WO2018128255A1

WO2018128255A1 - Compound for organic optoelectronic element, composition for organic optoelectronic element, organic optoelectronic element, and display device

Info

Publication number: WO2018128255A1
Application number: PCT/KR2017/011928
Authority: WO
Inventors: 류진현; 김창우; 유은선; 장기포; 정호국; 조영경
Original assignee: 삼성에스디아이 주식회사
Priority date: 2017-01-05
Filing date: 2017-10-26
Publication date: 2018-07-12

Abstract

The present invention relates to a compound expressed by chemical formula 1 for an organic optoelectronic element, a composition for an organic optoelectronic element, an organic optoelectronic element employing the same, and a display device. The details of chemical formula 1 are as defined in the specification.

Description

【Specification]

[Name of invention]

Compound for organic optoelectronic devices.Composition for water organic optoelectronic devices, organic optoelectronic devices and display devices

Technical Field

A compound for organic optoelectronic devices, a composition for organic optoelectronic devices, an organic optoelectronic device, and a display device.

Background Art

Organic optoelectronic diodes are devices that can switch electrical energy and light energy.

Organic optoelectronic devices can be divided into two types according to the principle of operation. One is an optoelectronic device in which an exciton formed by light energy is separated into electrons and holes, and the electrons and holes are transferred to the other electrode to generate electrical energy, and the other is to supply voltage or current to the electrodes. To generate light energy from electrical energy.

Examples of the organic optoelectronic device may be 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 recently attracted much attention as demand for flat panel displays increases. The organic light emitting device converts electrical energy into light by applying an electric current to the organic light emitting material. The organic light emitting device has a structure in which an organic layer is inserted between an anode and a cathode. The organic layer may include a light emitting layer and an auxiliary layer, and the auxiliary layer may be, for example, a hole injection layer and a hole transport layer to increase the efficiency and stability of the organic light emitting device. It may include at least one layer selected from an electron blocking layer, an electron transport layer, an electron injection charge and a hole blocking layer.

The performance of the organic light emitting device is greatly influenced by the characteristics of the organic layer, and in particular, by the organic materials included in the organic layer.

In particular, the organic light emitting diode is applied to a large flat panel display. In order to increase the mobility of holes and electrons, it is necessary to develop organic materials that can increase electrochemical stability.

[Detailed Description of the Invention] ^"

[Technical problem]

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

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

Yet another embodiment provides an organic optoelectronic device including the compound.

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

ί technical solution

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

One ]

In Chemical Formula 1,

Ζ ¹ to Ζ ³ are each independently Ν or CR ^a ,

At least two of Z ¹ to Z ³ are N,

X is 0 or S,

L is a single bond, a substituted or unsubstituted C6 to C30 arylene group, or a substituted or unsubstituted C2 to C30 heteroarylene group,

Ar is a substituted or unsubstituted C6 to C30 aryl group,

R ^a and R ¹ to R ¹⁰ are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a combination thereof, "Substituted" means that at least one hydrogen is substituted with deuterium, C1 to C20 alkyl group C6 to C30 aryl group, or C2 to C30 heteroaryl group.

According to another embodiment, the compound for a first organic optoelectronic device described above; And a second organic optoelectronic device compound including a carbazole moiety represented by Formula 2 below.

2]

In Chemical Formula 2,.

Y ¹ is a single bond, a substituted or unsubstituted C6 to C30 arylene group, or a substituted or unsubstituted C2 to C30 heteroarylene group,

A ¹ is a substituted or unsubstituted C6 to C30 aryl group, or-a substituted or unsubstituted C2 to C30 heterocyclic group,

. R ¹¹ to. Each R ¹⁶ is independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group,

R ¹³ to R ¹⁶ are each independently present or adjacent groups of R ¹³ to R ¹⁶ are connected to form a substituted or unsubstituted aliphatic, aromatic or heteroaromatic monocyclic or polycyclic ring,

The "substituted", at least one hydrogen is hydrogen, C1 to C4 alkyl group,

Substituted with a C6 to C18 aryl group or a C2 to C30 heteroaryl group;

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

According to yet another embodiment a display comprising the organic optoelectronic device Provide the device.

【Effects of the Invention】

High efficiency long life organic optoelectronic devices can be implemented.

[Brief Description of Drawings]

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

[Form for implementation of invention]

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

In the present specification, "substituted" 'unless otherwise defined, at least one hydrogen of a substituent or a compound is a deuterium, a halogen group, a hydroxyl group, an amino group, a 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, It is substituted with a C2 to C30 heteroaryl group, a C1 to C20 alkoxy group / C1 to C10 trifluoroalkyl group, a cyano group, or a combination thereof.

In one embodiment of the present invention, "substituted" means that at least one hydrogen of 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 a heterocycloalkyl group, a C6 to C30 aryl group, a C2 to C30 heteroaryl group. Also in of eu embodiments of the ^invention, one example, a "substituted" shall have at least one hydrogen in the substituent or a compound means that the heavy hydrogen, C1 to C20 alkyl groups, C6 to C30 aryl group, or a C2 to C30 heteroaryl group substituted . In addition, in one specific embodiment of the present invention, "substituted" means that at least one hydrogen of the substituent or compound is deuterium, C1 to C5 alkyl group, C6 to C18 aryl group, pyridinyl group, quinolinyl group, isoquinolinyl group, di Mean substituted by a benzofuranyl group, a dibenzothiophenyl group, or a carbazolyl group. In addition, in a specific embodiment of the present invention, "substituted" means that at least one hydrogen of the substituent or compound is deuterium, C1 to C5 alkyl group, C6 to It means substituted with a C18 aryl group, dibenzofuranyl group or dibenzothiophenyl group. In addition, in a specific embodiment of the present invention, "substituted" means that at least one hydrogen of the substituent or compound is deuterium, methyl, ethyl, Mean substituted by propaneyl group, butyl group, phenyl group, biphenyl group, terphenyl group, naphthyl group, triphenyl group, dibenzofuranyl group or dibenzothiophenyl group.

