KR102559469B1 - Novel compound and organic electroluminescent divice including the same - Google Patents

Abstract

The present application relates to a novel arylamine compound, and when used as a hole transport layer (HTL), a light emitting auxiliary layer (HT prime), or a hole injection layer (HIL), hole injection and transport properties can be increased to provide high efficiency and long lifespan effects of the device.

Description

Novel compound and organic light emitting device containing the same {NOVEL COMPOUND AND ORGANIC ELECTROLUMINESCENT DIVICE INCLUDING THE SAME}

The present application relates to a novel compound and an organic light emitting device including the same.

Materials used as organic layers in organic light emitting diodes can be largely classified into light emitting materials, hole injection materials, hole transport materials, electron transport materials, electron injection materials, and the like according to their functions. The light emitting materials can be classified into high molecular weight and low molecular weight according to molecular weight, and can be classified into fluorescent materials derived from singlet excited states of electrons and phosphorescent materials derived from triplet excited states of electrons according to light emitting mechanisms, and light emitting materials can be classified into blue, green, and red light emitting materials and yellow and orange light emitting materials necessary to realize better natural colors according to the light emitting color. In addition, in order to increase color purity and increase light emitting efficiency through energy transfer, a host/dopant system may be used as a light emitting material. The principle is that when a small amount of a dopant having a smaller energy band gap and higher luminous efficiency than the host constituting the light emitting layer is mixed in the light emitting layer in a small amount, excitons generated in the host are transported to the dopant to emit light with high efficiency. At this time, since the wavelength of the host moves to the wavelength of the dopant, light of a desired wavelength can be obtained according to the type of dopant and host used.

Until now, various compounds have been known as materials used in organic light emitting devices, but in the case of organic light emitting devices using known materials, development of new materials is continuously required due to high driving voltage, low efficiency, and short lifespan. Therefore, efforts have been made to develop an organic light emitting device having low voltage driving, high luminance, and long lifespan using a material having excellent characteristics.

Japanese Patent Publication 10-2015-530735

The present application is intended to provide a novel compound, and an organic light emitting device including the same.

However, the problem to be solved by the present application is not limited to the problem described above, and other problems not described will be clearly understood by those skilled in the art from the description below.

A first aspect of the present application provides a compound represented by Formula 1 below:

[Formula 1]

In Formula 1,

Ar ₁ to Ar ₄ are each independently a C ₆ ~ C ₃₀ aryl group which may be substituted or a C ₅ ~ C ₃₀ heteroaryl group which may be substituted;

Ar ₅ is an aryl group of C ₆ to C ₁₀ which may be substituted;

R, R`, R ₁ and R ₂ are each independently hydrogen, a substituted C ₁ ~ C ₃₀ alkyl group, a substituted C ₂ ~ C ₃₀ alkenyl group, a substituted C ₆ ~ C ₃₀ aryl group, or a substituted C ₅ ~ C ₃₀ heteroaryl group,

l is an integer from 0 to 4, and m is an integer from 0 to 3.

A second aspect of the present application provides an organic light emitting device comprising a compound according to the present application.

The present invention relates to a novel compound of an arylamine structure into which a fluorene structure and a linear aryl are introduced, and specifically, a fluorene structure and a linear aryl are directly bonded to arylamine to form a deep HOMO and a high LUMO at the same time, so electron blocking is easy, and pi conjugation is increased by expansion of four or more aryl groups connected in a linear manner and thin film arrangement of molecules is excellent, so that a roll-off phenomenon through fast hole mobility can be suppressed and a device with a long lifespan can be realized. In addition, by fixing the aryl group on one side other than the linearly connected aryl group of the arylamine to an aryl group of C ₁₀ or less, excitons in the light emitting layer are efficiently formed by maintaining appropriate HOMO and LUMO and high T1, enabling the implementation of a high-efficiency organic light emitting device. In addition, by extending four or more linearly connected aryl groups, recrystallization can be prevented when driven at a high Tg even at a relatively small molecular weight, thereby increasing driving stability of the device.

When the compound of the present invention is used as a hole transport layer (HTL), a light emitting auxiliary layer (HT prime), or a hole injection layer (HIL), hole injection and transport properties can be increased, thereby providing high efficiency and long lifespan effects of the device. The compound of the present invention can maintain high triplet energy and exhibit high efficiency, and can maintain high Tg due to a substituent composed of 4 or more linear aryl groups, thereby exhibiting thin film stability and long lifespan effects during device operation.

