KR102650409B1 - Novel compound and organic electroluminescent divice including the same - Google Patents

Abstract

The present application relates to novel compounds and organic light-emitting devices containing the same.

Description

Novel compounds and organic light-emitting devices containing the same {NOVEL COMPOUND AND ORGANIC ELECTROLUMINESCENT DIVICE INCLUDING THE SAME}

The present application relates to novel compounds and organic light-emitting devices containing the same.

Materials used as organic layers in organic light-emitting diodes can be broadly classified into light-emitting materials, hole injection materials, hole transport materials, electron transport materials, and electron injection materials, depending on their function. In addition, the light-emitting materials can be classified into high molecules and low molecules according to their molecular weight, and can be classified into fluorescent materials derived from the singlet excited state of electrons and phosphorescent materials derived from the triplet excited state of electrons depending on the luminescence mechanism, Light-emitting materials can be divided into blue, green, and red light-emitting materials according to their emission color, and yellow and orange light-emitting materials necessary to realize better natural colors. Additionally, in order to increase color purity and increase luminous efficiency through energy transfer, a host/dopant system can be used as a luminescent material. The principle is that when a small amount of dopant, which has a smaller energy band gap and higher luminous efficiency than the host that mainly constitutes the light-emitting layer, is mixed into the light-emitting layer, excitons generated in the host are transported to the dopant, producing highly efficient light. At this time, since the wavelength of the host moves to the wavelength of the dopant, light of the desired wavelength can be obtained depending on the type of dopant and host used.

To date, various compounds are known as materials used in such organic light-emitting devices, but in the case of organic light-emitting devices using known materials, the development of new materials is continuously required due to high driving voltage, low efficiency, and short lifespan. Accordingly, efforts have been made to develop organic light-emitting devices with low-voltage operation, high brightness, and long lifespan using materials with excellent properties.

Japanese published patent 10-2015-530735

The present application seeks to provide novel organic compounds, methods for producing the same, and organic light-emitting devices containing the same.

However, the problem to be solved by the present application is not limited to the problems 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 the following formula (1):

[Formula 1]

In Formula 1,

R ₁ is hydrogen, deuterium, C ₁ -C ₆ alkyl group, or C ₆ to C ₃₀ aryl group,

Ar ₁ to Ar ₄ are each independently a substituted or unsubstituted C ₆ -C ₃₀ aryl group, a substituted or unsubstituted C ₁₀ -C ₂₅ condensed aryl group, or a substituted or unsubstituted C ₅ -C ₃₀ heteroaryl group, Ar ₃ and Ar ₄ may or may not form a ring with each other,

L is each independently a direct bond, a C ₆ -C ₃₀ arylene group, or a C ₅ -C ₃₀ heteroarylene group,

Ar is a substituted or unsubstituted C ₆ -C ₁₀ aryl group, a substituted or unsubstituted C ₁₀ -C ₂₅ condensed aryl group, or a substituted or unsubstituted C ₅ -C ₃₀ heteroaryl group,

l is an integer from 1 to 4, and m is an integer from 1 to 3.

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

The present invention uses phenyl-substituted diarylfluorene and an arylamine containing a phenyl group and a condensed aryl group to form a HOMO that is easy for hole injection and transport, and at the same time, maintains a high LUMO through substitution of the diarylfluorene moiety, thereby achieving electron blocking. A high-efficiency organic light-emitting device was realized by allowing excitons to be formed efficiently in the light-emitting layer. In addition, some of the aryls bonded to amines are aryl or condensed aryl with 6 to 10 carbon atoms, resulting in excellent thin film and interface arrangement of molecules, suppressing roll-off phenomenon through rapid hole mobility and realizing long-life devices. Arylamine compounds Even with a relatively single molecule, a high Tg can be maintained, preventing recrystallization of the thin film, thereby increasing driving stability.

The compound of the present invention has effects such as high luminous efficiency and high color purity, and can greatly contribute to the OLED industry such as flexible displays and lighting by applying it to organic light-emitting devices, organic light devices for solar power generation, etc.

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

Hereinafter, with reference to the attached drawings, implementation examples and embodiments of the present invention will be described in detail so that those skilled in the art can easily implement the present invention.

However, the present application may be implemented in various different forms and is not limited to the implementation examples and examples described herein. In order to clearly explain the present invention in the drawings, parts that are not related to the description are omitted, and similar parts are given similar reference numerals throughout the specification.