As used herein, "hetero" means one to three heteroatoms selected from the group consisting of N, 0, S, P, and Si in one functional group, and the rest are carbon unless otherwise defined. .

As used herein, unless otherwise defined, an "alkyl group" means an aliphatic hydrocarbon group. Alkyl groups may be "saturated alkyl groups" that do not contain any double or triple bonds.

The alkyl group may be an alkyl group of C1 to C30. 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 methyl, ethyl, propyl, iso-propyl, n-butyl, iso-butyl. sec-butyl and t-butyl.

Specific examples of the alkyl group include methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, t-butyl group, pentyl group, nucleosil group, cyclopropyl group, cyclobutyl group, cyclopentyl group and cyclonucleus. It means a practical skill. As used herein, an "aryl group" refers to a group of groups having one or more hydrocarbon aromatic moieties.

All of the elements of the hydrocarbon aromatic moiety have a P-orbital, and these P-orbitals form a conjugate (conj ugat i on), such as a phenyl group, a naphthyl group, and the like.

Two or more hydrocarbon aromatic moieties are linked via sigma bonds, such as biphenyl groups, terphenyl groups, quarterphenyl groups, etc.

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

Aryl groups include monocyclic, polycyclic or fused ring polycyclic (ie, rings having adjacent pairs of carbon atoms) functional groups. As used herein, the term "heterocyc lic group" is a higher concept including a heteroaryl group, and N, 0 instead of carbon (C) in a ring compound such as an aryl group, a cycloalkyl group, a fused ring thereof, or a combination thereof. It means that it contains at least one hetero atom selected from the group consisting of S, P and Si. In the case where the heterocyclic group is a fused ring, the heterocyclic group may include one or more heteroatoms for all or each ring.

For example, "heteroaryl group" means containing at least one hetero atom selected from the group consisting of N, 0, S, P and Si in the aryl group. 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, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an 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 is 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 m-terphenyl group, substituted or unsubstituted 0-terphenyl group, substituted or unsubstituted chrysenyl group, substituted or unsubstituted triphenylene group, substituted or unsubstituted perenyl group, substituted or unsubstituted fluorenyl 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 imidazolyl group, Substituted or unsubstituted triazolyl group, substituted or unsubstituted oxazolyl group, substituted or unsubstituted thiazolyl group, substituted or unsubstituted oxadiazoleyl group, substituted or unsubstituted thiadiazoleyl group, substituted or unsubstituted A substituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or Unsubstituted triazinyl group, substituted or unsubstituted benzofuranyl group, substituted or unsubstituted benzothiophenyl group, substituted or unsubstituted benzimidazolyl group, substituted or unsubstituted indolyl group, substituted or unsubstituted quinoli Neil group. Substituted tc unsubstituted isoquinolinyl group, substituted or unsubstituted quinazolinyl group, substituted or unsubstituted quinoxalinyl group, substituted or unsubstituted naphthyridinyl group, substituted unsubstituted benzoxazinyl group, substituted or unsubstituted Substituted benzthiazinyl group, substituted C unsubstituted acridinyl group, substituted or unsubstituted phenazineyl group, substituted c unsubstituted phenothiazineyl group, substituted or unsubstituted phenoxazineyl group, substituted unsubstituted The dibenzofuranyl group CC may be a 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 capable of forming holes by donating electrons when an electric field is applied, and as a light emitting layer of a hole formed at the anode having a conductive property along the HOMO quasi-level. It means the characteristic that facilitates the injection, movement of the holes formed in the light emitting layer to the anode and movement in the light emitting layer.

^■ In addition to referring to properties that can receive e-electronic properties when applied and is the electric field. It has a conductive property along the LIJM0 level, which means that the electrons formed in the cathode are easily injected into the light emitting layer, the electrons formed in the light emitting layer move to the cathode, and are easily moved in the light emitting layer. Hereinafter, a compound for an organic optoelectronic device according to one embodiment is described.

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

In Chemical Formula 1,

Z ¹ to Z ³ are each independently N or CR ^a , At least two of Z ¹ to V are N,

X is 0 or S,

Ar is a substituted or unsubstituted C6 to C30 aryl group,

R ^a and R ¹ to R ¹⁰ are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a combination thereof,

The "substituted" means that at least one hydrogen is substituted with deuterium, a C1 to C20 alkyl group, a C6 to C30 aryl group, or a C2 to C30 heteroaryl group.

In a specific embodiment of the present invention, the "substituted" may mean that at least one hydrogen is substituted with deuterium, C1 to C20 alkyl group, or C6 to C30 aryl group, more specifically at least one hydrogen is deuterium, C1 To C10 alkyl group, phenyl group, biphenyl group, or naphthyl group. It may mean substituted.

