KR102430046B1 - Compound for organic optoelectronic device, composition for organic optoelectronic device and organic optoelectronic device and display device - Google Patents

Abstract

It relates to a compound for an organic optoelectronic device represented by Formula 1, a composition for an organic optoelectronic device including the same, an organic optoelectronic device, and a display device.
Definitions for Chemical Formula 1 are the same as defined in the specification.

Description

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

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

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

Organic optoelectronic devices can be roughly 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 electrons and holes are transferred to different electrodes, and the other is electrical energy by supplying voltage or current to the electrode It is a light emitting device that generates light energy from

Examples of the organic optoelectronic device include an organic optoelectronic 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 attracted much 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 an organic material positioned between electrodes.

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

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

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

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

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

[Formula 1]

In Formula 1,

R ¹ and R ² are each independently hydrogen, an unsubstituted phenyl group or an unsubstituted biphenyl group,

At least one of R ¹ and R ² is an unsubstituted phenyl group or an unsubstituted biphenyl group,

R ³ and R ⁴ are each independently an unsubstituted phenyl group or an unsubstituted biphenyl group,

R ⁵ to R ⁹ are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C20 aryl group.

According to another embodiment, there is provided a composition for an organic optoelectronic device comprising a first compound for an organic optoelectronic device, and a second compound for an organic optoelectronic device.

The first compound for an organic optoelectronic device includes the compound for an organic optoelectronic device described above, and the second compound for an organic optoelectronic device includes a compound for an organic optoelectronic device represented by Chemical Formula 2 below.

[Formula 2]

In Formula 2,

Y ¹ and Y ² are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group,

Ar ¹ and Ar ² are each independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,

R ¹⁰ to R ¹⁵ are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, a cyano group, or It is a combination of these.

According to another embodiment, it includes an anode and a cathode facing each other, and at least one organic layer positioned between the anode and the cathode, wherein the organic layer comprises the compound for an organic optoelectronic device or a composition for an organic optoelectronic device An organic optoelectronic device is provided.

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

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

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

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

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

In one embodiment of the present invention, "substitution" means that at least one hydrogen in a 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, or a cyano group. In addition, in a specific embodiment of the present invention, "substitution" means that at least one hydrogen in a substituent or compound is substituted with deuterium, a C1 to C20 alkyl group, a C6 to C30 aryl group, or a cyano group. In addition, in a specific embodiment of the present invention, "substitution" means that at least one hydrogen in a substituent or compound is substituted with deuterium, a C1 to C5 alkyl group, a C6 to C18 aryl group, or a cyano group. In addition, in a specific example of the present invention, "substitution" means that at least one hydrogen in a substituent or compound is substituted with deuterium, a cyano group, a methyl group, an ethyl group, a propanyl group, a butyl group, a phenyl group, a biphenyl group, a terphenyl group or a naphthyl group means it has been

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

As used herein, the term "aryl group" is a concept that encompasses 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. It contains a form that forms, for example, a phenyl group, a naphthyl group, etc., and includes a form in which two or more hydrocarbon aromatic moieties are connected through a sigma bond, such as a biphenyl group, a terphenyl group, a quaterphenyl group, etc., and two or more hydrocarbon aromatic moieties They may include a fused non-aromatic fused ring, such as a fluorenyl group, directly or indirectly.

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

In the present specification, "heterocyclic group" is a higher concept including a heteroaryl group, and instead of carbon (C), N, O, It means containing at least one hetero atom selected from the group consisting of S, P and Si. When the heterocyclic group is a fused ring, the entire heterocyclic group or each ring may include one or more heteroatoms.

For example, "heteroaryl group" means containing at least one hetero atom selected from the group consisting of N, O, S, P and Si in the aryl group. Two or more heteroaryl groups may be directly connected through a sigma bond, or when 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 include 1 to 3 heteroatoms.

More specifically, a substituted or unsubstituted C6 to C30 aryl group includes 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 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 o- Terphenyl group, substituted or unsubstituted chrysenyl group, substituted or unsubstituted triphenylene group, substituted or unsubstituted perylenyl group, substituted or unsubstituted fluorenyl group, substituted or unsubstituted indenyl group, substituted or unsubstituted It may be a cyclic furanyl group, or a combination thereof, but is not limited thereto.

