KR102555494B1 - Composition for optoelectronic device and organic optoelectronic device and display device - Google Patents

Abstract

An organic photoelectron comprising a first compound, a second compound, and a third compound, wherein the first compound is represented by Formula I, the second compound is represented by Formula II, and the third compound is represented by Formula III It relates to a composition for a device, and an organic optoelectronic device and display device including the same.
Details of Formula I, Formula II and Formula III are as described in the specification.

Description

Composition for organic optoelectronic devices, organic optoelectronic devices and display devices

It relates to a composition for an organic optoelectronic device, an organic optoelectronic device, and a display device.

An organic optoelectronic diode is a device capable of converting between electrical energy and light energy.

Organic optoelectronic devices can be largely divided into two types according to their operating principles. 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, respectively. It is a light emitting device that generates light energy from

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

Among them, organic light emitting diodes (OLEDs) have recently been attracting great attention due to an increase in demand for flat panel display devices. An organic light emitting device is a device that converts electrical energy into light, and the performance of the organic light emitting device is greatly affected by organic materials positioned between electrodes.

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

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

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

According to one embodiment, it includes a first compound, a second compound, and a third compound, wherein the first compound is represented by Formula I, the second compound is represented by II, and the third compound is To provide a composition for an organic optoelectronic device, represented by Formula Ⅲ.

[Formula I]

In Formula I,

Z ¹ to Z ³ are N or CL ^a -R ^a ;

at least two of Z ¹ to Z ³ are N;

L ^a and L ¹ to L ³ are each independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heterocyclic group, or a combination thereof;

R ¹ and R 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 ^a , R ³ and R ⁴ are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a substituted or an unsubstituted silyl group, a substituted or unsubstituted amine group, a halogen, a cyano group, or a combination thereof;

Ring A is represented by any one of Formulas I-1 to Formula I-7 below:

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

[Formula Ⅰ-5] [Formula Ⅰ-6] [Formula Ⅰ-7]

In Formula 1-1 to Formula 1-7,

X ¹ is O, S or NR ^b ;

R ^b and R ⁵ to R ¹² are each independently hydrogen, heavy hydrogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a substituted or an unsubstituted silyl group, a substituted or unsubstituted amine group, a halogen, a cyano group, or a combination thereof;

* is the connection point;

[Formula II]

In Formula II,

L ⁴ is a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heterocyclic group, or a combination thereof;

Ar ¹ is a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a combination thereof;

R ¹³ and R ¹⁴ are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, a substituted or unsubstituted A silyl group, a substituted or unsubstituted amine group, a halogen, a cyano group, or a combination thereof,

Ring B is represented by any of the following formulas II-1 to II-4:

[Formula Ⅱ-1] [Formula Ⅱ-2]

[Formula Ⅱ-3] [Formula Ⅱ-4]

In Formula II-1 to Formula II-4,

L ⁵ and L ⁶ are each independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heterocyclic group, or a combination thereof;

L ⁸ is a single bond or a substituted or unsubstituted C6 to C20 arylene group;

Ar ² and Ar ³ are a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a combination thereof;

R ¹⁵ to R ²¹ are each independently hydrogen, heavy hydrogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, a substituted or unsubstituted A silyl group, a substituted or unsubstituted amine group, a halogen, a cyano group, or a combination thereof,

* is the connection point;

[Formula III]

In the above formula Ⅲ,

L ⁷ is a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heterocyclic group, or a combination thereof;

R ²² to R ³³ are each independently hydrogen, heavy hydrogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, a substituted or unsubstituted a silyl group, a substituted or unsubstituted amine group, a halogen group, a cyano group, or a combination thereof.

According to another embodiment, an organic optoelectronic device including an anode and a cathode facing each other, and at least one organic layer disposed between the anode and the cathode, wherein the organic layer includes the composition for an organic optoelectronic device.

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

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

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

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

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

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

In this specification, unless otherwise defined, "hetero" means containing 1 to 3 heteroatoms selected from the group consisting of N, O, S, P and Si in one functional group, and the rest being carbon. .

In the present specification, "aryl group" is a general concept of a group having one or more hydrocarbon aromatic moieties, and all elements of the hydrocarbon aromatic moiety have p-orbitals, and these p-orbitals are conjugated Forming a form, for example, including a phenyl group, a naphthyl group, etc., including a form in which two or more hydrocarbon aromatic moieties are connected through a sigma bond, for example, a biphenyl group, a terphenyl group, a quaterphenyl group, etc., and two or more hydrocarbon aromatic moieties may include a non-aromatic fused ring in which they are directly or indirectly fused, such as a fluorenyl group and the like.

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

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

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

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

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

In the present specification, the hole characteristic refers to a characteristic that can form holes by donating electrons when an electric field is applied, and has conduction characteristics along the HOMO level, so that holes formed at the anode are injected into the light emitting layer, the light emitting layer It means a property that facilitates the movement of holes formed in the anode to the anode and in the light emitting layer.

In addition, electronic properties refer to the characteristics of receiving electrons when an electric field is applied, and has conductivity along the LUMO level, so that electrons formed in the cathode are injected into the light emitting layer, electrons formed in the light emitting layer move to the cathode, and in the light emitting layer A property that facilitates movement.

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

A composition for an organic optoelectronic device according to an embodiment is a mixture including three types of compounds, specifically, a first compound having electronic properties, a second compound having hole properties, and a third compound having buffer properties. include

The third compound is a compound having a wide range of HOMO-LUMO band gaps including both the HOMO-LUMO band gaps of the first compound and the second compound, and has a higher hole mobility than the hole mobility of the second compound having hole characteristics. It has a low hole mobility, thereby slowing down hole injection characteristics, thereby reducing hole traps.

In addition, as the light emitting layer region has a lower electron mobility than the electron mobility of the first compound and is relatively moved toward the hole transport auxiliary layer, exciton quenching at the interface of the electron transport auxiliary layer and thus deterioration It is possible to obtain the effect of reducing the lifespan can be increased.

The first compound having the above electronic properties has a structure in which a nitrogen-containing 6-membered ring is substituted with carbazole or a carbazole derivative, and is represented by the following formula (I).

[Formula I]

In Formula I,

Z ¹ to Z ³ are N or CL ^a -R ^a ;

at least two of Z ¹ to Z ³ are N;

L ^a and L ¹ to L ³ are each independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heterocyclic group, or a combination thereof;

R ¹ and R 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 ^a , R ³ and R ⁴ are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a substituted or an unsubstituted silyl group, a substituted or unsubstituted amine group, a halogen, a cyano group, or a combination thereof;

Ring A is represented by any one of Formulas I-1 to Formula I-7 below:

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

[Formula Ⅰ-5] [Formula Ⅰ-6] [Formula Ⅰ-7]

In Formula 1-1 to Formula 1-7,

X ¹ is O, S or NR ^b ;

R ^b and R ⁵ to R ¹² are each independently hydrogen, heavy hydrogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a substituted or an unsubstituted silyl group, a substituted or unsubstituted amine group, a halogen, a cyano group, or a combination thereof;

* is a connection point.

Specifically, Z ¹ to Z ³ in Formula 1 are each independently N or CH, and at least two of Z ¹ to Z ³ may be N.

For example, Z ¹ to Z ³ may each be N.

For example, Z ¹ and Z ³ may be N, and Z ² may be CH.

L ¹ to L ³ of Formula 1 may each independently be a single bond, a phenylene group, a biphenylene group, a carbazolylene group, a dibenzofuranylene group, a dibenzothiophenylene group, or a pyridinylene group.

R ¹ and R ² in Formula 1 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 carba Zolyl group, substituted or unsubstituted indolocarbazolyl group, substituted or unsubstituted dibenzofuranyl group, substituted or unsubstituted dibenzothiophenyl group, substituted or unsubstituted fused carbazolyl group, substituted or unsubstituted Fused dibenzofuranyl group, substituted or unsubstituted fused dibenzothiophenyl group, substituted or unsubstituted fused indolocarbazolyl group, substituted or unsubstituted pyridinyl group, substituted or unsubstituted pyrimidinyl group, substituted or unsubstituted An unsubstituted triazinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted quinazolinyl group, or a substituted or unsubstituted benzo It may be a quinazolinyl group.