The compound for an organic optoelectronic device according to the present invention has a T core containing an N-containing six-membered ring, which includes a substituent directly connected without a linking group at position 2 of dibenzofuran or dibenzothiophene, thereby effectively expanding the LUM0 energy band and forming a molecular structure. The planarity of the structure may be increased, and thus the structure may easily receive electrons when an electric field is applied, thereby lowering the driving voltage of the organic optoelectronic device to which the compound for an organic optoelectronic device is applied. In addition, the expansion of LUM0 and the fusion of rings increase the stability of the electrons of the ΕΤ core, which is effective in improving device life.

In addition, since the diaryl fluorene is substituted, the glass transition degree (Tg) of the compound is higher than that of the dialkyl fluorene-substituted structure, thereby increasing stability of the compound during the process and preventing deterioration when applied to the device.

The glass transition temperature (Tg) may be related to the thermal stability of the compound and the device to which it is applied. That is, the compound for an organic optoelectronic device having a high glass transition temperature (Tg), when applied to the organic light emitting device in the form of a thin film, is a subsequent process, such as after deposition of the compound for the organic optoelectronic device In the encapsulat ion process, it is prevented from being degraded by temperature, thereby ensuring the life characteristics of the organic compound and the device.

In particular, since the diphenyl fluorene is substituted at the 4 position, it is possible to secure a much lower deposition temperature at the same molecular weight than the structure in which fluorene is substituted at another position, thereby preventing deterioration during high temperature storage or deposition process. . Accordingly, the driving voltage, efficiency, and lifespan characteristics of the organic optoelectronic device to which the compound for organic optoelectronic devices is applied may be improved.

In one embodiment of the present invention, Formula 1 may be represented by any one of the following Formula 1A, Formula 1B and Formula 1C, depending on the position of substitution of diphenyl fluorene.

1A] [Formula IB]

^{In the} above Formulas 1A, 1B, and 1C, the definitions of Z ¹ to Z ³ , X, L, Ar, and R ¹ to R ¹⁰ are as described above.

In addition, in one embodiment of the present invention, Formula 1 may be represented by any one of the following Formula 1-1, Formula 1-Π and formula im depending on the number and position of N included in Z ¹ to Z ³ .

[Formula 1-1] [Formula 1-Π]

In Formula 1-1, Formula 1-I, and Formula 1-m, X, L, Ar, and R to R ¹⁰ are the same as described above, and R ^al to R ^a3 are the same as the definitions of R ^a .

In a specific embodiment of the present invention, a structure represented by the general formula 1-I wherein Z ¹ to Z ³ are all N is preferred.

Specifically, L of Chemical Formula 1 may be a single bond. More specifically, of Chemical Formula 1A, Xing-group Chemical Formula 1B, Chemical Formula 1C, Chemical Formula, Chemical Formula ι-π and Chemical Formula l-m. [May be a single combination.

For example, Chemical Formula 1 is preferably a structure represented by Chemical Formula 1C or Chemical Formula 1-1, and most preferably, a structure represented by Chemical Formula 1C.

In one specific embodiment of the present invention, Ar is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted flu Orenyl group. Specifically, Ar may be a phenyl group, a biphenyl group, or a terphenyl group. More specifically, the biphenyl group may be a met a—biphenyl group or a para-biphenyl group, and the terphenyl group may be a meta-terphenyl group, a terphenyl group connected to met a in an i so form.

In one specific embodiment of the present invention, R ¹ to R ¹⁰ are each independently hydrogen, deuterium, methyl group, ethyl group, n-propyl group, i so-propyl group, It may be a substituted or unsubstituted phenyl group, or a substituted or unsubstituted naphthyl group, specifically, R ¹ to R ¹⁰ may be each independently hydrogen, methyl group, ethyl group, or phenyl group, the most specific embodiment of the present invention In an example, R ¹ to R ¹⁰ may be hydrogen or a phenyl group, and more specifically, R ¹ to R ¹⁰ may be all hydrogen.

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

[Group 1]

-1] [A-2] [A-3] [A-41

[Α-17ΠΑ— 18] [A-19] [A— 20]

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

Composition for an organic optoelectronic device according to another embodiment of the present invention is a compound for a first organic optoelectronic device described above; And a second organic optoelectronic device compound including a carbazole moiety represented by Formula 2 below.

In Chemical Formula 2,

A ¹ is a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group,

Rll to Rl ⁶ are each independently hydrogen, deuterium, substituted or unsubstituted

A C1 to C20 alkyl group substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group,

R ¹³ to R ¹⁶ are each independently present or adjacent groups of R ¹³ to R ¹⁶ are connected to form a substituted or unsubstituted aliphatic aromatic or heteroaromatic monocyclic or polycyclic ring.

"Substituted" means that at least one hydrogen is deuterium, a C1 to C4 alkyl group, a C6 to C18 aryl group, or a C2 to C30 heteroa _; Mean substituted by a aryl group. In a specific embodiment of the present invention, the "substituted". It means that at least one hydrogen is substituted with deuterium, phenyl group, or tho-biphenyl group, met a-biphenyl group, para-biphenyl group, terphenyl group, naphthyl group, dibenzofuranyl group or dibenzothiophenyl group.

