KR102133665B1 - Multicyclic compound and organic light emitting device comprising the same - Google Patents

Abstract

The present specification provides a compound represented by Chemical Formula 1 or Chemical Formula 2 and an organic light emitting device including the same.

Description

Polycyclic compound and an organic light emitting device comprising the same{MULTICYCLIC COMPOUND AND ORGANIC LIGHT EMITTING DEVICE COMPRISING THE SAME}

The present invention claims the benefit of the filing date of Korean Patent Application No. 10-2018-0007646 filed with the Korean Intellectual Property Office on January 22, 2018, the entire contents of which are incorporated herein.

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

In the present specification, the organic light emitting device is a light emitting device using an organic semiconductor material, and requires the exchange of holes and/or electrons between the electrode and the organic semiconductor material. The organic light emitting device can be roughly divided into two types according to the operation principle. First, excitons are formed in the organic layer by photons introduced into the device from an external light source, and the excitons are separated into electrons and holes, and the electrons and holes are transferred to different electrodes to be used as a current source (voltage source). It is a light emitting device of the form. The second is a light emitting device in which holes and/or electrons are injected into a layer of an organic semiconductor material that interfaces with an electrode by applying voltage or current to two or more electrodes, and operated by the injected electrons and holes.

In general, the organic light emitting phenomenon refers to a phenomenon that converts electrical energy into light energy using an organic material. An organic light emitting device using an organic light emitting phenomenon usually has a structure including an anode and a cathode and an organic material layer therebetween. Here, in order to increase the efficiency and stability of the organic light emitting device, the organic material layer is often composed of a multi-layered structure composed of different materials, for example, may be formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. When a voltage is applied between two electrodes in the structure of the organic light emitting device, holes are injected at the anode, and electrons are injected at the cathode, and an exciton is formed when the injected holes meet the electrons. When it falls to the ground again, it will shine. It is known that such an organic light emitting device has characteristics such as self-luminescence, high luminance, high efficiency, low driving voltage, wide viewing angle, and high contrast.

Materials used as the organic material layer in the organic light emitting device may be classified into light emitting materials and charge transport materials, such as hole injection materials, hole transport materials, electron transport materials, and electron injection materials, depending on their function. The light emitting materials include blue, green, and red light emitting materials, and yellow and orange light emitting materials necessary for realizing a better natural color depending on the light emitting color.

In addition, a host/dopant system may be used as a light emitting material in order to increase color purity and increase light emission efficiency through energy transfer. The principle is that when a small amount of a dopant having a smaller energy band gap and a higher luminous efficiency is mixed with a light emitting layer than a host mainly constituting the light emitting layer, excitons generated from the host are transported as a dopant to produce high efficiency light. At this time, since the wavelength of the host moves to the wavelength of the dopant, light of a desired wavelength can be obtained according to the type of the dopant used.

In order to sufficiently exhibit the excellent characteristics of the above-described organic light-emitting device, a material forming an organic material layer in the device, such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, etc. Development of new materials continues to be required.

Korea Patent Publication No. 2011-108575

A polycyclic compound and an organic light emitting device including the same are described herein.

An exemplary embodiment of the present specification is to provide a compound represented by the following formula 1 or formula 2.

[Formula 1]

[Formula 2]

In Formula 1 and Formula 2,

X1 to X3 are each independently N or CR,

At least two of X1 to X3 are N,

R is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

L1 is a direct bond; A substituted or unsubstituted arylene group having 6 to 10 carbon atoms; Or a substituted or unsubstituted heterocyclic group,

L2 is a substituted or unsubstituted arylene group having 6 to 10 carbon atoms; Or a substituted or unsubstituted heterocyclic group,

R1 is a substituted or unsubstituted aryl group,

R2 and R3 are each independently hydrogen; Or deuterium,

a is an integer from 0 to 7,

b is an integer from 0 to 8,

When a and b are each independently 2 or more, the substituents in parentheses are the same or different from each other, and adjacent R2 or R3 may combine with each other to form a substituted or unsubstituted indolocarbazole or indenocarbazole.

In addition, according to an exemplary embodiment of the present specification, the first electrode; A second electrode provided to face the first electrode; And an organic light emitting device including one or more organic material layers provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes the compound.

The compounds described herein can be used as a material for the organic material layer of the organic light emitting device. The compound according to at least one embodiment can improve the lifespan characteristics and/or in the organic light emitting device. In particular, the compounds described herein can be used as a material for a hole injection layer, a hole transport layer, an electron suppression layer, a light emitting layer, a hole suppression layer, an electron transport layer, and an electron injection layer.

1 shows an example of an organic light emitting device including a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4.
2 shows an example of an organic light-emitting device comprising a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8 and a cathode 4 It is done.

Hereinafter, this specification will be described in more detail.

The present specification provides a compound represented by the following Chemical Formula 1 or Chemical Formula 2. When the compound represented by the following Chemical Formula 1 or Chemical Formula 2 is used in the organic material layer of the organic light emitting device, the efficiency of the organic light emitting device is always maintained.

[Formula 1]

[Formula 2]

In Formula 1 and Formula 2,

X1 to X3 are each independently N or CR,

At least two of X1 to X3 are N,

R is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

L1 is a direct bond; A substituted or unsubstituted arylene group having 6 to 10 carbon atoms; Or a substituted or unsubstituted heterocyclic group,

L2 is a substituted or unsubstituted arylene group having 6 to 10 carbon atoms; Or a substituted or unsubstituted heterocyclic group,

R1 is a substituted or unsubstituted aryl group,

R2 and R3 are each independently hydrogen; Or deuterium,

a is an integer from 0 to 7,

b is an integer from 0 to 8,

When a and b are each independently 2 or more, the substituents in parentheses are the same or different from each other, and adjacent R2 or R3 may combine with each other to form indolocarbazole or indenocarbazole.