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

Throughout the specification of the present application, when a part "includes" a certain component, this means that it may further include other components rather than excluding other components unless specifically stated to the contrary. As used throughout the specification, the terms “about,” “substantially,” and the like are used to mean at or close to a numerical value when manufacturing and material tolerances inherent in the stated meaning are given, and are used to convey the understanding of the present application. Precise or absolute figures are used to assist in preventing unscrupulous infringers from taking unfair advantage of stated disclosures. As used throughout the specification, the terms “step of” or “step of” do not mean “step for.”

Throughout this specification, the term "combination thereof" included in the Markushi format expression means a mixture or combination of one or more components selected from the group consisting of the components described in the Markushi format expression, It means including one or more selected from the group consisting of.

Throughout this specification, description of “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 benzyl, phenyl, naphthyl, biphenyl, terphenyl, fluorene, phenanthrenyl, triphenylenyl, peryl. It means containing an aromatic ring such as nyl, chrysenyl, fluoranthenyl, benzofluorenyl, benzotriphenylenyl, benzochrysenyl, anthracenyl, stilbenyl, pyrenyl, etc., and “heteroaryl” means at least one ring. An aromatic ring containing a hetero atom, for example, pyrrolyl, pyrazinyl, pyridinyl, indolyl, isoindolyl, furyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, benzothiophenyl, di Benzothiophenyl, 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, thiophene ring, oxazole Aromatics formed from rings, oxadiazole rings, benzoxazole rings, thiazole rings, thiadiazole rings, benzothiazole rings, triazole rings, imidazole rings, benzoimidazole rings, pyran rings, and dibenzofuran rings. It means containing a heterocyclic group.

Throughout this specification, the term “alkyl” may include linear or branched, saturated or unsaturated C ₁ -C ₆ alkyl, such as methyl, ethyl, propyl, butyl, pentyl, hexyl or any of these. It may include all possible isomers, but may not be limited thereto.

Throughout the specification herein, “substituted” in the term “substituted or unsubstituted” refers to deuterium, halogen, amino group, nitrile group, nitro group or C ₁ to C ₂₀ alkyl group, C ₂ to C ₂₀ alkenyl group, C ₁ to C ₂₀ to be substituted with one or more groups selected from the group consisting of an alkoxy group, C ₃ ~ C ₂₀ cycloalkyl group, C ₃ ~ C ₂₀ heterocycloalkyl group, C ₆ ~ C ₃₀ aryl group, and C ₅ ~ C ₃₀ heteroaryl group. It means that you can.

Additionally, the same symbols throughout the specification may have the same meaning unless otherwise specified.

A first aspect of the present application provides a compound represented by the following formula (1):

[Formula 1]

In Formula 1,

R ₁ is hydrogen, deuterium, C ₁ -C ₆ alkyl group, or C ₆ to C ₃₀ aryl group,

Ar ₁ to Ar ₄ are each independently a substituted or unsubstituted C ₆ -C ₃₀ aryl group, a substituted or unsubstituted C ₆ -C ₃₀ condensed aryl group, or a substituted or unsubstituted C ₅ -C ₃₀ heteroaryl group, Ar ₃ and Ar ₄ may or may not form a ring with each other,

L is each independently a direct bond, a C ₆ -C ₃₀ arylene group, or a C ₅ -C ₃₀ heteroarylene group,

Ar is a substituted or unsubstituted C ₆ -C ₁₀ aryl group, a substituted or unsubstituted C ₁₀ -C ₂₅ condensed aryl group, or a substituted or unsubstituted C ₅ -C ₃₀ heteroaryl group,

l is an integer from 1 to 4, and m is an integer from 1 to 3.

In one embodiment of the present invention, Ar ₃ and Ar ₄ may combine with each other to form a ring, for example, fluorene.

In one embodiment of the present invention, when Ar is an aryl group, it may be phenyl, etc., and when Ar is a condensed aryl group, it may be naphthyl, phenanthrene, triphenylene, etc. Due to this limitation of substituents, high LUMO can be formed, excellent thin film and interfacial arrangement of molecules can be induced, and low temperature can be controlled during the deposition process.

In one embodiment of the present invention, the compound of Formula 1 may include a compound represented by Formula 2 or 3 below:

[Formula 2]

[Formula 3]

In the above formulas,

Ar, Ar ₁ , Ar ₂ , Ar ₄ , L, l and m are as defined in Formula 1, and R ₂ to R ₅ are each independently hydrogen, deuterium, C ₁ -C ₆ alkyl group, C ₆ -C ₃₀ aryl group or C ₅ -C ₃₀ heteroaryl group.