More specifically, a substituted or unsubstituted C2 to C30 heterocyclic group is a substituted or unsubstituted thiophenyl group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted pyrazolyl group, a substituted or 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, a substituted or unsubstituted A substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted benzofuranyl group, a substituted or 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, a 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, substituted or unsubstituted phenazine A diyl group, a substituted or unsubstituted phenothiazinyl group, a substituted or unsubstituted phenoxazinyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophene It may be a diary, or a combination thereof, but is not limited thereto.

As used herein, the hole property refers to a property capable of forming a hole by donating electrons when an electric field is applied. It refers to a property that facilitates the movement of holes formed in the anode and in the light emitting layer.

In addition, the electronic property refers to a property that can receive electrons when an electric field is applied. It has conduction properties along the LUMO level, so electrons formed in the cathode are injected into the light emitting layer, electrons formed in the light emitting layer are moved to the cathode, and in the light emitting layer. properties that facilitate movement.

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

The compound for an organic optoelectronic device according to an embodiment is represented by the following Chemical Formula 1.

[Formula 1]

In Formula 1,

R ¹ and R ² are each independently hydrogen, an unsubstituted phenyl group or an unsubstituted biphenyl group,

At least one of R ¹ and R ² is an unsubstituted phenyl group or an unsubstituted biphenyl group,

R ³ and R ⁴ are each independently an unsubstituted phenyl group or an unsubstituted biphenyl group,

R ⁵ to R ⁹ are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C20 aryl group.

The compound represented by Formula 1 improved the stability of the material by introducing a kinked terphenyl group into the indolocarbazole, and at the same time, the kinked terphenyl group was additionally substituted with a C6 to C12 aryl group to allow electron mobility Due to the effect of improving the deposition film according to the improvement, device characteristics with low driving efficiency and long life can be realized.

The compound for an organic optoelectronic device represented by Chemical Formula 1 may be, for example, represented by any one of the following Chemical Formulas 1A to 1C according to an aryl group further substituted with a terphenyl group.

[Formula 1A] [Formula 1B]

[Formula 1C]

In Formulas 1A to 1C, R ³ to R ⁹ are the same as described above.

More specifically, Chemical Formula 1A may be represented by any one of Chemical Formulas 1A-1 to 1A-3 below.

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

[Formula 1A-3]

In Formulas 1A-1 to 1A-3, R ³ to R ⁹ are the same as described above.

More specifically, Chemical Formula 1B may be represented by any one of Chemical Formulas 1B-1 to 1B-6 below.

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

[Formula 1B-3] [Formula 1B-4]

[Formula 1B-5] [Formula 1B-6]

In Formulas 1B-1 to 1B-6, R ³ to R ⁹ are the same as described above.

More specifically, Chemical Formula 1C may be represented by any one of the following Chemical Formulas 1C-1 to 1C-9.

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

[Formula 1C-3] [Formula 1C-4]

[Formula 1C-5] [Formula 1C-6]

[Formula 1C-7] [Formula 1C-8] [Formula 1C-9]

In Formulas 1C-1 to 1C-9, R ³ to R ⁹ are the same as described above.

The compound for an organic optoelectronic device according to an embodiment of the present invention may be represented by Chemical Formula 1A-2.

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

[Group 1]

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

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

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

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

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

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

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

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

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

[A-46] [A-47] [A-48] [A-49]

[A-50] [A-51] [A-52] [A-53] [A-54]

[A-55] [A-56] [A-57] [A-58] [A-59]

[A-60] [A-61] [A-62] [A-63] [A-64]

[A-65] [A-66] [A-67] [A-68] [A-69]

The composition for an organic optoelectronic device according to another exemplary embodiment includes the above-described compound (hereinafter, “a first compound for an organic optoelectronic device”), and a second compound for an organic optoelectronic device represented by the following Chemical Formula 2.

In an embodiment, the composition for an organic optoelectronic device may be a mixture of a first compound for an organic optoelectronic device and a second compound for an organic optoelectronic device.

