KR102500012B1 - Novel compound and organic electroluminescent divice including the same - Google Patents

Abstract

The present application relates to a novel compound and an organic light emitting device including the same, and the novel compound according to one embodiment of the present invention is applied to an organic light emitting device to achieve high efficiency, long lifespan, low driving voltage and driving stability of the organic light emitting device. can be secured

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. And 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, Light emitting materials can be classified into blue, green, and red light emitting materials and yellow and orange light emitting materials required 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 range of the dopant, light having 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.

Korean Patent Publication 10-2015-0086721

The present application provides a novel organic compound, a method for preparing the same, 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,

X is O, S, or CR ₁ R ₂ And, R ₁ and R ₂ are each independently a substituted or unsubstituted C ₁ ~ C ₃₀ alkyl group, or a substituted or unsubstituted C ₆ ~ C ₃₀ aryl group,

Ar ₁ is a substituted or unsubstituted C ₆ ~ C ₃₀ aryl group or a substituted or unsubstituted C ₃ ~ C ₃₀ heteroaryl group;

L is a direct bond or a substituted or unsubstituted C ₆ to C ₁₈ arylene group;

Ar ₂ and Ar ₃ are each independently a substituted or unsubstituted C ₆ ~ C ₃₀ aryl group or a substituted or unsubstituted C ₃ ~ C ₃₀ heteroaryl group (provided that Ar ₁ , Ar ₂ and Ar ₃ are triphenyl not Rengi),

H is hydrogen;

A second aspect of the present application provides an organic light emitting device including an organic material layer containing a compound according to the present application between a first electrode and a second electrode.

The compound according to one embodiment of the present invention is one in which dibenzofuran, dibenzothiophene, or fluorene is bonded to the 6-position of carbazole and arylamine is bonded to the 3-position of carbazole. can be used for Since the compound according to the present invention has the structure of Chemical Formula 1, it can be adjusted to a HOMO energy level that facilitates hole injection and hole transport, and thus can have a low driving voltage.

In addition, since the compound according to one embodiment of the present invention is a combination of carbazole and dibenzofuran, dibenzothiophene or fluorene, it can maintain high triplet energy and can be applied to a phosphorescent device, achieving high efficiency can do.

In addition, the compound according to one embodiment of the present invention can achieve high efficiency and long lifespan by suppressing a roll-off phenomenon by increasing hole mobility.

In addition, recrystallization of the thin film can be prevented by having a high glass transition temperature, and thus thermal stability is increased and driving stability can be secured.

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 approximating that value when manufacturing and material tolerances inherent in the stated meaning are given, and do not convey the understanding of this application. Accurate or absolute figures are used to help prevent exploitation by unscrupulous infringers of 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 one or more mixtures or combinations selected from the group consisting of the components described in the expression of the Markush form, and the components It means including one or more selected from the group consisting of.

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 a C _5-30 aromatic hydrocarbon ring group, such as phenyl, benzyl, naphthyl, biphenyl, terphenyl, fluorene, phenanthrenyl, triphenylenyl, peryle It means containing an aromatic ring such as yl, chrysenyl, fluoranthenyl, benzofluorenyl, benzotriphenylenyl, benzochrysenyl, anthracenyl, stilbenyl, pyrenyl, etc., and "heteroaryl" means at least one As a C _3-30 aromatic ring containing a hetero atom, for example, pyrrolyl, pyrazinyl, pyridinyl, indolyl, isoindolyl, furyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, Benzothiophenyl, dibenzothiophenyl, quinolyl group, isoquinolyl, quinoxalinyl, carbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, thienyl, and pyridine ring, pyrazine 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, thio Ofene ring, oxazole ring, oxadiazole ring, benzooxazole ring, thiazole ring, thiadiazole ring, benzothiazole ring, triazole ring, imidazole ring, benzoimidazole ring, pyran ring, dibenzofuran It may mean including a heterocyclic group formed from a ring.

Throughout the specification, the term "which may be substituted" refers to deuterium, halogen, amino group, nitrile group, nitro group, or C ₁ ~ C ₂₀ alkyl group, C ₂ ~ C ₂₀ alkenyl group, C ₁ ~ C ₂₀ alkoxy group, C ₃ ~ C ₂₀ cycloalkyl group, C ₃ ~ C ₂₀ heterocycloalkyl group, C ₆ ~ C ₃₀ aryl group and C ₃ ~ C ₃₀ means that can be substituted with one or more groups selected from the group consisting of a heteroaryl group can do. 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,

X is O, S, or CR ₁ R ₂ , R ₁ and R ₂ are each independently a substituted or unsubstituted C ₁ to C ₃₀ alkyl group or a substituted or unsubstituted C ₆ to C ₃₀ aryl group,

Ar ₁ is a substituted or unsubstituted C ₆ ~ C ₃₀ aryl group or a substituted or unsubstituted C ₃ ~ C ₃₀ heteroaryl group;

L is a direct bond or a substituted or unsubstituted C ₆ -C ₁₈ arylene group.

Ar ₂ and Ar ₃ are each independently a substituted or unsubstituted C ₆ ~ C ₃₀ aryl group or a substituted or unsubstituted C ₃ ~ C ₃₀ heteroaryl group (provided that Ar ₁ , Ar ₂ and Ar ₃ are triphenyl not Rengi)

H is hydrogen.

In the compound of Formula 1 according to an embodiment of the present invention, dibenzofuran, dibenzothiophene, or fluorene is bonded to the 6-position of carbazole, and arylamine is bonded to the 3-position of carbazole. .

Since the compound according to the present invention has the structure of Chemical Formula 1, it can be adjusted to a HOMO energy level that facilitates hole injection and hole transport, and thus can have a low driving voltage.

In addition, since the compound according to one embodiment of the present invention is a combination of carbazole and dibenzofuran, dibenzothiophene or fluorene, it can maintain high triplet energy and can be applied to a phosphorescent device, achieving high efficiency can do.

