阅读说明：本技术 新颖化合物及包含其的有机发光器件 (Novel compound and organic light emitting device comprising the same ) 是由 咸昊完 安贤哲 姜京敏 金熙宙 金东骏 闵丙哲 韩政佑 林东焕 林大喆 权桐热 于 2019-08-07 设计创作，主要内容包括：本发明涉及新颖化合物及包含其的有机发光器件,根据本发明的一实例的新颖化合物适用于有机发光器件,可确保有机发光器件的高效率、长寿命、低的驱动电压及驱动稳定性。(The present invention relates to a novel compound and an organic light emitting device including the same, and the novel compound according to an embodiment of the present invention is suitable for an organic light emitting device, and can ensure high efficiency, long life, low driving voltage, and driving stability of the organic light emitting device.)

1. A compound represented by the following chemical formula 1,

chemical formula 1

In the chemical formula 1, the first and second organic solvents,

Ar₁to Ar₃Each independently is substituted or unsubstituted C₆～C₅₀Aryl of (2), or substituted or unsubstituted C₅～C₅₀Heteroaryl of Ar₁To Ar₃At least one of the following chemical formulas 1-1, Ar₁To Ar₃In the case where one of the following chemical formulae 1-1 is present, Ar remains₁To Ar₃At least one of which is substituted or unsubstituted C₁₀～C₅₀Or the following chemical formula 1-1,

chemical formula 1-1

X is O, S, CRR' or NAr, and Ar is substituted or unsubstituted C₆～C₅₀Aryl of (2), or substituted or unsubstituted C₅～C₅₀R and R' are each independently hydrogen, deuterium, halogen, nitro, nitrile, substituted or unsubstituted C₁～C₃₀Alkyl, substituted or unsubstituted C₂～C₃₀Alkenyl of (a), substituted or unsubstituted C₁～C₃₀Alkoxy group of (2), or substituted or unsubstituted C₁～C₃₀The thioether group of (a) is,

R₁to R₆Independently of each other, hydrogen, deuterium, halogen, nitro, nitrile, or a salt thereofSubstituted or unsubstituted C₁～C₃₀Alkyl, substituted or unsubstituted C₂～C₃₀Alkenyl of (a), substituted or unsubstituted C₁～C₃₀Alkoxy, substituted or unsubstituted C₁～C₃₀Or a substituted or unsubstituted C₆～C₃₀Aryl of (A), adjacent multiple R₃R is₄R is₅R is₆Can form a ring or not form a ring therebetween,

L₁and L₂Each independently is a direct bond, substituted or unsubstituted C₆～C₃₀Or substituted or unsubstituted C₅～C₃₀The heteroarylene group of (a) is,

l, m and o are each independently 0 or an integer of 1 to 3, and n and p are each independently 0 or an integer of 1 to 4.

2. The compound of claim 1, wherein L is₂Relative to the NAr₁Ar₂Bonded in the meta position to the phenylene group.

3. The compound according to claim 1, wherein the compound is represented by the following chemical formula 2 or the following chemical formula 3,

chemical formula 2

Chemical formula 3

In the chemical formula 2 or chemical formula 3,

R₇and R₈Each independently hydrogen, deuterium, halogen, nitro, nitrile, substituted or unsubstituted C₁～C₃₀Alkyl, substituted or unsubstituted C₂～C₃₀Alkenyl, substituted orUnsubstituted C₁～C₃₀Alkoxy, substituted or unsubstituted C₁～C₃₀Or a substituted or unsubstituted C₆～C₃₀The aryl group of (a) is,

q and r are each independently 0 or an integer of 1 to 4.

4. The compound of claim 1, wherein the compound is represented by one of the following chemical formula 4 or chemical formula 7,

chemical formula 4

Chemical formula 5

Chemical formula 6

Chemical formula 7

5. The compound according to claim 1, wherein the compound is represented by one of the following chemical formulas 8 to 10,

chemical formula 8

Chemical formula 9

Chemical formula 10

In the chemical formulas 8 to 10,

R₇and R₈Each independently hydrogen, deuterium, halogen, nitro, nitrile, substituted or unsubstituted C₁～C₃₀Alkyl, substituted or unsubstituted C₂～C₃₀Alkenyl of (a), substituted or unsubstituted C₁～C₃₀Alkoxy, substituted or unsubstituted C₁～C₃₀Or a substituted or unsubstituted C₆～C₃₀Aryl group of (1).