In a specific example of the present invention, L ¹ to L ³ of Formula 1 may each independently be a single bond, an m-phenylene group, or a p-phenylene group.

For example, R ¹ and R ² in Formula 1 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 carbazolyl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted terphenyl group. may be an indolocarbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

Formula 1 may be represented by any one of the following Formulas 1A to 1J according to specific structures of carbazole and carbazole derivatives.

[Formula ⅠA] [Formula ⅠB] [Formula ⅠC]

[Formula ID] [Formula IE] [Formula IF]

[Formula IG] [Formula IH]

[Formula Ⅰ] [Formula ⅠJ]

In Formulas IA to 1J, definitions of Z ¹ to Z ³ , L ¹ to L ³ , R ¹ to R ¹² , and X ¹ are as described above.

Specifically, R ³ to R ⁶ in Formula 1A are each independently hydrogen, deuterium, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, or a substituted or unsubstituted carbazolyl group. , It may be a substituted or unsubstituted indolocarbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

For example, Formula 1A may be represented by any one of Formulas 1A-1 to 1A-7.

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

[Formula IA-5] [Formula IA-6] [Formula IA-7]

In Formulas IA-1 to Formula IA-7, Z ¹ to Z ³ , L ¹ to L ³ , R ¹ and R ² are defined as described above, and R ³ to R ⁵ are each independently substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted indolocarbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or It may be a substituted or unsubstituted dibenzothiophenyl group.

Specifically, R ³ , R ⁴ and R ⁷ to R ⁹ in Formulas 1B to 1D are each independently hydrogen, deuterium, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group. , A substituted or unsubstituted carbazolyl group, a substituted or unsubstituted indolocarbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

For example, Formula 1A may be represented by Formula 1A-1 or Formula 1A-4.

For example, Formula 1B may be represented by Formula 1B-1 or Formula 1B-2.

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

In Formula IB-1 and Formula IB-2, Z ¹ to Z ³ , L ¹ to L ³ , R ¹ and R ² are defined as described above, and R ⁸ is a substituted or unsubstituted phenyl group, or a substituted or It may be an unsubstituted biphenyl group.

For example, Formula 1C may be represented by Formula 1C-1 or Formula 1C-2.

[Formula ⅠC-1] [Formula ⅠC-2]

In Formulas 1C-1 and 1C-2, Z ¹ to Z ³ , L ¹ to L ³ , R ¹ and R ² are defined as described above, and R ⁸ is a substituted or unsubstituted phenyl group, or a substituted or It may be an unsubstituted biphenyl group.

For example, Chemical Formula 1D may be represented by Chemical Formula 1D-1.

[Formula ⅠD-1]

In Formula ID-1, Z ¹ to Z ³ , L ¹ to L ³ , R ¹ and R ² are defined as described above.

Specifically, R ³ , R ⁴ and R ¹⁰ to R ¹² in Formulas IE to 1J are each independently hydrogen, deuterium, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group. , A substituted or unsubstituted carbazolyl group, a substituted or unsubstituted indolocarbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

For example, Chemical Formula IE may be represented by any one of Chemical Formulas IE-1 to IE-5.

[Formula IE-1] [Formula IE-2] [Formula IE-3]

[Formula IE-4] [Formula IE-5]

In Formulas IE-1 to IE-5, Z ¹ to Z ³ , L ¹ to L ³ , R ¹ , R ² and X ¹ are defined as described above, and R ³ to R ¹¹ are each independently substituted. Alternatively, it may be an unsubstituted phenyl group, or a substituted or unsubstituted biphenyl group.

For example, Formula IF may be represented by Formula IF-1 or Formula IF-2.

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

In Formula IF-1 and Formula IF-2, Z ¹ to Z ³ , L ¹ to L ³ , R ¹ , R ² and X ¹ are defined as described above, R ³ is a substituted or unsubstituted phenyl group, Or it may be a substituted or unsubstituted biphenyl group.

For example, Chemical Formula IG may be represented by Chemical Formula IG-1 or Chemical Formula IG-2.

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

In Formulas IG-1 and Formula IG-2, Z ¹ to Z ³ , L ¹ to L ³ , R ¹ , R ² and X ¹ are defined as described above, R ³ is a substituted or unsubstituted phenyl group, Or it may be a substituted or unsubstituted biphenyl group.

For example, Chemical Formula IH may be represented by Chemical Formula IH-1.

[Formula ⅠH-1]

In Formula IH-1, Z ¹ to Z ³ , L ¹ to L ³ , R ¹ , R ² and X ¹ are defined as described above.

For example, Formula 1I may be represented by Formula 1I-1 or Formula 1I-2.

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

In Formulas II-1 and Formulas II-2, Z ¹ to Z ³ , L ¹ to L ³ , R ¹ , R ² and X ¹ are defined as described above, R ³ is a substituted or unsubstituted phenyl group, Or it may be a substituted or unsubstituted biphenyl group.

For example, R ³ to R ⁶ in Formula 1A may each independently be hydrogen, a phenyl group, a biphenyl group, a carbazolyl group, a dibenzofuranyl group, or a dibenzothiophenyl group.

For example, R ³ , R ⁴ and R ⁷ to R ⁹ in Formulas 1B to 1D may each independently be a hydrogen or a phenyl group.

For example, R ³ , R ⁴ and R ¹⁰ to R ¹² in Formulas IE to 1J may each independently represent hydrogen or a phenyl group.

For example, the first compound may be represented by Formula 1A and Formulas 1E to 1H.

As a specific example, the first compound may be represented by Formula 1A or Formula 1E.

For example, the first compound may be represented by Chemical Formula 1A.

According to a specific embodiment of the present invention, in Formula 1A, L ¹ to L ³ are each independently a single bond or a substituted or unsubstituted phenylene group, and R ¹ and R ² are each independently a substituted or unsubstituted phenyl group , A substituted or unsubstituted biphenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group, and R ³ to R ⁶ may each independently be hydrogen or a substituted or unsubstituted phenyl group. However, it is not limited thereto.

The first compound may be, for example, one selected from compounds listed in Group 1 below.

[Group 1]

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

[1-5] [1-6] [1-7] [1-8]

[1-9] [1-10] [1-11] [1-12]

[1-13] [1-14] [1-15] [1-16]

[1-17] [1-18] [1-19] [1-20]

[1-21] [1-22] [1-23] [1-24]

[1-25] [1-26] [1-27] [1-28]

[1-29] [1-30] [1-31] [1-32]

[1-33] [1-34] [1-35] [1-36]

[1-37] [1-38] [1-39] [1-40]

[1-41] [1-42] [1-43] [1-44]

[1-45] [1-46] [1-47] [1-48]

[1-49] [1-50] [1-51] [1-52]

[1-53] [1-54] [1-55] [1-56]

[1-57] [1-58] [1-59] [1-60]

[1-61] [1-62] [1-63] [1-64]

[1-65] [1-66] [1-67] [1-68]

[1-69] [1-70] [1-71] [1-72]

[1-73] [1-74] [1-75] [1-76]

[1-77] [1-78] [1-79] [1-80]

[1-81] [1-82] [1-83] [1-84]

[1-85] [1-86]

The second compound having the hole property is a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group in carbazole or a carbazole derivative. It is a structure and is represented by Formula II below.

