KR20210133043A - Compound for organic optoelectronic device, organic optoelectronic device and display device - Google Patents

Abstract

It relates to a compound for an organic optoelectronic device represented by chemical formula 1, and an organic optoelectronic device and a display apparatus including the same. The content of chemical formula 1 is as defined in the specification. According to one embodiment, provided is the compound for the organic optoelectronic device represented by chemical formula 1. The present invention can realize a high-efficiency, long-lifespan organic optoelectronic device.

Description

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

It relates to a compound 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 may 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 an organic optoelectronic device including the compound for an organic optoelectronic device.

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,

L ¹ is a substituted or unsubstituted C6 to C30 arylene group or a substituted or unsubstituted C2 to C30 heterocyclic group,

L ^{2 To} L ⁶ are each independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, or a substituted or unsubstituted C2 to C30 heterocyclic group,

R ¹ to R ⁷ are each independently hydrogen, deuterium, a cyano group, a halogen group, a substituted or unsubstituted C1 to C30 alkyl group, or a substituted or unsubstituted C6 to C30 aryl group,

Ar ¹ to Ar ⁴ are each independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group.

According to another embodiment, there is provided an organic optoelectronic device comprising 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 includes the compound 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 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 presented 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 example of the present invention, "substitution" means that at least one hydrogen in a substituent or compound is substituted with deuterium, a C1 to C20 alkyl group, a C6 to C30 aryl group, or a 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 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, "hetero" means that, unless otherwise defined, 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, and the like, and two or more hydrocarbon aromatic moieties. They may include a non-aromatic fused ring fused directly or indirectly, such as a fluorenyl group, and the like.

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,

L ¹ is a substituted or unsubstituted C6 to C30 arylene group or a substituted or unsubstituted C2 to C30 heterocyclic group,

L ^{2 To} L ⁶ are each independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, or a substituted or unsubstituted C2 to C30 heterocyclic group,

R ¹ to R ⁷ are each independently hydrogen, deuterium, a cyano group, a halogen group, a substituted or unsubstituted C1 to C30 alkyl group, or a substituted or unsubstituted C6 to C30 aryl group,

Ar ¹ to Ar ⁴ are each independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group.

The compound represented by Formula 1 has a structure in which a substituted or unsubstituted amine group is substituted at the 4th position of carbazole and a substituted or unsubstituted triazinyl group is substituted at the 9th position of the carbazole.

As the carbazole is substituted with an amine group and a triazine group at the same time, it is possible to separate the HOMO electron cloud and the LUMO electron cloud molecularly, thereby reducing the energy difference (ΔEst) between T1 and S1 to manufacture a high-efficiency/long-life device.

In particular, since the amine group is substituted at the 4th position of the carbazole, it has a faster hole mobility compared to the conventional bipolar host, and the triazinyl group is substituted at the 9th position of the carbazole, resulting in faster hole mobility and electron mobility. Thus, it may have an effect of reducing the driving voltage.

In addition, since the substituted or unsubstituted amine group ^{is substituted through the linking group L 1} , ΔEst may become narrower, and thus the efficiency in the device may be further improved.

In Formula 1, L ¹ may be a substituted or unsubstituted phenylene group.

For example, L ¹ may be a substituted or unsubstituted para-phenylene group.

The L ² to L ⁶ may each independently be a single bond or a substituted or unsubstituted phenylene group.

For example, each of L ² to L ⁴ may be a single bond.

For example, L ⁵ and L ⁶ may each independently represent a single bond, or a substituted or unsubstituted phenylene group.

wherein Ar ¹ and Ar ² are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted di It may be a benzothiophenyl group.

For example, Ar ¹ and Ar ² may each be a substituted or unsubstituted phenyl group.

In a specific example, the *-L ² -Ar ¹ and *-L ³ -Ar ² may each independently be selected from the substituents listed in Group I below.

[Group I]

Ar ³ and Ar ⁴ may each independently be a substituted or unsubstituted phenyl group, or a substituted or unsubstituted biphenyl group.