In addition, the compound according to one embodiment of the present invention can achieve high efficiency and long lifespan by suppressing a roll-off phenomenon by increasing hole mobility.

In addition, recrystallization of the thin film can be prevented by having a high glass transition temperature, and thus thermal stability is increased and driving stability can be secured.

Also, in one embodiment of the present invention, X is CR ₁ R ₂ , and R ₁ and R ₂ may each independently be methyl or phenyl. In this case, the lifetime of the device can be increased by lowering the crystallinity.

Also, in one embodiment of the present invention, the X may be O or S. In this case, the lifetime of the device can be increased by lowering the crystallinity.

In addition, in one embodiment of the present invention, the L may be a substituted or unsubstituted C ₆ ~ ₁₂ arylene. In this case, the HOMO energy level may be deeper, and accordingly, the HOMO energy level suitable for the light emitting auxiliary layer may be obtained.

Further, in one embodiment of the present invention, Ar ₁ , Ar ₂ , and Ar ₃ are each independently a substituted or unsubstituted C ₆ ~ C ₁₅ aryl group or a substituted or unsubstituted C ₃ ~ C ₁₈ heteroaryl group. can

Further, in one embodiment of the present invention, Ar ₁ is phenyl, biphenyl, terphenyl, or naphthyl, and Ar ₂ and Ar ₃ may each independently be phenyl, biphenyl, terphenyl, or fluorene. .

In addition, in one embodiment of the present invention, the compound may be represented by any one of Formulas 2 to 5 below.

[Formula 2]

[Formula 3]

[Formula 4]

[Formula 5]

In Formulas 2 to 5,

L' is a direct bond or phenylene. In this case, the HOMO energy level can go a little deeper.

The compounds represented by Chemical Formulas 2 to 5 may have a molecular weight of 900 or less, so that a low deposition temperature may be formed.

In addition, L' is selected as a direct bond or phenylene and Ar ₂ Alternatively, the HOMO energy level may be changed depending on the presence or absence of fluorene in Ar ₃ , and accordingly, the application may be selected as a light emitting auxiliary layer or a hole transport layer. More specifically, when L' is a direct bond, a hole transport layer, L' is phenylene, and Ar ₂ Or, when Ar ₃ is fluorene, and the bonding position with N is 2, the hole transport layer, L' is phenylene, and Ar ₂ Alternatively, when Ar ₃ is biphenyl or fluorene, and the bonding position with N is 4, it may have an appropriate HOMO energy level for the light emitting auxiliary layer.

In addition, the compound represented by Formula 2, Formula 4, or Formula 5 has a relatively small solid angle with carbazole by connecting No. 2 of fluorene and No. 4 of dibenzofuran or dibenzothiophene as a connection position. It can have fast mobility (mobility) when forming a thin film.

In addition, the compound represented by Chemical Formula 3 has a large value of solid angle with carbazole by connecting fluorene number 4, thereby increasing the lifespan of the device due to its increased bulk.

According to one embodiment of the present invention, the compounds represented by Chemical Formulas 2 to 5 may be specified as follows, but may not be limited thereto.

In one embodiment of the present invention, the compound represented by Formula 1 may be any one of the compounds 1 to 577 shown below, but may not be limited thereto:

A second aspect of the present application provides an organic light emitting device including a compound represented by any one of Chemical Formulas 1 to 5. The organic light emitting device may include one or more organic material layers containing the compound according to the present disclosure between the first electrode and the second electrode.

In one embodiment of the present invention, the organic material layer may be a hole injection layer, a hole transport layer and a light emitting auxiliary layer, but may not be limited thereto. In addition, the compound of the present invention may be used alone or in combination with known compounds when forming an organic layer.

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. According to one embodiment of the present invention, as described above, the compound of Formula 1 may be represented by any one of Formulas 2 to 5.

The organic light emitting device includes an organic material layer such as a hole injection layer (HIL), a hole transport layer (HTL), a light emitting layer (EML), an electron transport layer (ETL), and an electron injection layer (EIL) between an anode and a cathode. May contain more than one floor.

For example, the organic light emitting device may be manufactured as shown in FIG. 1 . The organic light emitting element is composed 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 layer 600) from the bottom The injection electrode 2000) may be stacked in order.

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

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 200, the desired structure and thermal characteristics of the hole injection layer, etc., but generally 50-500 The temperature, the degree of vacuum of 10 ^{- 8} to 10 ^{- 3} torr, the deposition rate of 0.01 to 100 Å/sec, and the layer thickness range of 10 Å to 5 μm can be appropriately selected.

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 300 may use the compound according to the present invention, and as described above, the compound according to the present invention may be used alone or a known compound may be used together. In addition, according to one embodiment of the present invention, the hole transport layer 300 may have one or more layers, and may include a hole transport layer formed of only known materials. In addition, according to one embodiment of the present invention, an auxiliary light emitting layer may be formed on the hole transport layer 300 .

The light emitting layer 400 may be formed by depositing a material for the light emitting layer on the hole transport layer 300 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, an oxadiazole derivative, a triazole derivative, a phenanthroline derivative, or a hole blocking material described in Japanese Patent Laid-Open No. 11-329734 (A1) may be mentioned, and typically Balq (bis(8-hydroxy) oxy-2-methylquinolinato)-aluminum biphenoxide), phenanthrolines-based compounds (eg UDC BCP (vasocuproin)), and the like 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 an electron injection layer 600. It can be formed by methods such as law.

The hole injection layer 200, the hole transport layer 300, the light emitting layer 400, and the electron transport layer 500 of the organic light emitting device may use the compound according to the present invention or the following materials, or according to the present invention A compound and a known substance can 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 can have a structure of various organic light emitting devices as well as an 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. It is also possible to further form a layer or two intermediate layers.

As described above, the thickness of each organic material layer formed according to the present invention may be adjusted according to a required degree, specifically, 10 to 1,000 nm, and more specifically, 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 in 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]

intermediate synthesis

To synthesize the target compound, intermediate I-1 was synthesized as follows, and the synthesized intermediates are shown in Table 1 below.