In one embodiment of the present invention, Formula 2 is represented by the following Formula 2A. Or a composition for an organic optoelectronic device, which is one selected from a combination of Formulas 2B-1 and 2B-2:

[Formula 2A] [Formula 2B-1] [Formula 2B-2]

In Formula 2A, Formula 2B-1, and Formula 2B-2,

Y ¹ to Y 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,

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

R ¹¹ to R ¹³ , and R ¹⁷ to R ²¹ 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 hetero Ring groups, or a combination thereof.

m is one of the integers of 0-2. More preferably ni = 0.

In one embodiment of the present invention, Formula 2 may be represented by the following Formula 2A or Formula 2C.

In Chemical Formulas 2A and 2C,

Y ² and Y ³ are the same as the definition of Y ¹ described above, A ² and A ³ are the same as the definition of A ¹ described above, R ¹⁷ to R ²¹ are the same as the definition of R ¹¹ to R ¹⁶ described above, m is one of the integers of 0-2.

In a specific embodiment of the present invention, Y ¹ to Y ³ of Formula 2A, Formula 2B-1, Formula 2B-2, and Formula 2C each independently represent a single bond, or a substituted or unsubstituted C6 to C18 arylene. It may be a flag. Specifically, it may be a single bond, met a-phenylene group, or para-phenylene group.

In a specific embodiment of the present invention, A ¹ to A ³ of Formula 2A, Formula 2B-1, Formula 2B-2, and Formula 2C are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group. ， Substituted or unsubstituted Terphenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted anthracenyl group substituted or unsubstituted triphenylene group, substituted or unsubstituted pyridinyl group, substituted or unsubstituted dibenzothiophenyl group, substituted or Unsubstituted dibenzofuranyl group, substituted or unsubstituted carbazolyl group, substituted or unsubstituted fluorenyl group, or a combination thereof. Specifically, substituted or unsubstituted phenyl group, substituted or unsubstituted biphenyl group, substituted or unsubstituted terphenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted triphenylene group, substituted or unsubstituted dibenzo It may be a thiophenyl group, or a substituted or unsubstituted dibenzofuranyl group. In one embodiment of the present invention, in Formula 2A, Formula 2B-1, Formula 2B-2, Formula 2C, R ¹¹ to R ¹³ , and R ¹⁷ to R ²¹ are each independently hydrogen, deuterium, or substituted or unsubstituted. It may be a C6 to C12 aryl group. Specifically, it may be hydrogen or a phenyl group.

In a specific embodiment of the present invention, m in Formula 2A may be 0 or 1, preferably m = 0.

In addition, when ni = 0 in Formula 2A, the binding position of carbazoles in the core of biscarbazole is more preferably 2, 3-bond, 3, 3-bond or 2, 2-bond, and 3 _: 3. Bonding is more preferred.

In one more specific embodiment of the present invention, Formula 2A is one of the structures listed in Group I below, and * SE and * —Y ² — A ² may be one of the substituents listed in Group ^II below.

[Group I]

In the groups I and Π, * is the point of attachment.

The compound for the organic optoelectronic device 2 is represented by Formula 2 may be selected from, for example, the compounds listed in Group 2.

[Group 2]

[E-1] [Ε-2] [Ε— 3] [Ε-4] [Ε-5]

[E-31] [E-32] [E-33] [E-34] [E-35] 8ΐ

Ζ6ΐΐ0 / Ζ.ΐ0ΖΗΜ / Χ3 <Ι

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

Ζ6ΐΐΟ / Ζ.ΐΟΖΗΜ / Χ3 <Ι

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

S

o

The compound for the first organic optoelectronic device and the compound for the second organic optoelectronic device described above may prepare various compositions by various combinations.

The composition according to an embodiment of the present invention may include a compound represented by Formula 1C as a first host, and may include a compound represented by Formula 2A or 2C as a second host. In this case, Z ¹ to Z ³ of Formula 1C may be all N. In the case of the formula 2A, can be a structure represented by formula C-8 or C-17 of the group I, ^ -Α ¹ and -Y ² -A ² are to the * groups Π B-1, B-2 , And B-3.

The second compound for an organic optoelectronic device may improve the light emission efficiency by increasing the reliability it is 1, using the light-emitting ^layer, with a compound for an organic optoelectronic device to increase the mobility of charge and lifetime characteristics. In addition, the mobility of the charge may be controlled by controlling the ratio of the second organic optoelectronic device compound and the first organic optoelectronic device compound. When the composition of the present invention is used as a host, the combination ratio thereof may vary depending on the type of dopant used or the propensity of the dopant, or 0LED when the composition of the present invention is used in an electron transport layer or an electron transport auxiliary layer. Used in the device

Depending on the host and the dopant of the EML layer, the compound and the combination ratio of the composition of the present invention may vary. For example, it may be included in a weight ratio of about 1: 9 to 9: 1, and specifically 1: 9 to 8: 2, 1: 9 to 7: 3, 1: 9 to 6: 4, 1: 9 to 5: 5 It may be included in the range, 2: 8 to 8: 2, 2: 8 to 7: 3, 2: 8 to

It may be included in the range of 6: 4, 2: 8 to 5: 5.

In addition, when the composition of the present invention is used as a host. I U ^'and the second compound for an organic optoelectronic device Sean 1 compound for an organic optoelectronic device: 9 to 5: 5, 2: 8 to 5: 5, 3: may be included in a weight ratio range of 5: 7 to 5. Specifically, the compound for the first organic optoelectronic device and the compound for the second organic optoelectronic device are 2: 8 to 8: 2,

3: 7 to 7: 3, 4: 6 to 6: 4, 4: 6 to 8: 2, and may be included in the range of 5: 5 to 8: 2, such as 2: 8 to 8: 2, It may be included in the range of 3: 7 to 7: 3. As a 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 3: 7 to 5: 5, for example, 3: 7 or 5: 5. By being included in the above range it is possible to improve efficiency and life at the same time.