For example, ^{one of Ar 3} and Ar ⁴ may be a substituted or unsubstituted phenyl group, and the other may be a substituted or unsubstituted biphenyl group.

As a specific example, *-L ⁵ -Ar ³ and *-L ⁶ -Ar ⁴ may each independently be selected from the substituents listed in Group II below.

[Group II]

Each of R ¹ to R ⁷ may independently represent hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C12 aryl group.

For example, each of R ¹ to R ⁷ may be hydrogen, or ^{any one of R 1} to R ⁷ may be a phenyl group and all others may be hydrogen.

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

[Group 1]

In addition to the above-described compound for an organic optoelectronic device, one or more compounds may be further included.

For example, the compound for an organic optoelectronic device described above may be applied in the form of a composition further comprising a known host material.

The compound for an organic optoelectronic device described above may further include a dopant.

The dopant may be for example a phosphorescent dopant, for example a red, green or blue phosphorescent dopant, for example a red or green phosphorescent dopant.

A dopant is a material that emits light by being mixed in a small amount in a compound or composition for an organic optoelectronic device, and a material such as a metal complex that emits light by multiple excitation that excites it to a triplet state or more is generally used. can 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 ⁷ MX

In Formula Z, M is a metal, and L ⁷ and X 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 ⁷ and X are, for example, Biden It may be a tate ligand.

The compound for an organic optoelectronic device described above 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 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 diode 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 may include the aforementioned compound for an organic optoelectronic device or a composition for an organic optoelectronic device.

The organic layer 105 may include the emission layer 130 , and the emission layer 130 may include the aforementioned compound for an organic optoelectronic device.

The composition for an organic optoelectronic device further comprising a dopant may be, for example, a green light-emitting composition.

The emission layer 130 may include, for example, the above-described compound for an organic optoelectronic device as a phosphorescent host.

The organic layer may further include an auxiliary layer in addition to the emission layer.

The auxiliary layer may be, for example, the hole auxiliary layer 140 .

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 include, for example, at least one of the compounds listed in Group D 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 D]

In the hole transport auxiliary layer, in addition to the compounds described above, known compounds described in US5061569A, JP1993-009471A, WO1995-009147A1, JP1995-126615A, JP1998-095973A, and the like, 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 a negative electrode 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, 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, unless otherwise specified.

(Production of compounds for organic optoelectronic devices)

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

Synthesis Example 1: Synthesis of Intermediate A

4-Bromo-9H-Carbazole 20 g 2-Chloro-4-phenyl-6-(4,4-biphenyl)-triazine 29.34 g (85.33 mmol) was suspended in 300 ml of DMF and sodium hydride 2.34 g (97.52 mmol) was added slowly and stirred for 12 hours. After completion of the reaction, the generated solid was filtered, washed with distilled water/acetone/methanol in the order, and recrystallized from monochlorobenzene to obtain 35 g (yield: 77 %) of the target compound, Intermediate A.

Synthesis Example 2: Synthesis of Comparative Compound 1

Intermediate A 10 g (18.06 mmol) and diphenylamine 3.21 g (18.97 mmol), Pd ₂ (dba) ₃ 0.5 g (0.54 mmol) NaO(t-Bu) 3.47 g (36.17 mmol), P ( t-Bu)3 0.22 g (1.08 mmol) was suspended in 100 ml of toluene and stirred under reflux for 12 hours. After completion of the reaction, distilled water is added and extracted. The reaction solution was filtered through silicagel and recrystallized from toluene to obtain 7 g (yield: 60%) of the target compound, Comparative Compound 17.

(LC/MS: theoretical value 641.76, measured value: 642.2)

Synthesis Example 3: Synthesis of compound 2

Intermediate A 10.73 g (19.39 mmol) synthesized in Synthesis Example 1, Intermediate B 9 g (24.24 mmol), Pd(PPh ₃ ) ₄ 0.67 g (0.58 mmol), K ₂ CO ₃ 5.36 g (38.75 mmol) were mixed with THF 100 After suspending in 50 ml of ml/distilled water, the mixture is stirred under reflux for 12 hours. After completion of the reaction, the resulting solid was filtered, washed with distilled water and acetone, and recrystallized from monochlorobenzene to obtain 9 g (yield: 64 %) of compound 2 as the target compound.