Preparation Example 1 : Intermediate (I-1) synthesis

Under argon or nitrogen atmosphere, dibenzo[b,d]furan-4-ylboronic acid 42.5g (200mM), 3,6-diiodo-9-phenyl-9H-carbazole 149g (300mM), tetrakis(triphenylphosphine)palladium(0) 600ml of toluene and 300ml of 2M Na ₂ CO ₃ aqueous solution were added to 4.7g (4mM), and the mixture was heated under reflux for 10 hours. After completion of the reaction, extraction with dichloromethane and MgSO ₄ was added and filtered. After removing the solvent from the filtered organic layer, it was purified by column chromatography to obtain 75 g of intermediate I-1 (3-(dibenzo[b,d]furan-4-yl)-6-iodo-9-phenyl-9H-carbazole). .

Preparation Example 2: Synthesis of Intermediate (I-2)

Intermediate I-2 (3-( 71.7 g of dibenzo[b,d]thiophen-4-yl)-6-iodo-9-phenyl-9H-carbazole) was obtained.

Preparation Example 3: Synthesis of Intermediate (I-3)

Intermediate I- 84.3 g of 3 (3-(9,9-dimethyl-9H-fluoren-2-yl)-6-iodo-9-phenyl-9H-carbazole) was obtained.

Preparation Example 4: Synthesis of Intermediate (I-4)

Intermediate I- 80.9 g of 4 (3-(9,9-dimethyl-9H-fluoren-4-yl)-6-iodo-9-phenyl-9H-carbazole) was obtained.

Preparation Example 5 : Intermediate (I-5) synthesis

Under argon or nitrogen atmosphere, 53.6g (100mM) of I-1, 40.2g (200mM) of 4-bromophenylboronic acid, 2.4g (2mM) of tetrakis(triphenylphosphine)palladium(0), 400ml of toluene, 2M Na ₂ CO ₃ aqueous solution 200 ml was added and heated under reflux for 8 hours. After completion of the reaction, extraction with dichloromethane and MgSO ₄ was added and filtered. After removing the solvent from the filtered organic layer, the intermediate I-5 (3-(4-bromophenyl)-6-(dibenzo[b,d]furan-4-yl)-9-phenyl-9H-carbazole was purified by column chromatography. ) to obtain 45.2 g.

Preparation Example 6: Synthesis of Intermediate (I-6)

Intermediate I-6 (3-(4-bromophenyl)-6-(9,9-dimethyl-9H-fluoren- 2-yl) -9-phenyl-9H-carbazole) 50.2 g was obtained.

Preparation Example 7: Synthesis of Intermediate (I-7)

Intermediate I-7 (3-(4-bromophenyl)-6-(9,9-dimethyl-9H-fluoren- 4-yl) -9-phenyl-9H-carbazole) 49.1 g was obtained.

Preparation Example 8: Synthesis of Intermediate (I-8)

Intermediate I-8 (3- 51.9 g of (4'-bromo-[1,1'-biphenyl]-4-yl)-6-(dibenzo[b,d]furan-4-yl)-9-phenyl-9H-carbazole) was obtained.

Preparation Example 9: Synthesis of Intermediate (I-9)

Preparation Example 5 in addition to using 55.2 g of I-2 instead of 53.6 g of I-1 and using 55.4 g of (4'-bromo-[1,1'-biphenyl]-4-yl)boronic acid instead of 40.2 g of 4-bromophenylboronic acid The reaction was carried out in the same manner as in Intermediate I-9 (3-(4'-bromo-[1,1'-biphenyl]-4-yl)-6-(dibenzo[b,d]thiophen-4-yl)- 9-phenyl-9H-carbazole) 51.9 g was obtained.

Preparation Example 10: Synthesis of Intermediate (I-10)

Preparation Example 5 in addition to using 56.2 g of I-3 instead of 53.6 g of I-1 and using 55.4 g of (4'-bromo-[1,1'-biphenyl]-4-yl)boronic acid instead of 40.2 g of 4-bromophenylboronic acid The reaction was carried out in the same manner as in Intermediate I-10 (3-(4'-bromo-[1,1'-biphenyl]-4-yl)-6-(9,9-dimethyl-9H-fluoren-2-yl )-9-phenyl-9H-carbazole) 55.4 g was obtained.

Preparation Example 11: Synthesis of Intermediate (I-11)

Preparation Example 5 in addition to using 56.2 g of I-4 instead of 53.6 g of I-1 and using 55.4 g of (4'-bromo-[1,1'-biphenyl]-4-yl)boronic acid instead of 40.2 g of 4-bromophenylboronic acid The reaction was carried out in the same manner as in Intermediate I-11 (3-(4'-bromo-[1,1'-biphenyl]-4-yl)-6-(9,9-dimethyl-9H-fluoren-4-yl )-9-phenyl-9H-carbazole) 54.7 g was obtained.

intermediate FD-MS transference number(%) I-1

m/z: 535.04 (100.0%), 536.05 (32.1%), 537.05 (2.9%), 537.05 (2.5%) 70 I-2

m/z: 551.02 (100.0%), 552.02 (32.1%), 553.02 (4.2%), 553.03 (2.9%), 553.03 (2.6%), 554.02 (1.9%) 65 I-3

m/z: 561.10 (100.0%), 562.10 (35.9%), 563.10 (3.4%), 563.10 (2.6%) 75 I-4

m/z: 561.10 (100.0%), 562.10 (35.4%), 563.10 (3.9%), 563.10 (2.5%) 72 I-5

m/z: 563.09 (100.0%), 565.09 (97.1%), 566.09 (37.7%), 564.09 (22.8%), 564.09 (16.3%), 567.09 (7.4%), 565.10 (4.7%), 565.10 (2.7%) ) 80 I-6