[Formula II]

In Formula II,

L ⁴ is a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heterocyclic group, or a combination thereof;

Ar ¹ is a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a combination thereof;

R ¹³ and R ¹⁴ are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, a substituted or unsubstituted A silyl group, a substituted or unsubstituted amine group, a halogen, a cyano group, or a combination thereof,

Ring B is represented by any of the following formulas II-1 to II-4:

[Formula Ⅱ-1] [Formula Ⅱ-2]

[Formula Ⅱ-3] [Formula Ⅱ-4]

In Formula II-1 to Formula II-4,

L ⁵ and L ⁶ are each independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heterocyclic group, or a combination thereof;

L ⁸ is a single bond or a substituted or unsubstituted C6 to C20 arylene group;

Ar ² and Ar ³ are a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a combination thereof;

R ¹⁵ to R ²¹ are each independently hydrogen, heavy hydrogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, a substituted or unsubstituted A silyl group, a substituted or unsubstituted amine group, a halogen, a cyano group, or a combination thereof,

* is a connection point.

Specifically, L ⁴ of Formula II may be a single bond or a C6 to C12 arylene group.

For example, L ⁴ of Formula II may be a single bond or a substituted or unsubstituted phenyl group.

Ar ¹ in Formula Ⅱ is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted Or it may be an unsubstituted dibenzothiophenyl group.

For example, Ar ¹ of Formula II may be a substituted or unsubstituted meta-biphenyl group or a substituted or unsubstituted para-biphenyl group.

Formula II may be represented, for example, by any one of the following Formulas IIA to IIF, depending on the specific structures of carbazole and carbazole derivatives.

[Formula ⅡA] [Formula ⅡB]

[Formula IIC] [Formula IIID]

[Formula IIE] [Formula IIF]

In Formulas IIA to IIF, L ⁴ to L ⁶ , L ⁸ , Ar ¹ to Ar ³ , and R ¹³ to R ²¹ are defined as described above.

Specifically, R ¹³ to R ¹⁸ in Formula ⅡA may each independently be hydrogen, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted carbazolyl group.

Specifically, L ⁵ of Formula IIA may be a single bond or a substituted or unsubstituted C6 to C12 arylene group.

Specifically, L ⁸ of Formula IIA may be a single bond or a substituted or unsubstituted C6 to C12 arylene group.

Specifically, Ar ² of Formula ⅡA 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, a substituted or unsubstituted anthracenyl group, or a substituted or unsubstituted terphenyl group. Alternatively, it may be an unsubstituted phenanthrenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

Specifically, R ¹³ , R ¹⁴ and R ¹⁹ to R ²¹ in Formulas ⅡB to ⅡF are each independently hydrogen, a substituted or unsubstituted phenyl group, a substituted or unsubstituted triphenylene group, or a substituted or unsubstituted carbazolyl group. can be

Specifically, L ⁶ of Formulas IIB to Formula IIF may be a single bond or a substituted or unsubstituted phenylene group.

Specifically, Ar ³ in Chemical Formulas ⅡB to ⅡF is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted triphenylene group, or a substituted or unsubstituted carbane group. It may be a zolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

For example, R ¹³ to R ¹⁸ in Formula ⅡA may each independently be hydrogen or a substituted or unsubstituted phenyl group.

For example, L ⁵ of Formula IIA may be a single bond or a substituted or unsubstituted phenylene group.

For example, L ⁸ of Formula IIA may be a single bond or a substituted or unsubstituted phenylene group.

For example, Ar ² of Formula ⅡA may be a substituted or unsubstituted phenyl group or a substituted or unsubstituted biphenyl group.

For example, R ¹³ , R ¹⁴ , and R ¹⁹ to R ²¹ in Formulas ⅡB to ⅡF may each independently be hydrogen or a substituted or unsubstituted phenyl group.

For example, L ⁶ of Formulas IIB to IIF may be a single bond or a substituted or unsubstituted phenylene group.

For example, Ar ³ in Formulas IIB to IIF may be a substituted or unsubstituted phenyl group or a substituted or unsubstituted biphenyl group.

For example, the second compound may be represented by Chemical Formula ⅡA or Chemical Formula ⅡF.

As a specific example, Chemical Formula ⅡA may be represented by any one of Chemical Formulas 2A-1 to 2A-3.

[Formula ⅡA-1] [Formula ⅡA-2]

[Formula ⅡA-3]

In Chemical Formulas IIA-1 to Chemical Formulas IIA-3, L ⁴ , L ⁵ , Ar ¹ , Ar ² , and R ¹³ to R ¹⁸ are defined as described above.

For example, the second compound may be represented by any one of Formula IIA-1, Formula IIA-2, and Formula IIF.

According to a specific embodiment of the present invention, in Chemical Formulas 2A-1 and 2A-2, L ⁴ and L ⁵ are each independently a single bond or a substituted or unsubstituted phenylene group,

Ar ¹ and Ar ² are each independently a substituted or unsubstituted phenyl group or a substituted or unsubstituted biphenyl group,

Each of R ¹³ to R ¹⁸ may be hydrogen or a phenyl group.

The second compound may be, for example, one selected from compounds listed in Group 2 below.

[Group 2]

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

[2-5] [2-6] [2-7] [2-8]

[2-9] [2-10] [2-11] [2-12]

[2-13] [2-14] [2-15]

[2-16] [2-17] [2-18] [2-19]

[2-20] [2-21] [2-22] [2-23]

[2-24] [2-25] [2-26] [2-27]

[2-28] [2-29] [2-30] [2-31]

[2-32] [2-33] [2-34] [2-35] [2-36]

[2-37] [2-38] [2-39] [2-40] [2-41]

[2-42] [2-43] [2-44] [2-45] [2-46]

[2-47] [2-48] [2-49] [2-50]

The third compound having the buffer property has a structure in which spirofluorene is substituted for triphenylene and is represented by the following Chemical Formula III.

[Formula III]

In the above formula Ⅲ,

L ⁷ is a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heterocyclic group, or a combination thereof;

R ²² to R ³³ are each independently hydrogen, heavy hydrogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, a substituted or unsubstituted a silyl group, a substituted or unsubstituted amine group, a halogen group, a cyano group, or a combination thereof.

Chemical Formula III may be represented by any one of the following Chemical Formulas III-1 to Chemical Formulas III-4 according to specific substitution points of spirofluorene substituted with triphenylene.

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

[Formula Ⅲ-3] [Formula Ⅲ-4]

In Formulas III-1 to Formulas III-4, L ⁷ and R ²² to R ³³ are defined as described above.

For example, Chemical Formula III may be represented by Chemical Formula III-4.

Specifically, L ⁷ in Formula III-4 may be a single bond or a substituted or unsubstituted phenylene group.

Specifically, R ²² to R ³³ in Formula III-4 may be hydrogen, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted carbazolyl group.

For example, L ⁷ in Chemical Formula III-4 may be a meta-phenylene group or a para-phenylene group.

For example, each of R ²² to R ³³ in Chemical Formula III-4 may be hydrogen.

The third compound may be, for example, one selected from compounds listed in Group 3 below.

[Group 3]

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

[3-5] [3-6] [3-7] [3-8]

[3-9] [3-10] [3-11] [3-12]

[3-13] [3-14] [3-15] [3-16]

[3-17] [3-18] [3-19]

The first compound includes a nitrogen-containing 6-membered ring having high electron transport characteristics, thereby stably and effectively transporting electrons to lower driving voltage, increase current efficiency, and implement long lifespan characteristics of the device.

The second compound has a structure including carbazole having high HOMO energy, and thus can effectively inject and transfer holes, thereby contributing to improvement of device characteristics.

The third compound has a wide HOMO-LUMO band gap, thereby controlling the hole and electron movement rates of the first compound and the second compound, thereby preventing hole trapping and preventing exciton quenching through relative movement of the light emitting layer region. This contributes to the improvement of life characteristics of the device.

By using a three-host composition comprising a first compound, a second compound, and a third compound, a two-host composition such as a composition comprising a first compound and a second compound or a composition comprising a first compound and a third compound An optimum balance can be achieved by more finely adjusting the electron/hole characteristics within the device stack compared to the composition, and the device characteristics can be greatly improved due to the appropriate charge balance.