In one embodiment of the present invention, the compound may include a compound represented by the following formula 4 or 5:

[Formula 4]

[Formula 5]

In the above formulas,

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

R ₆ and R ₇ are each independently hydrogen, deuterium, or C ₁ -C ₆ alkyl group,

R ₈ to R ₁₁ are each independently hydrogen, deuterium, C ₁ -C ₆ alkyl group, C ₆ -C ₃₀ aryl group, or C ₅ -C ₃₀ heteroaryl group,

Ar ₅ is a substituted or unsubstituted C ₆ -C ₃₀ aryl group, a substituted or unsubstituted C ₆ -C ₃₀ condensed aryl group, or a substituted or unsubstituted C ₅ -C ₃₀ heteroaryl group,

n is an integer from 0 to 3.

In one embodiment of the present invention, the compound may include a compound of the following formula 6 or 7:

[Formula 6]

[Formula 7]

In the above formula,

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

R ₆ to R ₁₁ and Ar ₅ are as defined in Formulas 2 to 5.

In one embodiment of the present invention, Ar in Formulas 1 to 7 may specifically be an unsubstituted C ₆ -C ₁₀ aryl group or an unsubstituted C ₁₀ -C ₂₅ fused aryl group.

In one embodiment of the present invention, Ar in Formulas 1 to 7 may be phenyl or naphthyl.

In one embodiment of the present invention, in Formulas 1 to 7, l is 1 and R ₁ may be hydrogen.

In one embodiment of the present invention, in Formulas 3, 5, and 7, R ₃ , R ₄ , R ₉ , and R ₁₀ may each independently be hydrogen, methyl, or phenyl.

In one embodiment of the present invention, the compound of Formula 1 may be prepared as shown in Scheme 1 below, but may not be limited thereto:

[Scheme 1]

In one embodiment of the present invention, the organic light-emitting compound may include, but may not be limited to, the following specific compounds:

Among the above specific compounds, the following compounds can have faster hole mobility by directly bonding N to the 2-position of at least one fluorene, thereby lowering the driving voltage and improving efficiency and lifespan.

In addition, among the above specific compounds, the following compounds may have faster hole mobility by combining L, phenylene, or N at the 2-position of diarylfluorene or diphenylfluorene, thereby lowering the driving voltage and improving efficiency. and lifespan can be further improved.

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 layers containing the compound according to claim 1 between the first electrode and the second electrode.

In one embodiment of the present invention, the organic layer may be one or more of a hole injection layer, a hole transport layer, and 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 as a known organic layer. Can be used with luminescent compounds.

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

The organic light-emitting device has an organic material layer 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. It may contain more than one.

For example, the organic light emitting device may be manufactured according to the structure shown in FIG. 1. The organic light emitting device consists of an 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) from below. Injection electrodes (2000) are stacked in that order.

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

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

The hole injection layer 200 may be formed by depositing a hole injection layer material on the anode electrode using a method such as vacuum deposition, spin coating, casting, or Langmuir-Blodgett (LB) method. When forming a hole injection layer by the vacuum deposition method, the deposition conditions vary depending on the compound used as the material for the hole injection layer 200, the structure and thermal characteristics of the desired hole injection layer, but generally 50-500 deposition. Temperature, vacuum degree of 10 ^-8 to 10 ^-3 torr, deposition rate of 0.01 to 100 Å/sec, and layer thickness of 10 Å to 5 ㎛ can be appropriately selected.

Next, the hole transport layer 300 can be formed by depositing a hole transport layer material on top of the hole injection layer 200 by a method such as vacuum deposition, spin coating, casting, or LB method. When forming a hole transport layer by the vacuum deposition method, the deposition conditions vary depending on the compound used, but it is generally better to select conditions within the same range as those for forming the hole injection layer. Thereafter, the light-emitting layer 400 can be formed by depositing a light-emitting layer material on top of the hole transport layer by a method such as vacuum deposition, spin coating, casting, or LB method. When forming a light-emitting layer by the vacuum deposition method, the deposition conditions vary depending on the compound used, but it is generally better to select conditions within the same range as those for forming the hole injection layer. Additionally, the light emitting layer material may use a known compound as a host or dopant.

