained by synthesizing in steps 1 and 2 of Synthesis Example 1 After dissolving chloro-1,3,5-Triazine 1.2eq (28.0g) in dimethylformamide, add 1.5eq (3.3g) of sodium hydride (in natural oil, 60%) and stir for 6 hours under reflux. When complete, the reactant is dropped into distilled water to solidify, the solid is filtered off and dissolved in dichloromethane. Then, the organic layer was dried over magnesium sulfate (MgSO ₄ ), filtered, and the filtrate was concentrated under reduced pressure. The organic solution was removed and the product solid obtained by column chromatography on silica gel with hexane:dichloromethane =7:3 (v/v) was recrystallized from monochlorobenzene to obtain compound 6 (12.4g, Y=30%).

LC-Mass (Theoretical value: 742.87 g/mol, Measurement value: M+ = 744 g/mol)

Synthetic example 4: Synthesis of Compound 7

Step 1: 2,4-dichloro-6-phenyl-1,3,5-Triazine 1eq (26.9g) and 1,3,2-Dioxaborolane, 4,4,5,5-tetramethyl-2-[1,1 After suspending':3',1''-terphenyl]-5'-yl- 1.1eq (46.7g) in 350ml of THF and 170ml of distilled water, Pd(PPh ₃ ) ₄ 0.05eq(6.8g) and potassium carbonate (K ₂ CO ₃ ) 2eq (32.9g) was added and stirred under reflux. When the reaction was completed, the solvent was dried, then dissolved in dichloromethane, dried over magnesium sulfate (MgSO ₄ ), filtered, and the filtrate was recrystallized with nucleic acid to obtain 29.7 g (Y=59%) of intermediate d-1.

(중간체 d-1)

(Intermediate d-1)

Step 2: Dissolve 1eq (20.0g) of intermediate a-2 and 1.2eq (28.0g) of intermediate d-1 in dimethylformamide and add 1.5eq (3.3g) of sodium hydride (in natural oil, 60%). When the reaction is completed by stirring and refluxing for 6 hours, the reactant is dropped into distilled water to solidify, the solid is filtered off and dissolved in dichloromethane. Then, the organic layer was dried over magnesium sulfate (MgSO ₄ ), filtered, and the filtrate was concentrated under reduced pressure. The organic solution was removed and the product obtained by column chromatography on silica gel with hexane:dichloromethane =7:3 (v/v) was recrystallized from monochlorobenzene to obtain compound 7 (11.2g, Y=27%).

LC-Mass (Theoretical value: 742.87 g/mol, Measurement value: M+ = 744 g/mol)

Synthetic example 5: Synthesis of Compound 14

Step 1: After 2,4-dichloro-6-phenyl-1,3,5-Triazine 1eq (31.6g) and (3-Dibenzofuranyl) boronic acid 1.1eq (32.6g) were suspended in 360 ml of THF and 180 ml of distilled water, Pd (PPh ₃ ) ₄ 0.05eq (8.1g) and potassium carbonate (K ₂ CO ₃ ) 2eq (38.6g) were added and stirred under reflux. After the reaction was completed, the solvent was dried, dissolved in dichloromethane, dried over magnesium sulfate (MgSO ₄ ), filtered, and the filtrate was recrystallized with nucleic acid to obtain 34.0 g (Y=68%) of intermediate e-1.

(중간체 e-1)

(Intermediate e-1)

Step 2: Dissolve the intermediate a-2 1eq (20.0g) and the intermediate e-1 1.2eq (23.9g) in Synthesis Example 1 in dimethylformamide, and then add 1.5eq (3.3) of sodium hydride (in natural oil, 60%). After adding g) and stirring under reflux for 6 hours, the reaction is dropped and solidified by dropping the reactant in distilled water. The solid is filtered and extracted and dissolved in dichloromethane. Then, the organic layer was dried over magnesium sulfate (MgSO ₄ ), filtered, and the filtrate was concentrated under reduced pressure. The organic solution was removed and the product obtained by column chromatography on silica gel with hexane:dichloromethane =7:3 (v/v) was recrystallized from monochlorobenzene to obtain compound 14 (8.5g,Y=22%).