In the most specific embodiment of the present invention, the first compound may be represented by the above-described Chemical Formula IA-1 or Chemical Formula IA-4, and the second compound may be represented by the above-described Chemical Formula IA-1, Chemical Formula IA-2, and Chemical Formula ⅡF It may be represented by any one of, and the third compound may be represented by the above-described Chemical Formula III-4.

A composition in which the first compound, the second compound, and the third compound are mixed may be included in a light emitting layer of an organic light emitting device to be described later, and may be included as, for example, a phosphorescent host.

In the composition for an organic optoelectronic device, the first compound is included in an amount of about 20% to 50% by weight based on the total weight of the first compound, the second compound, and the third compound, and the second compound is the first compound. , It is included in about 40% to 60% by weight based on the total weight of the second compound and the third compound, and the third compound is about 10% based on the total weight of the first compound, the second compound and the third compound. It may be included in wt% to 30 wt%.

Within the above range, for example, the first compound for an organic optoelectronic device is about 25% by weight to about 45% by weight based on the total weight of the first compound for an organic optoelectronic device, the second compound for an organic optoelectronic device, and the third compound for an organic optoelectronic device. % by weight, and the second compound for an organic optoelectronic device is about 45% to about 45% by weight based on the total weight of the first compound for an organic optoelectronic device, the second compound for an organic optoelectronic device, and the third compound for an organic optoelectronic device. 60% by weight, and the third compound for an organic optoelectronic device is about 10% by weight based on the total weight of the first compound for an organic optoelectronic device, the second compound for an organic optoelectronic device, and the third compound for an organic optoelectronic device to 25% by weight.

In addition, as a specific example, the first compound is included in about 30% to 40% by weight based on the total weight of the first compound, the second compound, and the third compound, and the second compound is the first compound, It is included in about 45% to 55% by weight based on the total weight of the second compound and the third compound, and the third compound is about 10% by weight based on the total weight of the first compound, the second compound, and the third compound. It may be included in wt% to 20 wt%.

As a more specific example, the composition for an organic optoelectronic device may include the first compound: the second compound: the third compound in a weight ratio of about 35:55:10 or about 32:48:20. By being included within the above range, the electron transport capability of the first compound, the hole transport capability of the second compound, and the buffering capability of the third compound are appropriately balanced to improve the efficiency and lifespan of the device.

The composition for an organic optoelectronic device may further include one or more compounds in addition to the above-described first compound, second compound, and third compound.

The composition for an organic optoelectronic device may further include a dopant. The dopant may be, for example, a phosphorescent dopant, for example, a red, green or blue phosphorescent dopant, and may be, for example, a green phosphorescent dopant.

A dopant is a material that causes light emission by being mixed in a small amount in a composition including the first compound, the second compound, and the third compound, and is generally a metal complex that emits light by multiple excitation excitation in a triplet state or higher ( metal complex) may be used. The dopant may be, for example, an inorganic, organic, or organic-inorganic compound, and may include one type or two or more types.

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

[Formula Z]

L ⁹ MX ²

In Formula Z, M is a metal, L ⁹ and X ² are the same as or different from each other and are ligands that form a complex with M.

M may be, for example, Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd or a combination thereof, and L ⁹ and X ² are, for example, bi It may be a dentate ligand.

Examples of the ligand represented by L ⁹ and X ² may be selected from the formulas listed in Group D below, but are not limited thereto.

[Group D]

In the group D,

R ³⁰⁰ to R ³⁰² are each independently hydrogen, deuterium, a C1 to C30 alkyl group with or without halogen substitution, a C6 to C30 aryl group with or without C1 to C30 alkyl substitution, or halogen,

R ³⁰³ to R ³²⁴ are each independently hydrogen, deuterium, halogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C3 to C30 cycloalkyl group, or a substituted Or an unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C1 to C30 heteroaryl group, a substituted or unsubstituted C1 to C30 amino group, a substituted or unsubstituted C6 to C30 arylamino group, SF ₅ , a trialkylsilyl group having a substituted or unsubstituted C1 to C30 alkyl group, a dialkylarylsilyl group having a substituted or unsubstituted C1 to C30 alkyl group and a C6 to C30 aryl group, or It is a triarylsilyl group having a substituted or unsubstituted C6 to C30 aryl group.

For example, a dopant represented by Chemical Formula IV below may be included.

[Formula IV]

In Formula IV,

R ¹⁰¹ to R ¹¹⁶ are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or -SiR ¹³² R ¹³³ R ¹³⁴ ;

Wherein R ¹³² to R ¹³⁴ are each independently a C1 to C6 alkyl group;

At least one of R ¹⁰¹ to R ¹¹⁶ is a functional group represented by Formula IV-1 below;

L ¹⁰⁰ is a bidentate ligand of a monovalent anion, and is a ligand that coordinates with iridium through an unshared electron pair of a carbon or heteroatom,

n1 and n2 are independently any one of integers from 0 to 3, n1 + n2 is any one of integers from 1 to 3,

[Formula IV-1]

In Formula IV-1,

R ¹³⁵ to R ¹³⁹ are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or -SiR ¹³² R ¹³³ R ¹³⁴ ;

* means a part connected to a carbon atom.

For example, a dopant represented by Chemical Formula Z-1 may be included.

[Formula Z-1]

In the above formula Z-1, rings A, B, C, and D each independently represent a 5- or 6-membered carbocyclic or heterocyclic ring;

R ^A , R ^B , R ^C , and R ^D each independently represent mono-, di-, tri-, or tetra-substituted, or unsubstituted;

L ^B , L ^C , and L ^D are each a direct bond, BR, NR, PR, O, S, Se, C=O, S=O, SO ₂ , CRR', SiRR', GeRR', and combinations thereof independently selected from the group consisting of;

When nA is 1, L ^E is a group consisting of a direct bond, BR, NR, PR, O, S, Se, C=O, S=O, SO ₂ , CRR', SiRR', GeRR', and combinations thereof is selected from; When nA is 0, L ^E is not present;

R ^A , R ^B , R ^C , R ^D , R , and R' are each hydrogen, deuterium, halogen, alkyl group, cycloalkyl group, heteroalkyl group, arylalkyl group, alkoxy group, aryloxy group, amino group, silyl group, alkenyl group , Cycloalkenyl group, heteroalkenyl group, alkynyl group, aryl group, heteroaryl group, acyl group, carbonyl group, carboxylic acid group, ester group, nitrile group, isonitrile group, sulfanyl group, sulfinyl group, sulfonyl group, phosphino group independently selected from the group consisting of, and combinations thereof; any adjacent R ^A , R ^B , R ^C , R ^D , R , and R' are optionally linked to form a ring; X ^B , X ^C , X ^D , and X ^E are each independently selected from the group consisting of carbon and nitrogen; Q ¹ , Q ² , Q ³ , and Q ⁴ each represent an oxygen or a direct bond.

A dopant according to an embodiment may be a platinum complex, and may be represented by Chemical Formula V below.

[Formula V]

In Formula V,

X ¹⁰⁰ is selected from O, S and NR ¹³¹ ;

R ¹¹⁷ to R ¹³¹ are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or - SiR ¹³² R ¹³³ R ¹³⁴ ;

Wherein R ¹³² to R ¹³⁴ are each independently a C1 to C6 alkyl group;

At least one of R ¹¹⁷ to R ¹³¹ is -SiR ¹³² R ¹³³ R ¹³⁴ or a tert-butyl group.

The composition for an organic optoelectronic device may be formed by a dry film formation method such as chemical vapor deposition.

Hereinafter, organic optoelectronic devices to which the above-described composition for organic optoelectronic devices is applied will be described.

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

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

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

Referring to FIG. 1 , an organic light emitting 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. include

The anode 120 may be made of, for example, a conductor having a high work function so as to smoothly inject holes, and may be made of, for example, metal, metal oxide, and/or conductive polymer. The anode 120 may be formed of, for example, a metal such as nickel, platinum, vanadium, chromium, copper, zinc, or gold or an alloy thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO and Al or SnO ₂ and Sb; conductive polymers such as poly(3-methylthiophene), poly(3,4-(ethylene-1,2-dioxy)thiophene) (polyehtylenedioxythiophene: PEDT), polypyrrole, and polyaniline; It is not.

