TW201942330A - Novel compound and organic electroluminescent device including the same - Google Patents

Abstract

The present application relates to a novel compound and an organic light-emitting device comprising same, the novel compound according to one embodiment of the present invention being applied to an organic light-emitting device to allow same to be highly effective, and have extended lifespan, low driving voltage and operational stability.

Description

Novel compound and organic light emitting device containing the same

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

In the organic light emitting diode, the material used as the organic substance layer can be roughly classified into a light emitting material, a hole injection material, a hole transport material, an electron transport material, an electron injection material, and the like according to functions. In addition, the above-mentioned light-emitting materials can be classified into high molecular and low-molecular materials according to molecular weight, and can be classified into fluorescent materials in a singlet excited state derived from electrons and phosphorescent materials in a triplet excited state derived from electrons. They are classified into blue, green, and red light-emitting materials and yellow and orange light-emitting materials required for better natural colors. In addition, in order to increase color purity and increase luminous efficiency through energy transfer, a matrix / dopant can be used as a luminescent substance. The principle is that if a small amount of dopants with a small band gap and excellent luminous efficiency are mixed in the auxiliary layer compared with the matrix that mainly constitutes the light-emitting layer, excitons generated in the matrix are transported to the dopants, thereby emitting high efficiency. Light. At this time, the wavelength of the substrate is shifted to the wavelength band of the dopant, so light having a desired wavelength can be obtained according to the type of the dopant and the substrate used.

Heretofore, as a substance used in such an organic light-emitting device, various compounds are well known. However, in the case of an organic light-emitting device using a conventionally well-known substance, development has been continuously demanded due to high driving voltage, low efficiency, and short life. New material. Therefore, efforts are continuously being made to develop organic light-emitting devices with low-voltage driving, high brightness, and long life using substances with excellent characteristics.

Known Technical Documents Patent Documents (Patent Document 1) Korean Published Patent 10-2015-0086721

The present invention provides a novel organic compound and an organic light emitting device including the same.

However, the problems to be solved by the present invention are not limited to the problems described above, and those with ordinary knowledge in the technical field to which the present invention pertains can clearly understand other problems not described based on the following description.

One embodiment of the present invention provides a compound represented by the following Chemical Formula 1.

Chemical formula 1

In the above Chemical Formula 1,
X is O, S or CRR ',
Ar ₁ is a substituted or unsubstituted C ₆ ~ C ₅₀ aryl group, or a substituted or unsubstituted C ₅ ~ C ₅₀ heteroaryl group,
Ar ₂ is a substituted or unsubstituted C ₁₂ ~ C ₅₀ aryl group,
R, R ', R ₁ to R ₆ are each independently hydrogen, halogen, nitro, nitrile, substituted or unsubstituted C ₁ to C ₃₀ alkyl, substituted or unsubstituted C ₂ to C ₃₀ olefin Group, substituted or unsubstituted C ₁ to C ₃₀ alkoxy group, substituted or unsubstituted C ₁ to C ₃₀ thioether group, substituted or unsubstituted C ₆ to C ₃₀ aryl group, or substituted or unsubstituted Substituted C ₅ to C ₃₀ heteroaryl groups, between adjacent R ₁ , R ₂ , R ₃ or R and R ′ can form a ring with each other or not, R ₄ and R ₆ Or R ₅ and R ₆ can form a ring with each other or not,
L ₁ is a directly bonded, substituted or unsubstituted C ₆ to C ₃₀ extended aryl group, or a substituted or unsubstituted C ₅ to C ₃₀ extended aryl group,
L ₂ is a substituted or unsubstituted C ₆ to C ₃₀ extended aryl group, or a substituted or unsubstituted C ₅ to C ₃₀ extended aryl group,
l is an integer of 0 or 1 to 4, and m and n are each independently an integer of 0 or 1 to 3. When l, m, or n is 2 or more, R ₁ , R _2, and R ₃ may be the same or different.

A second embodiment of the present invention provides an organic light emitting device including the organic substance layer containing the compound of the present invention between the first electrode and the second electrode.

According to an example compound of the present invention, a tricyclic condensed ring group (dibenzofuran, dibenzothiophene, or fluorene) and a dibenzofuran are connected to the nitrogen of an arylamine through a linker, thereby forming It is suitable for the highest occupied molecular orbital (HOMO) energy level of the light emitting auxiliary layer, thereby realizing a highly efficient organic light emitting device.

In addition, according to an example compound of the present invention, a tricyclic condensed ring group having excellent electron resistance is introduced on the arylamine side, maintaining a high minimum unoccupied molecular orbital (LUMO) and T1. The confinement effect of excitons in the light-emitting layer is maximized. Thereby, an organic light emitting device with high efficiency and long life can be realized.

In addition, according to the compound according to an example of the present invention, when the second or fourth position of the dibenzofuran having a small bulkiness is used as a connection position on the arylamine side to form a thin film, the molecular arrangement can be changed. Excellent. By realizing low voltage and suppressing the roll-off phenomenon, a long-life organic light emitting device can be realized.

In addition, according to an example compound of the present invention, one side of an arylamine is connected to dibenzofuran through a linking group, and an aryl group is provided on the other side, whereby a π-conjugate can be increased. As a result, hole mobility can be improved, and a low driving voltage can be realized when applied to an organic light emitting device.

In addition, the compound according to an example of the present invention includes a tricyclic condensed ring group expanded by dibenzofuran on the side of the arylamine to form a high Tg, which prevents recrystallization of the film, thereby ensuring Driving stability of organic light emitting device.

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

However, the present invention can be implemented in many different forms, and is not limited to the examples and embodiments described herein. In the drawings, in order to clearly illustrate the present invention, parts irrelevant to the description are omitted. Throughout the description, similar parts are marked with similar element symbols.

Throughout the description of the present invention, when a component is "on" another component, it includes not only the case where one component is in contact with another component, but also the case where other components are present between the two components.

Throughout the description of the present invention, when a part “includes” a structural element, unless there is a particular contrary description, it means that other structural elements may also be included instead of excluding other structural elements. The terms "about", "substantially" and the like used throughout the specification of the present invention are used in their meanings to imply inherent preparations and material tolerances in their numerical values or meanings close to their numerical values in order to prevent conscience. The infringer improperly makes use of disclosures that refer to exact or absolute numerical values in order to help understand the present invention. The term "~ (of) steps" or "~ steps" used throughout the present specification does not mean "steps for ~".

Throughout the description of the present invention, the term "combination" contained in the expression of Markush form means that it is selected from the group consisting of a plurality of structural elements described in the expression of Markush form Mixing or combining one or more of these means including one or more selected from the group consisting of the plurality of structural elements.

