KR102094942B1 - Compound for organic optoelectric device, composition for organic optoelectric device and organic optoelectric 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

COMPOUND FOR ORGANIC OPTOELECTRIC DEVICE, COMPOSITION FOR ORGANIC OPTOELECTRIC DEVICE AND ORGANIC OPTOELECTRIC DEVICE AND DISPLAY DEVICE}

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

Organic optoelectronic devices can be roughly divided into two types according to the operating principle. One is a photoelectric device that generates electrical energy as excitons formed by light energy are separated into electrons and holes, and the electrons and holes are transferred to different electrodes, and the other is to supply electricity by supplying voltage or current to the electrodes. 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 as demand for flat panel display devices has increased. The organic light-emitting device is a device that converts electrical energy into light by applying a current to the 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 be, for example, a hole injection layer, a hole transport layer, an electron blocking layer, an electron transport layer, or 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, it 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 increasing 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,

L ¹ to L ³ 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,

R ¹ to R ⁶ 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 C30 heterocyclic group, or a combination thereof ego,

At least one of R ¹ to R ³ is a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted Isoquinolinyl group, substituted or unsubstituted naphthyridinyl group, substituted or unsubstituted quinazolinyl group, substituted or unsubstituted benzoquinazolinyl group, substituted or unsubstituted benzimidazolyl group, substituted or unsubstituted benzofuran A pyrimidinyl group, a substituted or unsubstituted benzothiophenpyrimidinyl group, a substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted indolocarbazole group,

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 C18 heteroaryl group.

According to another embodiment, the compound for a first organic optoelectronic device described above; And a compound for at least one second organic optoelectronic device of a compound consisting of a compound represented by the following Chemical Formula 2 and a moiety represented by the following Chemical Formula 3 and a moiety represented by the following Chemical Formula 4: Provided is a composition.

[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,

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 ⁷ to R ¹² 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 C50 heterocyclic group, or combinations thereof,

m is an integer from 0 to 2;

[Formula 3] [Formula 4]

In Chemical Formulas 3 and 4,

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 ¹³ to R ¹⁶ 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 ego,

The two adjacent * in Formula 3 are connected to the two * in Formula 4 to form a fused ring, and * in the Formula 3 not forming a fused ring is each independently CR ^a ,

R ^a is each independently 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;

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 C18 heteroaryl group.

According to another embodiment, an anode and a cathode facing each other, and 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.

It is possible to realize a high-efficiency long-life organic optoelectronic device.

1 and 2 are cross-sectional views showing 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 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, C6 to C30 It means substituted with a C1 to C10 trifluoroalkyl group or a cyano group such as a heteroaryl group, a C1 to C20 alkoxy group, a fluoro group, or a trifluoromethyl group.

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 It means substituted with C30 heterocycloalkyl group, C6 to C30 aryl group, C6 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 C30 alkyl group, a C6 to C18 aryl group, or a C6 to C20 heteroaryl group. In the most specific example of the present invention, "substitution" means that at least one hydrogen in the substituent or compound is substituted with deuterium, a C1 to C4 alkyl group, a C6 to C18 aryl group, or a C2 to C18 heteroaryl group.

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

In the present specification, an “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, the 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 at least one hydrocarbon aromatic moiety,

While all the 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 connected 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, 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 phenanthryl 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 chrysenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted perenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted Nyl group, substituted or unsubstituted furanyl group, substituted or unsubstituted thiophenyl group, substituted or unsubstituted pyrrolyl group, substituted or unsubstituted pyrazolyl group, substituted or unsubstituted imidazolyl group, substituted or non- Substituted triazole group, substituted or unsubstituted oxazolyl group, substituted or unsubstituted thiazolyl group, substituted or unsubstituted oxadiazolyl group, substituted or unsubstituted thiadiazolyl group, substituted or unsubstituted pyridyl group , Substituted or unsubstituted pyrimidinyl group, substituted or unsubstituted pyrazinyl group, substituted or unsubstituted triazinyl group, substituted or unsubstituted benzofuranyl group, substituted or unsubstituted benzothiophenyl group, substituted or unsubstituted Benzimidazole group, substituted or unsubstituted indolyl group, substituted or unsubstituted quinolinyl group, substituted or unsubstituted isoquinolinyl group, substituted or unsubstituted quinazolinyl group, substituted or unsubstituted benzoquinazoli A nil group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted benzofuran pyrimidinyl group, a substituted or unsubstituted benzothiophenpyrimidinyl group, a substituted or unsubstituted naphthyridinyl group, A substituted or unsubstituted benzoxazine group, a substituted or unsubstituted benzthiazinyl group, a substituted or unsubstituted acridinyl group, a substituted or unsubstituted phenazinyl group, a substituted or unsubstituted phenothiazineyl group, substituted or Unsubstituted phenoxazinyl group, substituted or unsubstituted dibenzofuranyl group, substituted or unsubstituted dibenzothiophenyl group, or a combination thereof, 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 a conductive property along the HOMO level, injecting a hole formed at the anode into the light emitting layer, and emitting layer It means the property of facilitating the movement of the holes formed in the anode and the movement in 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,

L ¹ to L ³ 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,

R ¹ to R ⁶ 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 C30 heterocyclic group, or a combination thereof ego,

At least one of R ¹ to R ³ is a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted Isoquinolinyl group, substituted or unsubstituted naphthyridinyl group, substituted or unsubstituted quinazolinyl group, substituted or unsubstituted benzoquinazolinyl group, substituted or unsubstituted benzimidazolyl group, substituted or unsubstituted benzofuran A pyrimidinyl group, a substituted or unsubstituted benzothiophenpyrimidinyl group, a substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted indolocarbazole group,

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 C18 heteroaryl group.

In one example, the "substitution" means that at least one hydrogen is deuterium, C1 to C4 alkyl group, phenyl group, biphenyl group, fluorenyl group, naphthyl group, phenanthrenyl group, pyridinyl group, pyrimidinyl group, triazinyl group, It means that it is substituted with a quinazolinyl group, a benzoquinazolinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, or a carbazolyl group.

For example, the "substitution" means that at least one hydrogen is deuterium, C1 to C4 alkyl group, phenyl group, meta-biphenyl group, para-biphenyl group, naphthyl group, dibenzofuranyl group, dibenzothiophenyl group, or carbazole group Means substituted with.

The compound for an organic optoelectronic device according to the present invention has a non-planar skeleton having a bulky structure by introducing a phenanthro [9 ', 10': 4,5] imidazo [1,2-a] pyridine core, which increases the glass transition temperature. It can be raised to improve the thermal stability.

In addition, the non-planar skeleton of the bulky structure is a substituent having an electron characteristic or hole characteristic, that is, a structure in which a nitrogen-containing 6-membered ring containing at least one N is substituted, since injection of holes and electrons may occur more rapidly, It can exhibit device performance with low driving voltage, long life, and high efficiency.