The cathode 110 may be made of, for example, a conductor having a low work function so as to facilitate electron injection, and may be made of, for example, metal, metal oxide, and/or conductive polymer. The negative electrode 110 may be formed of, for example, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium, or alloys thereof; Multi-layered 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 the above-described composition for an organic optoelectronic device.

The organic layer 105 may include, for example, the light emitting layer 130, and the light emitting layer 130 may include, for example, the above-described composition for an organic optoelectronic device.

The above composition for an organic optoelectronic device may be, for example, a green light emitting composition.

The light emitting layer 130 may include, for example, each of the above-described first compound, second compound, and third compound as a phosphorescent host.

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

The hole auxiliary layer 140 may include, for example, at least one of the compounds listed in Group E below.

Specifically, the hole auxiliary layer 140 may include a hole transport layer between the anode 120 and the light emitting layer 130, and a hole transport auxiliary layer between the light emitting layer 130 and the hole transport layer. At least one of the listed compounds may be included in the hole transport auxiliary layer.

[Group E]

In addition to the compounds described above, known compounds described in US5061569A, JP1993-009471A, WO1995-009147A1, JP1995-126615A, JP1998-095973A, and similar structures may be used for the hole transport auxiliary layer.

In addition, in one embodiment of the present invention, it may be an organic light emitting device further including an electron transport layer, an electron injection layer, a hole injection layer, and the like as the organic layer 105 in FIG. 1 or 2 .

In the organic light emitting devices 100 and 200, after forming an anode or a cathode on a substrate, an organic layer is formed by a dry film method such as evaporation, sputtering, plasma plating, and ion plating, and then formed thereon. It can be prepared by forming a cathode or an anode.

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

The above-described implementation will be described in more detail through the following examples. However, the following examples are for illustrative purposes only and do not limit the scope of rights.

(Synthesis of first compound)

Synthesis Example 1: Synthesis of Intermediate Int-6

[Scheme 1]

Step 1: Synthesis of Intermediate Int-1

1-Bromo-4-chloro-2-fluorobenzene (61g, 291mmol), 2,6-Dimethoxyphenylboronic Acid (50.4g, 277mmol), K ₂ CO ₃ (60.4g, 437mmol) and Pd(PPh ₃ ) ₄ (10.1g , 8.7mmol) was put into a round bottom flask, dissolved in THF (500ml) and distilled water (200ml), and stirred under reflux for 12 hours at 60°C. After the reaction was completed, after removing the water layer, 38 g (51%) of intermediate Int-1 was obtained using column chromatography (Hexane: DCM (20%)).

Step 2: Synthesis of Intermediate Int-2

Intermediate Int-1 (38g, 142mmol) and Pyridine Hydrochloride (165g, 1425mmol) were put in a round bottom flask and stirred under reflux at 200℃ for 24 hours. Upon completion of the reaction, the mixture was cooled to room temperature, slowly poured into distilled water, and stirred for 1 hour. The solids were filtered to give 23 g (68%) of the intermediate Int-2.

Step 3: Synthesis of Intermediate Int-3

Intermediate Int-2 (23g, 96mmol) and K ₂ CO ₃ (20g, 144mmol) were put in a round bottom flask and dissolved in NMP (100ml), followed by stirring under reflux at 180°C for 12 hours. When the reaction is complete, the mixture is poured into an excess of distilled water. After filtering the solid, it was dissolved in ethyl acetate, dried over MgSO ₄ , and the organic layer was removed under reduced pressure. 16 g (76%) of intermediate Int-3 was obtained by column chromatography (Hexane: Ethyl Acetate (30%)).

Step 4: Synthesis of Intermediate Int-4

Intermediate Int-3 (16g, 73mmol) and Pyridine (12ml, 146mmol) were put in a round bottom flask and dissolved in DCM (200ml). After lowering the temperature to 0℃, trifluoromethanesulfonic anhydride (14.7ml, 88mmol) was slowly added dropwise. When the reaction was completed after stirring for 6 hours, an excess amount of distilled water was added, stirred for 30 minutes, and then extracted with DCM. The organic solvent was removed under reduced pressure and vacuum dried to obtain 22.5 g (88%) of intermediate Int-4.

Step 5: Synthesis of Intermediate Int-5

Intermediate Int-4 (25g, 71.29mmol) and 3-BiPhenylboronic acid (16.23g, 81.78mmol), K ₂ CO ₃ (14.78g, 106.93mmol) and Pd(PPh ₃ ) ₄ (4.12g, 3.56mmol) were used. and synthesized in the same manner as in step 1 to obtain 21 g (83%) of intermediate Int-5.

Step 6: Synthesis of Intermediate Int-6

Intermediate Int-5 (21g, 59.18mmol), Bis(pinacolato)diboron (19.54g, 76.94mmol), Pd(dppf)Cl ₂ (2.42g, 2.96mmol), Tricyclohexylphosphine (3.32g, 11.84mmol) and Potassium acetate ( 11.62g, 118.37mmol) into a round bottom flask and dissolved in DMF (320ml). The mixture is stirred at reflux for 10 hours at 120°C. When the reaction is complete, the mixture is poured into an excess of distilled water and stirred for 1 hour. The solids are filtered and dissolved in DCM. After removing moisture with MgSO ₄ , the organic solvent was filtered using a silica gel pad and removed under reduced pressure. The solid was recrystallized from ethyl acetate and hexane to obtain 18.49 g (70%) of intermediate Int-6.

Synthesis Example 2: Synthesis of Intermediate Int-14

[Scheme 2]

2,4-Dichloro-6-phenyl-1,3,5-triazine (30g, 132.71mmol), carbazole (17.75g, 106.17mmol), and sodium tert-butoxide (14.03g, 145.98mmol) were put in a round bottom flask and THF (650ml) and stirred at room temperature for 12 hours. The resulting solid was filtered and stirred in the water layer for 30 minutes. After filtering and drying, 20 g (42%) of intermediate Int-14 was obtained.

Synthesis Example 3: Synthesis of Compound 1-27

[Scheme 3]

Intermediate Int-14 (9.5 g, 26.62 mmol), intermediate Int-6 (14.26 g, 31.95 mmol), K ₂ CO ₃ (9.20 g, 66.56 mmol) and Pd(PPh ₃ ) ₄ (1.54 g, 1.33 mmol) Put in a round bottom flask, dissolve in THF (100ml) and distilled water (40ml), and stir under reflux for 12 hours at 70 ℃. After the reaction was completed, the mixture was added to 500 mL of methanol, and the crystallized solid was filtered, dissolved in monochlorobenzene, filtered through silica gel/celite, and after removing an appropriate amount of organic solvent, recrystallized with methanol to obtain 13.14 g of compound 1-27 ( 77%) was obtained.

(LC/MS theory: 640.23 g/mol, measured value: M+= 641.39 g/mol)

Synthesis Example 4: Synthesis of Compound 1-24

[Scheme 4]

Step 1: Synthesis of Intermediate Int-8

Add 23.4 g (87.3 mmol) of 2-Chloro-4,6-diphenyl-1,3,5-triazine to 100 mL of THF, 100 mL of Toluene, and 100 mL of distilled water, 0.9 equivalent of 4-Chlorophenylboronic acid, and 0.03 equivalent of Pd (PPh ₃ ) ₄ , K ₂ CO ₃ 2 equivalents were added and stirred at reflux for 6 hours under a nitrogen atmosphere. After removing the water layer, the organic layer was dried under reduced pressure. After washing the obtained solid with water and hexane, the solid was recrystallized with 200 mL of toluene to obtain 20 g (67%) of intermediate Int-8.