In the present specification, when a part “includes” a certain component, it means that the component may further include other components, not to exclude other components, unless otherwise stated.

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

Examples of the substituent in this specification are described below, but are not limited thereto.

The term "substitution" means that the hydrogen atom bonded to the carbon atom of the compound is replaced with another substituent, and the position to be substituted is not limited to a position where the hydrogen atom is substituted, that is, a position where the substituent is substitutable, and when two or more are substituted , 2 or more substituents may be the same or different from each other.

The term "substituted or unsubstituted" in this specification is deuterium; Halogen group; Cyano group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted aryl group; And substituted or unsubstituted heterocyclic groups, substituted with 1 or 2 or more substituents selected from the group, or substituted with 2 or more substituents among the exemplified substituents, or having no substituents. For example, "a substituent having two or more substituents" may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent to which two phenyl groups are connected.

Examples of the substituents are described below, but are not limited thereto.

In the present specification, examples of the halogen group include fluorine (F), chlorine (Cl), bromine (Br), or iodine (I).

In the present specification, the alkyl group may be straight chain or branched chain, and carbon number is not particularly limited, but is preferably 1 to 60. According to an exemplary embodiment, the alkyl group has 1 to 30 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms. Specific examples of the alkyl group are methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-ox Tilgi, and the like, but are not limited to these.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to an exemplary embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, a cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, and the like, but is not limited thereto.

In the specification, examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted triarylamine group. The aryl group in the arylamine group may be a monocyclic aryl group or a polycyclic aryl group. The arylamine group including the two or more aryl groups may include a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group at the same time.

Specific examples of the arylamine group include a phenylamine group, a naphthylamine group, a biphenylamine group, anthracenylamine group, 3-methyl-phenylamine group, 4-methyl-naphthylamine group, and 2-methyl-biphenylamine Group, 9-methyl-anthracenylamine group, diphenyl amine group, phenyl naphthyl amine group, biphenyl phenyl amine group, and the like, but is not limited thereto.

In the present specification, the aryl group is not particularly limited, but is preferably 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the carbon number of the aryl group is 6 to 30. According to one embodiment, the carbon number of the aryl group is 6 to 20. The aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc., as a monocyclic aryl group, but is not limited thereto. The polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, perylenyl group, triphenyl group, chrysenyl group, fluorenyl group, and the like, but is not limited thereto.

In the present specification, the fluorenyl group may be substituted, and two substituents may combine with each other to form a spiro structure.

,

등의 스피로플루오레닐기,

(9,9-디메틸플루오레닐기), 및

(9,9-디페닐플루오레닐기) 등의 치환된 플루오레닐기가 될 수 있다. 다만, 이에 한정되는 것은 아니다.When the fluorenyl group is substituted,

,

Spirofluorenyl groups, such as

(9,9-dimethylfluorenyl group), and

It may be a substituted fluorenyl group, such as (9,9-diphenylfluorenyl group). However, it is not limited thereto.

In the present specification, the heterocyclic group is a hetero atom and is a ring group containing one or more of N, O, P, S, Si, and Se, and carbon number is not particularly limited, but is preferably 2 to 60 carbon atoms. According to an exemplary embodiment, the heterocyclic group has 2 to 30 carbon atoms. Examples of the heterocyclic group include pyridyl group, pyrrol group, pyrimidyl group, pyridazinyl group, furanyl group, thiophenyl group, imidazole group, pyrazole group, dibenzofuranyl group, dibenzothiophenyl group, and the like. It is not limited to.

In the present specification, a description of the aforementioned heterocyclic group may be applied, except that the heteroaryl group is aromatic.

In this specification, "adjacent" A group may mean a substituent substituted on an atom directly connected to an atom in which the substituent is substituted, a substituent located closest in conformation to the substituent, or another substituent substituted on the atom in which the substituent is substituted. For example, two substituents substituted in the ortho position on the benzene ring and two substituents substituted on the same carbon in the aliphatic ring may be interpreted as "adjacent" to each other.

In the present specification, in a substituted or unsubstituted ring formed by bonding adjacent groups to each other, "ring" is a substituted or unsubstituted hydrocarbon ring; Or substituted or unsubstituted heterocyclic ring.

In the present specification, the hydrocarbon ring may be an aromatic, aliphatic or aromatic and aliphatic condensed ring, and may be selected from examples of the cycloalkyl group or aryl group except for the non-monovalent.

In this specification, the description of the aryl group can be applied, except that the aromatic hydrocarbon ring is monovalent.

In the present specification, the heterocycle is a non-carbon atom, and contains at least one heteroatom, specifically, the heteroatom contains at least one atom selected from the group consisting of N, O, P, S, Si and Se, etc. can do. The heterocycle may be monocyclic or polycyclic, and may be aromatic, aliphatic, or a condensed ring of aromatic and aliphatic, and the aromatic heterocycle may be selected from examples of the heteroaryl group except that it is not monovalent.

According to an exemplary embodiment of the present specification, the formula 1 is represented by any one of the following formulas 3 to 6.

[Formula 3]

[Formula 4]

[Formula 5]

[Formula 6]

In the formula 3 to 6,

X1 to X3, L1, R1, R2 and a are as defined above.

According to an exemplary embodiment of the present specification, X1 and X2 is N, X3 is CR.

According to an exemplary embodiment of the present specification, X1 and X3 is N, X2 is CR.