In addition, since phenanthro [9 ', 10': 4,5] imidazo [1,2-a] pyridine has good solubility, it can be applied to both OLED materials for deposition and solution processing.

On the other hand, unlike the structure of the present invention in which one of the two N's is contained in the terminal phenyl of the central core, Comparative Structure Examples 1 to 4, Comparative Structure Examples 6 and Comparative Structure Example 7 have two N's of the terminal phenyl of the central core. It is not included in all and has a structure located outside the terminal phenyl, and the compounds according to Comparative Structure Examples 1 to 4, Comparative Structure Examples 6 and Comparative Structure Example 7 have a relatively high deposition temperature, and have poor film characteristics during device fabrication. , Unlike the structure of the present invention, which has an adverse effect on the device result and includes two Ns in the center core, Comparative Structure Example 5, which includes only one N in the center core, has a relatively high LUMO value, resulting in a higher driving voltage. It is likely that the stability of the compound will deteriorate due to this.

In one embodiment of the present invention, R ¹ to R ⁶ of Formula 1 are each independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl group, substituted or unsubstituted phenyl group, substituted or unsubstituted biphenyl group, Substituted or unsubstituted terphenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted anthracenyl group, substituted or unsubstituted phenanthrenyl group, substituted or unsubstituted fluorenyl group, substituted or unsubstituted triphenyl Ren group, substituted or unsubstituted pyridinyl group, substituted or unsubstituted pyrimidinyl group, substituted or unsubstituted triazinyl group, substituted or unsubstituted quinolinyl group, substituted or unsubstituted isoquinolinyl group, substituted or Unsubstituted naphthyridinyl group, substituted or unsubstituted quinazolinyl group, substituted or unsubstituted benzoquinazolinyl group, substituted or unsubstituted benzimidazole group, substituted or unsubstituted benzofuranpy MIDI group, may be a carbazole group as a substituted or unsubstituted benzothiophen-pyrido the media group, a substituted or unsubstituted carbazole group, or a substituted or unsubstituted indole,

At least one of R ¹ to R ³ is a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted Isoquinolinyl group, substituted or unsubstituted naphthyridinyl group, substituted or unsubstituted quinazolinyl group, substituted or unsubstituted benzoquinazolinyl group, substituted or unsubstituted benzimidazolyl group, substituted or unsubstituted benzofuran It may be a pyrimidinyl group, a substituted or unsubstituted benzothiophenpyrimidinyl group, a substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted indolocarbazole group.

In a specific embodiment of the present invention, R ¹ to R ⁶ of Formula 1 are each independently hydrogen, deuterium, substituted or unsubstituted C1 to C4 alkyl group, substituted or unsubstituted phenyl group, substituted or unsubstituted pyridine Nyl group, substituted or unsubstituted pyrimidinyl group, substituted or unsubstituted triazinyl group, substituted or unsubstituted naphthyridinyl group, substituted or unsubstituted quinazolinyl group, substituted or unsubstituted benzofuran pyrimidinyl group, substituted Or an unsubstituted benzothiophenpyrimidinyl group, a substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted indolocarbazole group,

At least one of R ¹ to R ³ is a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted It may be a quinazolinyl group, a substituted or unsubstituted benzofuran pyrimidinyl group, a substituted or unsubstituted benzothiophenpyrimidinyl group, a substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted indolocarbazole group. ,

Each of L ¹ to L ³ may be independently a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group, for example, L ¹ to L ³ are each independently a single bond or substitution. Or it may be an unsubstituted meta-phenylene group, or a substituted or unsubstituted para-phenylene group.

When L ¹ to L ³ are the same as above, the distance between the phenanthro [9 ', 10': 4,5] imidazo [1,2-a] pyridine and the substituents exhibiting ET properties is shortened, and the molecular shape becomes spherical. It is possible to lower the deposition temperature from this and have excellent heat stability.

In an example of the present invention, R ⁴ to R ⁶ are each independently hydrogen, deuterium, substituted or unsubstituted C1 to C5 alkyl group, substituted or unsubstituted phenyl group, substituted or unsubstituted biphenyl group, substituted or unsubstituted Terphenyl group, or a substituted or unsubstituted naphthyl group. More specifically, R ⁴ to R ⁶ may be each independently hydrogen, deuterium, phenyl group, biphenyl group, terphenyl group or naphthyl group, for example, hydrogen or phenyl group.

In one embodiment of the present invention, at least one of R ¹ to R ³ is a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted quill Nolinyl group, substituted or unsubstituted isoquinolinyl group, substituted or unsubstituted naphthyridinyl group, substituted or unsubstituted quinazolinyl group, substituted or unsubstituted benzoquinazolinyl group, substituted or unsubstituted benzimidazolyl group , A substituted or unsubstituted benzofuranpyrimidinyl group, a substituted or unsubstituted benzothiophenpyrimidinyl group, a substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted indolocarbazole group.

In a specific embodiment of the present invention, any one of R ¹ to R ³ is a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted Quinolinyl group, substituted or unsubstituted isoquinolinyl group, substituted or unsubstituted naphthyridinyl group, substituted or unsubstituted quinazolinyl group, substituted or unsubstituted benzoquinazolinyl group, substituted or unsubstituted benziimi A polyzolyl group, a substituted or unsubstituted benzofuranpyrimidinyl group, a substituted or unsubstituted benzothiophenpyrimidinyl group, a substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted indolocarbazole group, R ¹ The rest of R ³ and R ⁴ to R ⁶ may be each independently hydrogen or a phenyl group.

In one of the most specific embodiments of the present invention, R ¹ is a substituted or unsubstituted triazinyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted benzofuranpyrimidinyl group , A substituted or unsubstituted benzothiophenpyrimidinyl group, a substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted indolocarbazole group, and R ² to R ⁶ may be hydrogen or a phenyl group.

In another specific embodiment of the present invention, R ² is a substituted or unsubstituted triazinyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted benzofuranpyrimidinyl group , A substituted or unsubstituted benzothiophenpyrimidinyl group, a substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted indolocarbazole group, R ¹ , and R ³ to R ⁶ are hydrogen, or a phenyl group You can.

In another specific embodiment of the present invention, R ³ is a substituted or unsubstituted triazinyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted benzofuran pyrimidi A nil group, a substituted or unsubstituted benzothiophenpyrimidinyl group, a substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted indolocarbazole group, R ¹ , R ² , and R ⁴ to R ⁶ are hydrogen Or, it may be a phenyl group.

Formula 1 is, for example, the following formula 1-A1, formula 1-A2, formula 1-B1, formula 1-B2, formula 1-C1, and formula 1- It can be expressed in any one of C2.

[Formula 1-A1] [Formula 1-A2] [Formula 1-B1]

[Formula 1-B2] [Formula 1-C1] [Formula 1-C2]

In Formula 1-A1, Formula 1-A2, Formula 1-B1, Formula 1-B2, Formula 1-C1, and Formula 1-C2, L ¹ to L ³ , and R ¹ to R ⁶ are as described above .