Step 2: Synthesis of Intermediate Int-9

After dissolving 35g (142mmol) of 3-Bromo-9H-carbazole in 500mL of THF, 17.3g (142mmol) of phenylboronic acid and 8.2g (7.1mmol) of Pd (PPh ₃ ) ₄ were added and stirred. Then, 49.1 g (356 mmol) of a saturated K ₂ CO ₃ aqueous solution was added and stirred under reflux at 80° C. for 12 hours. After completion of the reaction, water was added to the reaction mixture, extracted with DCM, and after removing moisture with MgSO ₄ , filtered and concentrated under reduced pressure. The resulting residue was separated and purified by column chromatography (Hexane: DCM (20%)) to obtain 22.0 g (64%) of intermediate Int-9.

Step 3: Synthesis of compounds 1-24

Intermediate Int-9 22.0 g (90.4 mmol), Intermediate Int-8 31.1 g (90.4 mmol), NaOtBu 13.1 g (135.6 mmol), Pd ₂ (dba) ₃ 2.5 g (2.7 mmol), P (t-Bu) ₃ 5.5 g (50% in toluene) was added to 300 mL of xylene and stirred under reflux for 12 hours under a nitrogen stream. After removing xylene, 200 mL of methanol was added to the mixture obtained therefrom to filter the crystallized solids, which were dissolved in MCB and filtered through silica gel, and 32 g (64%) of compound 1-24 was obtained by condensing with an appropriate amount of organic solvent.

(LC/MS theory: 550.22 g/mol, measured value: M+= 551.23 g/mol)

Synthesis Example 5: Synthesis of Compound 1-25

[Scheme 5]

Step 1: Synthesis of Intermediate A

After suspending 65.5 g (216.79 mmol) of 2-[1,1'-biphenyl]-4-yl-4,6-dichloro-1,3,5-triazine and 25 g (149.51 mmol) of Carbazole in 800 ml of THF, NaO ( t-Bu) 15.09 g (156.99 mmol) was slowly added. After stirring at room temperature for 12 hours, the resulting solid was filtered and washed in the order of distilled water, acetone, and hexane to obtain 40.15 g (62% yield) of intermediate A.

Step 2: Synthesis of compounds 1-25

Intermediate A 10 g (23.10 mmol) and 3- (9H-carbazol-9-yl) phenyl boronic acid 8.70 g (23.56 mmol), Pd (PPh ₃ ) ₄ 0.8 g (0.69 mmol), K ₂ CO ₃ 6.39 g (46.2 mmol) was suspended in 100 ml of THF and 50 ml of distilled water, and stirred under reflux for 12 hours. After completion of the reaction, after cooling to room temperature, the resulting solid is filtered and washed with distilled water and acetone. After heating and dissolving in 200ml of dichlorobenzene, silicagel filtering and filtering the resulting solid, it was recrystallized in 150ml of dichlorobenzene to obtain 11g of compound 1-25 (74% yield).

(LC/MS: theoretical value 639.75 g/mol, measured value: 640.40 g/mol)

(Synthesis of Second Compound)

Synthesis Example 6: Synthesis of Compound 2-2

It was synthesized in the same manner as described in KR10-2017-0037277A.

Synthesis Example 7: Synthesis of Compound 2-15

[Scheme 6]

Step 1: Synthesis of Intermediate 2-15-1

In a round bottom flask, 10.44 g (42.41 mmol) of 4-bromo-9H-carbazole and 11.88 g (42.41 mmol) of 4-iodo-1,1'-biphenyl (purchased from Aldrich), 0.388 g (42.41 mmol) of Pd ₂ (dba) ₃ 0.424mmol), P(t-Bu) 3 0.206g (0.848mmol), and NaO(t-Bu) 6.11g (63.61mmol) were suspended in 420ml of toluene and stirred at 60°C for 12 hours. After completion of the reaction, distilled water was added, stirred for 30 minutes, extracted, and only the organic layer was columned with a silica gel column (hexane/dichloromethane = 9: 1 (v/v)) to obtain 14.70 g (87% yield) of intermediate 2-15-1. .

Step 2: Synthesis of Intermediate 2-15-2

In a round bottom flask, 15.50 g (38.92 mmol) of the intermediate 2-15-1 synthesized above, 7.15 g (42.81 mmol) of (2-nitrophenyl)-boronic acid and 16.14 g (116.75 mmol) of potassium carbonate, tetrakis-(tri Phenylphosphine)palladium(0)(Pd(PPh ₃ ) ₄ ) 1.35g (1.17mmol) was suspended in 150ml of toluene and 70ml of distilled water, followed by reflux stirring for 12 hours. Then, extraction was performed with dichloromethane and distilled water, and the organic layer was filtered through silica gel. Subsequently, the organic solution was removed, and the product solid was recrystallized from dichloromethane and n-hexane to obtain 13.72 g of intermediate 2-15-2 (yield: 80%).

Step 3: Synthesis of Intermediate 2-15-3

In a round bottom flask, 22.46 g (51.00 mmol) of the intermediate 2-15-2 synthesized above and triethyl phosphite 52.8ml was added thereto, nitrogen substitution was performed, and the mixture was stirred at 160° C. for 12 hours. After completion of the reaction, 3 L of MeOH was added, stirred, filtered, and the filtrate was volatilized. Purification (Hexane) was performed by column chromatography to obtain 10.42 g (50% yield) of Intermediate 2-15-3.

Step 4: Synthesis of compounds 2-15

Compound 2-15 was synthesized in the same manner as in Step 1 of Synthesis Example 7 using the synthesized intermediate 2-15-3 and 1-iodo-3-phenylbenzene. (Yield: 60%)

(LC/MS: theoretical value 560.23 g/mol, measured value: 561.57 g/mol)

Synthesis Example 8: Synthesis of Compound 2-13

[Scheme 7]

Step 1: Synthesis of Intermediate 2-13-1

In a round bottom flask, 2-[9-([1,1'-biphenyl]-4-yl)-9H-carbazol-3-yl]-4,4,5,5-tetramethyl-1,3, 2-dioxaborolane 18.23 g (40.94 mmol), 2-bromo-9H-carbazole 11.08 g (45.03 mmol) and potassium carbonate 11.32 g (81.88 mmol), tetrakis-(triphenylphosphine)palladium (0 )(Pd(PPh ₃ ) ₄ ) 1.42g (1.23mmol) was suspended in 180ml of tetrahydrofuran (THF) and 75ml of distilled water, followed by reflux stirring for 12 hours. Then, extraction was performed with dichloromethane and distilled water, and the organic layer was filtered through silica gel. Subsequently, the organic solution was removed, and the product solid was recrystallized from dichloromethane and n-hexane to obtain 18.05 g of intermediate 2-13-1 (yield: 91%).

Step 2: Synthesis of compound 2-13

In a round bottom flask, 13.29 g (27.42 mmol) of intermediate 2-13-1, 6.39 g (27.42 mmol) of 1-bromo-4-phenylbenzene, 0.25 g (0.274 mmol) of Pd ₂ (dba) ₃ , P (t- After suspending 0.133 g (0.274 mmol) of Bu) ₃ and 3.95 g (41.13 mmol) of NaO (t-Bu) in 300 ml of toluene, the mixture was stirred at 60° C. for 12 hours. After completion of the reaction, distilled water was added, stirred for 30 minutes, extracted, and only the organic layer was columned with a silica gel column (hexane/dichloromethane = 9: 1 (v/v)) to obtain 15.37 g (88% yield) of compound 2-13.

LC-Mass (Theory: 636.26 g/mol, Measured: M+ = 637.40 g/mol)

(Synthesis of Third Compound)

Synthesis Example 9: Synthesis of Compound 3-1

[Scheme 8]

Step 1: Synthesis of Intermediate Int-3-1

4,4,5,5-Tetramethyl-2-(triphenylen-2-yl)-1,3,2-dioxaborolane 50.3 g (142.1 mmol), 1-Bromo-3-iodobenzene 40.2 g (142.1 mmol), K ₂ 29.5 g (213.2 mmol) of CO ₃ and 4.9 g (4.3 mmol) of Pd (PPh ₃ ) ₄ were suspended in 280 ml of THF and 110 ml of distilled water under a nitrogen stream, followed by reflux stirring for 8 hours. After the reaction was completed, after extraction with DCM, a solid was obtained using column chromatography (Hexane: DCM (20%)) to obtain 39.3 g (78%) of intermediate Int-3-1.