The composition may further include at least one organic compound in addition to the above-mentioned compound for the first organic optoelectronic device and the compound for the second organic optoelectronic device. 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 substance that is lightly mixed to cause light emission. Materials such as metal complexes that emit light by multiple excitation that excite triplet state subphases can be used. The dopant may be, for example, an inorganic, organic, or inorganic compound, and may be included in one kind or two or more kinds.

An example of the dopant may be a phosphorescent dopant, and an example of the phosphorescent dopant may be Ir, Pt, 0s, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd or And organometallic compounds containing a combination of these. The phosphorescent dopant may be, for example, a compound represented by Chemical Formula Z, but is not limited thereto.

[Formula Z]

L ₂ MX

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

M may be, for example, Ir, Pt, 0s, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or a combination thereof, wherein L and X are, for example, Tate ligand.

It will be described hereinafter the above-described organic optoelectronic devices for applying the organic optoelectronic devices compound, or a composition for organic optoelectronic ^devices,. :

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

The organic layer may include 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 may be a compound for the organic optoelectronic device. ， Or organic It may include a composition for an optoelectronic device.

The auxiliary layer further comprises an electron transport auxiliary layer adjacent to the light emitting layer J1, The electron transport auxiliary layer is the compound for the organic optoelectronic device. Or a composition for an organic optoelectronic device.

For example, when the compound for an organic optoelectronic device is included in the electron transport layer or the electron transport auxiliary layer, the compound for an organic optoelectronic device may be represented by Formula 1C or Formula 1-1.

The organic optoelectronic device is not particularly limited as long as the device can switch electrical energy and light energy. Examples thereof include an organic photoelectric device, an organic light emitting device, an organic solar cell, and an organic photosensitive drum.

Herein, an organic light emitting diode as an example of an organic optoelectronic device will be described with reference to the drawings.

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

The anode 120 may be made of a high work function conductor, for example, to facilitate hole injection, and may be made of metal, metal oxide and / or conductive polymer, for example. The anode 120 is, for example, a metal such as nickel, platinum, vanadium, cream, copper, zinc, gold or an alloy thereof; Metal oxides such as zinc oxide, indium oxide, sulphite tin πΤ0), and sulphite zinc oxide (IZ0); Combinations of oxides with metals such as ZnO and A1 or Sn0 ₂ and Sb; Conductive polymers such as poly (3l methylthiophene), poly (3,4 '(ethylene-1,2'dioxy) thiophene) (polyehtylenedioxythiophene: PEDT), polypyrrole and polyaniline, and the like. It is not limited.

The cathode 110 may be made of a low work function conductor, for example, to facilitate electron injection, and may be made of metal, metal oxide and / or conductive polymer, for example. The cathode 110 is, for example, magnesium, calcium, sodium, potassium, titanium. Indium, yttrium, lithium, gadolinium, aluminum, silver. Tin, lead, Metals such as cesium, barium, or alloys thereof; Multilayer structure materials such as LiF / Al, Li0 ₂ / Al, LiF / Ca, LiF / Al, and BaF ₂ / Ca, but are not limited thereto.

The organic layer 105 includes an emission layer 130 containing the compound for an organic optoelectronic device described above. . 2 is a cross-sectional view illustrating an organic light emitting device according to another embodiment. Referring to FIG. 2, the organic light emitting diode 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 not shown, the organic layer 105 of FIG. 1 or 2 is an electron injection insect. It may further include 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 thereof. The compound for an organic optoelectronic device of the present invention may be included in these organic layers. The organic light emitting device (100.200) is formed on the substrate by an anode or a cathode, and then evaporation. Sputtering ¾ dry film such as plasma plating and ion plating ¾; ^{Alternatively} , the organic layer may be formed by a wet film method such as spin coating, dipping, flow coating, or the like, followed by forming a cathode or an anode thereon.

The organic light emitting diode described above may be applied to an organic light emitting display device. The following presents specific embodiments of the present invention. However, the embodiments described below are merely for illustrating or explaining the present invention in detail, and thus the present invention is not limited thereto.

Hereinafter, starting materials and reaction materials used in Examples and Synthesis Examples were purchased from Signia-Aklrich, / ic or TCI, or synthesized through known methods, unless otherwise specified. (Production of Compound for Organic Optoelectronic Devices)

example. Compounds given as more specific examples of the compounds of the invention Synthesis through steps

(1st compound for organic optoelectronic device)

Synthesis Example 1 Synthesis of Compound A-1

a) Synthesis of Intermediate A-1-1

Into a 500 mL round bottom flask, 22.6 g (100 mmol) of 2,4-dichlorosulphate 6-phenyltriazine was added to 100 mL of tetrahydrofuran, 100 mL of toluene and 100 mL of distilled water, followed by dibenzofuran-3-boronic acid. 0.9 equivalent, tetrakistriphenylphosphine palladium 0.03 equivalent and potassium carbonate 2 equivalent are added and heated to reflux under a nitrogen atmosphere. After 6 hours, the reaction solution was cooled, the water repellent was removed, and the organic layer was dried under reduced pressure. The obtained solid was washed with water and nucleic acid, and the solid was recrystallized with 200 mL of toluene to obtain 21.4 g (60% yield) of Intermediate A 1.-1.