[Formula 2]

In Formula 2,

Y ¹ and Y ² are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group,

Ar ¹ and Ar ² are each independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,

R ¹⁰ to R ¹⁵ are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, a cyano group, or It is a combination of these.

The second compound for an organic optoelectronic device is a material having fast and stable hole transport properties, and it can be used in the light emitting layer together with the first compound for an organic optoelectronic device having fast and stable electron transport properties to balance charges, through which It has a high glass transition temperature compared to its molecular weight, so it can realize low driving and long life characteristics.

In one embodiment of the present invention, Ar ¹ and Ar ² of Formula 2 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted Naphthyl group, substituted or unsubstituted anthracenyl group, substituted or unsubstituted triphenylenyl group, substituted or unsubstituted carbazolyl group, substituted or unsubstituted dibenzothiophenyl group, substituted or unsubstituted dibenzofuran a diyl, a substituted or unsubstituted fluorenyl group, or a substituted or unsubstituted pyridinyl group, Y ¹ and Y ² are each independently a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenyl and a ren group, and R ¹⁰ to R ¹⁵ may each independently be hydrogen, deuterium, or a substituted or unsubstituted C6 to C12 aryl group.

"Substitution" in Formula 2 means that at least one hydrogen is substituted with deuterium, a C1 to C4 alkyl group, a C6 to C18 aryl group, or a C2 to C30 heteroaryl group.

For example, *-Y ¹ -Ar ¹ and *-Y ² -Ar ² in Formula 2 may be one of the substituents listed in Group I below.

[Group I]

In the above group I, * is a connection point.

For example, the compound represented by Formula 2 may be one selected from the compounds listed in Group 2 below, but is not limited thereto.

[Group 2]

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

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

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

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

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

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

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

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

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

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

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

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

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

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

[B-71] [B-72] [B-73]

The first compound for an organic optoelectronic device and the second compound for an organic optoelectronic device may be applied in the form of a composition (ie, a mixture).

For example, the compound for an organic optoelectronic device or the composition for an organic optoelectronic device described above may be a host.

The first compound for an organic optoelectronic device and the second compound for an organic optoelectronic device may be included, for example, in a weight ratio of 1:99 to 99:1. By being included in the above range, the efficiency and lifespan can be improved by matching an appropriate weight ratio by using the electron transport capability of the first compound for an organic optoelectronic device and the hole transport capability of the second compound for an organic optoelectronic device. Within the above range, for example, it may be included in a weight ratio of about 90:10 to 10:90, about 80:20 to 20:80, for example, about 80:20 to about 30:70, about 70:30 to about 30:70. It may be included as a weight ratio. As an example, it may be included in a weight ratio of 60:40 to 30:70, and as a specific example, it may be included in a weight ratio of 40:60.

The compound for an organic optoelectronic device or the composition for an organic optoelectronic device described above may further include a dopant. The dopant may be, for example, a phosphorescent dopant, such as a phosphorescent dopant of red, green or blue, such as a phosphorescent dopant of red or green.

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

Examples of the dopant 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. and organometallic compounds containing them. The phosphorescent dopant may be, for example, a compound represented by the following Chemical Formula Z, but is not limited thereto.

[Formula Z]

L ³ MX ^A

In Formula Z, M is a metal, and L ³ and X ^A are the same as or different from each other and are ligands forming 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 ⁴ and X are, for example, Biden It may be a tate ligand.

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

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

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

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

1 and 2 are cross-sectional views illustrating an organic light emitting diode 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 to facilitate hole injection, and may be made of, for example, a metal, a metal oxide, and/or a conductive polymer. The anode 120 may include, for example, a metal such as nickel, platinum, vanadium, chromium, copper, zinc, 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, but are limited thereto it is not

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

The organic layer 105 includes the light emitting layer 130 including the above-described compound or composition.

The light emitting layer 130 may include, for example, the above-described compound or composition.

Referring to FIG. 2 , the organic light emitting device 200 further includes a hole auxiliary layer 140 in addition to the emission layer 130 . The hole auxiliary layer 140 may further increase hole injection and/or hole mobility between the anode 120 and the emission 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 A 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 A]

In the hole transport auxiliary layer, in addition to the compounds described above, known compounds described in US5061569A, JP1993-009471A, WO1995-009147A1, JP1995-126615A, JP1998-095972A, etc. and compounds having a similar structure may also be used.