6. The compound according to claim 1, wherein the compound is represented by one of the following chemical formulas 11 to 13,

chemical formula 11

Chemical formula 12

Chemical formula 13

In the chemical formula 13, the first and second organic solvents,

R₂is substituted or unsubstituted C₆～C₃₀Aryl group of (1).

7. The compound of claim 1, wherein the 2 nitrogens of the diamine are each independently bound at the 2 nd or 3 rd position of a 3-ring condensed ring containing X, or at the 2 nd or 3 rd position of a 3-ring condensed ring dibenzothiophene containing S.

8. A compound according to any one of claims 1 to 6, wherein R is₁To R₈Each independently selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, and combinations thereof.

9. A compound according to any one of claims 1 to 6, wherein X is O.

10. A compound according to any one of claims 1 to 6, wherein X is S.

11. A compound according to any one of claims 1 to 6, wherein Ar is Ar₁To Ar₃At least one of which is selected from the group consisting of naphthyl, biphenyl, terphenyl, quaterphenyl, phenanthryl, triphenylene, and combinations thereof.

12. The compound of claim 1, wherein the compound is one of the following compounds,

13. an organic light-emitting device characterized by comprising an organic layer containing the compound according to any one of claims 1 to 12 between a first electrode and a second electrode.

14. The organic light-emitting device according to claim 13, wherein the organic layer is one or more of a hole injection layer, a hole transport layer, and a light-emission auxiliary layer.

15. The organic light-emitting device of claim 14, wherein the organic layer is a light-emitting auxiliary layer between the hole-transporting layer and the light-emitting layer.

Technical Field

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

Background

In the organic light emitting diode, materials used as the organic layer may be broadly classified into a light emitting material, a hole injecting material, a hole transporting material, an electron injecting material, and the like according to functions. The light-emitting materials may be classified into high-molecular and low-molecular materials according to molecular weight, fluorescent materials in a singlet excited state derived from electrons and phosphorescent materials in a triplet excited state derived from electrons according to a light-emitting mechanism, and blue, green and red light-emitting materials and yellow and orange light-emitting materials required for embodying a better natural color may be classified according to light emission colors. Also, in order to increase color purity and increase luminous efficiency by energy transfer, a host/dopant species may be used as a light emitting substance. The principle is that when a small amount of a dopant having a smaller energy band gap and excellent light emission efficiency than a host mainly constituting a light emitting layer is mixed in the light emitting layer, excitons generated in the host are transported to the dopant, and light with high efficiency is emitted. At this time, since the wavelength of the host is shifted to the wavelength band of the dopant, light having a desired wavelength can be obtained according to the type of the dopant and the host used.

Many compounds have been known as materials used in such organic light emitting devices, but in the case of organic light emitting devices using the materials known so far, development of new materials is continuously required due to high driving voltage, low efficiency and short lifetime. Accordingly, efforts are continuously made to develop an organic light emitting device having low voltage driving, high luminance, and long life using a substance having excellent characteristics.

Disclosure of Invention

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 above-described problems, and other problems not described may be clearly understood by those skilled in the art from 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-described chemical formula 1,

Ar₁to Ar₃Each independently is substituted or unsubstituted C₆～C₅₀Aryl of (2), or substituted or unsubstituted C₅～C₅₀Heteroaryl of Ar₁To Ar₃At least one of the following chemical formulas 1-1, Ar₁To Ar₃In the case where one of the following chemical formulae 1-1 is present, Ar remains₁To Ar₃At least one of which is substituted or unsubstituted C₁₀～C₅₀Or the following chemical formula 1-1,

chemical formula 1-1

X is O, S, CRR' or NAr, and Ar is substituted or unsubstituted C₆～C₅₀Aryl of (2), or substituted or unsubstituted C₅～C₅₀Heteroaryl of (a), the aboveR and R' are each independently hydrogen, deuterium, halogen, nitro, nitrile, substituted or unsubstituted C₁～C₃₀Alkyl, substituted or unsubstituted C₂～C₃₀Alkenyl of (a), substituted or unsubstituted C₁～C₃₀Alkoxy group of (2), or substituted or unsubstituted C₁～C₃₀The thioether group of (a) is,

R₁to R₆Each independently hydrogen, deuterium, halogen, nitro, nitrile, substituted or unsubstituted C₁～C₃₀Alkyl, substituted or unsubstituted C₂～C₃₀Alkenyl of (a), substituted or unsubstituted C₁～C₃₀Alkoxy, substituted or unsubstituted C₁～C₃₀Or a substituted or unsubstituted C₆～C₃₀Aryl of (A), adjacent multiple R₃R is₄R is₅R is₆Can form a ring or not form a ring therebetween,

L₁and L₂Each independently is a direct bond, substituted or unsubstituted C₆～C₃₀Or substituted or unsubstituted C₅～C₃₀The heteroarylene group of (a) is,

l, m and o are each independently 0 or an integer of 1 to 3, and n and p are each independently 0 or an integer of 1 to 4.