Formula 1-A1) and (1-A2 of R ^1, Formula 1-B1) and (1-B2 of R ^2, and R ³ are each independently a substituted or unsubstituted of Formula 1-C1) and (1-C2 Pyridinyl group, substituted or unsubstituted pyrimidinyl group, substituted or unsubstituted triazinyl group, substituted or unsubstituted naphthyridinyl group, substituted or unsubstituted quinolinyl group, substituted or unsubstituted isoquinolinyl group , Substituted or unsubstituted quinazolinyl group, substituted or unsubstituted benzoquinazolinyl group, substituted or unsubstituted benzimidazole group, substituted or unsubstituted benzofuran pyrimidinyl group, substituted or unsubstituted benzothiophene pyri It may be a midinyl group, a substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted indolocarbazole group,

Specifically, the formula 1-A1) and (1-A2 of R ^1, Formula 1-B1) and (1-B2 of R ^2, and Formula 1-C1) and (1-C2 of R ³ is substituted, each independently Or an unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted benzo It may be a furan pyrimidinyl group, a substituted or unsubstituted benzothiophenpyrimidinyl group, a substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted indolocarbazole group,

For example, it may be selected from the substituents listed in Group I below.

[Group Ⅰ]

In Group I, * is a connection point.

Formula 1-A1) and (1-A2 of R ^1, Formula 1-B1) and (1-B2 of R ^2, and substituted or unsubstituted as the specific example of Formula 1-C1) and (1-C2 R ³ of Substituted triazinyl group, substituted or unsubstituted naphthyridinyl group, substituted or unsubstituted quinazolinyl group, substituted or unsubstituted benzofuranpyrimidinyl group, substituted or unsubstituted benzothiophenpyrimidinyl group, substituted or unsubstituted A substituted carbazolyl group, or a substituted or unsubstituted indolocarbazole group.

In one embodiment of the present invention, L ¹ to L ³ of Formula 1A-2 and Formula 1C-2 is a single bond, and R ¹ of Formula 1A-2 is a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted tria A carbonyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted benzofuranpyrimidinyl group, or a substituted or unsubstituted benzothiophenpyrimidinyl group, R ² to R ⁶ are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C4 alkyl group, or a substituted or unsubstituted C6 to C18 aryl group,

R ³ of Formula 1C-2 is a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted benzo Furan pyrimidinyl group, or a substituted or unsubstituted benzothiophenpyrimidinyl group, R ¹ , R ² and R ⁴ to R ⁶ are each independently hydrogen, deuterium, substituted or unsubstituted C1 to C4 alkyl group or substituted or It may be an unsubstituted C6 to C18 aryl group.

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 compound for a first organic optoelectronic device described above 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 it may include at least one compound for a second organic optoelectronic device of the compound consisting of a compound represented by the following formula (2), and a moiety represented by the following formula (4) and a moiety represented by the following formula (3).

[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,

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 ⁷ to R ¹² 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 C50 heterocyclic group, or combinations thereof,

m is an integer from 0 to 2;

[Formula 3] [Formula 4]

In Chemical Formulas 3 and 4,

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 ¹³ to R ¹⁶ 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 ego,

The two adjacent * in Formula 3 are connected to the two * in Formula 4 to form a fused ring, and * in the Formula 3 not forming a fused ring is each independently CR ^a ,

R ^a is each independently 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;

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 C18 heteroaryl 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, and in a specific embodiment, a single bond, or substitution Or it may be an unsubstituted phenylene group.

In one embodiment of the present invention, Ar ¹ and Ar ² in Chemical Formula 2 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, or a substituted or unsubstituted Naphthyl group, substituted or unsubstituted anthracenyl group, substituted or unsubstituted triphenylenyl group, substituted or unsubstituted pyridinyl group, substituted or unsubstituted dibenzothiophenyl group, substituted or unsubstituted dibenzofuran It may be a diary, a substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted fluorenyl group, and in one specific embodiment, a substituted or unsubstituted phenyl group, a substituted or unsubstituted meta-biphenyl group, or a substituted or It may be an unsubstituted para-biphenyl group.

In one embodiment of the present invention, R ⁷ to R ¹² in Formula 2 may be each independently hydrogen, deuterium, or a substituted or unsubstituted C6 to C12 aryl group, and in a specific embodiment, hydrogen or phenyl group. have.

In one embodiment of the present invention, m in Formula 2 may be 0 or 1, and in a specific embodiment, 0 may be 0.

In a more specific embodiment of the present invention, Formula 2 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. Can be

[Group Ⅱ]

[Group Ⅲ]

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

Specifically, Formula 2 is represented by C-8 or C-17 of Group II, and * -Y ¹ -Ar ¹ , and * -Y ² -Ar ² are B-1 to B- of Group III. It can be represented by any of the four.

More specifically, the * -Y ¹ -Ar ¹ , and * -Y ² -Ar ² may be selected from B-1, B-2, B-3 of Group III and combinations thereof. The compound for a second organic optoelectronic device represented by Formula 2 may be, for example, a compound listed in Group 2 below, but is not limited thereto.

[Group 2]

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

In one embodiment of the present invention, the compound for a second organic optoelectronic device consisting of a combination of a moiety represented by Formula 3 and a moiety represented by Formula 4 is represented by at least one of the following Formulas 3-I to 3-V. You can.

[Formula 3-Ⅰ] [Formula 3-Ⅱ] [Formula 3-Ⅲ]

[Formula 3-IV] [Formula 3-Ⅴ]

In Chemical Formulas 3-I to 3-V, Y ³ , Y ⁴ , Ar ³ , Ar ⁴ , and R ¹³ to R ¹⁶ are as described above.

In an embodiment of the present invention, Y ³ and Y ⁴ of Chemical Formulas 3-I to 3-V may be a single bond, a phenylene group, a biphenylene group, a pyridylene group, or a pyrimidinylene group.

In an embodiment of the present invention, Ar ³ and Ar ⁴ of Chemical Formulas 3-I to 3-V are substituted or unsubstituted phenyl groups, substituted or unsubstituted biphenyl groups, substituted or unsubstituted pyridyl groups, substituted or unsubstituted It may be a pyrimidinyl group, or a substituted or unsubstituted triazinyl group.

In an embodiment of the present invention, R ¹³ to R ¹⁶ of Chemical Formulas 3-I to 3-V may be hydrogen.

The compound for a second organic optoelectronic device consisting of a combination of a moiety represented by Formula 3 and a moiety represented by Formula 4 may be, for example, a compound listed in Group 3 below, but is not limited thereto.