LC-Mass (Theoretical value: 680.75 g/mol, Measurement value: M+ = 682 g/mol)

Synthesis Example 6: Synthesis of Compound 16

Step 1: Synthesis Example 2 was synthesized in the same manner as in Example 1, except that 4-iodo-biphenyl was used instead of Bromobenzene to obtain intermediate f-1 (51.7 g, Y=86%).

(중간체 f-1)

(Intermediate f-1)

Step 2: Intermediate f-1 1eq (51.7 g) was synthesized in the same manner as in Step 2 of Synthesis Example 2 to obtain Intermediate f-2 (44.3 g, Y=79%).

(중간체 f-2)

(Intermediate f-2)

Step 3: Intermediate f-2 1eq (44.3g) and 1,2-diaminobenzene 1eq (13.8g) dissolved in 300ml of dimethylformamide (DMF) in a flask of sodium meta bisulfate 1.2eq (31.9g) in distilled water 300ml And then slowly drop it under a stream of nitrogen at room temperature. When the reaction was completed, the organic layer was dissolved in dichloromethane and recrystallized with acetone to obtain intermediate f-3 (31.0 g, Y=56%).

(중간체 f-3)

(Intermediate f-3)

Step 4: Dissolve the intermediate f-3 1eq (31.0g) and 2-Chloro-4,6-diphenyltriazine 1.2eq (22.9g) in dimethylformamide, and then add sodium hydride (NaH) (in natural oil, 60%). After adding 1.5eq (4.3g) and stirring under reflux for 6 hours, the reaction was completed. After extraction in dichloromethane and distilled water, the organic layer was dried over magnesium sulfate (MgSO ₄ ), filtered and the filtrate was concentrated under reduced pressure. The organic solution was removed, and silica gel column was used with hexane:dichloromethane =7:3 (v/v) to recrystallize the product solid with monochlorobenzene to obtain compound 16 (9.8g, Y=21%).

LC-Mass measurement (theoretical value: 666.77 g/mol, measured value: M+ = 668 g/mol)

Synthetic example 7: Synthesis of Compound 18

Step 1: Synthesis Example 1, except that 3-Bromo-aldehyde was used instead of 4-Bromo-aldehyde in Step 1, and synthesized in the same manner as in Step 1 and Step 2 of Synthesis Example 1, intermediate g-2 (38.3 g, Y =77%).

(중간체 g-2)

(Intermediate g-2)

Step 2: Synthesis of the intermediate g-2 1eq (10.3g) and 2-Chloro-4,6-diphenyl-1,3,5-Triazine 1.2eq (9.2g) using the same method as in Step 3 of Synthesis Example 1 And recrystallized from chloroform to obtain compound 18 (3.2 g, Y=19%).

LC-Mass measurement (theoretical value: 590.67 g/mol, measured value: M+ = 592 g/mol)

Synthetic example 8: Synthesis of Compound 20

Step 1: After dissolving 3-(3-Bromophenyl)-9-phenyl-9H-carbazole 1eq (57.3 g) in 500 ml of anhydrous tetrahydrofuran (THF, anhydrous), lower the reactor temperature to below 0°C. After slowly dropping 1-eq (57.6 ml) of n-butyl lithium (2.5M) and slowly adding DMF,anhydrous 1.5eq (15.8 g) when lithium replacement is complete, and extracting in distilled water when the reaction is completed at room temperature, the organic layer is magnesium sulfate ( It was dried over MgSO ₄ ), filtered and the filtrate was concentrated under reduced pressure. The organic solution was removed and recrystallized from dichloromethane and nucleic acid to obtain intermediate h-1 (34.1 g, Y=68%).

Step 2: Intermediate h-1 1eq (34.1 g) was obtained using the same method as in Step 2 of Synthesis Example 1 to obtain intermediate h-2 (20.0 g, Y=47%).

Step 3: Synthesis of intermediate h-2 1eq (20.0g) and 2-Chloro-4,6-diphenyl-1,3,5-Triazine 1.2eq (14.7g) using the same method as in Step 3 of Synthesis Example 1 And recrystallized with monochlorobenzene to give compound 20 (13.2 g, Y=43%).

