WO2019143223A9 - Polycyclic compound and organic light-emitting diode comprising same - Google Patents

Abstract

The present specification provides a compound represented by chemical formula (1) or chemical formula (2) and an organic light-emitting diode comprising same.

Description

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

In general, organic light emitting phenomenon refers to a phenomenon of converting 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, a cathode and an organic material layer therebetween. In this case, the organic material layer is often made of a multi-layer structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device, for example, it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer. When the voltage is applied between the two electrodes in the structure of the organic light emitting device, holes are injected into the organic material layer at the anode, and electrons are injected into the organic material layer, and excitons are formed when the injected holes and the electrons meet each other. When it falls back to the ground, it glows. Such organic light emitting devices are known to have characteristics such as self-luminous, high brightness, high efficiency, low driving voltage, wide viewing angle, and high contrast.

The material used as the organic material layer in the organic light emitting device may be classified into a light emitting material and a charge transport material such as a hole injection material, a hole transport material, an electron transport material, an electron injection material and the like according to a function. The light emitting materials include blue, green, and red light emitting materials, and yellow and orange light emitting materials required to realize better natural colors, depending on the light emission color.

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

In order to fully exhibit the excellent characteristics of the above-described organic light emitting device, a material constituting the 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., is supported by a stable and efficient material. The development of new materials continues to be demanded.

In the present specification, a polycyclic compound and an organic light emitting device including the same are described.

One embodiment of the present specification is to provide a compound represented by the following formula (1) or formula (2).

[Formula 1]

[Formula 2]

In Chemical Formula 1 and Chemical 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; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

L 1 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 of 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.

Further, according to one embodiment of the present specification, the first electrode; A second electrode provided to face the first electrode; And at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound.

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

FIG. 1 shows an example of an organic light emitting element composed of a substrate 1, an anode 2, a light emitting layer 3 and a cathode 4. As shown in FIG.

2 shows an example of an organic light emitting element consisting of 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.

<Code description>

1: substrate

2: anode

3: light emitting layer

4: cathode

5: hole injection layer

6: hole transport layer

7: light emitting layer

8: electron transport layer

Hereinafter, the present specification will be described in more detail.

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

 [Formula 1]

[Formula 2]

In Chemical Formula 1 and Chemical 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; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

L 1 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 of 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, this means that it may further include other components, without excluding other components, unless specifically stated otherwise.

In this specification, when a member is located "on" another member, this includes not only when one member is in contact with another member but also when another member exists between the two members.

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

The term "substituted" means that a hydrogen atom bonded to a 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 can be substituted, if two or more substituted , Two or more substituents may be the same or different from each other.

As used herein, the term "substituted or unsubstituted" is deuterium; Halogen group; Cyano group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted aryl group; And it is substituted with one or two or more substituents selected from the group consisting of a substituted or unsubstituted heterocyclic group, or two or more of the substituents exemplified above are substituted with a substituent, or means that do not have any substituents. For example, "a substituent to which two or more substituents are linked" 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 linked.

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 linear or branched chain, 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 include 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 and n-jade Although there exist a tilt group, it is 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 one 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, 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, may be a polycyclic aryl group. The arylamine group including two or more aryl groups may simultaneously include a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group.

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

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

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

When the fluorenyl group is substituted,

Spirofluorenyl groups such as

(9,9-dimethylfluorenyl group), and

Substituted fluorenyl groups such as (9,9-diphenylfluorenyl group). However, the present invention is not limited thereto.

In the present specification, the heterocyclic group is a ring group including one or more of N, O, P, S, Si, and Se as hetero atoms, and the 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, pyrrole group, pyrimidyl group, pyridazinyl group, furanyl group, thiophenyl group, imidazole group, pyrazole group, dibenzofuranyl group, dibenzothiophenyl group, and the like. It is not limited only to.

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

In the present specification, "adjacent" The group may mean a substituent substituted with an atom directly connected to an atom in which the corresponding substituent is substituted, a substituent positioned closest to the substituent in stereo structure, or another substituent substituted with an atom in which the substituent is substituted. For example, two substituents substituted at the ortho position in the benzene ring and two substituents substituted at the same carbon in the aliphatic ring may be interpreted as "adjacent" groups.

In the present specification, in a substituted or unsubstituted ring in which adjacent groups are bonded to each other, a “ring” means a substituted or unsubstituted hydrocarbon ring; Or a substituted or unsubstituted hetero ring.

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

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

In the present specification, the heterocycle includes one or more atoms other than carbon and heteroatoms, and specifically, the heteroatoms include one or more atoms selected from the group consisting of N, O, P, S, Si, and Se. 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, Chemical Formula 1 is represented by any one of the following Chemical Formulas 3 to 6.