According to an exemplary embodiment of the present specification, X2 and X3 is N, X1 is CR.

According to an exemplary embodiment of the present specification, X1 to X3 is N.

According to an exemplary embodiment of the present specification, R is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, R is hydrogen; Or deuterium.

According to an exemplary embodiment of the present specification, L1 is a direct bond; A substituted or unsubstituted arylene group having 6 to 10 carbon atoms; Or a substituted or unsubstituted heterocyclic group.

According to an exemplary embodiment of the present specification, L2 is a substituted or unsubstituted arylene group having 6 to 10 carbon atoms; Or a substituted or unsubstituted heterocyclic group.

According to an exemplary embodiment of the present specification, L1 is a direct bond.

According to an exemplary embodiment of the present specification, L1 and L2 are each independently a substituted or unsubstituted arylene group having 6 to 10 carbon atoms or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, L1 and L2 are each independently a substituted or unsubstituted arylene group having 6 to 10 carbon atoms or a substituted or unsubstituted heterocyclic group having 2 to 15 carbon atoms.

According to an exemplary embodiment of the present specification, L1 and L2 are each independently an substituted or unsubstituted arylene group having 6 to 10 carbon atoms.

According to an exemplary embodiment of the present specification, L1 and L2 are each independently a substituted or unsubstituted phenylene group.

According to an exemplary embodiment of the present specification, R1 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, R1 is a substituted or unsubstituted aryl group having 6 to 15 carbon atoms.

According to an exemplary embodiment of the present specification, R1 is a substituted or unsubstituted phenyl group.

According to an exemplary embodiment of the present specification, R1 is a phenyl group.

According to an exemplary embodiment of the present specification, R2 and R3 are each independently hydrogen; Or deuterium.

According to an exemplary embodiment of the present specification, R2 and R3 are hydrogen.

According to an exemplary embodiment of the present specification, R2 is hydrogen, or may combine with an adjacent group to form a substituted or unsubstituted indolocarbazole or indenocarbazole.

According to an exemplary embodiment of the present specification, R2 is hydrogen, or may combine with an adjacent group to form a ring of the following structure.

In the above structure, A1 to A5 are each independently hydrogen; heavy hydrogen; Halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, a1 and a2 are each an integer of 0 to 4, * indicates a position to be substituted.

According to an exemplary embodiment of the present specification, the formula 2 is represented by any one of the following formulas 7 to 9.

[Formula 7]

[Formula 8]

[Formula 9]

In the formulas 7 to 9,

L2 is as defined above,

A1 to A5 are each independently hydrogen; heavy hydrogen; Halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

A6 to A8 are each independently hydrogen or deuterium,

a1 and a2 are each an integer from 0 to 4,

a6 and a7 are each an integer from 0 to 6,

a8 is an integer from 0 to 8.

According to an exemplary embodiment of the present specification, A1 and A2 is hydrogen.

According to an exemplary embodiment of the present specification, A3 to A5 are each independently substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

According to an exemplary embodiment of the present specification, A3 to A5 are each independently substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.

According to an exemplary embodiment of the present specification, A3 and A4 are each independently a substituted or unsubstituted alkyl group.

According to an exemplary embodiment of the present specification, A3 and A4 are a methyl group.

According to an exemplary embodiment of the present specification, A5 is a substituted or unsubstituted aryl group.

According to an exemplary embodiment of the present specification, A5 is a substituted or unsubstituted phenyl group.

According to an exemplary embodiment of the present specification, A5 is a phenyl group.

According to an exemplary embodiment of the present specification, A6 to A8 are each independently hydrogen or deuterium.

According to an exemplary embodiment of the present specification, A6 to A8 is hydrogen.

According to an exemplary embodiment of the present specification, a and b are 0 or 1.

According to an exemplary embodiment of the present specification, when a and b are each independently 2 or more, adjacent R2 or R3 may combine with each other to form a substituted or unsubstituted indolocarbazole or indenocarbazole.

According to an exemplary embodiment of the present specification, when a and b are each independently 2 or more, adjacent R2 or R3 is bonded to each other to replace indolocarbazole or indenocarbazole unsubstituted or substituted with an aryl group having 6 to 30 carbon atoms. Can form.

According to an exemplary embodiment of the present specification, when a and b are each independently 2 or more, adjacent R2 or R3 is bonded to each other to replace indolocarbazole or indenocarbazole unsubstituted or substituted with an aryl group having 6 to 15 carbon atoms. Can form.

According to an exemplary embodiment of the present specification, when a and b are each independently 2 or more, adjacent R2 or R3 may be bonded to each other to form indolocarbazole or indenocarbazole unsubstituted or substituted with a phenyl group.

According to an exemplary embodiment of the present specification, the formula 1 is represented by any one of the following structures.

According to an exemplary embodiment of the present specification, the formula 2 is represented by any one of the following structures.

Substituents of the compound of Formula 1 or Formula 2 herein may be combined by methods known in the art, and the type, location, and number of substituents may be changed according to techniques known in the art.

The conjugation length of the compound and the energy band gap are closely related. Specifically, the longer the conjugation length of the compound, the smaller the energy band gap.

In the present invention, compounds having various energy band gaps can be synthesized by introducing various substituents to the core structure as described above. In addition, in the present invention, the HOMO and LUMO energy levels of the compound can be adjusted by introducing various substituents to the core structure having the above structure.

In addition, by introducing various substituents to the core structure of the structure as described above, it is possible to synthesize a compound having intrinsic properties of the introduced substituents. For example, by introducing a substituent mainly used for a hole injection layer material, a hole transport material, a light emitting layer material, and an electron transport layer material used in manufacturing an organic light emitting device into the core structure, a material satisfying the conditions required for each organic material layer can be synthesized. Can.