m/z: 589.14 (100.0%), 591.14 (97.2%), 590.14 (42.1%), 592.14 (41.2%), 593.15 (8.6%), 591.15 (5.0%), 591.15 (3.4%), 594.15 (1.2%) ) 85 I-7

m/z: 589.14 (100.0%), 591.14 (97.4%), 590.14 (42.3%), 592.14 (41.1%), 593.15 (8.5%), 591.15 (5.1%), 591.15 (3.2%), 594.15 (1.1%) ) 83 I-8

m/z: 639.12 (100.0%), 641.12 (97.5%), 640.12 (45.7%), 642.12 (44.3%), 643.12 (9.5%), 641.13 (5.2%), 641.13 (4.8%), 644.13 (0.9%) ) 81 I-9

m/z: 655.10 (100.0%), 657.09 (97.1%), 656.10 (45.7%), 658.10 (44.5%), 659.10 (9.9%), 657.10 (5.3%), 657.10 (5.1%), 657.09 (4.1%) ), 659.09 (4.2%), 658.10 (2.3%), 660.09 (2.0%), 658.11 (1.2%), 660.10 (1.0%) 79 I-10

m/z: 665.17 (100.0%), 667.17 (97.6%), 666.18 (48.9%), 668.17 (47.6%), 669.18 (11.1%), 667.18 (6.1%), 667.18 (5.2%), 670.18 (1.1%) ) 83 I-11

m/z: 665.17 (100.0%), 667.17 (97.2%), 666.18 (48.4%), 668.17 (47.1%), 669.18 (11.2%), 667.18 (6.7%), 667.18 (5.4%), 670.18 (1.6%) ) 82

compound synthesis

Target compounds 1 to 32 were synthesized using the intermediates I-1 to I-11, and the results are shown in Tables 2 and 3 below.

synthesis example 1: Synthesis of Compound S1

Under argon or nitrogen atmosphere, I-5 24.5 g (50 mM), 9,9-dimethyl-N-phenyl-9H-fluoren-2-amine 28.6 g (100 mM), Pd ₂ (dba) 31.6 g (1.7 mM), Toluene 300ml was added to 50% P(t-Bu) 32ml (4mM), NaOt-Bu 14.7g (152mM), and heated while refluxing for 15 hours. After completion of the reaction, the mixture was filtered immediately, extracted with dichloromethane, and MgSO ₄ was added thereto and filtered. After removing the solvent from the filtered organic layer, it was purified by column chromatography to obtain compound S1 (N-(4-(6-(dibenzo[b,d]furan-4-yl)-9-phenyl-9H-carbazol-3-yl ) phenyl) -9,9-dimethyl-N-phenyl-9H-fluoren-2-amine) 31.9 g was obtained.

synthesis example 2: Synthesis of Compound S2

The reaction was the same as in Synthesis Example 1 except that 28.6 g of 9,9-dimethyl-N-phenyl-9H-fluoren-4-amine was used instead of 28.6 g of 9,9-dimethyl-N-phenyl-9H-fluoren-2-amine. Proceed to compound S2 (N-(4-(6-(dibenzo[b,d]furan-4-yl)-9-phenyl-9H-carbazol-3-yl)phenyl)-9,9-dimethyl-N- phenyl-9H-fluoren-4-amine) to obtain 31.5 g.

synthesis example 3: Synthesis of Compound S3

N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-9H-fluoren-2-amine instead of 9,9-dimethyl-N-phenyl-9H-fluoren-2-amine 28.6g Compound S3 (N-([1,1'-biphenyl]-4-yl)-N-(4-(6-(dibenzo[b,d] 34.7 g of furan-4-yl)-9-phenyl-9H-carbazol-3-yl)phenyl)-9,9-dimethyl-9H-fluoren-2-amine) was obtained.

synthesis example 4: Synthesis of Compound S4

N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-9H-fluoren-4-amine instead of 9,9-dimethyl-N-phenyl-9H-fluoren-2-amine 28.6g Compound S4 (N-([1,1'-biphenyl]-4-yl)-N-(4-(6-(dibenzo[b,d] 35.1 g of furan-4-yl)-9-phenyl-9H-carbazol-3-yl)phenyl)-9,9-dimethyl-9H-fluoren-4-amine) was obtained.

synthesis example 5: Synthesis of Compound S5

The reaction was carried out in the same manner as in Synthesis Example 1 except that 24.6 g of N-phenyl-[1,1'-biphenyl]-4-amine was used instead of 28.6 g of 9,9-dimethyl-N-phenyl-9H-fluoren-2-amine Compound S5 (N-(4-(6-(dibenzo[b,d]furan-4-yl)-9-phenyl-9H-carbazol-3-yl)phenyl)-N-phenyl-[1,1' -biphenyl] -4-amine) to obtain 29.5 g.

synthesis example 6: Synthesis of Compound S6

The reaction was carried out in the same manner as in Synthesis Example 1 except that 24.6 g of N-phenyl-[1,1'-biphenyl]-2-amine was used instead of 28.6 g of 9,9-dimethyl-N-phenyl-9H-fluoren-2-amine Compound S6 (N-(4-(6-(dibenzo[b,d]furan-4-yl)-9-phenyl-9H-carbazol-3-yl)phenyl)-N-phenyl-[1,1' -biphenyl] -2-amine) to obtain 29.9 g.

synthesis example 7: Synthesis of Compound S7

The reaction proceeds in the same manner as in Synthesis Example 1 except that 32.2 g of di([1,1'-biphenyl]-4-yl)amine was used instead of 28.6 g of 9,9-dimethyl-N-phenyl-9H-fluoren-2-amine Compound S7 (N-([1,1'-biphenyl]-4-yl)-N-(4-(6-(dibenzo[b,d]furan-4-yl)-9-phenyl-9H-carbazol -3-yl)phenyl)-[1,1'-biphenyl]-4-amine) 33.4g was obtained.