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

According to the diamine compound of one embodiment of the present invention, the diamine includes dibenzothiophene and one or more 3-ring condensed rings as a substituent of the diamine, and has a phenylene linker in which 2 nitrogens of the diamine are bonded to an ortho-position or a meta-position, thereby forming a deep Highest Occupied Molecular Orbital (HOMO) level and a high Lowest Unoccupied Molecular Orbital (LUMO) level at which electrons are easily blocked, maintaining a high T1, and having an excellent electron and exciton blocking effect, thereby realizing a low voltage and high efficiency organic light emitting device.

Further, the diamine compound according to an embodiment of the present invention has a 3-ring condensed ring (dibenzofuran, dibenzothiophene, carbazole, or fluorene) having excellent electron resistance, thereby improving durability and increasing the lifetime of the organic light emitting device.

Also, the diamine compound according to an embodiment of the present invention has an aryl group or a heteroaryl group having 10 or more carbon atoms as a substituent, thereby increasing pi-conjugation, facilitating molecular alignment, improving hole mobility (holemobilty), and realizing a long-life organic light emitting device by suppressing a roll-off phenomenon.

Further, according to the diamine compound of the embodiment of the present invention, the dibenzothiophene and the 3-ring are condensed to form a high Tg, and recrystallization of the thin film is prevented, thereby ensuring driving stability of the organic light emitting device.

Drawings

Fig. 1 shows a schematic view of an organic light emitting device according to an embodiment of the present invention.

Description of reference numerals

100: substrate

200: hole injection layer

300: hole transport layer

400: luminescent layer

500: electron transport layer

600: electron injection layer

1000: anode

2000: cathode electrode

Detailed Description

Examples and embodiments of the present invention are described in detail below with reference to the accompanying drawings so that those skilled in the art can easily implement the invention.

However, the present invention can be realized in various forms and is not limited to the examples and embodiments described herein. In the drawings, for the purpose of clearly explaining the present invention, portions not related to the explanation are omitted, and like reference numerals are given to like portions throughout the specification.

Throughout the present specification, when an element is "on" another element, it includes not only the case where the element is in contact with the other element, but also the case where the other element is present between the two elements.

Throughout the present specification, when a portion "includes" a structural element, it is meant that other structural elements may be included, but not excluded, unless otherwise stated. The terms "about," "substantially," and the like, as used throughout the specification are used in the sense of their numbers or close to their numbers to indicate inherent preparation and material tolerances, so as to prevent an assiduous intruder from inadvertently making use of the disclosure in which exact or absolute numbers are mentioned to assist in understanding the invention. The term "step(s)" or "step(s)" used throughout the present specification does not mean "step(s) used for.

Throughout the present specification, the term "combination thereof" contained in an expression of Markush (Markush) means a mixture or combination of one or more kinds selected from the group consisting of a plurality of structural elements described in an expression of Markush, and means including one or more kinds selected from the group consisting of the plurality of structural elements.

Throughout the present specification, the expression "A and/or B" means "A or B, or A and B".

Throughout the present specification, the term "aryl" is meant to encompass C_5-30The aromatic hydrocarbon ring group of (2), for example, phenyl, benzyl, naphthyl, biphenyl, terphenyl, fluorene, phenanthryl, triphenylalkenyl, phenylalkenyl,