[Formula 3]

[Formula 4]

[Formula 5]

[Formula 6]

In Chemical Formulas 3 to 6,

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

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

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

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

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

According to an exemplary embodiment of the present disclosure, R is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; 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 disclosure, R is hydrogen; Or deuterium.

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

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

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

According to an exemplary embodiment of the present disclosure, R2 and R3 is hydrogen.

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

According to an exemplary embodiment of the present disclosure, R2 is hydrogen, or may be combined with adjacent groups to form a ring of the following structure.

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

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

[Formula 7]

[Formula 8]

[Formula 9]

In Chemical Formulas 7 to 9,

L2 is as defined above,

A1 to A5 are each independently hydrogen; heavy hydrogen; Halogen group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; 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 of 0 to 4,

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

a8 is an integer of 0-8.

According to an exemplary embodiment of the present disclosure, A1 and A2 are hydrogen.

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

According to an exemplary embodiment of the present specification, A3 to A5 are each independently a 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 disclosure, A6 to A8 is hydrogen.

According to an exemplary embodiment of the present specification, a and b is 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 are bonded to each other to form an indolocarbazole or indenocarbazole unsubstituted or substituted with an aryl group having 6 to 30 carbon atoms. Can be formed.

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

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 combined with each other to form an indolocarbazole or indenocarbazole substituted or unsubstituted with a phenyl group.

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

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

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

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

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

Moreover, the compound which has the intrinsic property of the introduced substituent can be synthesize | combined by introducing various substituents into the core structure of the above structure. For example, by introducing a substituent mainly used in the hole injection layer material, the hole transport material, the light emitting layer material and the electron transport layer material used in the manufacture of the organic light emitting device to the core structure to synthesize a material that meets the requirements for each organic material layer. Can be.

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

The organic light emitting device of the present invention may be manufactured by a conventional method and material for manufacturing an organic light emitting device, except that at least one organic material layer is formed using the above-described compound.

The compound may be formed as an organic layer by a solution coating method as well as a vacuum deposition method in the manufacture of the organic light emitting device. Here, the solution coating method means spin coating, dip coating, inkjet printing, screen printing, spraying method, roll coating and the like, but is not limited thereto.

The organic material layer of the organic light emitting device of the present invention may have a single layer structure, but may have a multilayer 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 and the like as an organic material layer. However, the structure of the organic light emitting device is not limited thereto and may include a smaller number of 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 the 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, the hole injection layer or hole transport layer may include a compound represented by the formula (1) or (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 may include 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. Organic compounds, metals or metal compounds may be included as dopants.

As another example, the organic material layer including the compound represented by Formula 1 or Formula 2 includes the compound represented by Formula 1 or Formula 2 as a host, further includes a fluorescent host or a phosphorescent host, and includes an iridium-based ( 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 a 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 illustrates 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 form a metal oxide or a metal oxide or an alloy thereof on a substrate. It can be prepared by depositing an anode to form an anode, 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 the above method, an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

The organic material layer may have a multilayer 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 may be formed by using a variety of polymer materials, and by using a method such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer, rather than a deposition method. It can be prepared in layers.

As the anode material, a material having a large work function is usually preferred 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), indium zinc oxide (IZO); A combination of a metal and an 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, and the like, but are not limited thereto.

It is preferable that the cathode material is a material having a small work function to facilitate electron injection into the 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; Multilayer structure materials such as LiF / Al or LiO ₂ / Al, and the like, but are not limited thereto.

The hole injection material is a material capable of well injecting holes from the anode at a low voltage, and the highest occupied molecular orbital (HOMO) of the hole injection material is preferably between the work function of the anode material and the HOMO of the surrounding organic material layer. Specific examples of hole injection materials include metal porphyrine, oligothiophene, arylamine-based organics, hexanitrile hexaazatriphenylene-based organics, quinacridone-based organics, and perylene-based Organic materials, anthraquinone and polyaniline and polythiophene-based conductive polymers, but are not limited thereto.

As the hole transporting material, a material capable of transporting holes from the anode or the hole injection layer and transferring the holes to the light emitting layer is suitable. Specific examples thereof include an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together, but are not limited thereto.

The emission layer may emit red, green, or blue light, and may be formed of a phosphor or a fluorescent material. The light emitting material is a material capable of emitting light in the visible region by receiving and combining holes and electrons from the hole transporting layer and the electron transporting layer, respectively, and a material having good quantum efficiency with respect to fluorescence or phosphorescence is preferable. Specific examples thereof include 8-hydroxyquinoline aluminum complex (Alq ₃ ); Carbazole series compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compound; Benzoxazole, benzthiazole and benzimidazole series compounds; Poly (p-phenylenevinylene) (PPV) -based polymers; Spiro compounds; Polyfluorene, rubrene and the like, but are not limited thereto.