b) Synthesis of Compound A-1

20 g of the intermediate A-1-1 synthesized above in a 500 rnL equipotential bottom flask

(55.9 mmol) was added 200 mL of tetrahydrofuran and 100 mL of distilled water, and 2— (9,9-diphenal-9H-fluoren-4-yl) -4,4,5,5-tetramethyl-1, 3,2-dioxaborolane compound 1. 1 equivalent, tetrakistriphenylphosphine palladium 0.03 equivalent and potassium carbonate 2 equivalent are added and heated to reflux under a nitrogen atmosphere. After 18 hours, the reaction solution was cooled down, the precipitated solid was filtered off, and washed with 500 niL of water. The solid was recrystallized from 500 mL of monochlorobenzene to give 26 g of Compound A-1. Synthesis Example 2 Synthesis of Compound A-13

[Bungungsik 2]

2- (9,9-diphenyl-9H-fluoren-4-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane compound instead of 2- (9,9- Compound A-13 was prepared in the same manner as in Synthesis Example 1 using diphenyl-9H-fluorene- 2-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane compound. 28g was obtained.

Synthesis of Compound for Second Organic Optoelectronic Device

Synthesis Example 3 Synthesis of Compound F-55

Exact Mass: 649.25

To the intermediate phenyl-indolocarbazole in a nitrogen environment, 1.2 equivalents of 4-bromophenyl-carbazole, 0.03 equivalents of bisdibenzylideneacetonepalmatur (0), 1 equivalent of tri-t-butylphosphine, sodium t— 2 equivalents of butoxide were added to toluene and heated to reflux for 16 hours. After the reaction was completed, the reaction solution was filtered once at high temperature, and the solution was concentrated after stirring once after treatment with act ivated carbon while stirring the solution. The concentrated solution was added dropwise to methyl alcohol to obtain crystals, which were then filtered. The residue thus obtained was separated and purified through column chromatography to obtain Compound F-55 (83%).

LC-Mass (Theoretical value: 649.25 g / mol, Measured value: M + = 649 g / mo l) Comparative Synthesis Example 1 Synthesis of Comparative Compound 1

Comparative Compound 1 was obtained in the same manner with reference to paragraph 830 of Korean Patent Registration Publication No. KR1542714.

(Production of Organic Light Emitting Device)

Example 1

The glass substrate coated with ITO (Indium tin oxide) to a thickness of 1500A was washed with distilled water ultrasonic waves. After the washing using distilled water was isopropyl _alkoeul. Ultrasonic washing with a solvent such as acetone, methanol, and the like was dried and then transferred to a plasma cleaner, and then the substrate was cleaned for 10 minutes using an oxygen plasma, and then the substrate was transferred to a vacuum evaporator. Compound A was vacuum deposited on the IT0 substrate using the prepared IT0 transparent electrode as an anode to form a hole injection layer having a thickness of 700 A, and then compound C was deposited to a thickness of 50 A on the injection layer. Depositing a thickness of 1020 A to form a hole transport layer. Compound A-1 of Synthesis Example 1 was used as a host on the hole transport layer, and dostrotris ((2- [1,1'-biphenyl] -3-yl) pyridine) iridium (ΙΠΚ or less GDI) was added to 10%. Doped to form a light emitting layer of 400A thickness by vacuum deposition. Subsequently, compound D and Liq are simultaneously vacuum deposited at a ratio of 1: 1 on the emission layer to form an electron transport layer having a thickness of 300 A, and Liq 15A and Al 1200A are sequentially vacuum deposited on the electron transport layer to form a cathode. The device was produced.

The organic light emitting device has a structure having five layers of organic thin film worms, specifically as follows.

IT0 / Compound A (700A) / Compound B (50A) / Compound C (1020A) / EML [Compound A-

1: GD 1 = 90%: 10 wt%] (400 A) / Compound D: Liq (300 A) / Liq (15 A) / Al (1200 A). Compound A: N4, N4 '-di pheny 1 -N4, N4' -bis (9-pheny 1 -9H-car bazo 1 -3- yl) bi phenyl 一 4 ， 4 'ᅳ diamine

Compound B: 1,4,5,8,9,11-hexaazat r i pheny 1 ene-hexacarbon i t r i 1 e (HAT-CN) ，

Compound C: N- (biphenyl-4-yl) -9,9-dimethyl— N— (4- (9— phenyl-9H-carbazol-3-yl) henyl) -9H- f 1 uor en-2-am i ne

Compound D: 8- (4- (4, 6-cl i (napht ha 1 en-2-y l) -l, 3,5-triazi n-2-yl) phenyl) quinol ine Example 2

An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound A-1 and Compound E-99 were deposited together at a weight ratio of 30:70 to form a light emitting layer. The configuration of the light emitting layer of the organic light emitting device is as follows.

EML [Compound A-1: Compound E-99: GD1] = 27wt%: 63wt%: 10wt%] (400A) Example 3

An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound A-1 and Compound F-55 were deposited together at a weight ratio of 30:70 to form a light emitting layer. The configuration of the light emitting layer of the organic light emitting device is as follows.