Fluoranthenyl, benzofluorenyl, benzotrichenyl, benzotriphenylenyl, benzo

An aromatic ring such as a phenyl group, an anthracenyl group, a stilbene group, or a pyrenyl group, and a "heteroaryl group" is a group containing at least one hetero element C_3-30The aromatic ring of (A) is meant to comprise a ring formed by, for example, pyrrolinyl, pyrazinyl, pyridyl, indolyl, substituted pyridyl,Isoindolyl, furyl, benzofuryl, isobenzofuryl, dibenzofuryl, benzothienyl, dibenzothiophenyl, quinolyl, isoquinolyl, quinoxalinyl, carbazolyl, phenanthryl cry yl, acridinyl, phenanthrolinyl, thienyl, and heterocyclic groups formed from a pyridine ring, a pyrazine ring, a pyrimidine ring, a pyridazine ring, a triazine ring, an indole ring, a quinoline ring, an acridine ring, a pyrrolidine ring, a dioxane ring, a piperidine ring, a morpholine ring, a piperazine ring, a carbazole ring, a furan ring, a thiophene ring, an oxazole ring, an oxadiazole ring, a benzoxazole ring, a thiazole ring, a thiadiazole ring, a benzothiazole ring, a triazole ring, an imidazole ring, a benzimidazole ring, a pyran ring, a dibenzofuran ring, or a dibenzothiophene ring.

Throughout the present specification, the term "substituted or unsubstituted" may be meant to be selected from the group consisting of deuterium, halogen, amino, nitrile, nitro or C₁～C₂₀Alkyl of (C)₂～C₂₀Alkenyl of, C₁～C₂₀Alkoxy group of (C)₃～C₂₀Cycloalkyl of, C₃～C₂₀Heterocycloalkyl of (A), C₆～C₃₀Aryl and C₃～C₃₀Or substituted or unsubstituted.

In addition, throughout the present specification, the same reference numerals may have the same meaning unless otherwise specified.

Throughout the description of the present invention, the term "fluorene" may comprise a hydrogen bonded to the carbon at position 9 and substituted or unsubstituted C_1-20Alkyl, substituted or unsubstituted C_5-30Aryl of (2), or substituted or unsubstituted C_3-30And (3) heteroaryl substituted.

A first embodiment of the present invention provides a compound represented by the following chemical formula 1.

Chemical formula 1

In the above-described chemical formula 1,

Ar₁to Ar₃Each independently is substituted or unsubstituted C₆～C₅₀Aryl of (2), or substituted or unsubstituted C₅～C₅₀Heteroaryl of Ar₁To Ar₃At least one of the following chemical formulas 1-1, Ar₁To Ar₃In the case where one of the following chemical formulae 1-1 is present, Ar remains₁To Ar₃At least one of which is substituted or unsubstituted C₁₀～C₅₀Or the following chemical formula 1-1,

chemical formula 1-1

X is O, S, CRR' or NAr, and Ar is substituted or unsubstituted C₆～C₅₀Aryl of (2), or substituted or unsubstituted C₅～C₅₀R and R' are each independently hydrogen, deuterium, halogen, nitro, nitrile, substituted or unsubstituted C₁～C₃₀Alkyl, substituted or unsubstituted C₂～C₃₀Alkenyl of (a), substituted or unsubstituted C₁～C₃₀Alkoxy group of (2), or substituted or unsubstituted C₁～C₃₀The thioether group of (a) is,

R₁to R₆Each independently hydrogen, deuterium, halogen, nitro, nitrile, substituted or unsubstituted C₁～C₃₀Alkyl, substituted or unsubstituted C₂～C₃₀Alkenyl of (a), substituted or unsubstituted C₁～C₃₀Alkoxy, substituted or unsubstituted C₁～C₃₀Or a substituted or unsubstituted C₆～C₃₀Aryl of (A), adjacent multiple R₃R is₄R is₅R is₆Can form a ring or not form a ring therebetween,

L₁and L₂Each independently is a direct bond, substituted or unsubstituted C₆～C₃₀Or substituted or unsubstituted C₅～C₃₀The heteroarylene group of (a) is,

l, m and o are each independently 0 or an integer of 1 to 3, and n and p are each independently 0 or an integer of 1 to 4.

In an embodiment of the present invention, when Ar is as described above₁To Ar₃When one of the compounds is represented by the above chemical formula 1-1, Ar remains₁To Ar₃At least one of which may be substituted or unsubstituted C₁₀～C₅₀Aryl group of (1). Although not limited thereto, C₁₀～C₅₀The aryl group of (a) may be selected from the group consisting of naphthyl, biphenyl, terphenyl, quaterphenyl, phenanthryl, triphenylene, and combinations thereof.

And when Ar is above₁To Ar₃When 2 or more of them are the above chemical formula 1-1, Ar remains₁、Ar₂Or Ar₃C which may be substituted or unsubstituted₆～C₅₀Aryl of (2), or substituted or unsubstituted C₅～C₅₀The heteroaryl group of (a).