In addition, in one embodiment of the present invention, as the organic layer 105 in FIG. 1 or FIG. 2 , 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.

After forming an anode or a cathode on a substrate, the organic light emitting devices 100 and 200 form an organic layer by a dry film deposition method such as vacuum deposition, sputtering, plasma plating and ion plating, etc. It can be manufactured by forming an anode or an anode.

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

The above-described embodiment 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.

Hereinafter, unless otherwise specified, starting materials and reactants used in Examples and Synthesis Examples were purchased from Sigma-Aldrich, TCI, Tokyo chemical industry, or P&H tech, or synthesized through a known method.

(Production of compounds for organic optoelectronic devices)

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

(Preparation of compound for first organic optoelectronic device)

Synthesis Example 1: Synthesis of Intermediate 1

[Scheme 1]

3-Bromo-5-chloro-1,1'-Biphenyl (30 g, 112.8 mmol), 3-Phenylbenzeneboronic acid (22.3 g, 112.8 mmol), K ₂ CO ₃ (34.2 g, 248 mmol) and Pd (PPh ₃ ) ₄ (6.5 g, 5.6 mmol) was placed in a round-bottom flask, dissolved in THF (300 ml) and distilled water (150 ml), and stirred under reflux at 80° C. for 20 hours. After the reaction was completed, 35 g (81%) of Intermediate 1 was obtained using column chromatography (Hexane: DCM (20%)) after removing the water layer.

Synthesis Example 2: Synthesis of Intermediate 2

[Scheme 2]

Intermediate 1 (25 g, 73.5 mmol) and 11, 12-Dihydroindolo [2, 3-a] carbazole (20.7 g, 80.8 mmol), Pd ₂ (dba) ₃ (2 g, 2.2 mmol), P(t-Bu) ₃ (1.4g, 7.4mmol) and sodium tert-butoxide (7.7g, 80.8mmol) were put in a round-bottom flask, and Xylene (220ml) was stirred under reflux at 140℃ for 20 hours. When the reaction is complete, it is cooled to room temperature, slowly poured into distilled water, and stirred for 1 hour. After filtering the solid, it was dissolved in ethyl acetate and dried over MgSO ₄ . The organic solvent was removed under reduced pressure and vacuum dried to obtain 32 g (78%) of Intermediate 2.

Synthesis Example 3: Synthesis of compound A-1

[Scheme 3]

Intermediate 2 (18.6g, 33.2mmol), 2-Chloro-4,6-diphenyl-1,3,5-triazine (11.5g, 43.1mmol), sodium hydride (1.2g, 49.8mmol) was placed in a round-bottom flask and DMF (130ml) was stirred at room temperature for 12 hours. The resulting solid was filtered and stirred in a water layer for 30 minutes. After filtering and drying, 22 g (83%) of Compound A-1 was obtained.

(Preparation of compound for second organic optoelectronic device)

Synthesis Example 4: Synthesis of compound B-71

Compound B-71 was synthesized by a known method.

(comparative synthesis example)

The following comparative compounds were synthesized by a known method.

(Comparative compound 1) (Comparative compound 2)

(Comparative compound 3) (Comparative compound 4) (Comparative compound 5)

(comparative compound 6)

(Production of organic light emitting device)

Example 1

A glass substrate coated with indium tin oxide (ITO) to a thickness of 1,500 Å was washed with distilled water. After washing with distilled water, ultrasonic cleaning was performed with a solvent such as isopropyl alcohol, acetone, methanol, etc., dried and transferred to a plasma cleaner. After cleaning the substrate for 10 minutes using oxygen plasma, the substrate was transferred to a vacuum evaporator. Using the prepared ITO transparent electrode as an anode, Compound A was vacuum deposited on the ITO substrate to form a hole injection layer with a thickness of 700 Å, and Compound B was deposited on the injection layer to a thickness of 50 Å, followed by Compound C with 1,020 Å A hole transport layer was formed by deposition to a thickness of . Compound A-1 obtained in Synthesis Example 3 was used as a host on the hole transport layer, and PhGD was doped at 7wt% as a dopant to form an emission layer with a thickness of 400 Å by vacuum deposition. Subsequently, compound D and Liq were simultaneously vacuum deposited on the light emitting layer at a weight ratio of 1:1 to form an electron transport layer with a thickness of 300 Å, and Liq 15 Å and Al 1,200 Å were sequentially vacuum deposited on the electron transport layer to form a cathode. A light emitting device was manufactured.