[Group 3]

[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]

In the composition according to the most specific embodiment of the present invention, the compound for a first organic optoelectronic device is represented by Formula 1A-2 or Formula 1C-2, wherein L ¹ to L ³ are a single bond, and Formula 1A- R ¹ of 2 is a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted benzofuran pyrimidi Or a substituted or unsubstituted benzothiophenpyrimidinyl group, R ² to R ⁶ are each independently hydrogen, deuterium, substituted or unsubstituted C1 to C4 alkyl group or substituted or unsubstituted C6 to C18 aryl group , R ³ of Formula 1C-2 is a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted Crude furan-pyrimidinyl group, or a substituted or unsubstituted, and a benzothiophene pyrimidinyl ring group, R ^1, R ² and R ⁴ to R ⁶ is a C1 to C4 alkyl group or a substituted each independently hydrogen, deuterium, substituted or unsubstituted Or it may be an unsubstituted C6 to C18 aryl group. For example, R ² to R ⁶ of Formula 1A-2 and R ¹ , R ² and R ⁴ to R ⁶ of Formula 1C-2 may be hydrogen.

In addition, the compound for a second organic optoelectronic device is represented by C-8 or C-17 of Group II, wherein * -Y ¹ -Ar ¹ , and * -Y ² -Ar ² are B-1 of Group III. , B-2, B-3 and combinations thereof.

Meanwhile, 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, and the compound for the first organic optoelectronic device and the compound for the second organic optoelectronic device 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, 3: 7 to 7: 3, 4: 6 to 6: 4, 4: 6 to 8: 2, and 3: 7 to 7: 3, 3: 7 to 6 : 4, 3: 7 to 5: 5, and for example, 4: 6 to 5: 5. As a most specific example, the mixing ratio of the compound for the first organic optoelectronic device and the compound for the second organic optoelectronic device may be 5: 5.

By being included in the above range, bipolar characteristics can be more effectively implemented 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. An organometallic compound containing is mentioned. 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.

Hereinafter, an organic optoelectronic device to which the above-described compound for an organic optoelectronic device or a 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 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 auxiliary layer may further include an electron transport auxiliary layer adjacent to the light emitting layer, and the electron transport auxiliary layer may include the compound for an organic optoelectronic device or 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 device 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, for example, a conductor having a high work function to facilitate hole injection, for example, 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.

Although the organic layer 105 of FIG. 1 or 2 is not illustrated, 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 may be further included. 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, followed by 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, the starting materials, reactants, and intermediates used in Examples and Synthesis Examples were purchased from Sigma-Aldrich or TCI, or synthesized through a known method, or the method described herein, unless otherwise specified. It was synthesized through the method.

(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.

(First organic optoelectronic device compound)

Synthetic example  1: Synthesis of intermediate A-3 and intermediate A-4

[Scheme 1]

First step : Synthesis of Intermediate A-1 and Intermediate A-2

(1) Synthesis of Intermediate A-1

9,10-dibromophenanthrene (87.58g, 260.64 mmol), 4-chloropyridin-2-amine (50.26g, 390.96 mmol), sodium t-butoxide 50.10 g (521.28 mmol), palladium (II) in a 3L flask ) Acetate 2.93 g (13.03 mmol) and tri-butylphosphine 12.66 g (50% in toluene) were mixed with 1.3 L of xylene and heated to reflux for 15 hours under a nitrogen stream. The obtained mixture was added to 3 L of methanol to filter the crystallized solid, dissolved in monochlorobenzene, filtered with silica gel / celite, and after removing an appropriate amount of the organic solvent, recrystallized with methanol to give Intermediate A-1 (85.01 g, 85% yield).

(2) Synthesis of Intermediate A-2

3-Chloropyridin-2-amine was used instead of 4-chloropyridin-2-amine to obtain Intermediate A-2 (82.46 g, 82% yield) in the same manner as Intermediate A-1.

Stage 2 : Synthesis of Intermediate A-3 and Intermediate A-4

(1) Synthesis of Intermediate A-3

In a 2 L flask, intermediate A-1 (85.0 g, 221.54 mmol), potassium carbonate (76.55 g, 553.86 mmol) tetrakis (triphenylphosphine) palladium (0) (5.12 g, 4.43 mmol) were N, N-di After putting in 1 L of methyl formamide, it was heated to 140 ° C. for 24 hours under a nitrogen stream. After separating and volatilizing the organic layer, adding to 3 L of water and filtering the crystallized solid, intermediate column A-3 (45.1 g, yield of 67%) was obtained using column chromatography (EA / Hexane).

(2) Synthesis of Intermediate A-4

Intermediate A-2 was used instead of Intermediate A-1 to obtain Intermediate A-4 (42.90 g, 66% yield) in the same manner as Intermediate A-3.

Synthetic example  2: Synthesis of Intermediate A-8 and Intermediate A-9

[Scheme 2]

First step : Synthesis of Intermediate A-5

In a 3L flask, 100.0 g (470.21 mol) of 2-chlorophenanthrene is mixed with 1.5 L of methylene dichloride and the internal temperature is lowered to -10 ° C. While slowly adding 175.8 g (987.45 mol) of N-bromosuccinimide, the internal temperature is maintained at -10 ° C. After the reaction is completed, the reaction solution is washed with an aqueous sodium thiosulfate solution. After separation and removal of the organic solvent, intermediate A-5 (154.3 g, yield of 89%) was obtained through column chromatography.

Stage 2 : Synthesis of Intermediate A-6 and Intermediate A-7

In a 3 L flask, intermediate A-5 (154.00 g, 415.7 mmol), 2-aminopyridine 39.51 g, 419.85 mmol), sodium t-butoxide 79.91 g (831.39 mmol), palladium (II) acetate 4.67 g (20.78 mmol) and Tri-butylphosphine 20.19 g (50% in toluene) was mixed with 1.6 L of xylene and heated to reflux under nitrogen flow for 18 hours. The obtained mixture was added to 3 L of methanol to filter the crystallized solid, dissolved in monochlorobenzene, filtered with silica gel / celite, and the organic solvent was removed in an appropriate amount, and recrystallized with methanol to prepare Intermediate A-6 and Intermediate A. -7 (121.6 g, 76% yield) was obtained.

Stage 3 : Synthesis of Intermediate A-8 and Intermediate A-9

In a 3 L flask, intermediate A-6, and intermediate A-7 (120.0 g, 312.77 mmol), potassium carbonate (108.07 g, 781.92 mmol) tetrakis (triphenylphosphine) palladium (0) (7.23 g, 6.26 mmol) Was added to 1 L of N, N-dimethylformamide, and heated to 140 ° C. for 24 hours under a nitrogen stream. After separating and volatilizing the organic layer, adding 3 L of water to filter the crystallized solid, and then using column chromatography (EA / Hexane) -MPLC, intermediate A-8, and intermediate A-9 (36.2 g, 38 % Yield of 7: 3).

Synthetic example  3: Intermediate A-13, and Intermediate A- 14 of  synthesis

[Scheme 3]

First step : Synthesis of Intermediate A-10

Intermediate A-10 (130.5 g, 86% yield) was obtained in the same manner as Intermediate A-5 of Synthesis Example 2 using 3-chlorophenanthrene instead of 2-chlorophenanthrene of Synthesis Example 2.