According to the diamine compound of one embodiment of the present invention, the diamine includes dibenzothiophene and one or more 3-ring condensed rings as a substituent of the diamine, and has a phenylene linker in which 2 nitrogens of the diamine are bonded to an ortho-position or a meta-position, thereby forming a deep Highest Occupied Molecular Orbital (HOMO) level and a high Lowest Unoccupied Molecular Orbital (LUMO) level at which electrons are easily blocked, maintaining a high T1, and having an excellent electron and exciton blocking effect, thereby realizing a low voltage and high efficiency organic light emitting device.

Further, the diamine compound according to an embodiment of the present invention has a 3-ring condensed ring (dibenzofuran, dibenzothiophene, carbazole, or fluorene) having excellent electron resistance, thereby improving durability and increasing the lifetime of the organic light emitting device.

Also, the diamine compound according to an embodiment of the present invention has an aryl group or a heteroaryl group having 10 or more carbon atoms as a substituent, thereby increasing pi-conjugation, facilitating molecular alignment, improving hole mobility (holemobilty), and realizing a long-life organic light emitting device by suppressing a roll-off phenomenon.

Further, according to the diamine compound of the embodiment of the present invention, the dibenzothiophene and the 3-ring are condensed to form a high Tg, and recrystallization of the thin film is prevented, thereby ensuring driving stability of the organic light emitting device.

In an embodiment of the present invention, L is₂Relative to the NAr₁Ar₂And may be bonded in the meta position of the phenylene group.

In one example of the present invention, the above compound may be represented by the following chemical formula 2 or the following chemical formula 3.

Chemical formula 2

Chemical formula 3

In the above chemical formula 2 or chemical formula 3,

R₇and R₈Each independently hydrogen, deuterium, halogen, nitro, nitrile, substituted or unsubstituted C₁～C₃₀Alkyl, substituted or unsubstituted C₂～C₃₀Alkenyl of (a), substituted or unsubstituted C₁～C₃₀Alkoxy, substituted or unsubstituted C₁～C₃₀Or a substituted or unsubstituted C₆～C₃₀The aryl group of (a) is,

q and r are each independently 0 or an integer of 1 to 4.

The compound represented by the above chemical formula 2 is Ar in the above chemical formula 1₁Is a chemical formula 1-1 and L₁And L₂When the compound is a substituted or unsubstituted phenylene group, the compound represented by the above chemical formula 3 is Ar in the above chemical formula 1₃Is a chemical formula 1-1 and L₁And L₂The case is specified by a substituted or unsubstituted phenylene group. In this case, high T1 can be formed, and thus excitons can be effectively blocked.

In one example of the present invention, the above compound may be represented by one of the following chemical formulas 4 to 7.

Chemical formula 4

Chemical formula 5

Chemical formula 6

Chemical formula 7

The compound represented by the above chemical formula 4 is Ar in the above chemical formula 1₁Is a chemical formula 1-1 and L₁And L₂In the case of direct bonding, the compound represented by the above chemical formula 5 is Ar in the above chemical formula 1₃Is a chemical formula 1-1 and L₁And L₂In the case of direct bonding, the compound represented by the above chemical formula 6 is Ar in the above chemical formula 1₁And Ar₂Is a chemical formula 1-1 and L₁And L₂In the case of direct bonding, the compound represented by the above chemical formula 7 is Ar in the above chemical formula 1₁To Ar₃Is a chemical formula 1-1 and L₁And L₂In the case of direct bonding. In this case, there is a fast hole mobility, and thus the driving voltage can be effectively improved.

In one example of the present invention, the above compound may be represented by one of the following chemical formulas 8 to 10.

Chemical formula 8

Chemical formula 9

Chemical formula 10

In the above chemical formulas 8 to 10,

R₇and R₈Each independently hydrogen, deuterium, halogen, nitro, nitrile, substituted or unsubstituted C₁～C₃₀Alkyl, substituted or unsubstituted C₂～C₃₀Alkenyl of (a), substituted or unsubstituted C₁～C₃₀Alkoxy, substituted or unsubstituted C₁～C₃₀Or a substituted or unsubstituted C₆～C₃₀Aryl group of (1).