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

Iridium complex used as the dopant of the light emitting layer is as follows, but is not limited thereto.

As the electron transporting material, a material capable of injecting electrons well from the cathode and transferring the electrons to the light emitting layer is suitable. Specific examples include Al complexes 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 top emission type, a bottom emission type or a double-sided emission type depending on the material used.

Hereinafter, the present invention will be described in detail with reference to Examples. However, embodiments according to the present disclosure 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. 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 to 1D

Preparation Example 1-1 Synthesis of Intermediate 1A

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 800 ml of tetrahydrofuran and stirred in a nitrogen atmosphere. Potassium carbonate (61.4 g, 444.5 mmol) was added while dissolved in water. Then heated to reflux tetrakis (triphenylphosphine) palladium (0) (2.6 g, 1 mol%) was slowly added. After the reaction proceeds for about 9 hours the reaction was terminated. After the reaction was completed, the temperature was lowered to room temperature (25 ° C.), and the produced solid was filtered. The filtered solid was dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, stirred, and filtered. The filtrate was distilled under reduced pressure. The concentrate was purified through a silica column using chloroform and ethyl acetate to prepare an intermediate 1A (40.0 g, yield: 49%) as a white solid compound.

MS: [M + H] &lt; + &gt; = 368

Preparation Example 1-2 Synthesis of Intermediate 1B

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

MS: [M + H] &lt; + &gt; = 444

Preparation Example 1-3 Synthesis of Intermediate 1C

Intermediate as in Synthesis of Intermediate 1B of Preparation Example 1-2, except that (3-chlorophenyl) boronic acid (20.0g, 89.9mmol) was used instead of (4-chlorophenyl) boronic acid (20.0g, 89.9mmol) 1C (24.9 g, yield: 69%) was prepared.

MS: [M + H] &lt; + &gt; = 444

Preparation Example 1-4 Synthesis of Intermediate 1D

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

MS: [M + H] &lt; + &gt; = 444

I. Synthesis of Intermediates 2A and 2B

Preparation Example 2-1 Synthesis of Intermediate 2A

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 800 ml of tetrahydrofuran and stirred in a nitrogen atmosphere. Potassium carbonate (61.4 g, 444.5 mmol) was added while dissolved in water. Then heated to reflux tetrakis (triphenylphosphine) palladium (0) (2.6 g, 1 mol%) was slowly added. After the reaction proceeds for about 9 hours the reaction was terminated. After the reaction was completed, the temperature was lowered to room temperature (25 ° C.), and the produced solid was filtered. The filtered solid was dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, stirred, and filtered. The filtrate was distilled under reduced pressure. The concentrate was purified through a silica column using chloroform and ethyl acetate to give an intermediate 2A (47.3 g, yield: 58%) as a white solid compound.

MS: [M + H] &lt; + &gt; = 368

Preparation Example 2-2 Synthesis of Intermediate 2B

In a nitrogen atmosphere, Chemical Formulas 2A (30.0 g, 81.7 mmol) and (4-chlorophenyl) boronic acid (20.0 g, 89.9 mmol) were added to 400 ml of tetrahydrofuran and potassium carbonate (33.9 g, 245.2 mmol) was dissolved in water with stirring. Added. After heating, tetrakis (triphenylphosphine) palladium (0) (2.8 g, 3 mol%) was slowly added at reflux. After the reaction proceeded for about 4 hours and the reaction was terminated. After the reaction was completed, the temperature was lowered to room temperature (25 ° C.), and the produced solid was filtered. The filtered solid was dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, stirred, and filtered. The filtrate was distilled under reduced pressure. The concentrate was purified through a silica column using chloroform and ethyl acetate to give an intermediate 2B (25.3 g, yield: 70%) as a white solid compound.

MS: [M + H] &lt; + &gt; = 444

All. Synthesis of Intermediates 3A and 3B

Preparation Example 3-1 Synthesis of Intermediate 3A

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 800 ml of tetrahydrofuran and stirred in a nitrogen atmosphere. Potassium carbonate (61.4 g, 444.5 mmol) was added while dissolved in water. Then heated to reflux tetrakis (triphenylphosphine) palladium (0) (2.6 g, 1 mol%) was slowly added. After the reaction proceeds for about 9 hours the reaction was terminated. After the reaction was completed, the temperature was lowered to room temperature (25 ° C.), and the produced solid was filtered. The filtered solid was dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, stirred, and filtered. The filtrate was distilled under reduced pressure. The concentrate was purified through a silica column using chloroform and ethyl acetate to give an intermediate 3A (40.8 g, yield: 50%) as a white solid compound.