In addition, the organic light emitting device according to the present invention includes a first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer comprises a compound of Formula 1 or Formula 2.

The organic light-emitting device of the present invention can be manufactured by a conventional manufacturing method and material of an organic light-emitting device, except that one or more organic material layers are formed using the above-described compound.

The compound may be formed as an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device. Here, the solution application method means spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited to these.

The organic material layer of the organic light emitting device of the present invention may have a single layer structure, but may have a multi-layer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, etc. as an organic material layer. However, the structure of the organic light emitting device is not limited to this, and may include fewer organic material layers.

In the organic light emitting device of the present invention, the organic material layer may include an electron transport layer or an electron injection layer, and the electron transport layer or electron injection layer may include a compound represented by Formula 1 or Formula 2.

In the organic light emitting device of the present invention, the organic material layer may include a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer may include a compound represented by Formula 1 or Formula 2.

In another exemplary embodiment, the organic material layer includes a light emitting layer, and the light emitting layer includes a compound represented by Formula 1 or Formula 2.

According to another exemplary embodiment, the organic material layer includes a light emitting layer, and the light emitting layer may include a compound represented by Formula 1 or Formula 2 as a host of the light emitting layer.

In another exemplary embodiment, the organic material layer including the compound represented by Chemical Formula 1 or Chemical Formula 2 includes the compound represented by Chemical Formula 1 or Chemical Formula 2 as a host, and further includes a fluorescent host or a phosphorescent host, and other Organic compounds, metals or metal compounds may be included as dopants.

As another example, the organic material layer including the compound represented by Chemical Formula 1 or Chemical Formula 2 includes the compound represented by Chemical Formula 1 or Chemical Formula 2 as a host, and further includes a fluorescent host or a phosphorescent host. Ir) Can be used with dopants.

In one embodiment of the present specification, the first electrode is an anode, and the second electrode is a cathode.

According to another exemplary embodiment, the first electrode is a cathode, and the second electrode is an anode.

The structure of the organic light emitting device of the present invention may have a structure as shown in FIGS. 1 and 2, but is not limited thereto.

1 illustrates the structure of an organic light emitting device in which an anode 2, a light emitting layer 3, and a cathode 4 are sequentially stacked on a substrate 1. In such a structure, the compound may be included in the light emitting layer 3.

2 shows an organic light emitting device in which an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8, and a cathode 4 are sequentially stacked on a substrate 1 The structure is illustrated. In such a structure, the compound may be included in the hole injection layer 5, the hole transport layer 6, the light emitting layer 7 or the electron transport layer 8.

For example, the organic light emitting device according to the present invention uses a metal vapor deposition (PVD) method, such as sputtering or e-beam evaporation, to have a metal or conductive metal oxide on the substrate or alloys thereof It can be prepared by depositing an anode to form an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer thereon, and then depositing a material that can be used as a cathode thereon. In addition to this method, an organic light emitting device may be made by sequentially depositing a cathode material, an organic material layer, and a cathode material on a substrate.

The organic material layer may have a multi-layer structure including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer, but is not limited thereto, and may have a single layer structure. In addition, the organic material layer has a smaller number of solvent processes, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer, using a variety of polymer materials. Can be prepared in layers.

The positive electrode material is usually a material having a large work function to facilitate hole injection into the organic material layer. Specific examples of the positive electrode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); A combination of metal and oxide such as ZnO: Al or SnO ₂ : Sb; Conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole and polyaniline, but are not limited thereto.

The cathode material is preferably a material having a small work function to facilitate electron injection into an organic material layer. Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof; There is a multilayer structure material such as LiF/Al or LiO ₂ /Al, but is not limited thereto.

The hole-injecting material is a material that can be easily injected holes from the anode at a low voltage, and it is preferable that the high-occupied molecular orbital (HOMO) of the hole-injecting material is between the work function of the anode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include metal porphyrine, oligothiophene, arylamine-based organic substances, hexanitrile hexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based substances. Organic materials, anthraquinones, and polyaniline and polythiophene-based conductive polymers, but are not limited thereto.

As the hole transport material, a material capable of receiving holes from the anode or the hole injection layer and transporting them to the light emitting layer is suitable for a material having high mobility for holes. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers having a conjugated portion and a non-conjugated portion, but are not limited thereto.

The light emitting layer may emit red, green, or blue light, and may be made of a phosphorescent material or a fluorescent material. As the light-emitting material, a material capable of emitting light in the visible region by receiving and bonding holes and electrons from the hole transport layer and the electron transport layer, respectively, is preferably a material having good quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compound; Benzoxazole, benzthiazole and benzimidazole compounds; Poly(p-phenylenevinylene) (PPV)-based polymers; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited to these.

The host material of the light emitting layer includes a condensed aromatic ring derivative or a heterocyclic compound. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, and ladder types Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

The iridium-based complex used as a dopant in the light emitting layer is as follows, but is not limited thereto.

[Ir(piq) ₃ ] [Btp ₂ Ir(acac)]

[Ir(ppy) ₃ ] [Ir(ppy) ₂ (acac)]

[Ir(mpyp) ₃ ] [F ₂ Irpic]

[(F ₂ ppy) ₂ Ir(tmd)] [Ir(dfppz) ₃ ]

　　　

　　　

As the electron transport material, a material capable of receiving electrons from the cathode well and transferring them to the light emitting layer, a material having high mobility for electrons is suitable. Specific examples include the Al complex of 8-hydroxyquinoline; Complexes including Alq ₃ ; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited thereto.