synthesis example 8: Synthesis of Compound S8

N-([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-2-amine instead of 9,9-dimethyl-N-phenyl-9H-fluoren-2-amine 28.6 g 32.2 g The reaction was carried out in the same manner as in Synthesis Example 1 except for the use of compound S8 (N-([1,1'-biphenyl]-4-yl)-N-(4-(6-(dibenzo[b,d]furan -4-yl)-9-phenyl-9H-carbazol-3-yl)phenyl)-[1,1'-biphenyl]-2-amine) 33.8g was obtained.

synthesis example 9: Synthesis of Compound S9

Compound S9 (N-(4-(6-(9,9-dimethyl-9H-fluoren-2-yl) -9-phenyl-9H-carbazol-3-yl)phenyl)-9,9-dimethyl-N-phenyl-9H-fluoren-2-amine) 33.8g was obtained.

synthesis example 10: Synthesis of Compound S10

Compound S10 (N-(4-(6-(9,9-dimethyl-9H-fluoren-2-yl) -9-phenyl-9H-carbazol-3-yl)phenyl)-9,9-dimethyl-N-phenyl-9H-fluoren-4-amine) 33.4g was obtained.

synthesis example 11: Synthesis of Compound S11

Compound S11 (N-([1,1'-biphenyl]-4-yl)-N-(4-( 6-(9,9-dimethyl-9H-fluoren-2-yl)-9-phenyl-9H-carbazol-3-yl)phenyl)-9,9-dimethyl-9H-fluoren-2-amine) 36.2 g got it

synthesis example 12: Synthesis of compound S12

Compound S12 (N-([1,1'-biphenyl]-4-yl)-N-(4-( 6-(9,9-dimethyl-9H-fluoren-2-yl)-9-phenyl-9H-carbazol-3-yl)phenyl)-9,9-dimethyl-9H-fluoren-4-amine) 36.6 g got it

synthesis example 13: Synthesis of Compound S13

Compound S13 (N-(4-(6-(9,9-dimethyl-9H-fluoren-2-yl) 32.1 g of -9-phenyl-9H-carbazol-3-yl) phenyl) -N-phenyl- [1,1'-biphenyl] -4-amine) was obtained.

synthesis example 14: Synthesis of Compound S14

Compound S14 (N-(4-(6-(9,9-dimethyl-9H-fluoren-2-yl) 32 g of -9-phenyl-9H-carbazol-3-yl) phenyl) -N-phenyl- [1,1'-biphenyl] -2-amine) was obtained.

synthesis example 15: Synthesis of Compound S15

Compound S15 (N-([1,1'-biphenyl]-4-yl)-N-(4-( 34.5 g of 6-(9,9-dimethyl-9H-fluoren-2-yl)-9-phenyl-9H-carbazol-3-yl)phenyl)-[1,1'-biphenyl]-4-amine) was obtained. .

Synthesis Example 16: Synthesis of Compound S16

Compound S16 (N-([1,1'-biphenyl]-4-yl)-N-(4-( 34 g of 6-(9,9-dimethyl-9H-fluoren-2-yl)-9-phenyl-9H-carbazol-3-yl)phenyl)-[1,1'-biphenyl]-2-amine) was obtained.

Synthesis Example 17: Synthesis of Compound S17

Compound S17 (N-(4-(6-(9,9-dimethyl-9H-fluoren-4-yl) -9-phenyl-9H-carbazol-3-yl)phenyl)-9,9-dimethyl-N-phenyl-9H-fluoren-2-amine) 33g was obtained.

Synthesis Example 18: Synthesis of Compound S18

Compound S18 (N-(4-(6-(9,9-dimethyl-9H-fluoren-4-yl) 32.2 g of -9-phenyl-9H-carbazol-3-yl) phenyl) -9,9-dimethyl-N-phenyl-9H-fluoren-4-amine) was obtained.

Synthesis Example 19: Synthesis of Compound S19

Compound S19 (N-([1,1'-biphenyl]-4-yl)-N-(4-( 6-(9,9-dimethyl-9H-fluoren-4-yl)-9-phenyl-9H-carbazol-3-yl)phenyl)-9,9-dimethyl-9H-fluoren-2-amine) 34.8 g got it

Synthesis Example 20: Synthesis of Compound S20

Compound S20 (N-([1,1'-biphenyl]-4-yl)-N-(4-( 6-(9,9-dimethyl-9H-fluoren-4-yl)-9-phenyl-9H-carbazol-3-yl)phenyl)-9,9-dimethyl-9H-fluoren-4-amine) 35.3 g got it

Synthesis Example 21: Synthesis of Compound S21

Compound S21 (N-(4-(6-(9,9-dimethyl-9H-fluoren-4-yl) 31 g of -9-phenyl-9H-carbazol-3-yl) phenyl) -N-phenyl- [1,1'-biphenyl] -4-amine) was obtained.

Synthesis Example 22: Synthesis of Compound S22

Compound S22 (N-(4-(6-(9,9-dimethyl-9H-fluoren-4-yl) 31.3 g of -9-phenyl-9H-carbazol-3-yl) phenyl) -N-phenyl- [1,1'-biphenyl] -2-amine) was obtained.

Synthesis Example 23: Synthesis of Compound S23

Compound S23 (N-([1,1'-biphenyl]-4-yl)-N-(4-( 31.4 g of 6-(9,9-dimethyl-9H-fluoren-4-yl)-9-phenyl-9H-carbazol-3-yl)phenyl)-[1,1'-biphenyl]-4-amine) was obtained. .

Synthesis Example 24: Synthesis of Compound S24

Compound S24 (N-([1,1'-biphenyl]-4-yl)-N-(4-( 30.6 g of 6-(9,9-dimethyl-9H-fluoren-4-yl)-9-phenyl-9H-carbazol-3-yl)phenyl)-[1,1'-biphenyl]-2-amine) was obtained. .