Stage 2 : Synthesis of Intermediate A-11 and Intermediate A-12

Using intermediate A-10 instead of intermediate A-5 of synthesis example 2, intermediate A-6 of synthesis example 2, and intermediate A-11 and intermediate A-12 in the same manner as intermediate A-7 (106.3 g, 73%) Yield).

Stage 3 : Synthesis of Intermediate A-13 and Intermediate A-14

Intermediate A-13 of Synthesis Example 2 and Intermediate A-13 of Intermediate A-13 and Intermediate A-9 in the same manner as Intermediate A-13 and Intermediate A-9 were used instead of Intermediate A-6 of Intermediate A-7 and Intermediate A-7. And intermediate A-14 (37.4 g, 40% yield).

Synthetic example  4: Synthesis of Compound 3

[Reaction Scheme 4]

First step : Synthesis of Intermediate 1-1

Intermediate A-3 (50.0 g, 165.15 mmol), 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl-2,2'-bi (1,3, 2-Dioxabororan) (50.3 g, 198.18 mmol), potassium acetate (KOAc, 48.63 g, 495.4 mmol) and 1,1'-bis (diphenylphosphino) ferrocene-palladium (II) dichloride (8.1 g , 9.91 mmol) and tricyclohexylphosphine (13.9 g, 24.8 mmol) were added to 500 mL of N, N-dimethylformamide, followed by stirring at 130 ° C for 24 hours. After completion of the reaction, the reaction solution was extracted with water and EA to remove moisture using magnesium sulfate and concentrated, purified by column chromatography to give Intermediate 1-1 as a white solid (49.2 g, yield = 76 %).

Stage 2 : Synthesis of Compound 3

In a 100 ml flask, intermediate 1-1, (3.0 g, 7.89 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (2.11 g, 7.89 mmol), potassium carbonate (2.73 g, 19.72 mmol) Tetrakis (triphenylphosphine) palladium (0) (0.18 g, 0.16 mmol) was added to 30 mL of 1,4-dioxane and 15 mL of water, followed by heating at 100 ° C. for 12 hours under a nitrogen stream. The organic layer was separated and added to 300 mL of methanol to filter the crystallized solid, dissolved in monochlorobenzene, filtered with silica gel / celite, and after removing an appropriate amount of the organic solvent, recrystallized with monochlorobenzene to give compound 3 (2.9 g, 74 % Yield).

calcd. C34H21N5: C, 81.74; H, 4.24; N, 14.02; found: C, 81.74; H, 4.24; N, 14.02

Synthetic example  5: Synthesis of Compound 4

[Scheme 5]

First step : Synthesis of Intermediate 1-2

Cyanuric chloride (200.0 g, 1.085 mmol) and anhydrous THF 1.4L were added to a 3L flask, and Phenyl magnesium bromide (3M, 361.4 mL) was slowly added dropwise at 0 ° C. After completion of the reaction, water was poured into the reaction solution and stirred for 30 minutes, and then the organic layer was separated, and water was removed and concentrated using magnesium sulfate, and purified by methanol and hexane to give Intermediate 1-2 as a white solid (127.4 g, Yield = 52%).

Stage 2 : Synthesis of Intermediate 1-3

In a 2L round flask, intermediate 1-2 60.0 g 265.4 mmol), 3-biphenyl boronic acid 50.0 g (252.0 mmol), potassium carbonate 91.6 g (660.0 mmol), tetrakis (triphenylphosphine) palladium (0) 8.0 g (9.2 mmol) was added to 880 mL of 1,4-dioxane and 440 mL of water, and heated to reflux for 16 hours under a nitrogen stream. The obtained mixture was added to 3000 L of methanol to filter the crystallized solid, then dissolved in toluene, filtered with silica gel / celite, and after removing an appropriate amount of the organic solvent, recrystallized with methanol to obtain Intermediate 1-3 (63.6 g, 70 % Yield).

Stage 3 : Synthesis of Compound 4

Compound 4 (4.17 g, yield of 69%) was obtained by the same method as compound 3 of Synthesis Example 4 using intermediates 1-3 and intermediate 1-1.

 calcd. C40H25N5: C, 83.46; H, 4.38; N, 12.17. found: C, 83.46; H, 4.38; N, 12.17

Synthetic example  6 to 25

The starting material and the reacting material were as shown in Table 1 below, and the reaction method was synthesized in the same manner as in Compound 3 of Synthesis Example 4 to synthesize the compounds according to the present invention.

Synthetic example Starting material Reactants Final product Yield
(yield) Final product
Property data Synthesis Example 6

중간체 1-1

Intermediate 1-1

Intermediate 1-4

Compound 5 3.75 g, (62%) calcd. C40H25N5: C, 83.46; H, 4.38; N, 12.17. found: C, 83.46; H, 4.38; N, 12.17 Synthesis Example 7 Intermediate 1-1

Intermediate 1-5

Compound 6 4.31 g, (65%) calcd. C40H25N5: C, 83.46; H, 4.38; N, 12.17. found: C, 83.46; H, 4.37; N, 12.17
Synthesis Example 8 Intermediate 1-1

Intermediate 1-6

Compound 7 5.89 g, (65%) calcd. C40H23N5O: C, 81.48; H, 3.93; N, 11.88. O, 2.71; found: C, 81.48; H, 3.93; N, 11.88. O, 2.70
Synthesis Example 9 Intermediate 1-1

Intermediate 1-7

Compound 12 3.66g (61%) calcd. C39H24N4: C, 85.38; H, 4.41; N, 10.21. found: C, 85.38; H, 4.41; N, 10.21 Synthesis Example 10 Intermediate 1-1

Intermediate 1-8

Compound 13 4.18 g, (64%) calcd. C39H24N4: C, 85.38; H, 4.41; N, 10.21. found: C, 85.38; H, 4.41; N, 10.21
Synthesis Example 11 Intermediate 1-1

Intermediate 1-9

Compound 14 6.03 g, (62%) calcd. C39H22N4O: C, 83.26; H, 3.94; N, 9.96. O, 2.84; found: C, 83.26; H, 3.94; N, 9.96. O, 2.84
Synthesis Example 12 Intermediate 1-1

Intermediate 1-10

Compound 16 5.88 g, (66%) calcd. C39H23N5: C, 83.40; H, 4.13; N, 12.47. found: C, 83.40; H, 4.13; N, 12.47
Synthesis Example 13 Intermediate 1-1

Intermediate 1-11

Compound 40 4.79g, (67%) calcd. C39H24N4: C, 85.38; H, 4.41; N, 10.21. found: C, 85.38; H, 4.41; N, 10.21
Synthesis Example 14

Intermediate A-3

Intermediate 1-12

Compound 42 6.37g, (67%) calcd. C43H26N4: C, 86.26; H, 4.38; N, 9.36. found: C, 86.26; H, 4.38; N, 9.36
Synthesis Example 15 Intermediate A-3

Intermediate 1-13

Compound 43 5.52 g, (38%) calcd. C43H26N4: C, 86.26; H, 4.38; N, 9.36. found: C, 86.26; H, 4.38; N, 9.36
Synthesis Example 16