(LC/MS: theoretical value 717.86, measured value: 718.4)

Synthesis Example 4: Synthesis of Comparative Compound 2

10 g (yield: 63%) was obtained.

(LC/MS: Theoretical value 717.86, Measured value: 718.6)

(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 using oxygen plasma for 10 minutes, 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 2 of Synthesis Example 3 was used as a host on the hole transport layer, and PhGD was doped at 7 wt% 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 in a 1:1 ratio to form an electron transport layer having 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. The device was fabricated.

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 2: PhGD (7wt%)] (400 Å) / Compound D: Liq (300 Å) / Liq (15 Å) / Al (1,200 Å) 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

Comparative Examples 1 and 2

An organic light emitting diode was manufactured in the same manner as in Example 1, except that Comparative Compounds 1 or 2 of Comparative Synthesis Examples 1 and 2 were used instead of Compound 2.

(evaluation)

Example 1, Comparative Examples 1 and 2

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

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

(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) Current efficiency measurement

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

(4) Lifetime measurement

Luminance (cd / m ²⁾ to maintain a 6,000cd / m ^2, and time of the current efficiency (cd / A) is decreased by 97% to obtain a result.

(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) Life Ratio Calculation

Using the lifetime value measured in Comparative Example 1 as a reference value, each relative value was calculated and the results are shown.

(7) Calculation of driving voltage ratio

Based on the driving voltage measured in Comparative Example 1, each relative value was calculated and the results are shown.

division host T90 Life Ratio (%) drive voltage ratio
(%) Example 1 compound 2 140% 97% Comparative Example 1 Comparative compound 1 100% 100% Comparative Example 2 Comparative compound 2 120% 98%

Referring to Table 1, it can be seen that the organic light emitting device according to Example 1 has somewhat improved driving voltage characteristics, and in particular, remarkably improved lifespan characteristics compared to the organic light emitting devices according to Comparative Examples 1 and 2.

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 (11)

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

In Formula 1,
L ¹ is a substituted or unsubstituted C6 to C30 arylene group or a substituted or unsubstituted C2 to C30 heterocyclic group,
L ^{2 To} L ⁶ are each independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, or a substituted or unsubstituted C2 to C30 heterocyclic group,
R ¹ to R ⁷ are each independently hydrogen, deuterium, a cyano group, a halogen group, a substituted or unsubstituted C1 to C30 alkyl group, or a substituted or unsubstituted C6 to C30 aryl group,
Ar ¹ to Ar ⁴ are each independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group. According to claim 1,
Wherein L ¹ is a substituted or unsubstituted phenylene group compound for an organic optoelectronic device. Wherein L ^{2 To} L ^{6 Are} each independently a single bond or a substituted or unsubstituted phenylene group compound for an organic optoelectronic device. According to claim 1,
wherein Ar ¹ and Ar ² are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted di A benzothiophenyl group, a compound for an organic optoelectronic device. According to claim 1,
The *-L ² -Ar ¹ and *-L ³ -Ar ² are each independently one selected from the substituents listed in the following group I compound for an organic optoelectronic device:
[Group I]

In the above group I, * is a connection point. According to claim 1,
Wherein Ar ³ and Ar ⁴ are each independently a substituted or unsubstituted phenyl group, or a substituted or unsubstituted biphenyl group, a compound for an organic optoelectronic device. According to claim 1,
The *-L ⁵ -Ar ³ and *-L ⁶ -Ar ⁴ are each independently one selected from the substituents listed in the following group II compound for an organic optoelectronic device:
[Group II]

In group II above, * is a connection point. According to claim 1,
A compound for an organic optoelectronic device, which is one selected from the compounds listed in Group 1:
[Group 1]

. positive and negative poles 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 compound for an organic optoelectronic device according to any one of claims 1 to 8. 10. The method of claim 9,
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. A display device comprising the organic optoelectronic device according to claim 9 .

Images