The compound of the present invention has the effect of high luminous efficiency, improvement of driving voltage, and long lifespan, and can greatly contribute to OLED industries such as flexible displays and lighting by applying to organic light emitting devices and organic light emitting devices for photovoltaic power generation.

1 shows a schematic diagram of an organic light emitting device according to an embodiment of the present application.

Hereinafter, with reference to the accompanying drawings, embodiments and embodiments of the present application will be described in detail so that those skilled in the art can easily practice the present invention.

However, the present disclosure may be embodied in many different forms and is not limited to the implementations and examples described herein. And in order to clearly explain the present invention in the drawings, parts irrelevant to the description are omitted, and similar reference numerals are attached to similar parts throughout the specification.

Throughout the present specification, when a member is said to be located “on” another member, this includes not only a case where a member is in contact with another member, but also a case where another member exists between the two members.

Throughout the present specification, when a part "includes" a certain component, it means that it may further include other components without excluding other components unless otherwise stated. As used throughout this specification, the terms "about," "substantially," and the like are used at or near a value when manufacturing and material tolerances inherent in the stated meaning are given, and to aid in the understanding of this application, exact or absolute values are used to prevent unscrupulous infringers from exploiting the disclosed disclosure. The term "step of (doing)" or "step of" as used throughout the present specification does not mean "step for".

Throughout the present specification, the term "combination thereof" included in the expression of the Markush form means a mixture or combination of one or more selected from the group consisting of the components described in the expression of the Markush form, and includes one or more selected from the group consisting of the components.

Throughout this specification, reference to "A and/or B" means "A or B, or A and B".

Throughout this specification, the term "aryl" refers to C_6-30An aromatic hydrocarbon ring group of, for example, phenyl, benzyl, naphthyl, biphenyl, terphenyl, fluorene, phenanthrenyl, triphenylenyl, perylenyl, chrysenyl, fluoranthenyl, benzofluorenyl, benzotriphenylenyl, benzochrysenyl, anthracenyl, stilbenyl, pyrenyl means containing an aromatic ring, and "heteroaryl" is C containing at least one heteroatom_5-30As an aromatic ring of, for example, pyrrolyl, pyrazinyl, pyridinyl, indolyl, isoindolyl, furyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, benzothiophenyl, dibenzothiophenyl, quinolyl group, isoquinolyl, quinoxalinyl, carbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, thienyl, and pyridine rings, p Razine ring, pyrimidine ring, pyridazine ring, triazine ring, indole ring, quinoline ring, acridine ring, pyrrolidine ring, dioxane ring, piperidine ring, morpholine ring, piperazine ring, carbazole ring, furan ring, thiophene ring, oxazole ring, oxadiazole ring, benzooxazole ring, thiazole ring, thiadiazole ring, benzothiazole ring, triazole ring, imidazole ring, It means including an aromatic heterocyclic group formed from a benzoimidazole ring, a pyran ring, and a dibenzofuran ring.

Throughout this specification, the term "alkyl" may include linear or branched, saturated or unsaturated C ₁ -C ₆ alkyl, for example, methyl, ethyl, propyl, butyl, pentyl, hexyl, or all possible isomers thereof, but may not be limited thereto.

Throughout the present specification, the term "which may be substituted" or "substituted" refers to a halogen, an amino group, a nitrile group, a nitro group, a silane group, an alkyl group, or a C ₁ ~ C ₂₀ alkyl group, an alkenyl group, or a C ₂ ~ C ₂₀ alkenyl group, an alkoxy group, or a C ₁ ~ C ₂₀ alkoxy group, a cycloalkyl group, or a C ₃ ~ C ₂₀ cycloalkyl group, a heterocycloalkyl group, or a C ₃ ~C ₂ It means that it may be substituted with one or more groups selected from the group consisting of a 0 heterocycloalkyl group, a C ₅ ~ C ₃₀ aryl group, or a C ₅ ~ C ₃₀ heteroaryl group. In addition, the same symbol throughout the present specification may have the same meaning unless otherwise specified.