EML [Compound A-1: Compound F-55: GD1] = 27wt: 63wt%: 10wt%] (400A) Examples 4 to 6

An organic light emitting device was manufactured in the same manner as in Examples 1 to 3, except that Compound A-13 was used instead of Compound A-1. The configuration of the light emitting layer of the organic light emitting device is as follows.

Example 4: EML [Compound A-13: GD1] = 90 wt%: 10 wt] (400 A)

Example 5: EML [Compound A-13: Compound E-99: GD1] = 27wt: 63wt%: 10wt%] (400A)

Example 6: EML [Compound A—13: Compound F-55: GD1] = 27 wt: 63 wt%: 10 wt%] (400 A) Comparative Example 1

As shown in Table 1, an organic light emitting device was manufactured in the same manner as in Example 1, using Comparative Compound 1 instead of Compound A-1 in the emission layer. Example 7 (electron transport layer)

Glass substrates coated with ITO (Indium tin oxide) to a thickness of 1500 A were washed with distilled water ultrasonically. After the washing of distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, and the like was dried and transferred to a plasma cleaner, and then the substrate was cleaned for 10 minutes using an oxygen plasma, and then the substrate was transferred to a vacuum evaporator. Compound A was vacuum deposited on the IT0 substrate using the prepared IT0 transparent electrode as an anode to form a hole injection layer having a thickness of 700 A, and then compound C was deposited to a thickness of 50 A on top of the injection charge, and then Compound C was deposited. Depositing a thickness of 1020 A to form a hole transport layer. BH113 and BD370 (purchased from SFC Co., Ltd.) were doped with a blue fluorescence emitting host and a dopant to a dopant concentration of 5% to form a 200 A thick layer of fire ^: layer. Thereafter, the upper layer of the light emitting layer compound A-1 and Liq are simultaneously vacuum deposited at a weight ratio of 1: 1 to form an electron transport layer having a thickness of 300 A, and q 15A and Al 1200A are sequentially vacuum deposited on the electron transport layer to form a cathode. Thus, an organic light emitting device was manufactured. Materials used for fabricating the organic device are as follows.

Compound A: N4, N4 ¹ -di pheny ¹ -N4, N4 '-bis (9-pheny 1 -9H-car bazo 1 -3- yl) biphenyl 一 4,4' 一 diamine

Compound B: 1,4,5,8,9,11-hexaazat r i pheny 1 ene-hexacar boni t r i 1 e (HAT-CN) ，

Compound C: N- (bi pheny 1 4-y 1) -9, 9-di met hy 1 -N- (4- (9-pheny 1 -9H-carbazol-3-yl) henyl) -9H-f luoren-2-amine

Compound D: 8- (4- (4, 6-di (napht ha 1 en-2-y 1)-1, 3, 5- 1 ri az i n-2-yl) phenyl) quinol ine Example 8

An organic light emitting diode was manufactured according to the same method as Example 7 using Compound A-13 instead of Compound A-1 for the electron transport layer. Comparative Example 2

An organic light emitting diode was manufactured according to the same method as Example 7 using Comparative Compound 1 instead of Compound A-1 for the electron transport layer. Evaluation 1 (phosphorescent green host)

The luminous efficiency and lifespan characteristics of the organic light emitting diode according to Examples 1 to 6 and Comparative Example 1 were evaluated. Specific measurement methods are as follows, and the results are shown in Table 1.

(1) Measuring the change of current density according to the voltage change

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

(2) Measurement of luminance change according to voltage change

For the manufactured organic light emitting diode, the luminance at that time was measured using a luminance meter (Minol ta Cs_1000A) while increasing the voltage from 0V to 10V 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 brightness, current density and voltage measured from (1) and (2).

(4) life measurement

In the manufactured organic light emitting device. Using the Polaronics Lifetime Measurement System, the devices of Examples 1 to 3 and Comparative Example 1 were emitted at an initial luminance (c (l / m ² ) of 18000 cd / m ² , and the luminance was decreased over time. The time point when the brightness was reduced to 97% of the brightness was measured as the life of T97.

(5) Drive voltage measurement

Each device at 15 mA / cm ² using a current-voltmeter (Kei thl ey 2400) The driving voltage was measured and the result was obtained.

[Table 1] Phosphorescent green host device

Referring to Table 1, the organic light emitting device according to Examples 1 to 6 is a comparative example

Driving voltage compared to the organic light emitting element according to 1. The luminous efficiency and lifespan characteristics are all improved at the same time, and in particular, the lifespan and driving voltage can be seen to be improved. Evaluation 2 (Electronic Transport Layer)

For the organic light emitting diodes manufactured in Chassis Examples 7, 8 and Comparative Example 2, the current density change, luminance change, and luminous efficiency according to voltage were measured.

The specific measuring method is the same as in Evaluation 1, the life measuring method is as follows, and the results are shown in Table 2.

[Life measurement]

Using the Polaronics Lifetime Measurement System, the devices of Examples 7, 8 and Comparative Example ² were emitted with an initial luminance (cd / m ² ) of 750 cd / m ^{2 and} then over time. According to the decrease in luminance, the time point when the luminance was reduced to 97% of the initial luminance was measured as the life of T97.