Throughout the description of the present invention, the expression "A and / or B" means "A or B, or A and B".

Throughout this specification, the term "aryl" means an aromatic hydrocarbon ring group containing C _6-50 , such as phenyl, benzyl, naphthyl, biphenyl, terphenyl, fluorene, phenanthryl, Aromatics such as triphenylalkenyl, phenylalkenyl, fluorenyl, fluoranthenyl, benzofluorenyl, benzotriphenylenyl, benzofluorenyl, anthracenyl, stilbyl, and fluorenyl Family ring, "heteroaryl" as a C _5-50 aromatic ring containing at least one heteroatom, for example, meant to include from pyrrolinyl, pyrazinyl, pyridyl, indolyl, isoindolyl, Furyl, benzofuryl, isobenzofuryl, dibenzofuryl, benzophenylthio, dibenzophenylthio, quinolinyl, isoquinolinyl, quinoxalinyl, oxazolyl , Phenanthryl, acridinyl, phenanthroline, thienyl, and pyridine, pyrazine, pyrimidine, pyridazine, triazine, indole, quinoline, acridine, pyrrole Alkane ring, dioxane ring, pyrimidine ring, morpholine ring, oxazine ring, oxazole ring, furan ring, thiophene ring, oxazole ring, oxadiazole ring, benzoxazole ring, thiazole ring, Nitrogen ring, And a thiazole ring, a triazole ring, an imidazole ring, a benzimidazole ring, a pyran ring, a dibenzofuran ring, a dibenzothiophene ring formed heterocyclyl thiophene.

Throughout the description of the present invention, the term "substituted or unsubstituted" may mean a group selected from halogen, amino, nitrile, nitro or C ₁ to C ₂₀ alkyl, C ₂ to C ₂₀ alkenyl, C ₁ A group consisting of ～ 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 heteroaryl group More than one group in the group is substituted. In addition, throughout the specification of the present invention, the same element symbols may have the same meaning unless they are specifically mentioned.

Throughout the specification of the present invention, the term "fluorene" may include a C _1-20 alkyl group substituted or unsubstituted C _5-30 aryl group by a hydrogen bonded to the carbon at position 9 Or a substituted or unsubstituted C _3-30 heteroaryl group.

A first embodiment of the present invention provides a compound represented by the following Chemical Formula 1.

Chemical formula 1

In the above Chemical Formula 1,
X is O, S or CRR ',
Ar ₁ is a substituted or unsubstituted C ₆ ~ C ₅₀ aryl group, or a substituted or unsubstituted C ₅ ~ C ₅₀ heteroaryl group,
Ar ₂ is a substituted or unsubstituted C ₁₂ ~ C ₅₀ aryl group,
R, R ', R ₁ to R ₆ are each independently hydrogen, halogen, nitro, nitrile, substituted or unsubstituted C ₁ to C ₃₀ alkyl, substituted or unsubstituted C ₂ to C ₃₀ olefin Group, substituted or unsubstituted C ₁ to C ₃₀ alkoxy group, substituted or unsubstituted C ₁ to C ₃₀ thioether group, substituted or unsubstituted C ₆ to C ₃₀ aryl group, or substituted or unsubstituted Substituted C ₅ to C ₃₀ heteroaryl groups, between adjacent R ₁ , R ₂ , R ₃ or R and R ′ can form a ring with each other or not, R ₄ and R ₆ Or R ₅ and R ₆ can form a ring with each other or not,
L ₁ is a directly bonded, substituted or unsubstituted C ₆ to C ₃₀ extended aryl group, or a substituted or unsubstituted C ₅ to C ₃₀ extended aryl group,
L ₂ is a substituted or unsubstituted C ₆ to C ₃₀ extended aryl group, or a substituted or unsubstituted C ₅ to C ₃₀ extended aryl group,
l is an integer of 0 or 1 to 4,
m and n are each independently an integer of 0 or 1 to 3. When l, m or n is 2 or more, R ₁ , R ₂ and R ₃ may be the same or different.

According to an example compound of the present invention, a tricyclic condensed ring group (dibenzofuran, dibenzothiophene, or fluorene) and a dibenzofuran are connected to the nitrogen of an arylamine through a linker, thereby forming It is suitable for the HOMO energy level of the light emitting auxiliary layer, so that a highly efficient organic light emitting device can be realized.

In addition, according to an example compound of the present invention, a tricyclic condensed ring group having excellent electron resistance is introduced into the arylamine side, maintaining high LUMO and T1, easily blocking electrons, and enabling exciton confinement in the light-emitting layer. Maximize. Thereby, an organic light emitting device with high efficiency and long life can be realized.

In addition, according to the compound according to an example of the present invention, when the second or fourth position of the dibenzofuran having a small bulkiness is used as a connection position on the arylamine side to form a thin film, the molecular arrangement can be changed. Excellent. By realizing low voltage and suppressing the roll-off phenomenon, a long-life organic light emitting device can be realized.

In addition, the number of attachment positions of the tricyclic condensed ring compound can be shown below.

In addition, according to an example compound of the present invention, one side of an arylamine is connected to dibenzofuran through a linking group, and an aryl group is provided on the other side, whereby a π-conjugate can be increased. As a result, hole mobility can be improved, and a low driving voltage can be realized when applied to an organic light emitting device.

In addition, the compound according to an example of the present invention includes a tricyclic condensed ring group expanded by dibenzofuran on the side of the arylamine to form a high Tg, which prevents recrystallization of the film, thereby ensuring Driving stability of organic light emitting device.

In one embodiment of the present invention, the above-mentioned compound may be represented by the following Chemical Formula 2.

Chemical formula 2

In the above Chemical Formula 2,
X, Ar ₁ , Ar ₂ , R, R ′, R ₁ to R ₆ , 1, m and n are as defined in the chemical formula 1,
R ₇ is hydrogen, halogen, nitro, nitrile, substituted or unsubstituted C ₁ to C ₃₀ alkyl, substituted or unsubstituted C ₂ to C ₃₀ alkenyl, substituted or unsubstituted C ₁ to C ₃₀ alkoxy, substituted or unsubstituted C ₁ to C ₃₀ thioether group, substituted or unsubstituted C ₆ to C ₃₀ aryl group, or substituted or unsubstituted C ₅ to C ₃₀ heteroaryl group ,
o is an integer of 1 to 4, and p is an integer of 0 or 1 to 4. When the above o or p is 2 or more, R ₇ can be the same or different, and when o is 2 or more, p can be the same or different.