A first aspect of the present application provides a compound represented by Formula 1 below:

[Formula 1]

In Formula 1,

Ar ₁ to Ar ₄ are each independently a C ₆ ~ C ₃₀ aryl group which may be substituted or a C ₅ ~ C ₃₀ heteroaryl group which may be substituted;

Ar ₅ is an aryl group of C ₆ to C ₁₀ which may be substituted;

R, R`, R ₁ and R ₂ are each independently hydrogen, a substituted C ₁ ~ C ₃₀ alkyl group, a substituted C ₂ ~ C ₃₀ alkenyl group, a substituted C ₆ ~ C ₃₀ aryl group, or a substituted C ₅ ~ C ₃₀ heteroaryl group,

l is an integer from 0 to 4, and m is an integer from 0 to 3.

In one embodiment of the present invention, the Ar ₁ to Ar ₄ may each independently be phenyl, naphthyl, or phenanthrenyl. The group represented by -Ar ₁ -Ar ₂ -Ar ₃ -Ar ₄ in Formula 1 may have one or more meta or ortho bonds.

In one embodiment of the present invention, Ar ₅ may be phenyl or naphthyl.

In one embodiment of the present invention, R and R` may each independently be methyl or phenyl.

In one embodiment of the present invention, the R ₁ and R ₂ may each independently be hydrogen or phenyl.

In one embodiment of the present invention, the compound may be represented by Formula 2 below:

[Formula 2]

In Formula 2,

Ar ₁ to Ar ₄ , R, R`, R ₁ , R ₂ , l and m are as defined in Formula 1 above,

R ₃ is hydrogen, an optionally substituted C ₁ -C ₃₀ alkyl or an optionally substituted C ₂ -C ₃₀ alkenyl group,

n is an integer from 0 to 5;

In one embodiment of the present invention, the compound may be represented by Formula 3:

[Formula 3]

In Formula 3,

Ar ₄ , R ₁ , R ₂ , l and m are as defined in Formula 1 above,

R ₃ is hydrogen, an optionally substituted C ₁ -C ₃₀ alkyl or an optionally substituted C ₂ -C ₃₀ alkenyl group,

n is an integer from 0 to 5;

Ar and Ar' are each independently a C ₆ ~ C ₃₀ aryl group which may be substituted;

R ₆ to R ₈ are each independently hydrogen, an optionally substituted C ₁ -C ₃₀ alkyl group, an optionally substituted C ₂ -C ₃₀ alkenyl group, an optionally substituted C ₆ -C ₃₀ aryl group, or an optionally substituted C ₅ -C ₃₀ heteroaryl group.

In one embodiment of the present invention, the compound may be represented by Formula 4 below:

[Formula 4]

In Formula 4,

R ₁ , R ₂ , l and m are as defined in Formula 1 above,

R ₃ is hydrogen, an optionally substituted C ₁ to C ₃₀ alkyl group, or an optionally substituted C ₂ to C ₃₀ alkenyl group;

n is an integer from 0 to 5;

R ₄ and R ₅ are each independently hydrogen, a C ₁ ~ C ₃₀ alkyl group that may be substituted, a C ₂ ~ C ₃₀ alkenyl group that may be substituted, a C ₆ ~ C ₃₀ aryl group that may be substituted, or a C ₅ ~ C ₃₀ heteroaryl group that may be substituted;

R ₆ to R ₉ are each independently hydrogen, an optionally substituted C ₁ -C ₃₀ alkyl group, an optionally substituted C ₂ -C ₃₀ alkenyl group, an optionally substituted C ₆ -C ₃₀ aryl group, or an optionally substituted C ₅ -C ₃₀ heteroaryl group.

In one embodiment of the present invention, R ₃ may be hydrogen or n may be 0.

In one embodiment of the present invention, the R ₄ to R ₉ may be hydrogen.

In one embodiment of the present invention, the compound represented by Formula 1 may be synthesized by the reaction shown in Scheme 1 below, but may not be limited thereto:

[Scheme 1]

In the above reaction equation,

Ar ₁ to Ar ₅ , R, R`, R ₁ , R ₂ , l and m are as defined in Formula 1 above.

In one embodiment of the present invention, the compound represented by Formula 1 may include the following compounds, but may not be limited thereto:

For example, the compound represented by Chemical Formula 1 may include the following compounds, and these compounds may maintain a higher T1 by minimizing condensation groups, thereby maximizing the exciton confinement effect in the light emitting layer:

A second aspect of the present application provides an organic light emitting device including the compound represented by Formula 1 above. The organic light emitting device may include one or more organic material layers containing the compound according to the present invention between the first electrode and the second electrode.