Synthesis Example 25: Synthesis of Compound S25

Compound S25 (N-([1,1'-biphenyl]-4-yl)-4'-(6- (dibenzo[b,d]furan-4-yl)-9-phenyl-9H-carbazol-3-yl)-N-phenyl-[1,1'-biphenyl]-4-amine) to obtain 32.6 g.

Synthesis Example 26: Synthesis of Compound S26

Compound S26 (N-(4'-(6-(dibenzo[b,d]furan-4-yl)- 32.2 g of 9-phenyl-9H-carbazol-3-yl)-[1,1'-biphenyl]-4-yl)-N-phenyl-[1,1'-biphenyl]-2-amine) was obtained.

Synthesis Example 27: Synthesis of Compound S27

Compound S27 (N-([1,1'-biphenyl]-4-yl)-4'-(6- (dibenzo[b,d]thiophen-4-yl)-9-phenyl-9H-carbazol-3-yl)-N-phenyl-[1,1'-biphenyl]-4-amine) 32.4 g was obtained.

Synthesis Example 28: Synthesis of Compound S28

Compound S28 (N-(4'-(6-(dibenzo[b,d]thiophen-4-yl)- 32.9 g of 9-phenyl-9H-carbazol-3-yl)-[1,1'-biphenyl]-4-yl)-N-phenyl-[1,1'-biphenyl]-2-amine) was obtained.

Synthesis Example 29: Synthesis of Compound S29

Compound S29 (N-([1,1'-biphenyl] -4-yl) -4'-(6- (9,9-dimethyl-9H-fluoren-2-yl)-9-phenyl-9H-carbazol-3-yl)-N-phenyl-[1,1'-biphenyl]-4-amine) 33.7g was obtained .

Synthesis Example 30: Synthesis of Compound S30

Compound S30 (N-(4'-(6-(9,9-dimethyl-9H-fluoren-2-yl )-9-phenyl-9H-carbazol-3-yl)-[1,1'-biphenyl]-4-yl)-N-phenyl-[1,1'-biphenyl]-2-amine) 33.2 g was obtained .

Synthesis Example 31: Synthesis of Compound S31

Compound S31 (N-([1,1'-biphenyl] -4-yl) -4'-(6- (9,9-dimethyl-9H-fluoren-2-yl)-9-phenyl-9H-carbazol-3-yl)-N-phenyl-[1,1'-biphenyl]-4-amine) 32.4g was obtained .

Synthesis Example 32: Synthesis of Compound S32

Compound S32 (N-(4'-(6-(9,9-dimethyl-9H-fluoren-2-yl )-9-phenyl-9H-carbazol-3-yl)-[1,1'-biphenyl]-4-yl)-N-phenyl-[1,1'-biphenyl]-2-amine) 33.7 g was obtained .

compound transference number(%) FD-MS S1 83 m/z: 768.31 (100.0%), 769.32 (61.8%), 770.32 (18.6%), 771.32 (2.8%) S2 82 m/z: 768.31 (100.0%), 769.32 (61.9%), 770.32 (18.8%), 771.32 (2.5%) S3 82 m/z: 844.35 (100.0%), 845.35 (68.3%), 846.35 (22.7%), 847.36 (4.1%) S4 83 m/z: 844.35 (100.0%), 845.35 (68.2%), 846.35 (22.6%), 847.36 (4.3%) S5 81 m/z: 728.28 (100.0%), 729.29 (58.6%), 730.29 (16.3%), 731.29 (3.3%) S6 82 m/z: 728.28 (100.0%), 729.29 (58.2%), 730.29 (16.5%), 731.29 (3.5%) S7 83 m/z: 804.31 (100.0%), 805.32 (64.8%), 806.32 (20.6%), 807.32 (3.7%) S8 84 m/z: 804.31 (100.0%), 805.32 (64.7%), 806.32 (20.8%), 807.32 (3.6%) S9 85 m/z: 794.37 (100.0%), 795.37 (64.8%), 796.37 (20.6%), 797.38 (3.7%) S10 84 m/z: 794.37 (100.0%), 795.37 (64.8%), 796.37 (20.9%), 797.38 (3.4%) S11 83 m/z: 870.40 (100.0%), 871.40 (71.5%), 872.40 (25.2%), 873.41 (4.8%) S12 84 m/z: 870.40 (100.0%), 871.40 (71.2%), 872.40 (25.1%), 873.41 (5.2%) S13 85 m/z: 754.33 (100.0%), 755.34 (61.7%), 756.34 (18.8%), 757.34 (2.7%) S14 85 m/z: 754.33 (100.0%), 755.34 (61.8%), 756.34 (18.6%), 757.34 (2.8%) S15 83 m/z: 830.37 (100.0%), 831.37 (68.2%), 832.37 (22.9%), 833.38 (4.0%) S16 82 m/z: 830.37 (100.0%), 831.37 (68.0%), 832.37 (22.7%), 833.38 (4.5%) S17 83 m/z: 794.37 (100.0%), 795.37 (64.7%), 796.37 (20.8%), 797.38 (3.6%) S18 81 m/z: 794.37 (100.0%), 795.37 (64.9%), 796.37 (20.5%), 797.38 (3.7%) S19 80 m/z: 870.40 (100.0%), 871.40 (71.3%), 872.40 (25.3%), 873.41 (4.9%) S20 81 m/z: 870.40 (100.0%), 871.40 (71.1%), 872.40 (25.3%), 873.41 (5.1%) S21 82 m/z: 754.33 (100.0%), 755.34 (61.5%), 756.34 (18.9%), 757.34 (2.8%) S22 83 m/z: 754.33 (100.0%), 755.34 (61.9%), 756.34 (18.8%), 757.34 (2.5%) S23 83 m/z: 830.37 (100.0%), 831.37 (68.1%), 832.37 (22.8%), 833.38 (4.2%) S24 81 m/z: 830.37 (100.0%), 831.37 (68.4%), 832.37 (22.4%), 833.38 (4.4%) S25 81 m/z: 804.31 (100.0%), 805.32 (64.7%), 806.32 (20.6%), 807.32 (3.8%) S26 80 m/z: 804.31 (100.0%), 805.32 (64.8%), 806.32 (20.9%), 807.32 (3.4%) S27 79 m/z: 820.29 (100.0%), 821.29 (64.7%), 822.30 (20.6%), 822.29 (4.6%), 823.30 (3.8%), 823.29 (2.8%) S28 80 m/z: 820.29 (100.0%), 821.29 (64.7%), 822.30 (20.9%), 822.29 (4.7%), 823.30 (3.7%), 823.29 (2.5%) S29 81 m/z: 830.37 (100.0%), 831.37 (68.2%), 832.37 (22.7%), 833.38 (4.2%) S30 80 m/z: 830.37 (100.0%), 831.37 (68.3%), 832.37 (22.7%), 833.38 (4.1%) S31 78 m/z: 830.37 (100.0%), 831.37 (68.4%), 832.37 (22.7%), 833.38 (4.0%) S32 81 m/z: 830.37 (100.0%), 831.37 (68.5%), 832.37 (22.5%), 833.38 (4.1%)