Step 2: Synthesis of Intermediate Int-3-2

Intermediate Int3-1 77g (203.3mmol), Bis(pinacolato)diboron 59.4g (233.8mmol), Pd(dppf)Cl ₂ 4.8g (5.9mmol) and Potassium acetate 28.9g (294.8mmol) were put in a round bottom flask and DMF 400ml melt with The mixture is stirred at 120° C. for 12 hours at reflux. When the reaction is complete, the mixture is poured into an excess of distilled water and stirred for 1 hour. The solids are filtered and dissolved in DCM. After removing moisture with MgSO ₄ , the organic solvent was filtered using a silica gel pad and removed under reduced pressure. The solid was recrystallized from ethyl acetate and hexane to obtain 41.8 g (70%) of intermediate Int-3-2.

Step 3: Synthesis of Compound 3-1

Intermediate Int-3-2 61.2 g (142.1 mmol), 4-Bromo-9,9'-spirobi [9H-fluorene] 56.2 g (142.1 mmol), K ₂ CO ₃ 29.5 g (213.2 mmol), Pd (PPh ₃ ) ₄ 4.9g (4.3mmol) was suspended in 280ml of THF and 110ml of distilled water under a nitrogen stream, followed by reflux stirring for 8 hours. After the reaction was completed, after extraction with DCM, a solid was obtained using column chromatography (Hexane: DCM (20%)) to obtain 39.3 g (78%) of compound 3-1.

LC-Mass (Theory: 618.23 g/mol, Measured: M+ = 619.40 g/mol)

Synthesis Example 10: Synthesis of Compound 3-2

[Scheme 9]

Step 1: Synthesis of Intermediate Int-3-3

4,4,5,5-Tetramethyl-2-(triphenylen-2-yl)-1,3,2-dioxaborolane 50.3 g (142.1 mmol), 1-Bromo-4-iodobenzene 40.2 g (142.1 mmol), K ₂ 29.5 g (213.2 mmol) of CO ₃ and 4.9 g (4.3 mmol) of Pd (PPh ₃ ) ₄ were suspended in 280 ml of THF and 110 ml of distilled water under a nitrogen stream, followed by reflux stirring for 8 hours. After the reaction was completed, after extraction with DCM, a solid was obtained using column chromatography (Hexane: DCM (20%)) to obtain 43.6 g (80%) of intermediate Int-3-3.

Step 2: Synthesis of Intermediate Int-3-4

Intermediate Int3-3 77g (203.3mmol), Bis(pinacolato)diboron 59.4g(233.8mmol), Pd(dppf)Cl ₂ 4.8g(5.9mmol) and Potassium acetate 28.9g(294.8mmol) were put in a round bottom flask and DMF 400ml melt with The mixture is stirred at 120° C. for 12 hours at reflux. When the reaction is complete, the mixture is poured into an excess of distilled water and stirred for 1 hour. The solids are filtered and dissolved in DCM. After removing moisture with MgSO ₄ , the organic solvent was filtered using a silica gel pad and removed under reduced pressure. The solid was recrystallized from ethyl acetate and hexane to obtain 65.6 g (75%) of intermediate Int-3-4.

Step 3: Synthesis of Compound 3-2

Intermediate Int-3-4 61.2 g (142.1 mmol), 4-Bromo-9,9'-spirobi [9H-fluorene] 56.2 g (142.1 mmol), K ₂ CO ₃ 29.5 g (213.2 mmol), Pd (PPh ₃ ) ₄ 4.9g (4.3mmol) was suspended in 280ml of THF and 110ml of distilled water under a nitrogen stream, followed by reflux stirring for 8 hours. After the reaction was completed, after extraction with DCM, a solid was obtained using column chromatography (Hexane: DCM (20%)) to obtain 39.3 g (78%) of compound 3-2.

LC-Mass (Theory: 618.23g/mol, Measured: M+ = 619.39g/mol)

(Synthesis of dopant)

Synthesis Example 11: Synthesis of Dopant Compound PtGD

[PtGD]

It was synthesized in the same manner as described in KR1999337.

(Manufacture of organic light emitting device)

Example 1

A glass substrate coated with a thin film of ITO (Indium tin oxide) was washed with distilled water. After the distilled water cleaning was completed, the substrate was ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, or methanol, dried, transferred to a plasma cleaner, cleaned for 10 minutes using oxygen plasma, and then transferred to a vacuum evaporator. Using the prepared ITO transparent electrode as an anode, compound A doped with 3% NDP-9 (available from Novaled) was vacuum deposited on the ITO substrate to form a hole transport layer with a thickness of 1,400 Å, and the compound on the hole transport layer. B was deposited to a thickness of 350 Å to form a hole transport auxiliary layer. Compound 1-27, compound 2-2, and compound 3-2 were used as hosts at the same time on the hole transport auxiliary layer, and PtGD was doped at 15 wt% as a dopant to form a 400 Å-thick light emitting layer by vacuum deposition. Here, Compound 1-27, Compound 2-2 and Compound 3-2 were used in a weight ratio of 35:55:10, and the ratios were separately described in the following Examples and Comparative Examples. Subsequently, compound C was deposited on the light emitting layer to a thickness of 50 Å to form an electron transport auxiliary layer, and compound D and Liq were simultaneously vacuum deposited in a 1:1 ratio to form an electron transport layer with a thickness of 300 Å. An organic light emitting device was fabricated by forming a cathode by sequentially vacuum depositing 15 Å of LiQ and 1,200 Å of Al on the electron transport layer.

ITO / Compound A (3% NDP-9 doping, 1,400Å) / Compound B (350Å) / EML [1-27: 2-2: 3-2 [PtGD] (15wt%)] (400Å) / Compound C ( 50Å) / compound D: LiQ (300Å) / LiQ (15Å) / Al (1,200Å) structure.

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

Compound B: N,N-bis(9,9-dimethyl-9H-fluoren-4-yl)-9,9-spirobi(fluorene)-2-amine

Compound C: 2-(3-(3-(9,9-dimethyl-9H-fluoren-2-yl)phenyl)phenyl)-4,6-diphenyl-1,3,5-triazine

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

[PtGD]

Examples 2 and 3

Except for changing the composition to the host described in Tables 1 to 3, an organic light emitting device was manufactured in the same manner as in Example 1.

Comparative Examples 1 to 6

Except for changing the composition to the host described in Tables 1 to 3, an organic light emitting device was manufactured in the same manner as in Example 1.

evaluation

Efficiency and lifetime of the organic light emitting devices according to Examples 1 to 3 and Comparative Examples 1 to 6 were measured.

The specific measurement method is as follows, and the results are shown in Tables 1 to 3.

(1) Life measurement

The result was obtained by maintaining the luminance (cd/m ² ) at 24,000 cd/m ² and measuring the time for the current efficiency (cd/A) to decrease to 95%. Relative life ratios were shown based on the life values of Comparative Examples 1, 3, and 5, respectively.

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

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

(3) Measurement of luminance change according to voltage change

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

(4) Current efficiency measurement

The current efficiency (cd/A) of the required luminance of 9000 nit was calculated using the luminance, current density, and voltage measured from (1) and (2) above. Relative efficiency ratios were shown based on the current efficiency values of Comparative Examples 1, 3, and 5, respectively.