In one embodiment of the present invention, the organic material layer may be at least one layer of a hole injection layer, a hole transport layer, and a light emitting auxiliary layer, and may be, for example, a light emitting auxiliary layer, but may not be limited thereto. In this case, the compound of the present invention may be used alone or together with a known organic light emitting compound.

In the present invention, the light emitting auxiliary layer is a layer formed between the hole transport layer and the light emitting layer, and may be referred to as a second hole transport layer or a third hole transport layer according to the number of hole transport layers.

In one embodiment of the present invention, the organic light emitting device may include an organic material layer containing a hole transport material and an organic material layer containing a compound represented by Formula 1, but may not be limited thereto.

The organic light emitting device may include one or more organic material layers such as a hole injection layer (HIL), a hole transport layer (HTL), an emission layer (EML), an electron transport layer (ETL), and an electron injection layer (EIL) between an anode and a cathode.

For example, the organic light emitting device may be manufactured according to the structure illustrated in FIG. 1 . The organic light emitting device may be stacked from the bottom in the order of anode (hole injection electrode 1000) / hole injection layer 200 / hole transport layer 300 / light emitting layer 400 / electron transport layer 500 / electron injection layer 600 / cathode (electron injection electrode 2000).

In FIG. 1, the substrate 100 may be a substrate used in an organic light emitting device, and in particular, a transparent glass substrate excellent in mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and water resistance, or a flexible plastic substrate.

The hole injection electrode 1000 is used as an anode for hole injection of an organic light emitting device. A material having a low work function is used to enable injection of holes, and it may be formed of a transparent material such as indium tin oxide (ITO), indium zinc oxide (IZO), or graphene.

The hole injection layer 200 may be formed by depositing a hole injection layer material on the anode electrode by a method such as a vacuum deposition method, a spin coating method, a cast method, a Langmuir-Blodgett (LB) method, or the like. When the hole injection layer is formed by the vacuum deposition method, the deposition conditions vary depending on the compound used as the material of the hole injection layer, the desired structure and thermal characteristics of the hole injection layer, and the like, but in general, a deposition temperature of 50-500 ° C., 10 ^-8 to 10 ^-3 Torr, a deposition rate of 0.01 to 100 Å / sec, and a layer thickness of 10 Å to 5 μm.

Next, the hole transport layer 300 may be formed by depositing a hole transport layer material on the hole injection layer 200 by a method such as a vacuum deposition method, a spin coating method, a cast method, or an LB method. In the case of forming the hole transport layer by the vacuum deposition method, the deposition conditions vary depending on the compound used, but are generally selected within the same range of conditions as those for forming the hole injection layer. The hole transport layer may be one or more, and may be, for example, two layers of a first hole transport layer and a second hole transport layer (emission auxiliary layer). At least one of the first hole transport layer and the second hole transport layer may include the compound represented by Formula 1 according to the present invention.

Thereafter, the light emitting layer 400 may be formed by depositing a light emitting layer material on top of the hole transport layer or the light emitting auxiliary layer by a method such as a vacuum deposition method, a spin coating method, a cast method, or an LB method. In the case of forming the light emitting layer by the vacuum deposition method, the deposition conditions vary depending on the compound used, but it is generally preferable to select them within the same range of conditions as those for forming the hole injection layer. In addition, a known compound may be used as a host or dopant for the light emitting layer material.

In addition, when used with a phosphorescent dopant in the light emitting layer, a hole blocking material (HBL) may be additionally laminated by vacuum deposition or spin coating to prevent diffusion of triplet excitons or holes into the electron transport layer. The hole blocking material that can be used at this time is not particularly limited, but can be selected and used arbitrarily from known ones used as hole blocking materials. For example, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, or hole blocking materials described in Japanese Patent Laid-Open No. 11-329734 (A1) may be mentioned, and representatively, Balq (bis(8-hydroxy-2-methylquinolinato)-aluminum biphenoxide), phenanthrolines-based compounds (eg, UDC BCP (vasocuproin)), etc. can be used

An electron transport layer 500 is formed on the light emitting layer 400 formed as described above. At this time, the electron transport layer can be formed by a method such as a vacuum deposition method, a spin coating method, a cast method, or the like. In addition, although the deposition conditions of the electron transport layer vary depending on the compound used, it is generally preferable to select them within the same range of conditions as those for forming the hole injection layer.