The organic light emitting device according to the present invention may be a front emission type, a back emission type, or a double-sided emission type, depending on the material used.

Hereinafter, examples will be described in detail to specifically describe the present specification. However, the embodiments according to the present specification may be modified in various other forms, and the scope of the present application is not interpreted to be limited to the embodiments described below. The embodiments of the present application are provided to more fully describe the present specification to those skilled in the art.

[Synthesis example]

end. Synthesis of Intermediates 1A-1D

[Production Example 1-1] Synthesis of Intermediate 1A

In a nitrogen atmosphere, 2,4-dichloro-6-phenyl-1,3,5-triazine (50.0g, 222.2mmol) and phenanthren-9-ylboronic acid (49.4g, 222.2mmol) were added to 800ml of tetrahydrofuran and stirred. While potassium carbonate (61.4g, 444.5mmol) was dissolved in water and added. Thereafter, tetrakis(triphenylphosphine)palladium(0) (2.6 g, 1 mol%) was slowly added under heating under reflux. Thereafter, the reaction was completed for about 9 hours, and then the reaction was terminated. When the reaction was completed, the temperature was reduced to room temperature (25°C), and then the resulting solid was filtered. The filtered solid was dissolved in chloroform, and after washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and filtered to distill the filtrate under reduced pressure. The concentrate was purified through a silica column using chloroform and ethyl acetate to prepare Intermediate 1A (40.0 g, yield: 49%) as a white solid compound.

MS: [M+H] + = 368

[Production Example 1-2] Synthesis of Intermediate 1B

Formula 1A (30.0g, 81.7mmol) and (4-chlorophenyl)boronic acid (20.0g, 89.9mmol) were added to 400ml of tetrahydrofuran in a nitrogen atmosphere, and potassium carbonate (33.9g, 245.2 mmol) was dissolved in water while stirring. Was added. Then, tetrakis(triphenylphosphine)palladium(0) (2.8 g, 3 mol%) was slowly added under heating under reflux. Thereafter, the reaction was completed for about 4 hours, and then the reaction was terminated. When the reaction was completed, the temperature was reduced to room temperature (25°C), and then the resulting solid was filtered. The filtered solid was dissolved in chloroform, and after washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and filtered to distill the filtrate under reduced pressure. The concentrate was purified through a silica column using chloroform and ethyl acetate to prepare intermediate 1B (27.1 g, yield: 75%) as a white solid compound.

MS: [M+H] + = 444

[Production Example 1-3] Synthesis of intermediate 1C

(4-chlorophenyl)boronic acid (20.0g, 89.9mmol) instead of (3-chlorophenyl)boronic acid (20.0g, 89.9mmol), except for using the intermediate of the synthesis of Intermediate 1B of Preparation Example 1-2 1C (24.9 g, yield: 69%) was prepared.

MS: [M+H] + = 444

[Production Example 1-4] Synthesis of intermediate 1D

(4-chlorophenyl)boronic acid (20.0g, 89.9mmol) instead of (2-chlorophenyl)boronic acid (20.0g, 89.9mmol) except for using the intermediate of the synthesis of Intermediate 1B of Preparation Example 1-2 1D (21.0 g, yield: 58%) was prepared.

MS: [M+H] + = 444

I. Synthesis of Intermediates 2A and 2B

[Production Example 2-1] Synthesis of intermediate 2A

In a nitrogen atmosphere, 2,4-dichloro-6-phenyl-1,3,5-triazine (50.0g, 222.2mmol) and phenanthren-2-ylboronic acid (49.4g, 222.2mmol) were added to 800ml of tetrahydrofuran and stirred. While potassium carbonate (61.4g, 444.5mmol) was dissolved in water and added. Thereafter, tetrakis(triphenylphosphine)palladium(0) (2.6 g, 1 mol%) was slowly added under heating under reflux. Thereafter, the reaction was completed for about 9 hours, and then the reaction was terminated. When the reaction was completed, the temperature was reduced to room temperature (25°C), and then the resulting solid was filtered. The filtered solid was dissolved in chloroform, and after washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and filtered to distill the filtrate under reduced pressure. The concentrate was purified through a silica column using chloroform and ethyl acetate to prepare intermediate 2A (47.3 g, yield: 58%) as a white solid compound.

MS: [M+H] + = 368

[Production Example 2-2] Synthesis of Intermediate 2B

Formula 2A (30.0g, 81.7mmol) and (4-chlorophenyl)boronic acid (20.0g, 89.9mmol) were added to 400ml of tetrahydrofuran in a nitrogen atmosphere and potassium carbonate (33.9g, 245.2mmol) was dissolved in water while stirring. Was added. Thereafter, tetrakis(triphenylphosphine)palladium(0) (2.8 g, 3 mol%) was slowly added under reflux. Thereafter, the reaction was completed for about 4 hours, and then the reaction was terminated. When the reaction was completed, the temperature was reduced to room temperature (25°C), and then the resulting solid was filtered. The filtered solid was dissolved in chloroform, and after washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and filtered to distill the filtrate under reduced pressure. The concentrate was purified through a silica column using chloroform and ethyl acetate to prepare intermediate 2B (25.3 g, yield: 70%) as a white solid compound.