LC-Mass measurement (theoretical value: 666.77 g/mol, measured value: M+ = 668 g/mol)

Synthetic example 9: Synthesis of Compound 26

Step 1: Intermediate b-3 1eq (20.0g) and 2-[1,1'-biphenyl]-4-yl-4-chloro-6-phenyl-1,3,5-pyrimidine 1.2eq (22.9g) Compound 26 (6.7 g, Y = 18%) was obtained using the same method as in Step 3 of Synthesis Example 1.

Synthesis Example 10: Synthesis of Compound 65

Step 1: 2-bromo-dibenzofuran 1eq (37.8 g) was obtained using the same method as in Step 1 of Synthesis Example 8 to obtain the intermediate j-1 (24.5g, Y = 82%).

Step 2: Intermediate j-1 1eq (24.5g) was obtained using the same method as in Step 2 of Synthesis Example 1 to obtain intermediate j-2 (22.5g, Y=73%).

Step 3: Intermediate j-2 1eq (10.6g) and 2-[1,1'-biphenyl]-4-yl-4-chloro-6-phenyl-1,3,5-Triazine 1.2eq (15.3g) Compound 65 (10.4 g, Y=47%) was obtained using the same method as in Step 3 of Synthesis Example 1.

LC-Mass measurement (theoretical value: 591.66 g/mol, measured value: M+ = 593 g/mol)

Synthetic example 11: Synthesis of Compound 66

Step 1: Intermediate j-2 1eq (10.6g) and 2,4-bis([1,1'-biphenyl]-4-yl)-6-chloro-1,3,5-Triazine 1.2eq (18.9g) To obtain a compound 66 (11.0 g, Y = 44%) using the same method as in Step 3 of Synthesis Example 1.

LC-Mass measurement (theoretical value: 667.76 g/mol, measured value: M+ = 669 g/mol)

Synthetic example 12: Synthesis of Compound 77

Step 1: 2-[1,1'-biphenyl]-4-yl-4,6-dichloro-1,3,5-Triazine 1eq (42.2g) and 3-(4,4,5,5-tetramethyl- 1,3,2-dioxaborolan-2-yl)-Dibenzofuran 1.1eq (45.2g) was obtained in the same manner as in Step 1 of Synthesis Example 5 to obtain intermediate l-1 (33.5g, Y=67%).

(중간체 l-1)

(Intermediate l-1)

Step 2: Intermediate l-1 1.2eq (16.0g) and intermediate j-2 1eq (8.8g) were obtained in the same manner as in Step 3 of Synthesis Example 1 to obtain compound 77 (4.5g, Y=21%).

LC-Mass measurement (theoretical value: 681.74 g/mol, measured value: M+ = 683 g/mol)

Synthesis Example 13: Synthesis of Compound 82

Step 1: Using 3-bromo-dibenzofuran 1eq (63.0 g) instead of 3-(3-Bromophenyl)-9-phenyl-9H-carbazole of Step 1 of Synthesis Example 8, Step 1 and Step 2 of Synthesis Example 8 Compound 82 (3.5 g, Y=17%) was prepared by the same method as in Step 3 of Synthesis Example 1, using the same method as the sequential method, 1eq (8.8g) of intermediate product and 1.2eq (16.0g) of intermediate l-1 were produced. ).

LC-Mass measurement (theoretical value: 681.74 g/mol, measured value: M+ = 683 g/mol)

Synthesis Example 14: Synthesis of Compound 83

Step 1: 2-[1,1'-biphenyl]-4-yl-4,6-dichloro-1,3,5-Triazine 1eq(33.6) and 3-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-dibenzothiophen 1.1eq (37.9 g) was obtained using the same method as in Step 1 of Synthesis Example 8 to obtain the intermediate n-1 (28.3 g, Y = 57%).

(중간체 n-1)

(Intermediate n-1)

Step 2: Prepared in the same manner as in Synthesis Example 13, instead of Intermediate l-1, Intermediate n-1 1.2eq (15.3 g) was used to obtain Compound 83 (4.8 g, Y=16%).