Thereafter, an electron injection layer material may be deposited on the electron transport layer 500 to form the electron injection layer 600. At this time, the electron injection layer may be formed by a method such as a vacuum deposition method, a spin coating method, a cast method, or the like.

The hole injection layer 200, the hole transport layer 300, the light emitting layer 400, and the electron transport layer 500 of the device may use the compound according to the present invention or the following materials, or the compound according to the present invention and known materials may be used together.

A cathode 2000 for electron injection is formed on the electron injection layer 600 by a method such as vacuum deposition or sputtering. Various metals may be used as the cathode. Specific examples include materials such as aluminum, gold, and silver.

The organic light emitting device of the present invention may have various structures of the organic light emitting device as well as the organic light emitting device having an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and a cathode structure. If necessary, it is also possible to further form one or two intermediate layers.

As described above, the thickness of each organic material layer formed according to the present invention can be adjusted according to the required degree, specifically 10 to 1,000 nm, and more specifically preferably 20 to 150 nm.

In the present invention, since the thickness of the organic material layer including the compound represented by Chemical Formula 1 can be controlled in a molecular unit, the surface is uniform and the shape stability is excellent.

All of the contents described with respect to the first aspect of the present disclosure may be applied to the organic light emitting compound according to the present aspect, but may not be limited thereto.

Hereinafter, it will be described in more detail through examples of the present application, and the scope of the present application is not limited by the present examples.

[Example]

Preparation Example 1. Synthesis of IM

Preparation of IM for the synthesis of the target compound was synthesized through any one of the above steps, and may not be limited thereto.

The synthesis method of IM1 is as follows.

In a round bottom flask, 27.6 g of [1,1'-biphenyl] -4-ylboronic acid and 50.0 g of 4-bromo-4'-iodo-1,1'-biphenyl were dissolved in 800 ml of 1,4-dioxane, and K ₂ CO ₃ (2M) 210 ml and 4.8 g of Pd(PPh ₃ ) ₄ were added and stirred under reflux. The reaction was confirmed by TLC, and the reaction was terminated after adding water. The organic layer was extracted with MC, filtered under reduced pressure, and recrystallized to obtain 50.4 g of intermediate IM1 (yield: 74%).

The following IM2 to IM13 were synthesized by using different starting materials in the same manner as in IM1.

Preparation Example 2. Synthesis of OP

The synthesis method of OP1 is as follows.

In a round bottom flask, 15.0 g of 2-bromo-9,9-dimethyl-9H-fluorene, 5.6 g of aniline, 7.9 g of t-BuONa, 2.0 g of Pd ₂ (dba) ₃ , and 2.5 ml of (t-Bu) ₃ P were dissolved in 200 ml of toluene and stirred under reflux. The reaction was confirmed by TLC, and the reaction was terminated after adding water. The organic layer was extracted with MC, filtered under reduced pressure, and then recrystallized to obtain 11.75 g of OP1 (75% yield).

The following OP2 to OP3 were synthesized by using different starting materials in the same manner as in OP1.

Synthesis Example 1. Synthesis of Compound 1

After dissolving 5.0 g of IM1, 3.7 g of OP1, 1.9 g of t-BuONa, 0.5 g of Pd ₂ (dba) ₃ , and 0.5 ml of (t-Bu) ₃ P in 130 ml of toluene in a round bottom flask, the mixture was stirred under reflux. The reaction was confirmed by TLC, and the reaction was terminated after adding water. The organic layer was extracted with MC and filtered under reduced pressure, followed by column purification and recrystallization to obtain 5.36 g of Compound 1 (70% yield).

m/z: 589.28 (100.0%), 590.28 (49.1%), 591.28 (11.8%), 592.29 (1.8%)

Synthesis Example 2. Synthesis of Compound 2

Compound 2 was synthesized in the same manner as Compound 1 using OP2 instead of OP1. (Yield: 68%)

m/z: 639.29 (100.0%), 640.30 (53.4%), 641.30 (14.0%), 642.30 (2.4%)

Synthesis Example 3. Synthesis of Compound 3

Compound 3 was synthesized in the same manner as Compound 1 using OP3 instead of OP1. (Yield: 65%)

m/z: 713.31 (100.0%), 714.31 (60.3%), 715.31 (17.6%), 716.32 (3.4%)