The compound represented by the above chemical formula 8 is Ar in the above chemical formula 1₁Is of the formula 1-1, L₁Is a substituted or unsubstituted phenylene radical and L₂In the case of direct bonding, the compound represented by the above chemical formula 9 is Ar in the above chemical formula 1₁Is of the formula 1-1, L₁Is a direct bond and L₂In the case of a substituted or unsubstituted phenylene group, the compound represented by the above chemical formula 10 is Ar in the above chemical formula 1₁Is a chemical formula 1-1 and L₁And L₂In the case of substituted or unsubstituted phenylene radicals. In this case, a deep HOMO is present, and thus efficiency can be effectively improved.

In one example of the present invention, the above compound may be represented by one of the following chemical formulas 11 to 13.

Chemical formula 11

Chemical formula 12

Chemical formula 13

In the chemical formula 13 as described above,

R₂is substituted or unsubstituted C₆～C₃₀Aryl group of (1).

The compound represented by the above chemical formula 11 is Ar in the above chemical formula 1₁Is of the formula 1-1, L₁And L₂For direct bonding, R₁And R₂In the case where hydrogen is present and 2 nitrogens are bonded to the meta position (meta) of the phenylene group, the compound represented by the above chemical formula 12 is Ar in the above chemical formula 1₁Is of the formula 1-1, L₁And L₂For direct bonding, R₁And R₂In the case where hydrogen is present and 2 nitrogens are bonded to ortho positions (ortho) of the phenylene group, the compound represented by the above chemical formula 13 is Ar in the above chemical formula 1₁Is of the formula 1-1, L₁And L₂For direct bonding, R₁Is hydrogen, R₂Is a substituted or unsubstituted aryl group and 2 nitrogens are bonded in meta position (meta) of the phenylene group. In this case, the linker is minimized to form a high LUMO and T1, thereby effectively blocking the movement of unnecessary electrons.

According to an example of the present invention, in the above chemical formulas 1 to 13, 2 nitrogens of the diamine are each independently bound at the 2 nd or 3 rd position of the 3-ring condensed ring containing X, or may be bound at the 2 nd or 3 rd position of the 3-ring condensed ring containing S (dibenzothiophene).

The number of the connecting position of the 3-ring condensed ring including X or S is as follows.

According to an example of the present invention, 1 nitrogen of 2 nitrogens of the diamine may be bound at the 2 nd or 3 rd position of the 3-ring condensed ring containing X, and the other 1 nitrogen may be bound at the 2 nd or 3 rd position of the 3-ring condensed ring containing S (dibenzothiophene).

According to an embodiment of the present invention, in the above chemical formula 1-1, X may be O. In this case, the bulky characteristic is minimized and a lower driving voltage can be provided.

Also, according to an embodiment of the present invention, in the above chemical formula 1-1, X may be S. In this case, the electron donor function is prominent, and thus the efficiency and lifetime can be effectively improved.

According to an embodiment of the present invention, R is₁To R₈Each may be independently selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, and combinations thereof, and specifically may be hydrogen, phenyl, or biphenyl.

And, according to an embodiment of the present invention, Ar is as described above₁To Ar₃At least one of which may be selected from the group consisting of naphthyl, biphenyl, terphenyl, quaterphenyl, phenanthryl, triphenylene, and combinations thereof. In particular, it may be naphthyl, biphenyl or terphenyl.

According to an embodiment of the present invention, the compound represented by the above chemical formula 1 may be one of the following compounds, but may not be limited thereto.

A second embodiment of the present invention provides an organic light emitting device including the compound represented by the above chemical formula 1. The organic light emitting device described above may include 1 or more organic layers containing the compound of the present invention between the first electrode and the second electrode.

In an embodiment of the present invention, the organic layer may be a hole injection layer, a hole transport layer, and a light emission auxiliary layer, but may not be limited thereto. When the compound of the present invention is used to form an organic layer, it may be used alone or in combination with a known compound. In the present invention, the light-emission auxiliary layer is a layer formed between the hole transport layer and the light-emitting layer, and may be referred to as a 2 nd hole transport layer, a 3 rd hole transport layer, or the like depending on the number of hole transport layers.

In an embodiment of the present invention, the light-emitting auxiliary layer may comprise the compound of the present invention.

The organic light emitting device may include 1 or more organic layers such as a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), an emission layer (EML), an Electron Transport Layer (ETL), and an Electron Injection Layer (EIL) between a first electrode (anode) and a second electrode (cathode).