Intermediate 2-1

Intermediate 1-6

Compound 52 4.90 g, (65%) calcd. C40H23N5O: C, 81.48; H, 3.93; N, 11.88. O, 2.71; found: C, 81.48; H, 3.93; N, 11.88. O, 2.71
Synthesis Example 17 Intermediate 2-1

Intermediate 1-8

Compound 58 3.77 g, (71%) calcd. C39H24N4: C, 85.38; H, 4.41; N, 10.21. found: C, 85.38; H, 4.41; N, 10.21
Synthesis Example 18

Intermediate 3-1

Intermediate 1-6

Compound 97 4.33 g, (60%)
calcd. C40H23N5O: C, 81.48; H, 3.93; N, 11.88. O, 2.71; found: C, 81.48; H, 3.92; N, 11.88. O, 2.70
Synthesis Example 19 Intermediate 3-1 Intermediate 1-8

Compound 103 5.08g, (68%) calcd. C39H24N4: C, 85.38; H, 4.41; N, 10.21. found: C, 85.37; H, 4.41; N, 10.21 Synthesis Example 20

Intermediate 4-1 Intermediate 1-6

Compound 142 4.29 g, (67%) calcd. C40H23N5O: C, 81.48; H, 3.93; N, 11.88. O, 2.71; found: C, 81.48; H, 3.93; N, 11.88. O, 2.70
Synthesis Example 21 Intermediate 4-1 Intermediate 1-8

Compound 148 6.31g, (67%) calcd. C39H24N4: C, 85.38; H, 4.41; N, 10.21. found: C, 85.38; H, 4.41; N, 10.20 Synthesis Example 22

Intermediate 5-1 Intermediate 1-6

Compound 187 3.73 g, (62%) calcd. C40H23N5O: C, 81.48; H, 3.93; N, 11.88. O, 2.71; found: C, 81.48; H, 3.92; N, 11.88. O, 2.71 Synthesis Example 23 Intermediate 5-1 Intermediate 1-8

Compound 193 3.36g, (62%)
calcd. C39H24N4: C, 85.38; H, 4.41; N, 10.21. found: C, 85.37; H, 4.41; N, 10.21 Synthesis Example 24

Intermediate 6-1
Intermediate 1-6

Compound 232 5.74 g, (67%) calcd. C40H23N5O: C, 81.48; H, 3.93; N, 11.88. O, 2.71; found: C, 81.48; H, 3.93; N, 11.88. O, 2.71
Synthesis Example 25 Intermediate 6-1 Intermediate 1-8

Compound 238 3.93g, (74%) calcd. C39H24N4: C, 85.38; H, 4.41; N, 10.21. found: C, 85.38; H, 4.41; N, 10.21

Synthetic example  26: Synthesis of Compound 9

[Scheme 6]

First step : Synthesis of Intermediate 1-14

Compound intermediate 1-14 (51 g, yield of 47%) was obtained in the same manner as in Intermediate 1-3 of Synthesis Example 5.

Stage 2 : Synthesis of Compound 9

In a 100 mL flask, intermediate 1-14 (4.66 g, 10.19 mmol), carbazole (1.88, 11.21 mmol), sodium t-butoxide 1.96 g (20.39 mmol), tris (dibenzylideneacetone) dipalladium 0.59 g ( 1.02 mmol) and 0.86 g of tri-butylphosphine (50% in toluene) were mixed with 50 ml of xylene and heated to reflux under nitrogen flow for 24 hours. The obtained mixture was added to 200 L of methanol to filter the crystallized solid, then dissolved in monochlorobenzene, filtered with silica gel / celite, and after removing an appropriate amount of the organic solvent, recrystallized with methanol to give compound 9 (4.37 g, 73%) Yield).

calcd. C40H24N6: C, 81.61; H, 4.11; N, 14.28. found: C, 81.60; H, 4.11; N, 14.28

Synthetic example  27: Synthesis of Compound 32

[Scheme 7]

First step : Synthesis of Intermediate 1-16

In the same manner as in Intermediate 1-3 of Synthesis Example 5, Intermediate 1-16 (10.5 g, 62.4% yield) was obtained.

Stage 2 : Synthesis of Compound 32

Compound 32 (3.45 g, 58% yield) was obtained by the same method as compound 4 of Synthesis Example 5.

 calcd. C35H20N4S: C, 79.52; H, 3.81; N, 10.60; S, 6.07. found: C, 79.52; H, 3.81; N, 10.60; S, 6.06

Fabrication of organic light emitting device Ⅰ: Light emitting layer device -Single host ( Red )

Example  One

Compound 3 obtained in Synthesis Example 4 was used as a host, and (piq) ₂ Ir (acac) was used as a dopant to produce an organic light emitting device.

As an anode, ITO was used at a thickness of 1000 MPa, and as an anode, aluminum (Al) was used at a thickness of 1000 MPa. Specifically, when explaining the manufacturing method of the organic light emitting device, the anode was cut into ITO glass substrates having a sheet resistance value of 15 Ω / cm ² to a size of 50 mm ⅹ 50 mm ⅹ 0.7 mm, each in acetone, isopropyl alcohol, and pure water. After ultrasonic cleaning for minutes, UV ozone cleaning was used for 30 minutes.

N4, N4'-di (naphthalen-1-yl) -N4, N4'-diphenylbiphenyl-4,4 under conditions of vacuum degree 650 ⅹ 10 ^-7 Pa, deposition rate of 0.1 to 0.3 nm / s on the substrate '-Diamine (N4, N4'-di (naphthalene-1-yl) -N4, N4'-diphenylbiphenyl-4,4'-diamine: NPB) (80nm) was deposited to form a 800 정 hole transport layer. Subsequently, a light emitting layer having a film thickness of 300 Å was formed using Compound 3 obtained in Synthesis Example 4 under the same vacuum deposition conditions. At this time, a phosphorescent dopant (piq) ₂ Ir (acac) was simultaneously deposited. At this time, by adjusting the deposition rate of the phosphorescent dopant, when the total amount of the light emitting layer is 100% by weight, the compounding amount of the phosphorescent dopant was deposited to be 3% by weight.

Bis (2-methyl-8-quinolinolate) -4- (phenylphenolate) aluminum (bis (2-methyl-8-quinolinolate) -4- using the same vacuum deposition conditions on the light emitting layer.

(phenylphenolato) aluminium: BAlq) was deposited to form a hole blocking layer with a thickness of 50 Å. Subsequently, Alq 3 was deposited under the same vacuum deposition conditions to form an electron transport layer having a thickness of 200 mm 2. An organic optoelectronic device was fabricated by sequentially depositing LiF and Al as cathodes on the electron transport layer.

The structure of the organic optoelectronic device is ITO / NPB (80 nm) / EML (Compound 3 (97 wt%) + (piq) ₂ Ir (acac) (3 wt%), 30 nm) / Balq (5 nm) / Alq3 (20 nm) ) / LiF (1nm) / Al (100nm).