LC-Mass measurement (theoretical value: 697.80 g/mol, measured value: M+ = 699 g/mol)

Synthesis Example 15: Synthesis of Compound 95

Step 1: 2-bromo-dibenzofuran 1eq (49.6g) was obtained using the same method as in Step 1 of Synthesis Example 8 to obtain the intermediate o-1 (41.4g, Y = 69%).

(중간체 o-1)

(Intermediate o-1)

Step 2: 2-[1,1'-biphenyl]-4-yl-4-chloro-6-phenyl-1,3, in the same manner as in Step 3 of Synthesis Example 1, the intermediate o-1 1eq (41.4g) Reaction with 5-Triazine gave compound 95 (5.6 g, Y=37%).

LC-Mass measurement (theoretical value: 607.73 g/mol, measured value: M+ = 609 g/mol)

Synthetic example 16: Synthesis of Compound 96

The reaction was performed in the same manner as in Synthesis Example 15, but instead of 2-[1,1'-biphenyl]-4-yl-4-chloro-6-phenyl-1,3,5-Triazine, 2,4-bis([1, Compound 96 (5.2 g, Y=33%) was obtained using 1'-biphenyl]-4-yl)-6-chloro-1,3,5-Triazine.

LC-Mass measurement (theoretical value: 683.82 g/mol, measured value: M+ = 685 g/mol)

Synthetic example 17: Synthesis of Compound 106

The reaction was carried out in the same manner as in Synthesis Example 15, but instead of 2-[1,1'-biphenyl]-4-yl-4-chloro-6-phenyl-1,3,5-Triazine, the intermediate e-1 1.2eq (10.3 g ) To give compound 106 (3.5 g, Y=23%).

LC-Mass measurement (theoretical value: 621.71 g/mol, measured value: M+ = 623 g/mol)

Synthetic example 18: Synthesis of Compound 114

Reacted in the same manner as in Synthesis Example 15, but instead of 2-[1,1'-biphenyl]-4-yl-4-chloro-6-phenyl-1,3,5-Triazine, 4,6-di(biphenyl-4 Compound 114 (4.0 g, Y=25%) was obtained using -yl)-2-chloropyrimidine (11.8 g).

LC-Mass measurement (theoretical value: 682.83 g/mol, measured value: M+ = 684 g/mol)

Synthetic example 19: Synthesis of Compound 40

Intermediate a-2 1eq (5.6g) and 4-(biphenyl-4-yl)-2-chloroquinazoline 1.2eq (5.9g) in the same manner as in Step 3 of Synthesis Example 1 Compound 40 (2.5g, Y=25% Got)

LC-Mass measurement (theoretical value: 639.75 g/mol, measured value: M+ = 641 g/mol)

Synthetic example 20: Synthesis of Compound 42

4-(biphenyl-4-yl)-2-chloroquinazoline 1eq (5.6g) and intermediate b-3 1.2eq (5.9g) in the same manner as in Step 3 of Synthesis Example 1, Compound 42 (1.4g, Y=14% Got)

LC-Mass measurement (theoretical value: 639.75 g/mol, measured value: M+ = 641 g/mol)

Synthetic example 21: Synthesis of Compound 49

4-(biphenyl-4-yl)-2-chloroquinazoline 1eq (5.6g) and intermediate g-2 1.2eq obtained compound 49 (1.7g, Y=17%) in the same manner as in Step 3 of Synthesis Example 1.

LC-Mass measurement (theoretical value: 639.75 g/mol, measured value: M+ = 641 g/mol)

Synthetic example 22: Synthesis of Compound 55

Intermediate a-2 1eq (5.5g) and 2-chloro-4-(dibenzo[b,d]furan-3-yl)quinazoline

1.2eq (6.1g) was obtained in the same manner as in Step 3 of Synthesis Example 1 to obtain compound 55 (1.5g, Y=15%)

LC-Mass measurement (theoretical value: 653.73 g/mol, measured value: M+ = 655 g/mol)

Reference compound 1 Reference compound 2 Reference compound 3

Reference Synthesis Example One:

Intermediate b-3 1eq (5.4g) and 2-(3-chlorophenyl)-4,6-diphenyl- 1,3,5-Triazine 1eq (6.2g) in the same manner as in Step 3 of Synthesis Example 1 Reference compound 1 (1.7g, Y=17%).