The compound represented by the above Chemical Formula 2 is a case where L ₂ in the above Chemical Formula 1 contains a phenylene group, and one or more of dibenzofuran as a substituent of the arylamine and a nitrogen of the arylamine are bonded as a linking group Form of phenylene. In this case, while forming a HOMO suitable for the light-emitting auxiliary layer, the compound can maintain a high T1 due to the phenylene stretching, thereby more effectively blocking excitons.

In one embodiment of the present invention, the aforementioned compound may be represented by the following Chemical Formula 3.

Chemical formula 3

In the above Chemical Formula 3,
X, Ar ₁ , Ar ₂ , R, R ′, R ₁ to R ₆ , 1, m and n are as defined in the chemical formula 1,
R ₇ is hydrogen, halogen, nitro, nitrile, substituted or unsubstituted C ₁ to C ₃₀ alkyl, substituted or unsubstituted C ₂ to C ₃₀ alkenyl, substituted or unsubstituted C ₁ to C ₃₀ alkoxy, substituted or unsubstituted C ₁ to C ₃₀ thioether group, substituted or unsubstituted C ₆ to C ₃₀ aryl group, or substituted or unsubstituted C ₅ to C ₃₀ heteroaryl group ,
o is an integer from 1 to 4, p is an integer from 0 or 1 to 4,
When o or p is 2 or more, R ₇ can be the same or different, and when o is 2 or more, p can be the same or different.

In the case where the compound represented by the above Chemical Formula 3 is directly bonded in L ₁ in the above Chemical Formula 1, dibenzofuran and a tricyclic condensed ring group (dibenzofuran, dibenzothiophene, or fluorene series) are directly connected to form The deep HOMO energy level can realize a highly efficient organic light emitting device.

In one embodiment of the present invention, the compound may be represented by the following Chemical Formula 4 or Chemical Formula 5.

Chemical formula 4

Chemical formula 5

In the above Chemical Formula 4 and Chemical Formula 5,
Ar ₁ , Ar ₂ , R ₁ to R ₆ , l, m and n are as defined in Chemical Formula 1,
X is O or S,
R ₂ can be the same or different,
R ₇ is hydrogen, halogen, nitro, nitrile, substituted or unsubstituted C ₁ to C ₃₀ alkyl, substituted or unsubstituted C ₂ to C ₃₀ alkenyl, substituted or unsubstituted C ₁ to C ₃₀ alkoxy, substituted or unsubstituted C ₁ to C ₃₀ thioether group, substituted or unsubstituted C ₆ to C ₃₀ aryl group, or substituted or unsubstituted C ₅ to C ₃₀ heteroaryl group ,
o is an integer from 1 to 4, p is an integer from 0 or 1 to 4,
When o or p is 2 or more, R7 can be the same or different, and when o is 2 or more, p can be the same or different.

In this case, it is possible to maintain high LUMO while maintaining high hole mobility, which is effective for low-voltage driving and effectively blocks electrons flowing from the light-emitting layer into the hole-transporting layer.

In one embodiment of the present invention, the above compound may be represented by the following Chemical Formula 6.

Chemical formula 6

In the above Chemical Formula 6,
Ar ₁ , Ar ₂ , R, R ′, R ₁ to R ₆ , 1, m, and n are as defined in the chemical formula 1,
R ₇ is hydrogen, halogen, nitro, nitrile, substituted or unsubstituted C ₁ to C ₃₀ alkyl, substituted or unsubstituted C ₂ to C ₃₀ alkenyl, substituted or unsubstituted C ₁ to C ₃₀ alkoxy, substituted or unsubstituted C ₁ to C ₃₀ thioether group, substituted or unsubstituted C ₆ to C ₃₀ aryl group, or substituted or unsubstituted C ₅ to C ₃₀ heteroaryl group ,
o is an integer from 1 to 4, p is an integer from 0 or 1 to 4,
When o or p is 2 or more, R ₇ can be the same or different, and when o is 2 or more, p can be the same or different.

In this case, fast hole fluidity and high Tg can be achieved by 芴, which can be beneficial to improving low-voltage driving and driving stability.

In one embodiment of the present invention, the compound may be represented by the following Chemical Formula 7 or Chemical Formula 8.

Chemical formula 7

Chemical formula 8

In the above Chemical Formulas 7 and 8,
Ar ₁ , Ar ₂ , R ₁ to R ₆ , 1 and n are as defined in the above Chemical Formula 1,
X is O or S,
R ₂ can be the same or different,
R ₇ is hydrogen, halogen, nitro, nitrile, substituted or unsubstituted C ₁ to C ₃₀ alkyl, substituted or unsubstituted C ₂ to C ₃₀ alkenyl, substituted or unsubstituted C ₁ to C ₃₀ alkoxy, substituted or unsubstituted C ₁ to C ₃₀ thioether group, substituted or unsubstituted C ₆ to C ₃₀ aryl group, or substituted or unsubstituted C ₅ to C ₃₀ heteroaryl group ,
o is an integer from 1 to 4, p is an integer from 0 or 1 to 4,
When o or p is 2 or more, R ₇ can be the same or different, and when o is 2 or more, p can be the same or different.

In this case, it has high hole mobility and high LUMO and T1, which is easy to block electrons and excitons. By improving the roll-off phenomenon, the luminous efficiency and life can be effectively improved.

According to an example of the present invention, in the above Chemical Formulas 1 to 8, l, m, n, o, and p may all be 0. In addition, according to an example of the present invention, in the above Chemical Formulas 1 to 8, R ₁ to R ₇ may each independently be hydrogen, a C ₁ to C ₁₀ alkyl group, or a phenyl group. More specifically, R ₁ to R ₇ may be hydrogen or phenyl.

Furthermore, according to an example of the present invention, in the above Chemical Formulas 1 to 3 and Chemical Formula 6, R and R ′ may each independently be a C ₁ to C ₃ alkyl group.

In addition, according to an example of the present invention, in the above Chemical Formulas 1 to 5, Chemical Formula 7, and Chemical Formula 8, X may be O.

Furthermore, according to an example of the present invention, in the above Chemical Formulas 1 to 5, Chemical Formula 7, and Chemical Formula 8, X may be S.

According to an example of the present invention, in the above Chemical Formulas 1 to 8, Ar _{1 is} selected from the group consisting of phenyl, naphthyl, biphenyl, terphenyl, fluorenyl, dialkylfluorenyl, diarylfluorenyl, di In the group consisting of benzofuranyl, dibenzothienyl, and combinations thereof, the Ar _{2 is} selected from biphenyl, phenylnaphthyl, terphenyl, fluorenyl, dialkylfluorenyl, and diaryl. Fluorenyl, dibenzofuranyl, dibenzothienyl, and combinations thereof.