Synthesis Example 4. Synthesis of Compound 4

Compound 4 was synthesized in the same manner as Compound 1 using IM2 and OP3 instead of IM1 and OP1. (Yield: 72%)

m/z: 713.31 (100.0%), 714.31 (60.3%), 715.31 (17.6%), 716.32 (3.4%)

Synthesis Example 5. Synthesis of Compound 5

Compound 5 was synthesized in the same manner as Compound 1 using IM3 and OP3 instead of IM1 and OP1. (Yield: 65%)

m/z: 713.31 (100.0%), 714.31 (60.3%), 715.31 (17.6%), 716.32 (3.4%)

Synthesis Example 6. Synthesis of Compound 6

Compound 6 was synthesized in the same manner as Compound 1 using IM4 and OP3 instead of IM1 and OP1. (Yield: 67%)

m/z: 713.31 (100.0%), 714.31 (60.3%), 715.31 (17.6%), 716.32 (3.4%)

Synthesis Example 7. Synthesis of Compound 7

Compound 7 was synthesized in the same manner as Compound 1 using IM5 and OP3 instead of IM1 and OP1. (Yield: 62%)

m/z: 713.31 (100.0%), 714.31 (60.3%), 715.31 (17.6%), 716.32 (3.4%)

Synthesis Example 8. Synthesis of Compound 8

Compound 8 was synthesized in the same manner as Compound 1 using IM6 and OP3 instead of IM1 and OP1. (Yield: 63%)

m/z: 713.31 (100.0%), 714.31 (60.3%), 715.31 (17.6%), 716.32 (3.4%)

Synthesis Example 9. Synthesis of Compound 9

Compound 9 was synthesized in the same manner as Compound 1 using IM7 and OP3 instead of IM1 and OP1. (Yield: 63%)

m/z: 713.31 (100.0%), 714.31 (60.3%), 715.31 (17.6%), 716.32 (3.4%)

Synthesis Example 10. Synthesis of Compound 10

Compound 10 was synthesized in the same manner as Compound 1 using IM8 and OP3 instead of IM1 and OP1. (Yield: 60%)

m/z: 713.31 (100.0%), 714.31 (60.3%), 715.31 (17.6%), 716.32 (3.4%)

Synthesis Example 11. Synthesis of Compound 11

Compound 11 was synthesized in the same manner as Compound 1 using IM9 and OP3 instead of IM1 and OP1. (Yield: 56%)

m/z: 713.31 (100.0%), 714.31 (60.3%), 715.31 (17.6%), 716.32 (3.4%)

Synthesis Example 12. Synthesis of Compound 12

Compound 12 was synthesized in the same manner as Compound 1 using IM10 and OP3 instead of IM1 and OP1. (Yield: 60%)

m/z: 713.31 (100.0%), 714.31 (60.3%), 715.31 (17.6%), 716.32 (3.4%)

Synthesis Example 13. Synthesis of Compound 13

Compound 13 was synthesized in the same manner as Compound 1 using IM11 and OP3 instead of IM1 and OP1. (Yield: 58%)

m/z: 713.31 (100.0%), 714.31 (60.3%), 715.31 (17.6%), 716.32 (3.4%)

Synthesis Example 14. Synthesis of Compound 14

Compound 14 was synthesized in the same manner as Compound 1 using IM12 and OP3 instead of IM1 and OP1. (Yield: 60%)

m/z: 713.31 (100.0%), 714.31 (60.3%), 715.31 (17.6%), 716.32 (3.4%)

Synthesis Example 15. Synthesis of Compound 15

Compound 15 was synthesized in the same manner as Compound 1 using IM13 and OP3 instead of IM1 and OP1. (Yield 48%)

m/z: 713.31 (100.0%), 714.31 (60.3%), 715.31 (17.6%), 716.32 (3.4%)

Example 1: Manufacturing of organic light emitting device

A glass substrate coated with indium tin oxide (ITO) having a thickness of 1500 Å was washed with distilled water and ultrasonic waves. After washing with distilled water, it is ultrasonically washed with solvents such as isopropyl alcohol, acetone, and methanol, dried, transferred to a plasma cleaner, and then cleaned using oxygen plasma for 5 minutes. Then, using a thermal evaporator on top of the ITO substrate, HI01 600 Å, HATCN 50 Å?, NPB 250 Å as a hole transport layer, and Compound 1 100 Å as a light emitting auxiliary layer After forming a film, the light emitting layer was doped with 3% of BH01:BD01 to form a 250 Å film. Next, an organic light emitting device was manufactured by forming a 300 Å film of ET01:Liq (1:1) as an electron transport layer, forming a film of 10 Å LiF and 1000 Å of aluminum (Al), and encapsulating the device in a glove box.