LC-Mass measurement (theoretical value: 666.77 g/mol, measured value: M+ = 668 g/mol)

Reference Synthesis Example 2:

Step 1: 2-(4-chlorophenyl)-4,6-diphenyl-1,3,5-Triazine 1eq (61.1g) was prepared in the same manner as in Step 1 of Synthesis Example 8, intermediate-1 (15.6g,Y=26 %)

Step 2: Intermediate-1 1eq (15.6g) was obtained using the same method as in Step 2 of Synthesis Example 1 to obtain Intermediate-2 (5.7g, Y=29%).

Step 3: Intermediate-2 1 eq (5.7 g) and 9-(4-bromophenyl)-9H-Carbazole 1 eq (5.2 g) were prepared in the same manner as in Step 3 of Synthesis Example 1 and reference compound 2 (0.8 g, Y=9%) Got)

LC-Mass measurement (theoretical value: 666.77 g/mol, measured value: M+ = 668 g/mol)

Reference Synthesis Example 3( red ):

Step 1: 2-chloro-4-phenyl-Quinazoline 1eq (38.8g) and 4-Formylphenylboronic acid 1eq (26.6g) in the same manner as in Step 1 of Synthesis Example 5 Intermediate-3 (29.4g, Y = 59%) Got

Step 2: Intermediate-3 1eq (29.4g) was obtained using the same method as in Step 2 of Synthesis Example 1 to obtain Intermediate-4 (13.5g, Y=36%).

Step 3: Intermediate-4 1eq (6.2g) and 9-(4-bromophenyl)-9H-Carbazole 1eq (6.0g) in the same manner as in Step 3 of Synthesis Example 1 Reference compound 3 (1.5g,Y=15% Got)

LC-Mass measurement (theoretical value: 639.75 g/mol, measured value: M+ = 641 g/mol)

(Production of organic light emitting element)-Green element

Example One

The glass substrate coated with ITO (Indium tin oxide) with a thickness of 1500Å was washed with distilled water ultrasonically. After washing with distilled water, ultrasonic cleaning was performed with a solvent such as isopropyl alcohol, acetone, or methanol, dried and then transferred to a plasma scrubber, and then the substrate was cleaned using an oxygen plasma for 10 minutes and then transferred to a vacuum evaporator. Using this prepared ITO transparent electrode as an anode, vacuum deposition of Compound A on the top of the ITO substrate forms a hole injection layer having a thickness of 700 하고 and depositing Compound B on the top of the injection layer to a thickness of 50 Å, followed by compound C of 1020 Å. It was deposited to a thickness to form a hole transport layer. Compound 1 of Synthesis Example 1 was used as a host on the hole transport layer, and dopant tris(2-phenylpyridine) iridium(III) [Ir(ppy) ₃ ] was doped with 10 wt% to form a 400 µm thick light emitting layer by vacuum deposition. Did. Subsequently, an electron transport layer having a thickness of 300 증착 is formed by vacuum-depositing Compound D and Liq on the light emitting layer at a ratio of 1:1 simultaneously, and vacuum deposition of Liq 15 Å and Al 1200 에 on the electron transport layer sequentially forms a cathode to form an organic light emitting device. Was produced.

The organic light emitting device has a structure having five layers of organic thin films, and is specifically as follows.

ITO/Compound A(700Å)/Compound B(50Å)/Compound C(1020Å)/EML[Compound 1:Ir(ppy) ₃ = 90wt%:10wt%](400Å)/Compound D:Liq(300Å)/Liq (15 제작)/Al (1200Å).

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

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

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

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

Example 2 and Reference example One

The device of Example 2 and Reference Example 1 was manufactured in the same manner as in Example 1, using Compound 2 (Example 2) or CBP alone, instead of Compound 1.

Example 3

In Example 1, the organic light emitting device of Example 3 was manufactured in the same manner as in Example 1, except that Compound 1 and Compound E-136 were used in a 5:5 weight ratio instead of Compound 1 of Synthesis Example 1.