According to an example of the present invention, in the above Chemical Formula 1, L ₂ may be a substituted or unsubstituted C ₆ ~ C ₂₄ arylene group containing at least one 1,4-phenylene or 1,3-phenylene. .

According to an example of the present invention, in the above Chemical Formula 1, at least one of the Ar ₁ , Ar _2, and L ₂ may include a phenylene group having a meta bond.

According to an example of the present invention, in the above Chemical Formula 1, the Ar ₁ may be a biphenyl group having a meta bond or a terphenyl group having a meta bond, or the Ar ₂ may be a biphenyl group having a meta bond Or terphenyl with a meta bond.

In addition, according to an example of the present invention, in the above Chemical Formula 1, one or more of the following a) to c) may be satisfied:
a) Ar ₁ and Ar ₂ are biphenyl groups;
b) at least one of Ar ₁ and Ar ₂ is a C ₁₄ or more aryl group formed of only a six-membered ring; and
c) L ₂ is an arylene group having C ₁₀ or more.

According to an example of the present invention, in the above Chemical Formulas 1 to 8, the Ar _{1 is} selected from the group consisting of a phenyl group, a biphenyl group, a terphenyl group, a dimethylfluorenyl group, and a combination thereof, and the Ar ₂ And selected from the group consisting of biphenyl, terphenyl, dimethylfluorenyl, and combinations thereof.

According to an example of the present invention, the compound represented by the above Chemical Formula 1 may be one of the following compounds, and may not be limited thereto.

A second embodiment of the present invention provides an organic light-emitting device including the compound represented by the aforementioned Chemical Formula 1. The organic light emitting device may include one or more organic substance layers containing the compound of the present invention between the first electrode and the second electrode.

In an example of the present invention, the organic substance layer may be a hole injection layer, a hole transport layer, and a light emitting auxiliary layer, but it may not be limited by them. When the compound of the present invention forms an organic substance layer, it can be used alone or in combination with a conventional compound.

In an example of the present invention, the organic light emitting device may include an organic substance layer containing a hole transporting substance and an organic substance layer containing a compound represented by the above Chemical Formula 1, but it is not limited thereto.

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

For example, the organic light-emitting device can be prepared according to the structure described in FIG. 1. The organic light-emitting device can sequentially stack the anode 1000 (hole injection electrode) / hole injection layer 200 / hole transport layer 300 / light emitting layer 400 / electron transport layer 500 / electron injection layer 600 / cathode 2000 (electron injection electrode).

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

The hole injection electrode is used as an anode 1000 for injecting holes into an organic light emitting device. In order to be able to inject holes, a substance having a low work function is used, and can be formed of a transparent material 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 by a vacuum deposition method, a spin coating method, a casting method, a LB (Langmuir-Blodgett) method, or the like. When the hole injection layer is formed by the vacuum deposition method described above, the deposition conditions vary depending on the compound used as the material of the hole injection layer 200, the structure and thermal characteristics of the required hole injection layer, but usually It can be appropriately selected within a deposition temperature range of 50-500 ° C, a vacuum degree of 10 ^-8 to 10 ^-3 torr, a deposition speed of 0.01 to 100 Å / sec, and a layer thickness range of 10 Å to 5 μm.

Next, the hole transporting layer 300 can be formed by depositing a hole transporting layer substance on the hole injection layer 200 by a vacuum deposition method, a spin coating method, a casting method, an LB method, or the like. In the case where the hole transport layer is formed by the above-mentioned vacuum deposition method, the deposition conditions differ depending on the compound used, but generally, it is preferable to select within the same range of conditions as the formation of the hole injection layer. .

The hole transporting layer 300 may use the compound of the present invention. As described above, the compound of the present invention may be used alone or in combination with a conventional compound. In addition, the hole transporting layer 300 according to an example of the present invention may be one or more layers, and may include a hole transporting layer formed of only a conventional substance. In addition, according to an example of the present invention, a light emitting auxiliary layer may be formed on the hole transporting layer 300.

The light-emitting layer 400 can be formed by depositing a light-emitting layer substance on the hole transporting layer 300 or the light-emitting auxiliary layer by a method such as a vacuum deposition method, a spin coating method, a casting method, an LB method, or the like. In the case where the light-emitting layer is formed by the above-mentioned vacuum deposition method, the deposition conditions vary depending on the compound used, but generally, it is preferable to select within the same range of conditions as the formation of the hole injection layer. In addition, as the light emitting layer material, a conventional compound can be used as a host or a dopant.

In addition, in the case of using a phosphorescent dopant in the light emitting layer, in order to prevent the triplet excitons or holes from diffusing into the electron transport layer, a hole suppression material can be laminated by a vacuum deposition method or a spin coating method. (HBL). The hole-inhibiting substance that can be used at this time is not particularly limited, but any substance can be selected and used from conventional substances used as hole-inhibiting materials. For example, an oxadiazole derivative or a triazole derivative, a phenanthroline derivative, or a hole-inhibiting material described in Japanese Patent Application Laid-Open No. 11-329734 (A1) can be mentioned. Typically, Balq ( Bis (8-hydroxy-2-methylquinoline) -aluminum biphenate), phenanthrolines (such as BCP (Basso Coupoline) of Universal Display Corporation (UDC)).

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 vacuum deposition method, a spin coating method, a casting method, or the like. In addition, the deposition conditions of the above-mentioned electron transport layer vary depending on the compound used, but generally, it is preferable to select within the same range of conditions as the formation of the hole injection layer.

After that, an electron injection layer material may be deposited on the electron transport layer 500 to form an electron injection layer 600. At this time, the electron transport layer may be formed by conventional methods such as a vacuum deposition method, a spin coating method, and a casting method. Inject layer material.

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 of the present invention or the following substances, or may use the compound of the present invention and a known substance together. .

A cathode 2000 for injecting electrons is formed on the electron injection layer 600 by a method such as a vacuum deposition method or a sputtering method. As the cathode, various metals can be used. Specific examples include substances such as aluminum, gold, and silver.

The organic light-emitting device of the present invention can not only adopt 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, or a cathode structure, but also a structure of organic light-emitting devices of various structures. According to requirements, it is also possible to form 1 or 2 intermediate layers.

As described above, the thickness of each organic substance layer formed according to the present invention can be adjusted according to a desired degree, and is preferably 1 to 1000 nm, and more specifically 5 to 200 nm.