Examples 2 to 15: Preparation of organic light emitting device

Using the same method as in Example 1, but using Compounds 2 to 15 instead of Compound 1, an organic light emitting device in which a light emitting auxiliary layer was formed was manufactured.

Comparative Examples 1 to 9

An organic light emitting device was manufactured using the same method as in Example 1, but using the following Ref.1 to Ref.9 instead of Compound 1, respectively.

Experimental Example 1: Performance evaluation of organic light emitting device

By applying voltage to a Keithley 2400 source measurement unit, injecting electrons and holes, and measuring luminance when light is emitted using a Konica Minolta spectroradiometer (CS-2000), the performance of the organic light emitting devices of Examples and Comparative Examples was evaluated by measuring current density and luminance against applied voltage under atmospheric pressure conditions, and the results are shown in Table 1. was

As shown in Table 1, in the embodiments of the present invention, compared to Comparative Examples 1 to 9, the driving voltage is lower, and the efficiency and lifespan are increased.

More specifically, in the examples of the present invention, 1) compared to Comparative Examples 1 to 3, hole mobility can be increased by pi conjugation expansion through linear linkage of 4 phenyls, 2) compared to Comparative Examples 4 and 5, the aryl group on the other side, other than the linearly connected aryl, of the aryl group of the arylamine is C₁₀ By minimizing the following aryl groups, appropriate HOMO, LUMO, and high T1 can be maintained, 3) Compared to Comparative Examples 6 to 8, the molecular arrangement on the thin film is improved with aryl groups that are not branched, but linearly connected, so that it can have fast hole mobility, 4) Compared to Comparative Example 9, when the compound of the present invention, which does not undergo deuterium substitution and is easy to purify with high purity and can lead to long life of the organic light emitting device, the driving voltage is low. It can be seen that the efficiency and lifetime are greatly improved.

The above description of the present application is for illustrative purposes, and those skilled in the art will understand that it can be easily modified into other specific forms without changing the technical spirit or essential features of the present application. Therefore, the embodiments described above should be understood as illustrative in all respects and not limiting. For example, each component described as a single type may be implemented in a distributed manner, and similarly, components described as distributed may be implemented in a combined form.

The scope of the present application is indicated by the following claims rather than the detailed description above, and all changes or modifications derived from the meaning and scope of the claims, and equivalent concepts thereof, should be construed as being included in the scope of the present application.

100: substrate
200: hole injection layer
300: hole transport layer
400: light emitting layer
500: electron transport layer
600: electron injection layer
1000: anode
2000: Cathode

Claims (11)

A compound represented by Formula 3 below:
[Formula 3]

In Formula 3,
R ₁ to R ₃ , and R ₆ to R ₈ are hydrogen;
Ar and Ar' are C ₁ ~ C ₂₀ alkyl groups or C ₆ ~ C ₃₀ aryl groups;
Ar ₄ is unsubstituted phenyl;
l is an integer from 0 to 4, m is an integer from 0 to 3, and n is an integer from 0 to 5.
delete delete delete According to claim 1,
The compound is a compound represented by Formula 4:
[Formula 4]

In Formula 4,
R ₁ , R ₂ , l, m, n and R ₆ to R ₈ are as defined in claim 1,
R ₃ , R ₄ , R ₅ and R ₉ are each independently hydrogen.
delete According to claim 1,
In Formula 3 above A compound in which the group represented by has at least one meta or ortho linkage. According to claim 1,
The compound represented by Formula 3 is any one of the following compounds:



An organic light emitting device comprising an organic material layer containing the compound of claim 1 between the first electrode and the second electrode. According to claim 9,
The organic material layer is an organic light emitting device that is at least one layer of a hole injection layer, a hole transport layer, and a light emitting auxiliary layer. According to claim 10,
The organic material layer is an organic light emitting device that is a light emitting auxiliary layer.