Example  2 to Example  24

Compound 4, 5, 6, 7, 9, 12, 13, 14, 16, 32, 40, 42, 43, 52, 58, 97, 103, 142, 148, 187, 193 instead of compound 3 as a host when forming the light emitting layer , 232 and 238 were used, respectively, and the organic light emitting devices corresponding to Examples 2 to 24 were manufactured using the same method as in Example 1 above.

Comparative example  1 to 3

The organic light emitting device corresponding to Comparative Examples 1 to 3 was manufactured using the same method as in Example 1, except that Comparative Structure Examples 2 to 4 were used instead of Compound 3 as a host when forming the emission layer. The simulation data for Compound 52 and Comparative Structure Examples 1 to 7 are shown in Table 2 below.

T1 S1 HOMO LUMO Comparative Structure Example 1 2.75 3.309 -5.712 -1.982 Comparative Structure Example 2 2.483 3.217 -5.7 -2.119 Comparative Structure Example 3 2.494 2.951 -5.37 -2.009 Comparative Structure Example 4 2.34 2.945 -5.378 -2.097 Comparative Structure Example 5 2.328 2.806 -5.1 -1.866 Comparative Structure Example 6 2.59 3.51 -5.536 -1.654 Comparative Structure Example 7 2.091 3.352 -5.43 -1.759 Compound 52 2.451 2.867 -5.421 -2.110

(Comparative structural example 1) (Comparative structural example 2) (Comparative structural example 3) (Comparative structural example 4)

(Comparative structural example 5) (Comparative structural example 6) (Comparative structural example 7)

When comparing the simulation values of Comparative Structure Examples 1 to 7 and Compound 52, Comparative Structure Examples 1 and 7 do not smoothly transmit energy to the dopant because the T1 energy level is outside the Red region. And Comparative Structure Examples 5 and 6 have a high LUMO level, resulting in poor electron mobility or high driving voltage.

This is different from the structure of the present invention in which one of the two N's is contained in the terminal phenyl of the center core. In Comparative Structure Examples 1 to 4, Comparative Structure Examples 6 and 7 do not include both N's in the terminal phenyl of the center core. Since it is located outside the terminal phenyl of the center core, the deposition temperature is relatively high, and the film characteristics are not good during device fabrication, which adversely affects the device results. In the case of Comparative Structure Example 5, only one N is included in the center core. The LUMO value is relatively high, driving voltage is pushed, and the stability of the compound is likely to be degraded.

Evaluation example  1: Evaluation of characteristics of organic light emitting device (I)

The luminous efficiency and lifetime characteristics of the organic light emitting devices according to Examples 1 to 24 and Comparative Examples 1 to 3 were evaluated.

Specific measurement methods are as follows, and the results are shown in Table 3.

(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 manufactured 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) Driving voltage measurement

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

No. compound Driving voltage (V) Current efficiency
(cd / A) color
(EL color) Example 1 Compound 3 4.4 20.4 Red Example 2 Compound 4 4.2 21.3 Red Example 3 Compound 5 3.9 21.4 Red Example 4 Compound 6 4.2 21.7 Red Example 5 Compound 7 3.9 22.4 Red Example 6 Compound 9 4.0 22.0 Red Example 7 Compound 12 4.2 20.9 Red Example 8 Compound 13 4.0 22.2 Red Example 9 Compound 14 3.9 21.3 Red Example 10 Compound 16 4.0 21.1 Red Example 11 Compound 32 4.3 20.5 Red Example 12 Compound 40 3.7 22.0 Red Example 13 Compound 42 3.7 20.7 Red Example 14 Compound 43 3.9 20.5 Red Example 15 Compound 52 3.7 22.8 Red Example 16 Compound 58 3.9 21.5 Red Example 17 Compound 97 3.9 21.4 Red Example 18 Compound 103 4.0 20.9 Red Example 19 Compound 142 4.0 21.8 Red Example 20 Compound 148 4.2 21.4 Red Example 21 Compound 187 3.7 22.0 Red Example 22 Compound 193 3.8 22.4 Red Example 23 Compound 232 3.9 21.0 Red Example 24 Compound 238 4.1 20.7 Red Comparative Example 1 Comparative Structure Example 2 4.4 18.4 Red Comparative Example 2 Comparative Structure Example 3 4.6 17.3 Red Comparative Example 3 Comparative Structure Example 4 4.5 18.0 Red

Referring to Table 3, it can be seen that the organic light emitting devices of Examples 1 to 24 of the present invention have a low driving voltage and high efficiency compared to the organic light emitting devices of Comparative Examples 1 to 3.

In addition, it can be seen that it is a phosphorescent host material that has excellent charge-transporting properties and is a material that overlaps well with the absorption spectrum of the dopant, improving performance such as increasing efficiency and decreasing driving voltage, and maximizing its ability as an OLED material.

Fabrication of organic light emitting device ( Light emitting layer device -Mixed Host)

Example  25

On the hole transport layer, (piq) ₂ Ir (acac) (dopant), compound 52 (first host) and compound B-99 (second host) were co-deposited in a weight ratio of 3: 48.5: 48.5 to emit a 400 층 thick light emitting layer. An organic light emitting device was manufactured in the same manner as in Example 1, except that the light emitting layer was formed by forming.

Example  26 to Example  30

Examples 26 to 26 in the same manner as in Example 25, except that the first host and the second host shown in Table 4 were used instead of the first host compound 52 and the second host B-99 when forming the light emitting layer. Each of the organic light emitting devices of Example 30 was produced.

Evaluation example  2: Evaluation of characteristics of organic light emitting device (II)

The driving voltage, efficiency, brightness, and lifetime of the organic light emitting diodes of Examples 25 to 30 and Comparative Example 1 are supplied with power from a current voltmeter (Kethley SMU 236), and the brightness is PR650 Spectroscan Source Measurement Unit. (Product of PhotoResearch) Table 4 shows the results of the evaluation.

NO. Host 1 Host 2 Driving
Voltage (V) Current efficiency
(cd / A) EL color Example 25 52 B-99 3.6 23.0 Red Example 26 193 B-99 3.7 22.6 Red Example 27 52 B-130 3.8 22.6 Red Example 28 193 B-130 3.8 22.5 Red Example 29 52 B-137 3.7 22.8 Red Example 30 193 B-137 3.8 22.7 Red Comparative Example 1 Comparative structural example 2 4.4 18.4 Red

From Table 4, it can be seen that the organic light emitting devices of Examples 25 to 30, which are compounds of the present invention, have a low driving voltage or high efficiency by using the first host material and the second host material together.