In addition, in the present invention, the organic substance layer containing the compound represented by the above Chemical Formula 1 can adjust the thickness of the organic substance layer to a molecular unit, and therefore has the advantages of uniform surface and outstanding morphological stability.

Any of the organic light-emitting compounds of this embodiment can be applied to the contents described in the first embodiment of the present invention, but it is not limited thereto.

Hereinafter, the embodiments of the present invention will be described in more detail. The scope of the present invention is not limited to the embodiments.

Examples

Synthesis of compound represented by Chemical Formula 1

The compound represented by Chemical Formula 1 can be synthesized by the following reaction, but is not limited thereto.

Synthesis of intermediate IM

In order to synthesize the target compound, the intermediate IM can be synthesized by the following reaction without limitation.

Synthesis of intermediate IM1

Intermediate IM1 was synthesized by the following method.

In a round-bottomed flask, 20.0 g of dibenzo [b, d] furan-4-ylboronic acid and 35.5 g of 4,6-dibromodiphenyl And [b, d] thiophene (4,6-dibromodibenzo [b, d] thiophene) was dissolved in 900 ml of 1,4-dioxane (1,4-dioxan), and 140 ml of K ₂ CO ₃ ( 2M) and 3.3 g of Pd (PPh ₃ ) ₄ , and then stirred under reflux. The reaction was confirmed by thin layer chromatography (TLC), and after putting in water, the reaction was completed. The organic layer was extracted with methyl cellulose (MC), and after filtering under reduced pressure, 25.1 g (yield 62%) of intermediate IM1-1 was obtained by recrystallization.

In a round bottom flask, 25.0 g of the above IM1-1 and 20 g of bis (pinacolato) diboron were dissolved in 450 ml of 1,4-dioxan (1,4-dioxan ), And 17.2 g of KOAc and 0.2 g of Pd (dppf) Cl _{2 were} added, followed by stirring under reflux. The reaction was confirmed by thin layer chromatography (TLC), and after putting in water, the reaction was completed. The organic layer was extracted with methyl cellulose (MC), and after filtering under reduced pressure, 20.8 g (yield 75%) of intermediate IM1-2 was obtained by recrystallization.

In a round bottom flask, 22.0 g of the above IM1-2 and 14.9 g of 1-bromo-4-iodobenzene were dissolved in 550 ml of 1,4-dioxane (1,4 -dioxan), and 63 ml of K ₂ CO ₃ (2M) and 1.5 g of Pd (PPh ₃ ) _{4 were} added, followed by stirring under reflux. The reaction was confirmed by thin layer chromatography (TLC), and after putting in water, the reaction was completed. The organic layer was extracted with methyl cellulose (MC), and after filtering under reduced pressure, 14.0 g (yield 60%) of intermediate IM1 was obtained by recrystallization.

Synthesis of intermediates IM2 to IM11

As shown in Table 1 below, the following IM2 to IM11 were synthesized in the same manner as the above IM1 by changing the starting materials.

Table 1

Examples 1 to 20: Synthesis of compounds

The above-mentioned intermediates IM1 to IM11 were used to synthesize the target compound 1 to compound 20.

Example 1: Synthesis of Compound 1

In a round bottom flask, 3.0 g of IM1 and 2.17 g of di ([1,1'-biphenyl] -4-yl) amine (di ([1,1'-biphenyl] -4-yl) amine) 0.9 g of t-BuONa, 0.2 g of Pd ₂ (dba) ₃ , and 0.3 ml of (t-Bu) ₃ P were dissolved in 80 ml of toluene, followed by stirring under reflux. The reaction was confirmed by thin layer chromatography (TLC), and after putting in water, the reaction was completed. The organic layer was extracted with methyl cellulose (MC), and filtered under reduced pressure, and then purified and recrystallized through a column to obtain 3.0 g (yield 67%) of Compound 1.

m / z: 729.27 (100.0%), 730.27 (58.9%), 731.27 (17.4%), 732.28 (3.2%)

Example 2: Synthesis of Compound 2

Use N-([1,1'-biphenyl] -4-yl) naphthalen-1-amine (N-([1,1'-biphenyl] -4-yl) naphthalen-1-amine) instead of di ( [1,1'-biphenyl] -4-yl) amine (di ([1,1'-biphenyl] -4-yl) amine) was synthesized in the same manner as Compound 1 (yield: 63%) ).

m / z: 703.25 (100.0%), 704.25 (56.6%), 705.26 (16.2%), 706.26 (3.1%)

Example 3: Synthesis of Compound 3

Use N-([1,1'-biphenyl] -4-yl) naphthalen-2-amine (N-([1,1'-biphenyl] -4-yl) naphthalen-2-amine) instead of di ( [1,1'-biphenyl] -4-yl) amine (di ([1,1'-biphenyl] -4-yl) amine) was synthesized in the same manner as Compound 1 (yield 65%) ).

m / z: 703.25 (100.0%), 704.25 (56.6%), 705.26 (16.2%), 706.26 (3.1%)

Example 4: Synthesis of compound 4

Use N-([1,1'-biphenyl] -4-yl) -9,9-dimethyl-9H-fluoren-2-amine (N-([1,1'-biphenyl] -4-yl ) -9,9-dimethyl-9H-fluoren-2-amine) instead of di ([1,1'-biphenyl] -4-yl) amine (di ([1,1'-biphenyl] -4-yl amine), and compound 4 was synthesized by the same method as compound 1 (yield: 66%).

m / z: 769.30 (100.0%), 770.30 (62.5%), 771.30 (19.3%), 772.31 (4.1%)

Example 5: Synthesis of Compound 5

Use N-([1,1'-biphenyl] -4-yl) -9,9-dimethyl-9H-fluoren-3-amine (N-([1,1'-biphenyl] -4-yl ) -9,9-dimethyl-9H-fluoren-3-amine) instead of di ([1,1'-biphenyl] -4-yl) amine (di ([1,1'-biphenyl] -4-yl amine), and compound 5 was synthesized by the same method as compound 1 (yield: 65%).

m / z: 769.30 (100.0%), 770.30 (62.5%), 771.30 (19.3%), 772.31 (4.1%)

Example 6: Synthesis of Compound 6

Use N-([1,1'-biphenyl] -4-yl) -9,9-dimethyl-9H-fluoren-4-amine (N-([1,1'-biphenyl] -4-yl ) -9,9-dimethyl-9H-fluoren-4-amine) instead of di ([1,1'-biphenyl] -4-yl) amine (di ([1,1'-biphenyl] -4-yl amine), and compound 6 was synthesized by the same method as compound 1 (yield: 62%).