Example 4 to Example 6

As described in Table 2 below, devices corresponding to Examples 4 to 6 were manufactured using the first host, the second host, and their weight ratios, respectively.

Reference example 2 and Reference example 3

The devices of Reference Examples 2 and 3 were manufactured in the same manner as in Example 1, using Reference Compound 1 and Reference Compound 2 alone instead of Compound 1.

Reference example 4

The device of Reference Example 4 was manufactured in the same manner as in Example 3, except that Comparative Compound 1 was used as the first host instead of Compound 1.

(Production of organic light emitting device)- Red device

Example 7 and Reference example 5

Instead of Compound 1, Compound 40 (Example 7) or Reference Compound 3 was used alone, and [Ir(piq) ₂ acac] was doped with 5wt% instead of [Ir(ppy) ₃ ] as a dopant to form a thickness of 400Å by vacuum deposition. The devices of Example 7 and Reference Example 5 were manufactured in the same manner as in Example 1, except that the light emitting layer of FIG.

Example 8

It was prepared in the same manner as in Example 7, except that the host compound 40 and compound E-136 were used in a weight ratio of 4:6.

The organic light emitting device has a structure having five layers of organic thin films, and specifically

ITO/Compound A(700Å)/Compound B(50Å)/Compound C(1020Å)/EML[Compound 40: E-136: [Ir(piq) ₂ acac] = 38wt%: 57wt%: 5wt%] (400Å) / Compound D: Liq(300Å) / Liq(15Å) / Al(1200Å).

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

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

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

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

Example 9 to Example 11

The devices of Examples 9 to 11 were manufactured in the same manner as in Example 8 using the first host and the second host, respectively, as described in Table 3 below.

Reference example 6

The device of Reference Example 6 was manufactured in the same manner as in Example 7, except that instead of Compound 40, Reference Compound 3 and Compound E-136 were used in a 3:7 weight ratio.

evaluation

[Green]

The luminous efficiency and lifetime characteristics of the organic light emitting devices according to Examples 1 to 6 and Reference Examples 1 to 4 were evaluated. Specific measurement methods are as follows, and the results are shown in Table 1 and Table 2.

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

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

(2) Measurement of luminance change according to voltage change

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

(3) 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 (1) and (2) above.

(4) Life measurement

Using the polaronics life measurement system for the prepared organic light-emitting device, the devices of Examples 1 to 6 and Comparative Example 1 emit the initial luminance (cd/m ² ) at 5000 cd/m ² and decrease the luminance with time. By measuring, the time point when the luminance was reduced to 97% compared to the initial luminance was measured as the T97 life.

(5) Driving voltage measurement

The driving voltage of each device was measured at 15 mA/cm ² using a current-voltmeter (Keithley 2400).

Example Host Driving voltage (V) Luminous efficiency (cd/A) Life T97(h) Example 1 Compound 1 4.6 65 80 Example 2 Compound 2 4.5 54 50 Reference Example 1 CBP 7.20 19.5 One Reference Example 2 Reference compound 1 5.0 50 50 Reference Example 3 Reference compound 2 5.4 25 One

Example First host 2nd host Host 1:
Host 2
(wt/wt) Driving voltage
(V) Luminous efficiency
(cd/A) Life T97
(h) Example 3 Compound 1 E-136 5:5 4.0 65 150 Example 4 Compound 2 E-136 5:5 4.2 54 130 Example 5 Compound 14 E-136 5:5 3.9 75 170 Example 6 Compound 14 E-136 4:6 3.8 80 200 Reference Example 4 Reference compound 1 E-136 5:5 4.3 55 80

Referring to Tables 1 and 2, the organic light emitting diodes according to Examples 1 to 6 evaluated as a green host, compared with the organic light emitting diodes according to Reference Examples 1 to 4, have driving voltage, light emission efficiency, and lifetime characteristics at the same time. You can see the improvement.

[Red]

The luminous efficiency and lifetime characteristics of the organic light emitting devices according to Examples 7 to 11 and Reference Examples 5 and 6 were evaluated. The specific measuring method is the same as the above measuring method, and the results are shown in Tables 3 and 4.