In addition, when used with a phosphorescent dopant in the light emitting layer, a hole blocking material (HBL) can 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 any material can be selected from known hole blocking materials and used. For example, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, or hole blocking materials described in Japanese Patent Application Laid-Open No. 11-329734 (A1), etc., representative examples include Balq (bis (8-hyde) Roxy-2-methylquinolinolnato)-aluminum biphenoxide), phenanthrolines-based compounds (e.g., UDC's BCP (bassocuproin)), etc. can be used.

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

Thereafter, the electron injection layer material can be deposited on top of the electron transport layer 500 to form the electron injection layer 600. At this time, the electron transport layer is formed by using a typical electron injection layer material using vacuum deposition, spin coating, or cast. It can be formed through methods such as laws.

The hole injection layer 200, the hole transport layer 300, the light emitting layer 400, and the electron transport layer 500 of the above device can be formed using a compound according to the present invention or the following materials, or a compound according to the present invention and Known substances 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 can be used as the cathode. Specific examples include materials such as aluminum, gold, and silver.

The organic light emitting device of the present invention is capable of being an organic light emitting device having an anode, hole injection layer, hole transport layer, light emitting layer, electron transport layer, electron injection layer, and cathode structure, as well as various organic light emitting devices, depending on the need. It is also possible to further form a layer or an intermediate layer of two layers.

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

In addition, the present invention has the advantage that the organic material layer containing the compound represented by Formula 1 has a uniform surface and excellent morphological stability because the thickness of the organic material layer can be adjusted on a molecular basis.

All of the content described in the first aspect of the present application may be applied to the organic light-emitting compound according to this aspect, but may not be limited thereto.

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

[ Example ]

Manufacturing example One

IM's synthesis

To synthesize the target compound, IM was prepared through the same steps as the above reaction scheme.

The synthesis method of IM1 is as follows.

In a round bottom flask, dissolve 15.0 g of 2-bromo-9,9-dimethyl-9H-fluorene and 5.1 g of phenylboronic acid in 200 ml of 1,4-dioxane, add 60 ml of K ₂ CO ₃ (2M) and Pd(PPh ₃ ) 1.3 g of ₄ was added and then refluxed and stirred. 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 purified by column to obtain 10.43 g of intermediate IM1-1 (yield 63%).

The following IM2 to IM4 were synthesized using different starting materials in the same manner as IM1.

Synthesis of OP

h is a halogen atom.

To synthesize the target compound, OP was prepared through the same steps as the above reaction scheme.

The synthesis method of OP1 is as follows.

In a round bottom flask, 10.0 g of 2-bromo-9,9-diphenyl-9H-fluorene, 3.8 g of aniline, 5.3 g of t-BuONa, 1.4 g of Pd ₂ (dba) ₃ and 1.6 g of (t-Bu) ₃ P ml was dissolved in 150 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 and filtered under reduced pressure, followed by column purification and recrystallization to obtain 7.73g of OP1 (yield 74%).

The following OP2 to OP8 were synthesized using different starting materials in the same manner as OP1.

Synthesis example One : Compound 1 synthesis of

In a round bottom flask, 5.0 g of IM1, 3.3 g of OP1, 1.5 g of t-BuONa, 0.4 g of Pd ₂ (dba) ₃ and 0.5 ml of (t-Bu) ₃ P were dissolved in 100 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, then column purified and recrystallized to obtain 5.01 g of Compound 1 (yield 70%).

m/z: 677.31 (100.0%), 678.31 (57.1%), 679.31 (15.7%), 680.32 (2.9%)

Synthesis example 2 : Compound 2 synthesis of

Compound 2 was synthesized in the same manner as Synthesis Example 1 using IM2 instead of IM1 (yield 74%).

m/z: 677.31 (100.0%), 678.31 (57.1%), 679.31 (15.7%), 680.32 (2.9%)

Synthesis example 3: Compound 3 synthesis

Compound 3 was synthesized in the same manner as Synthesis Example 1 using IM3 instead of IM1 (yield 70%).

m/z: 677.31 (100.0%), 678.31 (57.1%), 679.31 (15.7%), 680.32 (2.9%)

Synthesis example 4 : Compound 4 synthesis

Compound 4 was synthesized in the same manner as Synthesis Example 1 using IM4 instead of IM1 (yield 65%).