TABLE 2 Driving voltage luminous efficiency element electron transport layer T97 (h)

(V) (cd / A)

Example 7 Compound A-1 3.76 114% 132% Example 8 Compound A-13 3.43 120% 151 Comparative Example 2 Comparative Compound 1 4.25 100% 100% Referring to Table 2, the organic according to Example 7 and Example 8 was obtained. The light emitting device compared to the organic light emitting device according to Comparative Example 2, it can be seen that the driving voltage, luminous efficiency and life characteristics are all broken at the same time.

The present invention is not limited to the above embodiments, but may be manufactured in various forms, and a person of ordinary skill in the art to which the present invention pertains does not change the technical spirit or essential features of the present invention. It will be appreciated that the present invention may be practiced as. Therefore, the above-described embodiments are to be considered in all respects as illustrative and not restrictive.

[Explanation of code]

100, 200 ： organic light emitting device

105 ： organic layer

110 ： cathode

120 ： anode

130 ： Luminescent

140 ： Hole auxiliary layer

Claims

[Range of request]

[Claim 11

Compound for an organic optoelectronic device represented by the formula

[Formula 1]

In Chemical Formula 1,

Z ¹ to Z ³ are each independently N or CR ^a ,

At least two of Z ¹ to Z ³ are N;

X is 0 or S,

Ar is a substituted or unsubstituted C6 to C30 aryl group,

R ^a and R ¹ wherein R ¹⁰ are each independently hydrogen, deuterium, a substituted or basubstituted C1 to C10 alkyl group. Substituted or unsubstituted C6 to C30 aryl group. Or a combination thereof,

"Substituted" means that at least one hydrogen is deuterium, C1 to C20 alkyl group C6 to C30 aryl group, or C2 to C30. Mean substituted by a heteroaryl group.

[Claim 2]

The method of claim 1,

A compound for an organic optoelectronic device, represented by any one of the following Formulas 1A and 1C:

[Formula 1A] [Formula 1C]

In Chemical Formula 1A and Chemical Formula 1C,

Z ¹ to Z ³ are each independently N or CR ^a ,

At least two of Z ¹ to Z ³ are N,

X is 0 or S,

Ar is a substituted or unsubstituted C6 to C30 aryl group,

R ^a and R ¹ to R ¹⁰ are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a combination thereof

Γclaim 3]

The method of claim 1,

Compound for an organic optoelectronic device represented by any one of the formula l.- i, formula ι-π and formula l-m:

-1] [Formula ι-π]

[Formula lm

In the formula l- i, formula i- π and formula i-m

X is 0 or s,

Ar is a substituted or unsubstituted C6 to C30 aryl group,

R ^al to R ^a3 , and R ¹ to R ¹⁰ are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a combination thereof.

[Claim 4]

The compound for an organic optoelectronic device of claim 2, wherein L is a single bond. [Claim 5]

The compound of claim 3, wherein L is a single bond. [Claim 6]

The method of claim 1 wherein ^'

Ar is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group or a substituted or unsubstituted naphthyl group compound for organic optoelectronic devices.

[Claim 7]

The method of claim 1,

Compounds for organic optoelectronic devices selected from compounds listed in Group 1:

[Group 1]

[Α- 1] [Α— 2ΠΑ-3 ΠΑ-4] o

[Claim 8]

A compound for a first organic optoelectronic device according to claim 1

An organic optoelectronic device composition comprising a compound for a second organic optoelectronic device comprising a carbazole moiety represented by Formula 2:

2]

The ^"in the formula ^(2),

R ¹¹ to R ¹⁶ are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group,

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

[Claim 9]

The method of claim 8,

Formula 2 is represented by the following Formula 2A 'or Formula 2B-1 and Formula 2B-

A composition for organic optoelectronic devices, wherein the composition is one selected from a combination of two:

[Formula 2A] [Formula 2B-1] [Formula 2B-2]

Formula 2A. In Chemical Formulas 2B-1 and 2B-2,

Y ¹ to Y ³ are each independently a single bond, a substituted or unsubstituted C 6 to C 30 arylene group. Substituted or unsubstituted C2 to C30 Heteroarylene group. Or a combination thereof,

R ¹¹ to R ¹³ , and R ¹⁷ to R ²¹ 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 hetero Ring groups, or a combination thereof,

m is one of the integers of 0-2.

[Claim 10]

The method of claim 9,

A ¹ to A ³ of Formula 2A, Formula 2B-1, and Formula 2B-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 group. A substituted naphthyl group, a substituted or unsubstituted anthracenyl group, or a substituted or unsubstituted triphenylene group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or An unsubstituted dibenzofuranyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted fluorenyl group, or a combination thereof. [Claim 11]

Positive and negative electrodes facing each other, 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 7. or

A valuable optoelectronic device comprising the composition for an organic optoelectronic device according to any one of claims 8 to 10.

[Claim 12]

The method of claim 11,

The organic layer includes a light emitting layer,

The light emitting layer is an organic optoelectronic device comprising the compound for an organic optoelectronic device or the composition for an organic optoelectronic device.

[Claim 13]

The method of claim 12,

The organic optoelectronic device compound or the organic optoelectronic device composition is included as a host of the light emitting layer.

[Claim 14]

The method of claim 11,

The organic layer further includes 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, the auxiliary layer further comprises an electron transport auxiliary layer adjacent to the light emitting layer. The electron transport auxiliary layer or the electron transport layer includes the compound for the organic optoelectronic device; Or an organic optoelectronic device comprising the composition for an organic optoelectronic device.

-Claim 15

A display device comprising the organic optoelectronic device of claim 11.