For example, the organic light emitting device may be prepared according to the structure described in fig. 1. The organic light emitting device may be stacked with an anode (hole injection electrode 1000)/a hole injection layer 200/a hole transport layer 300/a light emitting layer 400/an electron transport layer 500/an electron injection layer 600/a cathode (electron injection electrode 2000) in this order from bottom to top.

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

The hole injection electrode 1000 serves as an anode for injecting holes of the organic light emitting device. In order to inject holes, a material having a low work function may be used, and the material may be formed of a transparent material such as Indium Tin Oxide (ITO), Indium Zinc Oxide (IZO), or graphene (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, an LB (Langmuir-Blodgett) method, or the like. In the case of forming the hole injection layer by the above-described vacuum deposition method, the deposition conditions thereof vary depending on the compound used as the material of the hole injection layer 200, the structure and thermal characteristics of the hole injection layer, and the like, but may be generally at a deposition temperature of 50 to 500 ℃, 10 ℃ or the like^-8To 10^-3Vacuum degree of torr, 0.01 to

A deposition rate of/sec,The layer thickness range to 5 μm is suitably selected.

Next, a hole transport layer material is deposited on the hole injection layer 200 by a method such as a vacuum deposition method, a spin coating method, a casting method, or an LB method, thereby forming the hole transport layer 300. In the case of forming the hole transport layer by the above-described vacuum deposition method, the deposition conditions thereof vary depending on the compound used, but in general, it is preferable to select the conditions within the range substantially the same as the conditions for forming the hole injection layer.

The compound of the present invention can be used for the hole transport layer 300, and as described above, the compound of the present invention can be used alone or together with a known compound. The hole transport layer 300 according to an embodiment of the present invention may be 1 or more layers, and may include a hole transport layer formed only of a known material. Also, according to an embodiment of the present invention, a light-emission auxiliary layer may be formed on the hole transport layer 300.

The light-emitting layer 400 can be formed by depositing a light-emitting material on the hole transport layer 300 or the light-emitting auxiliary layer by a vacuum deposition method, a spin coating method, a casting method, an LB method, or the like. In the case of forming the light-emitting layer by the above-described vacuum deposition method, the deposition conditions thereof differ depending on the compound used, but in general, it is preferable to select the conditions within the range substantially the same as the conditions for forming the hole injection layer. In addition, the light-emitting layer material may use a known compound as a host or a dopant.

In addition, when the light-emitting layer is used together with a phosphorescent dopant, a hole-inhibiting material (HBL) may be further laminated by a vacuum deposition method or a spin coating method in order to prevent diffusion of triplet excitons or holes into the electron-transporting layer. The hole-inhibiting substance that can be used in this case is not particularly limited, but any substance can be selected from known substances used as hole-inhibiting materials and used. For example, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, or the hole-inhibiting materials described in jp 11-329734 a1 a may be mentioned, and Balq (bis (8-hydroxy-2-methylquinoline) -aluminum biphenoxide), and phenanthroline (phe nanthrolines) compounds (e.g., bcp (basocopoline) available from Universal Display (UDC)) may be used as representative examples.

The electron transport layer 500 is formed on the light emitting layer 400 formed as described above, and in this case, the electron transport layer may be formed by a method such as a vacuum deposition method, a spin coating method, or a casting method. The deposition conditions of the electron transport layer vary depending on the compound used, but in general, it is preferable to select the conditions within the range substantially the same as the conditions for forming the hole injection layer.

Thereafter, an electron injection layer material may be deposited on the electron transport layer 500 to form the electron injection layer 600, and at this time, the electron transport layer may be formed by a vacuum deposition method, a spin coating method, a casting method, or the like using a conventional electron injection layer material.

The compound of the present invention or the following substances may be used for 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, or the compound of the present invention and known substances may be used together.

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

The organic light-emitting device of the invention can adopt not only an anode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer and an organic light-emitting device with a cathode structure, but also structures of organic light-emitting devices with various structures, and can also form 1 layer or 2 layers of intermediate layers according to requirements.

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

In the present invention, the organic layer including the compound represented by chemical formula 1 has an advantage in that the surface is uniform and the morphological stability is excellent because the thickness of the organic layer can be adjusted to a molecular unit.

The organic light-emitting compound of the present embodiment can be applied to the content described in the first embodiment of the present invention, but may not be limited thereto.

Hereinafter, the present invention will be described more specifically with reference to examples, but the scope of the present invention is not limited to these examples.