m/z: 677.31 (100.0%), 678.31 (57.1%), 679.31 (15.7%), 680.32 (2.9%)

Synthesis example 5: Compound 5 synthesis

Compound 5 was synthesized in the same manner as Synthesis Example 1 using OP2 instead of OP1 (yield 71%).

m/z: 727.32 (100.0%), 728.33 (61.0%), 729.33 (18.3%), 730.33 (3.6%)

Synthesis example 6: Compound 6 synthesis

Compound 6 was synthesized in the same manner as Synthesis Example 1 using OP3 instead of OP1 (yield 75%).

m/z: 727.32 (100.0%), 728.33 (61.0%), 729.33 (18.3%), 730.33 (3.6%)

Synthesis example 7: Compound 7 synthesis

Compound 7 was synthesized in the same manner as Synthesis Example 1 using OP4 instead of OP1 (yield 70%).

m/z: 637.28 (100.0%), 638.28 (53.4%), 639.28 (14.0%), 640.29 (2.4%)

Synthesis example 8 : Compound 8 synthesis

Compound 8 was synthesized in the same manner as Synthesis Example 1 using OP5 instead of OP1 (yield 62%).

m/z: 687.29 (100.0%), 688.30 (57.7%), 689.30 (16.4%), 690.30 (3.0%)

Synthesis example 9: Compound 9 synthesis

Compound 9 was synthesized in the same manner as Synthesis Example 1 using OP6 instead of OP1 (yield 65%).

m/z: 687.29 (100.0%), 688.30 (57.7%), 689.30 (16.4%), 690.30 (3.0%)

Synthesis example 10: Compound 10 synthesis

Compound 10 was synthesized in the same manner as Synthesis Example 1 using OP7 instead of OP1 (yield 70%).

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

Synthesis example 11: Compound 11 synthesis

Compound 11 was synthesized in the same manner as Synthesis Example 1 using OP8 instead of OP1 (yield 72%).

m/z: 801.34 (100.0%), 802.34 (67.4%), 803.35 (22.5%), 804.35 (4.9%)

Preparation Example 2: Preparation of organic light emitting device

A glass substrate coated with a 1500 Å thin film of indium tin oxide (ITO) was washed with distilled water ultrasonic waves. After cleaning with distilled water, ultrasonic cleaning with solvents such as isopropyl alcohol, acetone, and methanol, drying, and transferring to a plasma cleaner, the substrate is cleaned for 5 minutes using oxygen plasma, and then a thermal vacuum evaporator (thermal vacuum evaporator) is placed on the top of the ITO substrate. Using an evaporator, 600 Å of HI01 as a hole injection layer, 50 Å of HATCN, and 600 Å of Compound 1 as a hole transport layer were formed, and then doped with 3% of BH01:BD01 as the emission layer to form a 250 Å film. Next, 300 Å of ET01:Liq (1:1) was deposited as an electron transport layer, followed by 10 Å of LiF and 1000 Å of aluminum (Al), and encapsulation of the device in a glove box to produce an organic light-emitting device (Example 1). was produced.

Organic light-emitting devices (Examples 2 to 11) were manufactured in the same manner as above using Compounds 2 to 11 instead of Compound 1.

Comparative example

An organic light-emitting device was manufactured in the same manner as Preparation Example 2, except that the following Ref.1 to Ref.8 (Comparative Examples 1 to 8) were used instead of Compound 1.

Experimental Example 1: 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 the current density and luminance with respect to the applied voltage under atmospheric pressure conditions, and the results are shown in Table 1.

Op. V mA/cm2 Cd/A lm/w CIEx CIey LT95 Example 1 3.901 10 7.47 6.84 0.140 0.109 192 Example 2 3.890 10 7.45 6.80 0.140 0.110 189 Example 3 3.890 10 7.45 6.79 0.141 0.110 190 Example 4 3.900 10 7.40 6.82 0.140 0.110 188 Example 5 3.900 10 7.31 6.65 0.141 0.110 170 Example 6 3.895 10 7.30 6.60 0.140 0.110 165 Example 7 3.926 10 7.43 6.73 0.140 0.110 185 Example 8 3.931 10 7.40 6.70 0.140 0.111 180 Example 9 3.933 10 7.44 6.72 0.139 0.111 185 Example 10 3.930 10 7.40 6.70 0.141 0.110 188 Example 11 3.940 10 7.40 6.70 0.140 0.110 190 Comparative Example 1 4.110 10 6.55 5.60 0.14 0.111 100 Comparative example 2 4.002 10 5.17 4.06 0.143 0.113 108 Comparative example 3 4.115 10 5.13 4.04 0.141 0.113 70 Comparative Example 4 4.112 10 6.36 5.28 0.141 0.112 73 Comparative Example 5 4.011 10 5.15 4.10 0.141 0.111 18 Comparative Example 6 4.020 10 6.50 5.64 0.142 0.112 110 Comparative example 7 4.060 10 5.32 4.23 0.141 0.113 115 Comparative example 8 4.250 10 6.72 6.00 0.140 0.115 30