S1 S2 S3

S4 S5 S6

S7 S8 S9

S10 S11 S12

S13 S14 S15

S16 S17 S18

S19 S20 S21

S22 S23 S24

S25 S26 S27

S28 S29 S30

S31 S32

Manufacture of organic light emitting devices

Example 1

A glass substrate coated with indium tin oxide (ITO) having a thickness of 1500 Å was washed with distilled water and ultrasonic waves. After cleaning with distilled water, it is ultrasonically cleaned with solvents such as isopropyl alcohol, acetone, and methanol, dried, transferred to a plasma cleaner, and then cleaned by using oxygen plasma for 5 minutes. evaporator) was used to form a hole injection layer HI01 600 Å, HATCN 50 Å, and a hole transport layer of 300 Å compound S1. Next, the light emitting layer was doped with 3% BH:BD to form a 250 Å film. Next, as an electron transport layer, 300 Å of ET:Liq (1:1) was formed, followed by 10 Å of LiF and 1000 Å of aluminum (Al), and the device was encapsulated in a glove box to manufacture an organic light emitting device.

Examples 2 to 20

An organic light emitting diode was manufactured in the same manner as in Example 1, except that instead of compound S1, compounds S3, S5 to S17, S19, and S21 to S24 were used as hole transport layers.

Comparative Examples 1 to 9

An organic light-emitting device was manufactured in the same manner as in Example 1, except that Ref.1 (NPB) to Ref.9 of Table 4 below were used as hole transport layers instead of Compound S1.

Ref.1 (NPB) Ref.2 Ref.3

Ref.4 Ref.5 Ref.6

Ref.7 Ref.8 Ref.9

Example 21

A glass substrate coated with indium tin oxide (ITO) having a thickness of 1500 Å was washed with distilled water and ultrasonic waves. After cleaning with distilled water, it is ultrasonically cleaned with solvents such as isopropyl alcohol, acetone, and methanol, dried, transferred to a plasma cleaner, and then cleaned by using oxygen plasma for 5 minutes. evaporator) was used to form a hole injection layer HI 600 Å, HATCN 50 Å, and 350 Å of NPB as the first hole transport layer, and then 150 Å of Compound S2 was formed as a second hole transport layer (light emitting auxiliary layer). Next, the light emitting layer was doped with 3% of BH:BD1 to form a 250 Å film. Next, as an electron transport layer, 300 Å of ET:Liq (1:1) was formed, followed by 10 Å of LiF and 1000 Å of aluminum (Al), and encapsulation of the device in a glove box to manufacture an organic light emitting device.

Examples 22 to 32

An organic light emitting device was manufactured in the same manner as in Example 21, except that instead of compound S2, compounds S4, S6, S18, S20, and S25 to S32 were used as the second hole transport layer (light emitting auxiliary layer).

Comparative Examples 10 to 12

An organic light emitting device was manufactured in the same manner as in Example 21, except that Ref.10 to Ref.12 of Table 5 were used as the second hole transport layer (light emitting auxiliary layer) instead of Compound S2.

Ref.10 Ref.11 Ref.12.

[Performance evaluation of organic light emitting device]

Apply voltage to the Keithley 2400 source measurement unit to inject electrons and holes, and measure the luminance when light is emitted using a Konica Minolta spectroradiometer (CS-2000) By doing so, the performance of the organic light emitting devices of Examples and Comparative Examples was evaluated by measuring current density and luminance with respect to applied voltage under atmospheric pressure conditions, and the results are shown in [Table 6] and [Table 7], respectively.

drive voltage
Op.V current density
mA/cm ² current efficiency
Cd/A color coordinates
CIEx color coordinates
CIEy LT95
@1000nit Example 1 3.76 10.00 6.82 0.140 0.120 185 Example 2 3.78 10.00 6.86 0.140 0.123 195 Example 3 3.89 10.00 6.68 0.140 0.122 170 Example 4 3.87 10.00 6.70 0.140 0.121 175 Example 5 3.85 10.00 6.75 0.140 0.123 175 Example 6 3.86 10.00 6.77 0.140 0.122 180 Example 7 3.75 10.00 6.81 0.140 0.123 180 Example 8 3.90 10.00 6.85 0.140 0.123 190 Example 9 3.75 10.00 6.83 0.140 0.122 185 Example 10 3.91 10.00 6.87 0.140 0.121 195 Example 11 3.89 10.00 6.71 0.140 0.122 170 Example 12 3.88 10.00 6.72 0.140 0.121 175 Example 13 3.83 10.00 6.74 0.140 0.121 170 Example 14 3.84 10.00 6.77 0.140 0.122 170 Example 15 3.76 10.00 6.82 0.140 0.123 180 Example 16 3.74 10.00 6.85 0.140 0.121 190 Example 17 3.88 10.00 6.71 0.140 0.120 175 Example 18 3.89 10.00 6.73 0.140 0.121 175 Example 19 3.85 10.00 6.77 0.140 0.122 180 Example 20 3.87 10.00 6.79 0.140 0.121 180 Comparative Example 1 4.21 10.00 4.95 0.140 0.132 55 Comparative Example 2 4.07 10.00 5.75 0.140 0.125 110 Comparative Example 3 4.12 10.00 5.64 0.140 0.126 120 Comparative Example 4 4.01 10.00 5.73 0.140 0.125 115 Comparative Example 5 3.93 10.00 5.89 0.140 0.124 130 Comparative Example 6 4.02 10.00 5.72 0.140 0.125 115 Comparative Example 7 3.95 10.00 5.87 0.140 0.125 130 Comparative Example 8 4.02 10.00 5.70 0.140 0.124 110 Comparative Example 9 3.99 10.00 5.69 0.140 0.123 115