Example Host 1 color Driving voltage (V) Luminous efficiency (cd/A) Example 7 Compound 40 Red 5.0 16.0 Reference Example 5 Reference compound 3 Red 5.2 7

* The luminance is 6000 cd / m ² or less of the element is not life measurement

Example First host 2nd host Host 1:
Host 2
(wt/wt) color Driving voltage
(V) Luminous efficiency
(cd/A) Example 8 Compound 40 E-136 4:6 Red 4.7 20.4 Example 9 Compound 42 E-136 4:6 Red 4.9 17.7 Example 10 Compound 55 E-136 4:6 Red 4.6 21.0 Example 11 Compound 55 E-136 3:7 Red 4.8 20.4 Reference Example 6 Reference compound 3 E-136 3:7 Red 4.9 9.4

* The luminance is 6000 cd / m ² or less of the element is not life measurement

Referring to Tables 3 and 4, it was confirmed that the organic light emitting devices according to Examples 7 to 11 evaluated as a red host had significantly improved driving voltage and luminous efficiency at the same time as compared with the organic light emitting devices according to Reference Examples 5 and 6. Can.

The present invention is not limited to the above embodiments, but may be manufactured in various different forms, and a person having ordinary skill in the art to which the present invention pertains may have other specific forms without changing the technical spirit or essential features of the present invention. It will be understood that can be carried out. Therefore, it should be understood that the embodiments described above are illustrative in all respects and not restrictive.

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

Claims (15)

A compound for a first organic optoelectronic device represented by the following Chemical Formula 1; And
Composition for an organic optoelectronic device comprising a compound for a second organic optoelectronic device represented by the following formula C-8:
[Formula 1]

In Chemical Formula 1,
Z ¹ to Z ⁵ are each independently N or CR ^a ,
At least two of Z ¹ to Z ⁵ are N,
R ^a is each independently hydrogen, deuterium, a substituted or unsubstituted C6 to C20 aryl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a combination thereof,
At least one of R ^a is a substituted or unsubstituted C6 to C20 aryl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a combination thereof,
R ^a are each independently or adjacent groups connected to each other to form a substituted or unsubstituted aliphatic, aromatic or heteroaromatic monocyclic or polycyclic ring,
R ¹ is a substituted or unsubstituted carbazolyl group,
L ¹ is a single bond, or a substituted or unsubstituted C6 to C30 arylene group,
R ² to R ⁵ are each hydrogen,
"Substitution" of Formula 1 means that at least one hydrogen is substituted with deuterium, a C1 to C20 alkyl group, a C6 to C30 aryl group, a dibenzofuranyl group, or a dibenzothiophenyl group;
[Chemical Formula C-8]

In Chemical Formula C-8,
Y ¹ and Y ² are each independently a single bond or a substituted or unsubstituted C6 to C30 arylene group,
A ¹ and A ² are each independently a substituted or unsubstituted C6 to C30 aryl group,
The "substitution" of the formula C-8 means that at least one hydrogen is substituted with deuterium, a C1 to C4 alkyl group, a C6 to C18 aryl group, or a C2 to C30 heteroaryl group. According to claim 1,
The first compound for an organic optoelectronic device is a composition for an organic optoelectronic device represented by the following formula 1A or formula 1B:
[Formula 1A] [Formula 1B]

In Formula 1A and Formula 1B,
Z ¹ to Z ⁵ are each independently N or CR ^a ,
At least two of Z ¹ to Z ⁵ are N,
R ^a is each independently hydrogen, deuterium, a substituted or unsubstituted C6 to C20 aryl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a combination thereof,
At least one of R ^a is a substituted or unsubstituted C6 to C20 aryl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a combination thereof,
R ^a are each independently or adjacent groups connected to each other to form a substituted or unsubstituted aliphatic, aromatic or heteroaromatic monocyclic or polycyclic ring,
L ¹ is a single bond, or a substituted or unsubstituted C6 to C30 arylene group,
R ^b , R ^c , R ^d , R ^e , R ^f , and R ² to R ⁵ are each hydrogen. According to claim 2,
The formula 1B is a composition for an organic optoelectronic device represented by the following formula 1B-I or formula 1B-II:
[Formula 1B-Ⅰ] [Formula 1B-Ⅱ]