The present invention is not limited to the above embodiments, but may be manufactured in various different forms, and those skilled in the art to which the present invention pertains 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 (13)

Compound for an organic optoelectronic device represented by the following formula (1):
[Formula 1]

In Chemical Formula 1,
L ¹ to L ³ 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,
R ¹ to R ⁶ 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 C30 heterocyclic group, or a combination thereof ego,
At least one of R ¹ to R ³ is a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted Isoquinolinyl group, substituted or unsubstituted naphthyridinyl group, substituted or unsubstituted quinazolinyl group, substituted or unsubstituted benzoquinazolinyl group, substituted or unsubstituted benzimidazolyl group, substituted or unsubstituted benzofuran A pyrimidinyl group, a substituted or unsubstituted benzothiophenpyrimidinyl group, a substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted indolocarbazole group,
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 C18 heteroaryl group. According to claim 1,
A compound for an organic optoelectronic device represented by any one of the following Chemical Formula 1-A1, Chemical Formula 1-A2, Chemical Formula 1-B1, Chemical Formula 1-B2, Chemical Formula 1-C1, and Chemical Formula 1-C2:
[Formula 1-A1] [Formula 1-A2] [Formula 1-B1]

[Formula 1-B2] [Formula 1-C1] [Formula 1-C2]

In Formula 1-A1 and Formula 1-A2,
L ¹ to L ³ are each independently a single bond, a substituted or unsubstituted C6 to C18 arylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, or a combination thereof,
R ¹ is substituted or unsubstituted pyridinyl group, substituted or unsubstituted pyrimidinyl group, substituted or unsubstituted triazinyl group, substituted or unsubstituted quinolinyl group, substituted or unsubstituted isoquinolinyl group, substituted Or an unsubstituted naphthyridinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted benzoquinazolinyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted benzofuranpyrimidinyl group, a substituted or An unsubstituted benzothiophenpyrimidinyl group, a substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted indolocarbazole group,
R ² to R ⁶ are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C5 alkyl group, a substituted or unsubstituted C6 to C18 aryl group, a substituted or unsubstituted C2 to C18 heterocyclic group, or a combination thereof ego;
In Formula 1-B1 and Formula 1-B2,
L ¹ to L ³ are each independently a single bond, a substituted or unsubstituted C6 to C18 arylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, or a combination thereof,
R ² is a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted Or an unsubstituted naphthyridinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted benzoquinazolinyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted benzofuranpyrimidinyl group, a substituted or An unsubstituted benzothiophenpyrimidinyl group, a substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted indolocarbazole group,
R ¹ and R ³ to R ⁶ are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C5 alkyl group, a substituted or unsubstituted C6 to C18 aryl group, a substituted or unsubstituted C2 to C18 heterocyclic group, or Combinations of these;
In Formula 1-C1 and Formula 1-C2,
L ¹ to L ³ are each independently a single bond, a substituted or unsubstituted C6 to C18 arylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, or a combination thereof,
R ³ is a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted Or an unsubstituted naphthyridinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted benzoquinazolinyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted benzofuranpyrimidinyl group, a substituted or An unsubstituted benzothiophenpyrimidinyl group, a substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted indolocarbazole group,
R ¹ , R ² and R ⁴ to R ⁶ are each independently hydrogen, deuterium, substituted or unsubstituted C1 to C5 alkyl group, substituted or unsubstituted C6 to C18 aryl group, substituted or unsubstituted C2 to C18 heterocycle Group, or a combination thereof. According to claim 1,
At least one of R ¹ to R ³ is a compound for an organic optoelectronic device selected from the substituents listed in Group I below:
[Group Ⅰ]

In Group I, * is a connection point. According to claim 1,
Compounds for organic optoelectronic devices, one selected from the compounds listed in Group 1 below:
[Group 1]

. The compound for a first organic optoelectronic device according to claim 1; And
For an organic optoelectronic device comprising a compound for at least one second organic optoelectronic device of a compound consisting of a compound represented by the following formula (2), and a moiety represented by the following formula (3) and a moiety represented by the following formula (4) Composition:
[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,
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 ⁷ to R ¹² 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 C50 heterocyclic group, or combinations thereof,
m is an integer from 0 to 2;
[Formula 3] [Formula 4]

In Chemical Formulas 3 and 4,
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 ¹³ to R ¹⁶ 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 ego,
The two adjacent * in Formula 3 are connected to the two * in Formula 4 to form a fused ring, and * in the Formula 3 not forming a fused ring is each independently CR ^a ,
R ^a is each independently 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;
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 C18 heteroaryl group. The method of claim 5,
Ar ¹ and Ar ² in the 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 naphthyl group, a substituted or unsubstituted ring unsubstituted ring Anthracenyl group, substituted or unsubstituted triphenylenyl group, substituted or unsubstituted pyridinyl group, substituted or unsubstituted dibenzothiophenyl group, substituted or unsubstituted dibenzofuranyl group, substituted or unsubstituted carba A composition for an organic optoelectronic device that is a zolyl group, a substituted or unsubstituted fluorenyl group, or a combination thereof. The method of claim 5,
Formula 2 is one of the structures listed in Group II below,
The * -Y ¹ -Ar ¹ , and * -Y ² -Ar ² is one of the substituents listed in Group III below, the composition for an organic optoelectronic device:
[Group Ⅱ]

[Group Ⅲ]

In group II and group III, * is a connection point. The method of claim 7,
Formula 2 is represented by C-8 or C-17 of Group II,
The * -Y ¹ -Ar ¹ , and * -Y ² -Ar ² is a composition for an organic optoelectronic device represented by any one of B-1 to B-4 of the group III. The method of claim 8,
The first compound for an organic optoelectronic device is a composition for an organic optoelectronic device represented by the following formula 1A-2 or formula 1C-2:
[Formula 1A-2] [Formula 1C-2]

In Formula 1A-2 and Formula 1C-2,
L ¹ to L ³ are a single bond,
R ¹ of Formula 1A-2 is a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted benzo Furan pyrimidinyl group, or a substituted or unsubstituted benzothiophenpyrimidinyl group, R ² to R ⁶ are each independently hydrogen, deuterium, substituted or unsubstituted C1 to C4 alkyl group or substituted or unsubstituted C6 to C18 Is an aryl group,
R ³ of Formula 1C-2 is a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted benzo Furan pyrimidinyl group, or a substituted or unsubstituted benzothiophenpyrimidinyl group, R ¹ , R ² and R ⁴ to R ⁶ are each independently hydrogen, deuterium, substituted or unsubstituted C1 to C4 alkyl group or substituted or Unsubstituted C6 to C18 aryl group. 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 a compound for an organic optoelectronic device according to any one of claims 1 to 4; or
An organic optoelectronic device comprising the composition for an organic optoelectronic device according to any one of claims 5 to 9. The method of claim 10,
The organic layer includes a light emitting layer,
The compound for an organic optoelectronic device or the composition for an organic optoelectronic device is included as a host of the light emitting layer. The method of claim 11,
The organic layer further includes an electron transport auxiliary layer adjacent to the light emitting layer,
The electron transport auxiliary layer is a compound for the organic optoelectronic device; Or an organic optoelectronic device comprising the composition for the organic optoelectronic device. A display device comprising the organic optoelectronic device according to claim 10.

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