MS: [M+H] + = 444

All. Synthesis of Intermediates 3A and 3B

[Production Example 3-1] Synthesis of intermediate 3A

In a nitrogen atmosphere, 2,4-dichloro-6-phenyl-1,3,5-triazine (50.0g, 222.2mmol) and phenanthren-3-ylboronic acid (49.4g, 222.2mmol) were added to 800ml of tetrahydrofuran and stirred. While potassium carbonate (61.4g, 444.5mmol) was dissolved in water and added. Thereafter, tetrakis(triphenylphosphine)palladium(0) (2.6 g, 1 mol%) was slowly added under heating under reflux. Thereafter, the reaction was completed for about 9 hours, and then the reaction was terminated. When the reaction was completed, the temperature was reduced to room temperature (25°C), and then the resulting solid was filtered. The filtered solid was dissolved in chloroform, and after washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and filtered to distill the filtrate under reduced pressure. The concentrate was purified through a silica column using chloroform and ethyl acetate to prepare white solid compound Intermediate 3A (40.8 g, yield: 50%).

MS: [M+H] + = 368

[Production Example 3-2] Synthesis of intermediate 3B

Formula 3A (30.0g, 81.7mmol) and (4-chlorophenyl)boronic acid (20.0g, 89.9mmol) were added to 400 ml of tetrahydrofuran in a nitrogen atmosphere and potassium carbonate (33.9 g, 245.2 mmol) was dissolved in water while stirring. Was added. Thereafter, tetrakis(triphenylphosphine)palladium(0) (2.8 g, 3 mol%) was slowly added under reflux. Thereafter, the reaction was completed for about 4 hours, and then the reaction was terminated. When the reaction was completed, the temperature was reduced to room temperature (25°C), and then the resulting solid was filtered. The filtered solid was dissolved in chloroform, and after washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and filtered to distill the filtrate under reduced pressure. The concentrate was purified through a silica column using chloroform and ethyl acetate to prepare intermediate 3B (27.8 g, yield: 77%) as a white solid compound.

MS: [M+H] + = 444

la. Synthesis of Compounds 1-14

[Synthesis Example 1] Synthesis of Compound 1

In a nitrogen atmosphere, intermediate 1A (15.0 g, 66.7 mmol) and (9-phenyl-9H-carbazol-1-yl)boronic acid (16.2 g, 66.7 mmol) were added to dioxane (200 mL), stirred and refluxed. Thereafter, potassium carbonate (27.6 g, 200.0 mmol) was dissolved in water, stirred sufficiently, and bis(tri-t-butylphosphine)palladium(0) (2.3 g, mol%) was added. After the reaction for 9 hours, the temperature was reduced to room temperature and filtered. The filtrate was extracted with chloroform and water, and then the organic layer was dried using magnesium sulfate. Then, the organic layer was distilled under reduced pressure and recrystallized using a mixed solution of tetrahydrofuran and ethyl acetate. The resulting solid was filtered and dried to prepare compound 1 (16.7 g, yield 46%).

MS: [M+H] + = 575

[Synthesis Example 2] Synthesis of Compound 2

(9-phenyl-9H-carbazol-2-yl)boronic acid (16.2 g, 66.7 mmol) was used instead of (9-phenyl-9H-carbazol-1-yl)boronic acid (16.2 g, 66.7 mmol) Then, in the same manner as in the synthesis of Compound 1 of Synthesis Example 1, Compound 2 (13.8 g, yield: 38%) was prepared.

MS: [M+H] + = 575

[Synthesis Example 3] Synthesis of Compound 3

(9-phenyl-9H-carbazol-3-yl)boronic acid (16.2 g, 66.7 mmol) was used instead of (9-phenyl-9H-carbazol-1-yl)boronic acid (16.2 g, 66.7 mmol) Then, in the same manner as in the synthesis of Compound 1 of Synthesis Example 1, Compound 3 (18.5 g, yield: 51%) was prepared.

MS: [M+H] + = 575

[Synthesis Example 4] Synthesis of Compound 4

(9-phenyl-9H-carbazol-4-yl)boronic acid (16.2 g, 66.7 mmol) was used instead of (9-phenyl-9H-carbazol-1-yl)boronic acid (16.2 g, 66.7 mmol) Then, compound 4 (10.9 g, yield: 30%) was prepared in the same manner as in the synthesis of compound 1 of Synthesis Example 1.

MS: [M+H] + = 575

[Synthesis Example 5] Synthesis of Compound 5

In a nitrogen atmosphere, intermediate 1B (15.0 g, 66.7 mmol) and (9-phenyl-9H-carbazol-2-yl)boronic acid (16.2 g, 66.7 mmol) were added to dioxane (200 mL), stirred and refluxed. Thereafter, potassium carbonate (27.6 g, 200.0 mmol) was dissolved in water, stirred sufficiently, and bis(tri-t-butylphosphine)palladium(0) (2.3 g, mol%) was added. After the reaction for 9 hours, the temperature was reduced to room temperature and filtered. The filtrate was extracted with chloroform and water, and then the organic layer was dried using magnesium sulfate. Then, the organic layer was distilled under reduced pressure and recrystallized using a mixed solution of tetrahydrofuran and ethyl acetate. The resulting solid was filtered and dried to prepare compound 5 (18.5 g, yield 51%).

MS: [M+H] + = 575

[Synthesis Example 6] Synthesis of Compound 6

Compound 6 (16.0 g, yield: 44%) was prepared in the same manner as in the synthesis of Compound 5 of Synthesis Example 5, except that Intermediate 1C was used instead of Intermediate 1B (15.0 g, 66.7 mmol).

[Synthesis Example 7] Synthesis of Compound 7

Compound 7 (9.1 g, yield: 25%) was prepared in the same manner as in Synthesis 5 of Synthesis Example 5, except that Intermediate 1D was used instead of Intermediate 1B (15.0 g, 66.7 mmol).