In Formula 1B-I and Formula 1B-II,
Z ¹ to Z ⁵ are each independently N or CR ^a ,
At least two of Z ¹ to Z ⁵ are N,
R ^a is each independently hydrogen, deuterium, a substituted or unsubstituted C6 to C20 aryl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a combination thereof,
At least one of R ^a is a substituted or unsubstituted C6 to C20 aryl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a combination thereof,
R ^a are each independently or adjacent groups connected to each other to form a substituted or unsubstituted aliphatic, aromatic or heteroaromatic monocyclic or polycyclic ring,
L ¹ is a single bond, or a substituted or unsubstituted C6 to C30 arylene group,
R ^d , R ^e , R ^f , and R ² to R ⁵ are each hydrogen. According to claim 1,
The first compound for an organic optoelectronic device is a composition for an organic optoelectronic device represented by any one of the following Formula 1-1 to Formula 1-5:
[Formula 1-1] [Formula 1-2] [Formula 1-3] [Formula 1-4] [Formula 1-5]

In Formula 1-1 to Formula 1-5,
R ^a2 to R ^a5 are each independently the same as the definition of R ^a in claim 1 and
R ^a6 and R ^a7 are each independently hydrogen, deuterium, a C6 to C20 aryl group, or a combination thereof,
R ¹ is a substituted or unsubstituted carbazolyl group,
L ¹ is a single bond, or a substituted or unsubstituted C6 to C30 arylene group,
R ² to R ⁵ are each hydrogen. According to claim 1,
Hexagonal ring containing Z ¹ to Z ⁵ of Formula 1 is a composition for an organic optoelectronic device selected from the substituents listed in Group I below:
[Group Ⅰ]

In group I above,
* Is the point of connection. According to claim 1,
The first compound for an organic optoelectronic device is a composition for an organic optoelectronic device selected from the compounds listed in Group 1 below:
[Group 1]

. delete According to claim 1,
A ¹ and A ² of Formula C-8 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 quarterphenyl group, a substituted or unsubstituted A composition for an organic optoelectronic device which is a substituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluorenyl group, or a combination thereof. According to claim 1,
*-Y ¹ -A ¹ and *-Y ² -A ² of Chemical Formula C-8 are one of the substituents listed in Group III below:
[Group Ⅲ]

In Group III, * is a connection point. The method of claim 9,
*-Y ¹ -A ¹ and *-Y ² -A ² of Chemical Formula C-8 is a composition for an organic optoelectronic device selected from B-1 to B-3 of Group III. delete According to claim 1,
The first compound for an organic optoelectronic device is a composition for an organic optoelectronic device represented by the following Formula 1-1 or Formula 1-5:
[Formula 1-1] [Formula 1-5]

In Formula 1-1 and Formula 1-5,
R ^a2 and R ^a4 are each independently hydrogen, deuterium, substituted or unsubstituted phenyl group, substituted or unsubstituted biphenyl group, substituted or unsubstituted terphenyl group, substituted or unsubstituted dibenzofuranyl group, or substituted or unsubstituted A substituted dibenzothiophenyl group,
At least one of R ^a2 and R ^a4 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzo Thiophyl group,
R ^a6 and R ^a7 are each independently hydrogen, deuterium, a C6 to C20 aryl group, or a combination thereof,
R ¹ is a substituted or unsubstituted carbazolyl group,
L ¹ is a single bond, or a substituted or unsubstituted C6 to C30 arylene group,
R ² to R ⁵ are each hydrogen;
*-Y ¹ -A ¹ and *-Y ² -A ² of Formula C-8 are represented by any one of the following B-1 to B-3:

. Positive and negative poles facing each other, and
And at least one organic layer positioned between the anode and the cathode,
The organic layer is an organic optoelectronic device comprising a composition for an organic optoelectronic device according to any one of claims 1 to 6 and 8 to 10 and 12. The method of claim 13,
The organic layer includes a light emitting layer,
The composition for an organic optoelectronic device is included as a host of the light emitting layer. A display device comprising the organic optoelectronic device according to claim 13.

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