MS: [M + H] &lt; + &gt; = 368

Preparation Example 3-2 Synthesis of Intermediate 3B

In a nitrogen atmosphere, chemical formulas 3A (30.0 g, 81.7 mmol) and (4-chlorophenyl) boronic acid (20.0 g, 89.9 mmol) were added to 400 ml of tetrahydrofuran, and potassium carbonate (33.9 g, 245.2 mmol) was dissolved in water while stirring. Added. After heating, tetrakis (triphenylphosphine) palladium (0) (2.8 g, 3 mol%) was slowly added at reflux. After the reaction proceeded for about 4 hours and the reaction was terminated. After the reaction was completed, the temperature was lowered to room temperature (25 ° C.), and the produced solid was filtered. The filtered solid was dissolved in chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, stirred, and filtered. The filtrate was distilled under reduced pressure. The concentrate was purified through a silica column using chloroform and ethyl acetate to give an intermediate 3B (27.8 g, yield: 77%) as a white solid compound.

MS: [M + H] &lt; + &gt; = 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) and stirred and refluxed. Thereafter, potassium carbonate (27.6 g, 200.0 mmol) was dissolved in water, and sufficiently stirred, followed by bis (tri-t-butylphosphine) palladium (0) (2.3 g, mol%). After 9 hours of reaction, the temperature was lowered to room temperature and filtered. The filtrate was extracted with chloroform and water, and the organic layer was dried over magnesium sulfate. After distilling under reduced pressure, the organic layer was 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] &lt; + &gt; = 575

Synthesis Example 2 Synthesis of Compound 2

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

MS: [M + H] &lt; + &gt; = 575

Synthesis Example 3 Synthesis of Compound 3

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

MS: [M + H] &lt; + &gt; = 575

Synthesis Example 4 Synthesis of Compound 4

Except for using (9-phenyl-9H-carbazol-4-yl) boronic acid (16.2 g, 66.7 mmol) 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 Synthesis of Compound 1 of Synthesis Example 1.

MS: [M + H] &lt; + &gt; = 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) and stirred and refluxed. Thereafter, potassium carbonate (27.6 g, 200.0 mmol) was dissolved in water, and sufficiently stirred, followed by bis (tri-t-butylphosphine) palladium (0) (2.3 g, mol%). After 9 hours of reaction, the temperature was lowered to room temperature and filtered. The filtrate was extracted with chloroform and water, and the organic layer was dried over magnesium sulfate. After distilling under reduced pressure, the organic layer was 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] &lt; + &gt; = 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 the synthesis of Compound 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 tert-butoxide (6.5 g, 67.7 mmol) was added to warm. Bis (tri tert-butylphosphine) palladium (0.5 g, 3 mol%) was added thereto, followed by stirring under reflux for 12 hours. After the reaction was completed, the temperature was lowered to room temperature, and the produced solid was filtered. The solid was dissolved in 700 mL of chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, stirred, and filtered. The filtrate was distilled under reduced pressure. The concentrated compound was purified through a silica column using chloroform and ethyl acetate to prepare a 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 (9.6 g, 33.8 mmol) was used instead of 9H-carbazole (5.7 g, 33.8 mmol) Compound 9 (7.7 g, yield: 33%) was prepared in the same manner 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 (9.6 g, 33.8 mmol) was used instead of 9H-carbazole (5.7 g, 33.8 mmol). Compound 10 (10.3 g, yield: 41%) was prepared in the same manner as 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) and stirred and refluxed. Thereafter, potassium carbonate (27.6 g, 200.0 mmol) was dissolved in water, and sufficiently stirred, followed by bis (tri-t-butylphosphine) palladium (0) (2.3 g, mol%). After 9 hours of reaction, the temperature was lowered to room temperature and filtered. The filtrate was extracted with chloroform and water, and the organic layer was dried over magnesium sulfate. After distilling under reduced pressure, the organic layer was 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] &lt; + &gt; = 575

Synthesis Example 12 Synthesis of Compound 12

Compound 12 (9.1 g, yield: 25%) was prepared in the same manner as in the 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 the synthesis of Compound 9 of Synthesis Example 9, except that 3B was used instead of Intermediate 1C (15.0 g, 33.9 mmol).