[Synthesis Example 8] Synthesis of Compound 8

Intermediate 1C (15.0 g, 33.9 mmol) and 9H-carbazole (5.7 g, 33.9 mmol) were added to 100 mL of xylene to dissolve, and sodium tertiary-butoxide (6.5 g, 67.7 mmol) was added to warm. Bis(tri tertiary-butylphosphine) palladium (0.5 g, 3 mol%) was added thereto, and the mixture was stirred at reflux for 12 hours. When the reaction was completed, the temperature was lowered to room temperature, and the resulting solid was filtered. The solid was dissolved in 700 mL of chloroform, and after washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and filtered to distill the filtrate under reduced pressure. The concentrated compound was purified through a silica column using chloroform and ethyl acetate to prepare pale pale green solid compound 8 (10.5 g, 54%).

MS:[M+H]+=575

[Synthesis Example 9] Synthesis of Compound 9

Compound of Synthesis Example 8, except that 7,7-dimethyl-5,7-dihydroindeno[2,1-b]carbazole (9.6g, 33.8 mmol) was used instead of 9H-carbazole (5.7 g, 33.8 mmol) Compound 9 (7.7 g, yield: 33%) was prepared as in the synthesis of 8.

MS:[M+H]+=691

[Synthesis Example 10] Synthesis of Compound 10

Compound 8 of Synthesis Example 8 except that 5-phenyl-5,7-dihydroindolo[2,3-b]carbazole (9.6g, 33.8 mmol) was used instead of 9H-carbazole (5.7 g, 33.8 mmol). Compound 10 (10.3 g, yield: 41%) was prepared as in the synthesis.

MS:[M+H]+=740

[Synthesis Example 11] Synthesis of Compound 11

In a nitrogen atmosphere, intermediate 2A (15.0 g, 66.7 mmol) and (9-phenyl-9H-carbazol-2-yl)boronic acid (16.2 g, 66.7 mmol) were added to dioxane (200 mL), stirred and refluxed. Thereafter, potassium carbonate (27.6 g, 200.0 mmol) was dissolved in water, stirred sufficiently, and bis(tri-t-butylphosphine)palladium(0) (2.3 g, mol%) was added. After the reaction for 9 hours, the temperature was reduced to room temperature and filtered. The filtrate was extracted with chloroform and water, and then the organic layer was dried using magnesium sulfate. Then, the organic layer was distilled under reduced pressure and recrystallized using a mixed solution of tetrahydrofuran and ethyl acetate. The resulting solid was filtered and dried to prepare compound 11 (7.7 g, yield 33%).

MS: [M+H] + = 575

[Synthesis Example 12] Synthesis of Compound 12

Compound 12 (9.1 g, yield: 25%) was prepared in the same manner as in Synthesis of Compound 11 of Synthesis Example 11, except that Intermediate 3A was used instead of Intermediate 2A (15.0 g, 66.7 mmol).

MS:[M+H]+=575

[Synthesis Example 13] Synthesis of Compound 13

Compound 13 (10.5 g, yield: 45%) was prepared in the same manner as in the synthesis of Compound 9 of Synthesis Example 9, except that 2B was used instead of Intermediate 1C (15.0 g, 33.9 mmol).

MS:[M+H]+=691

[Synthesis Example 14] Synthesis of Compound 14

Compound 14 (11.9 g, yield: 51%) was prepared in the same manner as in the synthesis of compound 9 of Synthesis Example 9, except that 3B was used instead of the intermediate 1C (15.0 g, 33.9 mmol).

MS:[M+H]+=691

[Experimental Example]

<Experimental Example 1>

A glass substrate coated with a thin film coated with ITO (indium tin oxide) at a thickness of 1,300 에 was placed in distilled water in which detergent was dissolved and washed with ultrasonic waves. At this time, Fischer (Fischer Co.) was used as the detergent, and distilled water filtered secondarily by a filter of Millipore Co. was used as the distilled water. After washing the ITO for 30 minutes, ultrasonic washing was repeated for 10 minutes by repeating it twice with distilled water. After washing with distilled water, ultrasonic cleaning was performed with a solvent of isopropyl alcohol, acetone, and methanol, followed by drying and transporting to a plasma cleaner. In addition, the substrate was washed for 5 minutes using oxygen plasma, and then transferred to a vacuum evaporator.

On the ITO transparent electrode prepared as above, the following HI-1 compound was thermally vacuum-deposited to a thickness of 50 Pa to form a hole injection layer. The following HT-1 compound was thermally vacuum-deposited to a thickness of 250 Pa on the hole injection layer to form a hole transport layer, and the following HT-2 compound was vacuum-deposited to a thickness of 50 Pa on the HT-1 deposition film to form an electron blocking layer. As a light emitting layer on the HT-2 deposited film, a compound 1 prepared in Preparation Example 1, the following YGH-1 compound, and a phosphorescent dopant YGD-1 were co-deposited in a weight ratio of 44:44:12 to form a 400 mm thick light emitting layer. An electron transport layer is formed by vacuum-depositing the following ET-1 compound to a thickness of 250 Pa on the light emitting layer, and the following ET-2 compound and Li are vacuum-deposited at a weight ratio of 98:2 on the electron transport layer to form an electron injection layer of 100 Pa thick. Formed. On the electron injection layer, aluminum was deposited to a thickness of 1000 MPa to form a cathode.

In the above process, the deposition rate of the organic material was maintained at 0.4 to 0.7 Å/sec, and the aluminum was maintained at the deposition rate of 2 Å/sec, and the vacuum degree during deposition was maintained at 1 × 10 ^-7 to 5 × 10 ^-8 torr. Did.