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

ITO / Compound A (700 Å) / Compound B (50 Å) / Compound C (1,020 Å) / EML [Compound A-1: PhGD (7wt%)] (400 Å) / Compound D: Liq (300 Å) / Liq (15 Å) /Al (1,200Å) was prepared in the structure.

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

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

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

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

Example 2 and Comparative Examples 1 to 12

An organic light emitting diode was manufactured in the same manner as in Example 1, except that the composition was changed to Table 1 and Table 2.

evaluation

Examples 1, 2 and The driving voltage, luminous efficiency, and lifespan characteristics of the organic light emitting diodes according to Comparative Examples 1 to 12 were evaluated.

Specific measurement methods are as follows, and the results are shown in Tables 1 and 2.

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

For the manufactured organic light emitting device, the current flowing through the unit device was measured using a current-voltmeter (Keithley 2400) while the voltage was increased 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 device, the luminance was measured at that time using a luminance meter (Minolta Cs-1000A) while increasing the voltage from 0V to 10V, and results were obtained.

(3) Measurement of luminous efficiency

The luminous efficiency (cd/A) of the same current density (10 mA/cm ² ) was calculated using the luminance, current density, and voltage measured from (1) and (2) above.

(4) Lifetime measurement

The result was obtained by measuring the time for the luminance (cd/m2) to be maintained at ^24,000 cd/m2 and the luminous efficiency (cd/A) to decrease to 95%.

(5) Measurement of driving voltage

A current-voltmeter (Keithley 2400) was used to measure the driving voltage of each device at 15mA/cm ² , and the results were obtained.

(6) T95 life ratio (%) calculation

The relative comparison value of T95(h) of the mixed host example (applying the first compound as the first host) and the mixed host comparative example (applying the comparative compound as the first host) to the single host evaluation or to applying the same second host indicates.

T95 life ratio (%) = {[T95(h) of [Example, Comparative Example (first compound alone or mixed host)) / [T95(h) of reference data (comparative compound alone or mixed host)]} X 100

(7) Calculation of driving voltage ratio (%)

Relative comparison values between the single host evaluation or the mixed host example (applying the first compound as the first host) and the mixed host comparative example (applying the comparative compound as the first host) to which the same second host is applied are shown.

Driving voltage ratio (%) = {[Drive voltage (V) of Examples, Comparative Examples (first compound alone or mixed host)] / [Drive voltage (V) of reference data (comparative compound alone or mixed host)] } X 100

(8) Calculation of power efficiency ratio (%)

Relative comparison values between the single host evaluation or the mixed host example (applying the first compound as the first host) and the mixed host comparative example (applying the comparative compound as the first host) to which the same second host is applied are shown.

Power efficiency ratio (%) = {[Power efficiency (Cd / A) of [Example, Comparative Example (first compound alone or mixed host)] / [Reference data (comparative compound alone or mixed host) power efficiency ( Cd/A)]} X 100

No. host color Driving voltage ratio (%) power
Efficiency ratio (%) T95
Life Ratio (%) Example 1 A-1 green 98% 103% 113% Comparative Example 1 Comparative compound 1 green 102% 101% 83% Comparative Example 2 Comparative compound 2 green 102% 100% 78% Comparative Example 3 Comparative compound 3 green 97% 99% 100% Comparative Example 4 Comparative compound 4 green 101% 102% 99% Comparative Example 5 Comparative compound 5 green 103% 96% 62% Comparative Example 6 Comparative compound 6 green 100% 100% 100%