m / z: 769.30 (100.0%), 770.30 (62.5%), 771.30 (19.3%), 772.31 (4.1%)

Example 7: Synthesis of compound 7

IM10 was used instead of IM1, and compound 7 was synthesized by the same method as compound 1 (yield: 67%).

m / z: 805.30 (100.0%), 806.30 (65.8%), 807.30 (21.4%), 808.31 (4.7%)

Example 8: Synthesis of compound 8

IM2 was used instead of IM1, and compound 8 was synthesized by the same method as compound 1 (yield: 69%).

m / z: 729.27 (100.0%), 730.27 (58.9%), 731.27 (17.4%), 732.28 (3.2%)

Example 9: Synthesis of Compound 9

IM3 was used instead of IM1, and compound 9 was synthesized by the same method as compound 1 (yield: 68%).

m / z: 729.27 (100.0%), 730.27 (58.9%), 731.27 (17.4%), 732.28 (3.2%)

Example 10: Synthesis of Compound 10

IM4 was used instead of IM1, and compound 10 was synthesized by the same method as compound 1 (yield 65%).

m / z: 729.27 (100.0%), 730.27 (58.9%), 731.27 (17.4%), 732.28 (3.2%)

Example 11: Synthesis of Compound 11

IM5 was used instead of IM1, and compound 11 was synthesized by the same method as compound 1 (yield: 62%).

m / z: 745.24 (100.0%), 746.25 (58.8%), 747.25 (17.7%), 747.24 (4.7%), 748.25 (3.5%), 748.24 (2.7%), 746.24 (1.2%)

Example 12: Synthesis of Compound 12

IM6 was used instead of IM1, and compound 12 was synthesized by the same method as compound 1 (65% yield).

m / z: 745.24 (100.0%), 746.25 (58.8%), 747.25 (17.7%), 747.24 (4.7%), 748.25 (3.5%), 748.24 (2.7%), 746.24 (1.2%)

Example 13: Synthesis of Compound 13

IM7 was used instead of IM1, and compound 13 was synthesized by the same method as compound 1 (yield: 62%).

m / z: 745.24 (100.0%), 746.25 (58.8%), 747.25 (17.7%), 747.24 (4.7%), 748.25 (3.5%), 748.24 (2.7%), 746.24 (1.2%)

Example 14: Synthesis of Compound 14

IM8 was used instead of IM1, and compound 14 was synthesized by the same method as compound 1 (yield 65%).

m / z: 745.24 (100.0%), 746.25 (58.8%), 747.25 (17.7%), 747.24 (4.7%), 748.25 (3.5%), 748.24 (2.7%), 746.24 (1.2%)

Example 15: Synthesis of Compound 15

IM9 was used instead of IM1, and compound 15 was synthesized by the same method as compound 1 (yield: 60%).

m / z: 755.32 (100.0%), 756.32 (62.1%), 757.33 (19.0%), 758.33 (3.9%)

Example 16: Synthesis of Compound 16

Using IM11 instead of IM1, compound 16 was synthesized by the same method as compound 1 (yield 65%).

m / z: 805.30 (100.0%), 806.30 (65.8%), 807.30 (21.4%), 808.31 (4.7%)

Example 17: Synthesis of Compound 17

Use N-phenyl- [1,1 ': 4', 1 ''-terphenyl] -4-amine (N-phenyl- [1,1 ': 4', 1 ''-terphenyl] -4-amine ) Instead of di ([1,1'-biphenyl] -4-yl) amine (di ([1,1'-biphenyl] -4-yl) amine), and compound 17 was synthesized by the same method as compound 1. (65% yield).

m / z: 729.27 (100.0%), 730.27 (58.9%), 731.27 (17.4%), 732.28 (3.2%)

Example 18: Synthesis of Compound 18

Use N-([1,1'-biphenyl] -4-yl)-[1,1 ': 3', 1 ''-terphenyl] -4-amine (N-([1,1'-biphenyl ] -4-yl)-[1,1 ': 3', 1 ''-terphenyl] -4-amine) instead of di ([1,1'-biphenyl] -4-yl) amine (di ([ 1,1'-biphenyl] -4-yl) amine), and compound 18 was synthesized by the same method as compound 1 (yield: 60%).

m / z: 805.30 (100.0%), 806.30 (65.8%), 807.30 (21.4%), 808.31 (4.7%)

Example 19: Synthesis of Compound 19

Using N- (4- (phenanthrene-9-yl) phenyl)-[1,1'-biphenyl] -4-amine (N- (4- (phenanthren-9-yl) phenyl)-[1,1 '-biphenyl] -4-amine) to replace di ([1,1'-biphenyl] -4-yl) amine (di ([1,1'-biphenyl] -4-yl) amine), and Compound 19 was synthesized in the same manner as Compound 1 (yield: 63%).

m / z: 829.30 (100.0%), 830.30 (68.0%), 831.30 (22.8%), 832.31 (5.2%)

Example 20: Synthesis of Compound 20

Use N-([1,1'-biphenyl] -4-yl) triphenylen-2-amine (N-([1,1'-biphenyl] -4-yl) triphenylen-2-amine) instead Di ([1,1'-biphenyl] -4-yl) amine (di ([1,1'-biphenyl] -4-yl) amine) was synthesized in the same manner as Compound 1 (yield) 64%).

m / z: 803.28 (100.0%), 804.29 (65.4%), 805.29 (21.4%), 806.29 (4.7%)

Examples 21 to 40: Preparation of organic light emitting devices

Example 21

A glass substrate coated with indium tin oxide (ITO) into a thin film at a thickness of 1500 Å was washed with distilled water ultrasonic waves. After the washing with distilled water is completed, ultrasonic cleaning is performed using a solvent such as isopropyl alcohol, acetone, methanol, etc., and then dried, and then transferred to a plasma cleaner, and then the substrate is cleaned with oxygen plasma for 5 minutes. On the top of the tin substrate, a thermal evaporator was used to form 600Å of HI01 as a hole injection layer, 50Å of HATCN was formed, and 250Å of HT01 was formed as a hole transporting layer as a luminous subsidy. After forming 100 Å of compound 1 into a layer, 3% of BH01: BD01 was doped as the light-emitting layer, and the film was formed at 250 Å. Next, after forming 300 层 of ET01: Liq (1: 1) as an electron transport layer, 10 ， of LiF and 1000 Å of aluminum (Al) were formed into a film, and the device was sealed in a glove box. Thus, an organic light emitting device was prepared.