No. 1
host 2nd
host 3rd
host 1st Host:
Second host:
3rd host
Ratio (wt:wt) efficiency ratio
(%) cost of life
(T95)
(%) Example 1 1-27 2-2 3-2 35:55:10 100 116 Comparative Example 1 1-27 2-2 - 35:65:0 100 100 Comparative Example 2 1-27 - 3-2 35:0:65 80 60

No. 1
host 2nd
host 3rd
host 1st Host:
Second host:
3rd host
Ratio (wt:wt) efficiency ratio
(%) cost of life
(T95)
(%) Example 2 1-24 2-15 3-1 35:55:10 100 116 Comparative Example 3 1-24 2-15 - 35:65:0 100 100 Comparative Example 4 1-24 - 3-1 35:0:65 80 70

No. 1
host 2nd
host 3rd
host 1st Host:
Second host:
3rd host
Ratio (wt:wt) efficiency ratio
(%) cost of life
(T95)
(%) Example 3 1-25 2-13 3-2 32:48:20 100 117 Comparative Example 5 1-25 2-13 - 35:65:0 100 100 Comparative Example 6 1-25 - 3-2 35:0:65 80 65

Referring to Tables 1 to 3, it can be seen that the lifespan of the organic light emitting device according to Examples 1 to 3 is significantly improved while maintaining equal or higher efficiency compared to the organic light emitting device according to Comparative Examples 1 to 6.

Although the preferred embodiments of the present invention have been described in detail above, the scope of the present invention is not limited thereto, and various modifications and improvements of those skilled in the art using the basic concept of the present invention defined in the following claims are also present. fall within the scope of the invention.

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

Claims (15)

first compound;
second compound; and
Including a third compound,
The first compound is represented by Formula I below,
The second compound is represented by Formula II below,
The third compound is a composition for an organic optoelectronic device represented by Formula III:
[Formula I]

In Formula I,
Z ¹ to Z ³ are N or CL ^a -R ^a ;
at least two of Z ¹ to Z ³ are N;
L ^a and L ¹ to L ³ are each independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heterocyclic group, or a combination thereof;
R ¹ and R 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 ^a , R ³ and R ⁴ are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a substituted or an unsubstituted silyl group, a substituted or unsubstituted amine group, a halogen, a cyano group, or a combination thereof;
Ring A is represented by any one of Formulas I-1 to Formula I-7 below:
[Formula Ⅰ-1] [Formula Ⅰ-2] [Formula Ⅰ-3] [Formula Ⅰ-4]

[Formula Ⅰ-5] [Formula Ⅰ-6] [Formula Ⅰ-7]

In Formula 1-1 to Formula 1-7,
X ¹ is O, S or NR ^b ;
R ^b and R ⁵ to R ¹² are each independently hydrogen, heavy hydrogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a substituted or an unsubstituted silyl group, a substituted or unsubstituted amine group, a halogen, a cyano group, or a combination thereof;
* is the junction point;
[Formula II]

In Formula II,
L ⁴ is a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heterocyclic group, or a combination thereof;
Ar ¹ is a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a combination thereof;
R ¹³ and R ¹⁴ are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, a substituted or unsubstituted A silyl group, a substituted or unsubstituted amine group, a halogen, a cyano group, or a combination thereof,
Ring B is represented by any of the following formulas II-1 to II-4:
[Formula Ⅱ-1] [Formula Ⅱ-2]

[Formula Ⅱ-3] [Formula Ⅱ-4]

In Formula II-1 to Formula II-4,
L ⁵ and L ⁶ are each independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heterocyclic group, or a combination thereof;
L ⁸ is a single bond or a substituted or unsubstituted C6 to C20 arylene group;
Ar ² and Ar ³ are a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a combination thereof;
R ¹⁵ to R ²¹ are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, a substituted or unsubstituted A silyl group, a substituted or unsubstituted amine group, a halogen, a cyano group, or a combination thereof,
* is the junction point;
[Formula III]

In the above formula Ⅲ,
L ⁷ is a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heterocyclic group, or a combination thereof;
R ²² to R ³³ are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, a substituted or unsubstituted a silyl group, a substituted or unsubstituted amine group, a halogen group, a cyano group, or a combination thereof. In paragraph 1,
The first compound is a composition for an organic optoelectronic device represented by Formula 1A or Formula 1E:
[Formula ⅠA] [Formula ⅠE]

In Formula 1A and Formula 1E,
Z ¹ to Z ³ , L ¹ to L ³ , R ¹ to R ¹² , and X ¹ are defined as in claim 1. In paragraph 2,
The first compound is a composition for an organic optoelectronic device represented by Formula IA. In paragraph 1,
The second compound is a composition for an organic optoelectronic device represented by the following formula ⅡA or formula ⅡF:
[Formula ⅡA] [Formula ⅡF]

In the above formulas ⅡA to ⅡF,
The definitions of L ⁴ to L ⁶ , L ⁸ , Ar ¹ to Ar ³ , and R ¹³ to R ²¹ are the same as in claim 1. In paragraph 4,
Formula ⅡA is a composition for an organic optoelectronic device represented by Formula 2A-1 or Formula 2A-2:
[Formula ⅡA-1] [Formula ⅡA-2]

In the above Chemical Formulas IIA-1 and Chemical Formulas IIA-2, L ⁴ , L ⁵ , Ar ¹ , Ar ² , and R ¹³ to R ¹⁸ are defined as in claim 1. In paragraph 1,
The third compound is a composition for an organic optoelectronic device represented by any one of Formulas III-1 to Formulas III-4:
[Formula III-1] [Formula III-2]

[Formula Ⅲ-3] [Formula Ⅲ-4]

In Formulas III-1 to Formulas III-4, L ⁷ and R ²² to R ³³ are defined as in claim 1. In paragraph 6,
The third compound is represented by Formula III-4,
L ⁷ of Formula III-4 is a single bond or a substituted or unsubstituted phenylene group;
R ²² to R ³³ are hydrogen, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted carbazolyl group, a composition for an organic optoelectronic device. In paragraph 1,
The first compound is represented by Formula IA-1 or Formula IA-4,
The second compound is represented by any one of the following Chemical Formulas IIA-1, Chemical Formulas IIA-2 and Chemical Formulas IIF,
The third compound is a composition for an organic optoelectronic device represented by Chemical Formula III-4:
[Formula IA-1] [Formula IA-4]

In Formula 1A-1 and Formula 1A-4, Z ¹ to Z ³ , L ¹ to L ³ , R ¹ and R ² are defined as defined in claim 1, R ³ is a substituted or unsubstituted phenyl group, A substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted indolocarbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted carbazolyl group. A cyclic dibenzothiophenyl group;
[Formula ⅡA-1] [Formula ⅡA-2]

[Formula IIF]

In the above formulas ⅡA-1, ⅡA-2 and ⅡF,
L ⁴ to L ⁶ , L ⁸ , Ar ¹ to Ar ³ , and R ¹³ to R ²¹ are defined as defined in claim 1;
[Formula III-4]

In Formula III-4,
The definitions of L ⁷ and R ²² to R ³³ are as defined in claim 1. anode and cathode facing each other,
At least one organic layer positioned between the anode and the cathode,
The organic layer is an organic optoelectronic device comprising the composition for an organic optoelectronic device according to any one of claims 1 to 8. According to claim 9,
The organic layer includes a light emitting layer,
The light emitting layer is an organic optoelectronic device comprising the composition for the organic optoelectronic device. According to claim 10,
The first compound, the second compound, and the third compound are each included as a phosphorescent host of the light emitting layer organic optoelectronic device. According to claim 11,
The first compound is included in about 20% to 50% by weight based on the total weight of the first compound, the second compound, and the third compound,
The second compound is included in about 40% to 60% by weight based on the total weight of the first compound, the second compound, and the third compound,
Wherein the third compound is contained in about 10% to 30% by weight based on the total weight of the first compound, the second compound and the third compound, the organic optoelectronic device. According to claim 10,
The organic optoelectronic device composition further comprises a dopant. According to claim 13,
The organic optoelectronic device composition is a green light-emitting composition. A display device comprising the organic optoelectronic device according to claim 9 .

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