No. host weight ratio
(First compound:
second compound) power
efficiency ratio
(%) T95
life ratio
(%) first
compound second
compound Example 2 A-1 B-71 4:6 102% 120% Comparative Example 7 Comparative compound 1 B-71 4:6 105% 62% Comparative Example 8 Comparative compound 2 B-71 4:6 100% 69% Comparative Example 9 Comparative compound 3 B-71 4:6 101% 101% Comparative Example 10 Comparative compound 4 B-71 4:6 103% 64% Comparative Example 11 Comparative compound 5 B-71 4:6 97% 40% Comparative Example 12 Comparative compound 6 B-71 4:6 100% 100%

Referring to Tables 1 and 2, the material of the present invention containing an additional phenyl group or a biphenyl group in the bent terphenyl structure is driven compared to the material that does not include the bent terphenyl structure or an additional substituent in the bent terphenyl structure It can be seen that the voltage and power efficiency are at the same level or higher, and the lifespan is significantly increased.

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

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

Claims (12)

A compound for an organic optoelectronic device represented by the following Chemical Formula 1:
[Formula 1]

In Formula 1,
R ¹ and R ² are each independently hydrogen, an unsubstituted phenyl group or an unsubstituted biphenyl group,
At least one of R ¹ and R ² is an unsubstituted phenyl group or an unsubstituted biphenyl group,
R ¹ and R ² are different from each other,
R ³ and R ⁴ are each independently an unsubstituted phenyl group or an unsubstituted biphenyl group,
R ⁵ to R ⁹ are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C20 aryl group. According to claim 1,
A compound for an organic optoelectronic device that is represented by the following Chemical Formula 1A or Chemical Formula 1C:
[Formula 1A]

[Formula 1C]

In Formula 1A and Formula 1C,
The definitions of R ³ to R ⁹ are the same as in claim 1. 3. The method of claim 2,
Formula 1A is a compound for an organic optoelectronic device represented by any one of Formulas 1A-1 to 1A-3 below:
[Formula 1A-1] [Formula 1A-2]

[Formula 1A-3]

In the formulas 1A-1 to 1A-3,
The definitions of R ³ to R ⁹ are the same as in claim 1. 4. The method of claim 3,
A compound for an organic optoelectronic device represented by Formula 1A-2. delete 3. The method of claim 2,
Formula 1C is a compound for an organic optoelectronic device represented by any one of Formulas 1C-1 to 1C-9:
[Formula 1C-1] [Formula 1C-2]

[Formula 1C-3] [Formula 1C-4]

[Formula 1C-5] [Formula 1C-6]

[Formula 1C-7] [Formula 1C-8] [Formula 1C-9]

In Formula 1C-1 to Formula 1C-9,
The definitions of R ³ to R ⁹ are the same as in claim 1. According to claim 1,
A compound for an organic optoelectronic device, which is one selected from the compounds listed in Group 1:
[Group 1]
[A-1] [A-2] [A-3] [A-4] [A-5]

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

[A-11] [A-12]

[A-49]

[A-50] [A-51] [A-52] [A-53] [A-54]

[A-55] [A-56] [A-57] [A-58] [A-59]

[A-60] [A-61] [A-62] [A-63] [A-64]

[A-65] [A-66] [A-67] [A-68] [A-69]

. A first compound for an organic optoelectronic device, and a second compound for an organic optoelectronic device,
The first compound for an organic optoelectronic device includes the compound for an organic optoelectronic device according to claim 1,
The second compound for an organic optoelectronic device is a composition for an organic optoelectronic device comprising a compound for an organic optoelectronic device represented by the following Chemical Formula 2:
[Formula 2]

In Formula 2,
Y ¹ and Y ² are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group,
Ar ¹ and Ar ² are each independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,
R ¹⁰ to R ¹⁵ are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, a cyano group, or It is a combination of these. 9. The method of claim 8,
The *-Y ¹ -Ar ¹ and *-Y ² -Ar ² are one of the substituents listed in the following group I composition for an organic optoelectronic device:
[Group I]

In the above group I, * is a connection point. positive and negative poles facing each other,
At least one organic layer positioned between the anode and the cathode,
The organic layer is a compound for an organic optoelectronic device according to any one of claims 1 to 4, 6 and 7; Or an organic optoelectronic device comprising the composition for an organic optoelectronic device according to claim 8 or 9. 11. The method of claim 10,
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. A display device comprising the organic optoelectronic device according to claim 10 .

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