<Experimental Examples 2 to 14>

An organic light emitting diode was manufactured according to the same method as Experimental Example 1 except for using the compound described in Table 1 below instead of compound 1 of Synthesis Example 1 in Experimental Example 1.

<Comparative Experimental Examples 1 to 6>

An organic light emitting diode was manufactured according to the same method as Experimental Example 1 except for using the compound shown in Table 1 below instead of compound 1 of Synthesis Example 1 in Experimental Example 1. The compounds of CE1 to CE6 in Table 1 are as follows.

In the Experimental Example and Comparative Experimental Example, the voltage and efficiency of the organic light emitting device were measured at a current density of 10 mA/cm ² , and life was measured at a current density of 50 mA/cm ² , and the results are shown in Table 1 below. At this time, LT ₉₅ means a time that becomes 95% of the initial luminance.

compound Voltage (V)
(@10mA/cm ² ) Efficiency (Cd/A)
(@10mA/cm ² ) Color coordinate
(x,y) Life (h)
(LT ₉₅ at 50mA/cm ² ) Experimental Example 1 Compound 1 4.0 80 0.46, 0.54 110 Experimental Example 2 Compound 2 3.8 84 0.45, 0.53 195 Experimental Example 3 Compound 3 4.1 81 0.46, 0.53 180 Experimental Example 4 Compound 4 3.9 85 0.45, 0.54 195 Experimental Example 5 Compound 5 3.8 85 0.46, 0.54 140 Experimental Example 6 Compound 6 3.7 88 0.46, 0.53 160 Experimental Example 7 Compound 7 3.9 86 0.46, 0.54 115 Experimental Example 8 Compound 8 3.8 88 0.46, 0.54 180 Experimental Example 9 Compound 9 4.0 83 0.46, 0.55 195 Experimental Example 10 Compound 10 4.1 80 0.46, 0.53 185 Experimental Example 11 Compound 11 3.8 83 0.46, 0.54 220 Experimental Example 12 Compound 12 3.8 84 0.46, 0.53 200 Experimental Example 13 Compound 13 4.0 80 0.46, 0.54 175 Experimental Example 14 Compound 14 4.0 82 0.46, 0.54 165 Comparative Experimental Example 1 CE1 4.5 70 0.46, 0.54 90 Comparative Experimental Example 2 CE2 5.0 64 0.46, 0.55 11 Comparative Experimental Example 3 CE3 4.2 80 0.46, 0.55 90 Comparative Experimental Example 4 CE4 4.4 79 0.47 0.60 20 Comparative Experimental Example 5 CE5 4.7 61 0.58, 0.61 5 Comparative Experimental Example 6 CE6 4.8 70 0.44, 0.53 One

As shown in Table 1, when the compound of the present invention is used as a light emitting layer material, it was confirmed that it exhibits excellent efficiency and lifetime compared to a comparative example. This is excellent in material stability, lifespan, etc. due to the excellent stability of the material due to the combination of triphenyl group to triazine unit and carbazole group to triazine unit. In addition, the distance between carbazole and triazine is more than 1, which is advantageous for life.

1: Substrate
2: anode
3: light emitting layer
4: Cathode
5: hole injection layer
6: hole transport layer
7: emitting layer
8: electron transport layer

Claims (9)

Compound represented by the following formula 1 or formula 2:
[Formula 1]

[Formula 2]

In Formula 1 and Formula 2,
X1 to X3 are each independently N or CR,
At least two of X1 to X3 are N,
R is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
L1 is a direct bond; Or a substituted or unsubstituted arylene group having 6 to 10 carbon atoms,
L2 is a substituted or unsubstituted arylene group having 6 to 10 carbon atoms; Or a substituted or unsubstituted heterocyclic group,
R1 is a substituted or unsubstituted aryl group,
R2 and R3 are each independently hydrogen; Or deuterium,
a is an integer from 0 to 7,
b is an integer from 0 to 8,
When a and b are each independently 2 or more, the substituents in parentheses are the same or different from each other, and adjacent R2 or R3 may combine with each other to form a substituted or unsubstituted indolocarbazole or indenocarbazole. The method according to claim 1,
Chemical Formula 1 is a compound represented by any one of the following Chemical Formulas 3 to 6:
[Formula 3]

[Formula 4]

[Formula 5]

[Formula 6]

In the formula 3 to 6,
X1 to X3, L1, R1, R2 and a are as defined in claim 1. The method according to claim 1,
Formula 2 is a compound represented by any one of the following formulas 7 to 9:
[Formula 7]

[Formula 8]

[Formula 9]

In the formulas 7 to 9,
L2 is as defined in claim 1,
A1 to A5 are each independently hydrogen; heavy hydrogen; Halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
A6 to A8 are each independently hydrogen or deuterium,
a1 and a2 are each an integer from 0 to 4,
a6 and a7 are each an integer from 0 to 6,
a8 is an integer from 0 to 8. The method according to claim 1,
Formula 1 is a compound represented by any one of the following structures:

. The method according to claim 1,
Formula 2 is a compound represented by any one of the structures:

. A first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein one or more of the organic material layers comprises a compound according to any one of claims 1 to 5 Light emitting element. The method according to claim 6,
The organic material layer includes a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer is an organic light emitting device comprising the compound of Formula 1 or Formula 2. The method according to claim 6,
The organic material layer includes an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer includes the compound represented by Formula 1 or Formula 2. The method according to claim 6,
The organic material layer includes a light emitting layer, the light emitting layer is an organic light emitting device comprising a compound represented by the formula (1) or formula (2).

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