Examples 22 to 40

In the same manner as in Example 21, Compound 2 to Compound 20 were used instead of Compound 1, thereby preparing an organic light-emitting device.

Comparative Example 1 to Comparative Example 11

In the same manner as in Example 21, the following Ref.1 to Ref.11 were used instead of Compound 1, thereby preparing an organic light-emitting device.

Performance evaluation of organic light emitting devices

The electrons and holes were injected using a voltage applied by the Kiethley 2400 source measurement unit, and the Konica Minolta spectroradiometer (CS-2000) was used to measure the brightness at the time of light emission. The performance of the organic light-emitting devices of Examples 21 to 40 and Comparative Examples 1 to 11 was measured by measuring the current density and brightness with respect to the applied voltage under atmospheric pressure conditions, and the results are shown in Table 2 below.

Table 2

As shown in Table 2 above, Examples 21 to 40 in which the compound of the present invention was used as a hole transporting layer were confirmed to have higher efficiency and longer life than Comparative Examples 1 to 11.

More specifically, the dibenzofurans of Examples 21 to 40 are linearly connected with dibenzothiophene, fluorene, or dibenzofuran as a tricyclic condensed ring compared to Comparative Examples 1 and 2, thereby having fast Hole mobility for low voltage characteristics.

Further, compared with Comparative Example 3, the dibenzofurans of Examples 21 to 40 are combined with dibenzothiophene, pyrene, or dibenzofuran as a tricyclic condensed ring, thereby forming deep HOMO, which can have excellent s efficiency.

Also, compared to Comparative Examples 4 and 5, Examples 21 to 40 include a linking group between the dibenzofuran and the nitrogen of the arylamine to form a deep HOMO while increasing the π-conjugation. Hole fluidity to achieve low voltage characteristics.

In addition, compared with Comparative Examples 6, 7, 8, and 9, Examples 21 to 40 are excellent in electronic resistance, and the dibenzofuran having a small bulkiness is bonded to the second or fourth position via a linking group. The nitrogen of the arylamine maintains HOMO and LUMO that can easily transport holes, and the intermolecular thin film is excellent in arrangement, and the roll-off phenomenon is suppressed by improving the fluidity in the thin film, thereby improving the life.

Furthermore, compared with Comparative Examples 10 and 11, the nitrogen of Examples 21 to 40 has dibenzofuran on one side and an aryl group having 12 or more carbon atoms on the other side, thereby increasing the π-conjugate By improving the fluidity of the hole, it can be seen that the low-voltage characteristic is achieved.

In addition, Examples 27 and 38 include a phenylene group having a meta bond and have a deeper HOMO, thereby further improving efficiency and life.

The above description of the present invention is for illustration, and those having ordinary knowledge in the technical field to which the present invention pertains can understand that it can be easily modified in other specific ways without changing the technical idea or necessary features of the present invention. Therefore, it should be understood that the various embodiments described above are illustrative in all aspects and not restrictive. For example, each structural element described as a single type may be implemented in a decentralized manner, and similarly, a plurality of structural elements described as dispersed may be implemented in a combined manner.

The scope of the present invention is indicated by the attached patent application patent scope, rather than the above-mentioned detailed description. The meaning and scope of the patent application patent scope and all changes or modifications derived from its equivalent concept should be construed as being included in this patent. Within the scope of the invention.

100‧‧‧ substrate

200‧‧‧ Hole injection layer

300‧‧‧ Electrode transport layer

400‧‧‧Light-emitting layer

500‧‧‧Electronic transport layer

600‧‧‧ electron injection layer

1000‧‧‧Anode

2000‧‧‧ cathode

FIG. 1 is a schematic diagram showing an organic light emitting device according to an example of the present invention.

Claims (20)