driving voltage
Op.V current density
mA/cm ² current efficiency
Cd/A color coordinates
CIEx color coordinates
CIEy LT95
@1000nit Example 21 4.08 10.00 6.32 0.140 0.128 125 Example 22 4.06 10.00 6.33 0.140 0.127 130 Example 23 4.08 10.00 6.32 0.140 0.128 125 Example 24 4.07 10.00 6.34 0.140 0.127 135 Example 25 4.08 10.00 6.27 0.140 0.127 120 Example 26 4.08 10.00 6.29 0.140 0.128 130 Example 27 4.09 10.00 6.25 0.140 0.129 135 Example 28 4.09 10.00 6.28 0.140 0.129 120 Example 29 4.08 10.00 6.24 0.140 0.127 125 Example 30 4.08 10.00 6.26 0.140 0.127 130 Example 31 4.07 10.00 6.28 0.140 0.127 135 Example 32 4.08 10.00 6.30 0.140 0.128 125 Comparative Example 10 4.12 10.00 5.42 0.140 0.129 85 Comparative Example 11 4.15 10.00 5.40 0.140 0.130 80 Comparative Example 12 4.11 10.00 5.52 0.140 0.128 95

Referring to Tables 6 and 7, the devices of Examples 1 to 32 using the compound of the present invention in which dibenzofuran or fluorene is substituted for arylamine-substituted carbazole have lower driving voltage and higher efficiency , it was confirmed that it exhibited long life characteristics.

More specifically, Table 6 is an evaluation of the characteristics of organic light emitting devices fabricated using the compound of the present invention and Ref.1 to Ref.9 as a hole transport layer. As shown in Table 6, dibenzofuran in carbazole , Compared to Comparative Example 2 and Comparative Example 3 using Ref.2 and Ref.3 materials having no substituent of dibenzothiophene or fluorene or substituted with a phenyl group, arylamine, dibenzofuran, and dibenzocyanate in carbazole, respectively Examples 1 to 20 using the compound substituted with opene or fluorene exhibited lower driving voltage, higher efficiency, and longer lifespan.

In addition, Comparative Examples 4 to 7 using Ref.4 to Ref.7 in which N (nitrogen) of carbazole is substituted with triphenylene instead of phenyl, and Ref.8 in which triphenylene is substituted for arylamine Compared to Comparative Example 8, Comparative Example 9 using Ref.9 where carbazole and dibenzofuran are not directly bonded but connected through a phenylene linking group, Examples 1 to 20 using the compound of the present invention have a lower driving voltage , exhibited high efficiency and long life characteristics.

Table 7 is an evaluation of the characteristics of an organic light emitting device manufactured using the compound of the present invention and Ref.10 to Ref.12 as a second hole transport layer (light emitting auxiliary layer). As shown in Table 7, carbazole Comparative Examples 10 and 11 using Ref.10 and Ref.11 having no substituent of dibenzofuran, dibenzothiophene or fluorene or substituted with a phenyl group, and carbazole and dibenzofuran not directly bonded, phenyl Compared to Comparative Example 12 using Ref.12 connected through a Ren connector, Examples 21 to 32 using the compound of the present invention exhibited lower driving voltage, higher efficiency, and longer lifespan.

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 1 below;
[Formula 1]

In Formula 1,
X is CR ₁ R ₂ , R ₁ and R ₂ are each independently a substituted or unsubstituted C ₁ to C ₃₀ alkyl group or a substituted or unsubstituted C ₆ to C ₃₀ aryl group,
Ar ₁ is a substituted or unsubstituted C ₆ ~ C ₃₀ aryl group;
L is a direct bond or a substituted or unsubstituted C ₆ ~ C ₁₈ arylene group;
Ar ₂ and Ar ₃ are each independently a substituted or unsubstituted C ₆ ~ C ₃₀ aryl group (provided that Ar ₁ , Ar ₂ and Ar ₃ are not triphenylene groups);
H is hydrogen; According to claim 1,
Wherein X is CR ₁ R ₂ , and R ₁ and R ₂ are each independently methyl or phenyl. delete According to claim 1,
Wherein L is a substituted or unsubstituted C ₆ ~ ₁₂ arylene compound. According to claim 1,
Wherein Ar ₁ , Ar ₂ , and Ar ₃ are each independently a substituted or unsubstituted C ₆ ~ C ₁₅ aryl group. According to claim 1,
Wherein Ar ₁ is phenyl, biphenyl, terphenyl, or naphthyl, and Ar ₂ and Ar ₃ are each independently phenyl, biphenyl, terphenyl, or fluorene. According to claim 1,
The compound is a compound represented by Formula 2 or 3;
[Formula 2]

[Formula 3]

In Formula 2 or 3,
L' is a direct bond or phenylene. According to claim 7,
The compound represented by Formula 2 or 3 is any one of the following compounds;

An organic light emitting device comprising an organic material layer containing the compound according to any one of claims 1, 2 and 4 to 8 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 9,
The organic light emitting device includes an organic material layer containing a hole transport material and an organic material layer containing a compound represented by Chemical Formula 1.

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