As shown in Table 1, the embodiments of the present invention show increased efficiency and lifespan compared to Comparative Examples 1 to 11. Comparing the examples of the present invention, 1) compared to Comparative Example 5, when it has a diphenylfluorene moiety, 2) compared to Comparative Examples 1 and 2, conjugate through diphenylfluorene part phenyl substitution In the case of gation expansion, 3) Compared to Comparative Examples 3 and 4, when maintaining LUMO, which facilitates electron blocking through phenyl substitution, 4) Compared to Comparative Examples 6, 7, and 8, one side of the arylamine It can be seen that the compound of the present invention, which is phenyl or naphthyl and the other side is not phenyl, has a low driving voltage and greatly improved efficiency and lifespan of the organic light-emitting device.

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

The scope of the present application is indicated by the claims described below rather than the detailed description above, and all changes or modified forms derived from the meaning and scope of the claims and their equivalent concepts 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 (12)

Compounds represented by formula 2 or 3 below:
[Formula 2]

[Formula 3]

In the above formulas,
R ₁ is hydrogen, deuterium, C ₁ -C ₆ alkyl group, or C ₆ -C ₃₀ aryl group,
R ₂ to R ₅ are each independently hydrogen, deuterium, C ₁ -C ₆ alkyl group, or C ₆ -C ₃₀ aryl group,
Ar ₁ , Ar ₂ and Ar ₄ are each independently a substituted or unsubstituted C ₆ -C ₃₀ aryl group, or a substituted or unsubstituted C ₆ -C ₃₀ condensed aryl group,
L is each independently a direct bond, a C ₆ -C ₃₀ arylene group, or a C ₅ -C ₃₀ heteroarylene group,
Ar is phenyl or naphthyl,
l is an integer from 1 to 4, and m is an integer from 1 to 3. According to claim 1,
The compound includes a compound represented by the following formula 4 or 5:
[Formula 4]

[Formula 5]

In the above formulas,
Ar, R ₁ , l and m are as defined in claim 1,
R ₆ and R ₇ are each independently hydrogen, deuterium, or C ₁ -C ₆ alkyl group,
R ₈ to R ₁₁ are each independently hydrogen, deuterium, C ₁ -C ₆ alkyl group, or C ₆ -C ₃₀ aryl group,
Ar ₅ is a substituted or unsubstituted C ₆ -C ₃₀ aryl group, or a substituted or unsubstituted C ₆ -C ₃₀ condensed aryl group,
n is an integer from 0 to 3. According to claim 1,
The compound includes a compound represented by Formula 6 or 7:
[Formula 6]

[Formula 7]

In the above formula,
Ar, R ₁ , l and m are as defined in claim 1,
R ₆ and R ₇ are each independently hydrogen, deuterium, or C ₁ -C ₆ alkyl group,
R ₈ to R ₁₁ are each independently hydrogen, deuterium, C ₁ -C ₆ alkyl group, or C ₆ -C ₃₀ aryl group,
Ar ₅ is a substituted or unsubstituted C ₆ -C ₃₀ aryl group, or a substituted or unsubstituted C ₆ -C ₃₀ condensed aryl group. The method according to any one of claims 1 to 3,
l is 1 and R ₁ is hydrogen. The method according to any one of claims 1 to 3,
R ₃ , R ₄ , R ₉ and R ₁₀ are each independently hydrogen, methyl or phenyl. According to claim 1,
The compound is any one of the following compounds.




















According to claim 1,
The compound is any one of the following compounds.






An organic light-emitting device comprising one or more organic material layers containing the compound according to claim 1 between the first electrode and the second electrode. According to claim 8,
An organic light-emitting device wherein the organic material layer is at least one of a hole injection layer, a hole transport layer, and a light-emitting auxiliary layer. delete delete delete