A compound represented by the following Chemical Formula 1, Chemical Formula 1: In Chemical Formula 1, X is O, S, or CRR ', Ar ₁ is a substituted or unsubstituted C ₆ to C ₅₀ aryl group, or a substituted or unsubstituted C ₅ to C ₅₀ heteroaryl group, and Ar ₂ is Substituted or unsubstituted C ₁₂ to C ₅₀ aryl groups, R, R ′, R ₁ to R ₆ are each independently hydrogen, halogen, nitro, nitrile, substituted or unsubstituted C ₁ to C ₃₀ alkane Group, substituted or unsubstituted C ₂ to C ₃₀ alkenyl group, substituted or unsubstituted C ₁ to C ₃₀ alkoxy group, substituted or unsubstituted C ₁ to C ₃₀ thioether group, substituted or unsubstituted C ₆ to C ₃₀ aryl, or substituted or unsubstituted C ₅ to C ₃₀ heteroaryl, between adjacent R ₁ , R ₂ , R ₃ , or R and R ′ To form a ring or not to form a ring with each other, R ₄ and R ₆ or R ₅ and R ₆ to form a ring or not to form a ring with each other, and L ₁ is a directly bonded, substituted or unsubstituted C ₆ to C ₃₀ arylene group Or substituted or unsubstituted C ₅ to C ₃₀ heteroaryl, L ₂ is substituted or unsubstituted C ₆ to C ₃₀ extended heteroaryl, or substituted or unsubstituted C ₅ to C ₃₀ extended heteroaryl Aryl, l is an integer of 0 or 1 to 4, m and n are each independently an integer of 0 or 1 to 3, l, m or n Is 2 or more, R _1, R ₂ and R ₃ are the same or different. The compound according to item 1 of the scope of patent application, wherein the compound is represented by the following Chemical Formula 2, In Chemical Formula 2, X, Ar ₁ , Ar ₂ , R, R ′, R ₁ to R ₆ , L ₁ , 1, m, and n are as defined in Chemical Formula 1, and R ₇ is hydrogen, halogen, nitro, or nitrile group. , Substituted or unsubstituted C ₁ to C ₃₀ alkyl, substituted or unsubstituted C ₂ to C ₃₀ alkenyl, substituted or unsubstituted C ₁ to C ₃₀ alkoxy, substituted or unsubstituted C ₁ to C ₃₀ thioether group, substituted or unsubstituted C ₆ to C ₃₀ aryl group, or substituted or unsubstituted C ₅ to C ₃₀ heteroaryl group, o is an integer from 1 to 4, p is 0 Or an integer of 1 to 4, when o or p is 2 or more, R ₇ is the same or different, and when o is 2 or more, p is the same or different. The compound according to item 1 of the scope of patent application, wherein the compound is represented by the following Chemical Formula 3, Chemical Formula 3 In Chemical Formula 3, X, Ar ₁ , Ar ₂ , R, R ′, R ₁ to R ₆ , 1, m, and n are as defined in Chemical Formula 1, and R ₇ is hydrogen, halogen, nitro, nitrile, substituted or Unsubstituted C ₁ to C ₃₀ alkyl, substituted or unsubstituted C ₂ to C ₃₀ alkenyl, substituted or unsubstituted C ₁ to C ₃₀ alkoxy, substituted or unsubstituted C ₁ to C ₃₀ thioether group, substituted or unsubstituted C ₆ to C ₃₀ aryl group, or substituted or unsubstituted C ₅ to C ₃₀ heteroaryl group, o is an integer of 1 to 4, p is 0 or 1 to Integer of 4, when o or p is 2 or more, R ₇ is the same or different, and when o is 2 or more, p is the same or different. The compound according to item 1 of the scope of patent application, wherein the compound is represented by the following Chemical Formula 4 or Chemical Formula 5, Chemical formula 5 In Chemical Formula 4 and Chemical Formula 5, Ar ₁ , Ar ₂ , R ₁ to R ₆ , 1, m, and n are as defined in Chemical Formula 1, X is O or S, R ₂ is the same or different, and R ₇ is hydrogen or halogen. , Nitro, nitrile, substituted or unsubstituted C ₁ to C ₃₀ alkyl, substituted or unsubstituted C ₂ to C ₃₀ alkenyl, substituted or unsubstituted C ₁ to C ₃₀ alkoxy, A substituted or unsubstituted C ₁ to C ₃₀ thioether group, a substituted or unsubstituted C ₆ to C ₃₀ aryl group, or a substituted or unsubstituted C ₅ to C ₃₀ heteroaryl group, o is 1 to 4 Is an integer of 0, p is an integer of 0 or 1 to 4, when o or p is 2 or more, R ₇ is the same or different, and when o is 2 or more, p is the same or different. The compound according to item 1 of the scope of patent application, wherein the compound is represented by the following Chemical Formula 6, In Chemical Formula 6, Ar ₁ , Ar ₂ , R, R ′, R ₁ to R ₆ , 1, m, and n are as defined in Chemical Formula 1, and R ₇ is hydrogen, halogen, nitro, nitrile, substituted or unsubstituted C ₁ to C ₃₀ alkyl, substituted or unsubstituted C ₂ to C ₃₀ alkenyl, substituted or unsubstituted C ₁ to C ₃₀ alkoxy, substituted or unsubstituted C ₁ to C ₃₀ Thioether group, substituted or unsubstituted C ₆ to C ₃₀ aryl group, or substituted or unsubstituted C ₅ to C ₃₀ heteroaryl group, o is an integer from 1 to 4, and p is 0 or 1 to 4 Integer, when o or p is 2 or more, R ₇ is the same or different, and when o is 2 or more, p is the same or different. The compound according to item 1 of the scope of patent application, wherein the compound is represented by the following Chemical Formula 7 or Chemical Formula 7, Chemical formula 8 In Chemical Formula 7 and Chemical Formula 8, Ar ₁ , Ar ₂ , R ₁ to R ₆ , 1 and n are as defined in Chemical Formula 1, X is O or S, R ₂ is the same or different, and R ₇ is hydrogen, halogen, nitrate Group, nitrile group, substituted or unsubstituted C ₁ to C ₃₀ alkyl group, substituted or unsubstituted C ₂ to C ₃₀ alkenyl group, substituted or unsubstituted C ₁ to C ₃₀ alkoxy group, substituted or Unsubstituted C ₁ to C ₃₀ thioether group, substituted or unsubstituted C ₆ to C ₃₀ aryl group, or substituted or unsubstituted C ₅ to C ₃₀ heteroaryl group, o is an integer from 1 to 4 , P is an integer of 0 or 1 to 4, when o or p is 2 or more, R ₇ is the same or different, and when o is 2 or more, p is the same or different. The compound according to item 1 of the scope of patent application, wherein R ₁ to R ₆ are each independently hydrogen or phenyl. The compound according to any one of claims 2 to 6 in the scope of patent application, wherein R ₁ to R ₇ are each independently hydrogen or phenyl. The compound according to any one of claims 1 to 3 or 5, in which R and R ′ are each independently a C ₁ to C ₃ alkyl group. The compound according to any one of claims 1 to 4 or 6 in the scope of patent application, wherein X is O. The compound according to any one of claims 1 to 4 or 6 in the scope of patent application, wherein X is S. The compound according to any one of claims 1 to 6, wherein Ar _{1 is} selected from the group consisting of phenyl, naphthyl, biphenyl, terphenyl, fluorenyl, dialkylfluorenyl, di In the group consisting of arylfluorenyl, dibenzofuranyl, dibenzothienyl, and combinations thereof, Ar _{2 is} selected from the group consisting of biphenyl, phenylnaphthyl, terphenyl, fluorenyl, and dialkylfluorene. Group, diarylfluorenyl, dibenzofuranyl, dibenzothienyl, and combinations thereof. The compound according to item 1 of the scope of patent application, wherein L ₂ is a substituted or unsubstituted C ₆ -C ₂₄ arylene group containing at least one 1,4-phenylene or 1,3-phenylene. The compound according to any one of claims 1 to 6, wherein Ar _{1 is} selected from the group consisting of phenyl, biphenyl, terphenyl, dimethylfluorenyl, and combinations thereof In the above, Ar _{2 is} selected from the group consisting of biphenyl, terphenyl, dimethylfluorenyl and combinations thereof. The compound as described in claim 1, wherein at least one of Ar ₁ , Ar ₂ and L ₂ contains a phenylene group having a meta bond. The compound according to item 15 of the scope of patent application, wherein Ar ₁ is a biphenyl group having a meta bond or a terphenyl group having a meta bond, or Ar ₂ is a biphenyl group having a meta bond or has a meta position Bonded terphenyl. The compound according to any one of claims 1 to 6 of the scope of patent application, which satisfies one or more of the following a) to c): a) Ar ₁ and Ar ₂ are biphenyl groups; b) Ar ₁ and At least one of Ar ₂ is an aryl group of C ₁₄ or more formed by only a six-membered ring; and c) L ₂ is an arylene group of C ₁₀ or more. The compound according to item 1 of the scope of patent application, wherein the compound is one of the following compounds, . An organic light-emitting device includes an organic layer containing a compound according to any one of the first to sixth items in the scope of patent application between a first electrode and a second electrode. The organic light-emitting device according to item 19 of the scope of the patent application, wherein the organic material layer is more than one of a hole injection layer, a hole transport layer, and a light-emitting auxiliary layer.