MS: [M + H] + = 691

Experimental Example

Experimental Example 1

The glass substrate coated with ITO (indium tin oxide) having a thickness of 1,300 kPa was put in distilled water in which detergent was dissolved and ultrasonically cleaned. In this case, Fischer Co. was used as a detergent, and distilled water was filtered secondly as a filter of Millipore Co. as a distilled water. After ITO was washed for 30 minutes, ultrasonic washing was performed twice with distilled water for 10 minutes. After the distilled water was washed, ultrasonic washing with a solvent of isopropyl alcohol, acetone, methanol, dried and transported to a plasma cleaner. In addition, the substrate was cleaned for 5 minutes using an oxygen plasma, and then the substrate was 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 kPa to form a hole injection layer. A hole transport layer was formed by thermal vacuum deposition of the following HT-1 compound to a thickness of 250 kPa on the hole injection layer, and an electron blocking layer was formed by vacuum depositing the following HT-2 compound to a thickness of 50 kPa on the HT-1 deposition film. Compound 1, the following YGH-1 compound, and phosphorescent dopant YGD-1, which were prepared in Preparation Example 1 as a light emitting layer on the HT-2 deposited film, were co-deposited at a weight ratio of 44:44:12 to form a light emitting layer having a thickness of 400 kHz. The following ET-1 compound was vacuum deposited to a thickness of 250 kPa on the light emitting layer to form an electron transport layer, and the following ET-2 compound and Li were vacuum deposited on the electron transport layer at a weight ratio of 98: 2 to form an electron injection layer having a thickness of 100 kW. Formed. Aluminum was deposited to a thickness of 1000 Å on the electron injection layer to form a cathode.

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

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 described 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 above experimental examples and comparative examples, the organic light emitting diodes were measured voltage and efficiency at a current density of 10 mA / cm ² , and lifespan was measured at a current density of 50 mA / cm ² , and the results are shown in Table 1 below. In this case, LT ₉₅ refers to a time when the luminance becomes 95% of the initial luminance.

	compound	Voltage (V) (@ 10mA / cm 2 )	Efficiency (Cd / A) (@ 10mA / cm 2 )	Color coordinates (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 Experiment 2	CE2	5.0	64	0.46, 0.55	11
Comparative Experiment 3	CE3	4.2	80	0.46, 0.55	90
Comparative Experiment 4	CE4	4.4	79	0.47, 0.60	20
Comparative Example 5	CE5	4.7	61	0.58, 0.61	5
Comparative Experiment 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 exhibits excellent efficiency and lifespan as compared to the comparative experimental example. This is a combination of a triphenyl group bond to a triazine unit and a carbazole group bond to a triazine unit, which is excellent in the stability of the material and excellent in efficiency, lifetime, and the like of the device. In addition, the distance between the carbazole and the triazine is about one long rather than far, which is advantageous for life.

Claims (9)

1. Compound represented by the following formula (1) or formula (2):

   [Formula 1]

   

   [Formula 2]

   

   In Chemical Formula 1 and Chemical 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; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

   L 1 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 of 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.
2. The method according to claim 1,

   Formula 1 is a compound represented by any one of the following formulas 3 to:

   [Formula 3]

   

   [Formula 4]

   

   [Formula 5]

   

   [Formula 6]

   

   In Chemical Formulas 3 to 6,

   X1 to X3, L1, R1, R2 and a are as defined in claim 1.
3. The method according to claim 1,

   Formula 2 is a compound represented by any one of the following formula 7 to 9:

   [Formula 7]

   

   [Formula 8]

   

   [Formula 9]

   

   In Chemical Formulas 7 to 9,

   L2 is as defined in claim 1,

   A1 to A5 are each independently hydrogen; heavy hydrogen; Halogen group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; 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 of 0 to 4,

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

   a8 is an integer of 0-8.
4. The method according to claim 1,

   Formula 1 is a compound represented by any one of the following structures:

   

   

   .
5. The method according to claim 1,

   Formula 2 is a compound represented by any one of the structures:

   

   .
6. A first electrode; A second electrode provided to face the first electrode; And at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers comprises a compound according to any one of claims 1 to 5. Light emitting element.
7. The method according to claim 6,

   The organic material layer comprises a hole injection layer or a hole transport layer, the hole injection layer or hole transport layer is an organic light emitting device comprising the compound of Formula 1 or Formula 2.
8. The method according to claim 6,

   The organic material layer comprises an electron transport layer or an electron injection layer, the electron transport layer or an electron injection layer is an organic light emitting device comprising a compound represented by the formula (1) or (2).
9. The method according to claim 6,

   The organic material layer comprises a light emitting layer, the light emitting layer is an organic light emitting device comprising a compound represented by the formula (1) or (2).

Images