WO2019143224A1 - 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 compounds and organic light emitting devices containing them

The present invention claims the benefit of Korean Patent Application No. 10-2018-0007648 filed on January 22, 2018 with the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference.

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

In the present specification, an organic light emitting element is a light emitting element 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 classified into two types according to the operating principle as described below. First, an exciton is formed in an organic material layer by a photon introduced into an element from an external light source. The exciton is separated into an electron and a hole, and the electrons and holes are transferred to different electrodes to be used as a current source Emitting device. The second type is a light emitting device that injects holes and / or electrons into an organic semiconductor material layer that interfaces with the electrode by applying a voltage or current to two or more electrodes, and operates by injected electrons and holes.

In general, organic light emission phenomenon refers to a phenomenon in which an organic material is used to convert electric energy into light energy. An organic light emitting device using an organic light emitting phenomenon generally has a structure including an anode, 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 may have a multi-layer structure composed of different materials and may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. When a voltage is applied between the two electrodes in the structure of such an organic light emitting device, holes are injected in the anode, electrons are injected into the organic layer in the cathode, excitons are formed when injected holes and electrons meet, When it falls back to the ground state, the light comes out. Such an organic light emitting device is known to have characteristics such as self-emission, high luminance, high efficiency, low driving voltage, wide viewing angle, and high contrast.

A material used as an organic material layer in an organic light emitting device can be classified into a light emitting material and a charge transporting material such as a hole injecting material, a hole transporting material, an electron transporting material, and an electron injecting material depending on functions. The luminescent material has blue, green and red luminescent materials and yellow and orange luminescent materials necessary for realizing a better natural color depending on the luminescent color.

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

In order to sufficiently exhibit the excellent characteristics of the organic light emitting device described above, materials constituting the organic material layer in the device, such as a hole injecting material, a hole transporting material, a light emitting material, an electron transporting material and an electron injecting material are supported by stable and efficient materials Development of new materials is continuously required.

In the present specification, polycyclic compounds and organic light emitting devices containing them are described.

Wherein one embodiment of the present specification is represented by the following general formula (1) or (2).

[Chemical Formula 1]

(2)

In formulas (1) and (2)

X1 to X6 and Y1 to Y6 each independently represent N or CR,

At least two of X1 to X3, at least two of X4 to X6, at least two of Y1 to Y3 and at least two of Y4 to Y6 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 and L2 are each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heterocyclic group,

R1 is a substituted or unsubstituted aryl group,

R2 and R3 are each independently selected from the group consisting of hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

a is an integer of 0 to 7,

b is an integer of 1 to 8,

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

Provided that when L2 is a direct bond, R < 3 > is deuterium; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or adjacent R3's are bonded to each other to form a ring.

According to an embodiment of the present invention, there is also provided a plasma display panel comprising: a first electrode; A second electrode facing the first electrode; And at least one organic compound layer disposed between the first electrode and the second electrode, wherein at least one of the organic compound layers includes the compound.

The compound described in this specification can be used as a material of an organic layer of an organic light emitting device. The compound according to at least one embodiment can improve the life characteristics in the organic light emitting device and / or the organic light emitting device. In particular, the compounds described in this specification can be used as materials for the hole injecting layer, the hole transporting layer, the electron blocking layer, the light emitting layer, the hole blocking layer, the electron transporting layer and the electron injecting layer.

Fig. 1 shows an example of an organic light-emitting device comprising a substrate 1, an anode 2, a light-emitting layer 3 and a cathode 4. Fig.

2 shows an example of an organic light emitting element comprising a substrate 1, an anode 2, a hole injecting layer 5, a hole transporting layer 6, a light emitting layer 7, an electron transporting layer 8 and a cathode 4 It is.

<Description of Symbols>

1: substrate

2: anode

3: light emitting layer

4: cathode

5: Hole injection layer

6: hole transport layer

7:

8: Electron transport layer

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

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

 [Chemical Formula 1]

(2)

In formulas (1) and (2)

X1 to X6 and Y1 to Y6 each independently represent N or CR,

At least two of X1 to X3, at least two of X4 to X6, at least two of Y1 to Y3 and at least two of Y4 to Y6 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 and L2 are each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heterocyclic group,

R1 is a substituted or unsubstituted aryl group,

R2 and R3 are each independently selected from the group consisting of hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

a is an integer of 0 to 7,

b is an integer of 1 to 8,

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

Provided that when L2 is a direct bond, R &lt; 3 &gt; is deuterium; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or adjacent R3's are bonded to each other to form a ring.

In this specification, when a part is referred to as "including " an element, it is to be understood that it may include other elements as well, without departing from the other elements unless specifically stated otherwise.

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

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

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

As used herein, the term " substituted or unsubstituted " A halogen group; Cyano; 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 a substituted or unsubstituted heterocyclic group, or that at least two of the substituents exemplified above are substituted with a substituent to which they are linked, or have no substituent. For example, "a substituent to which at least two substituents are connected" may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent in which two phenyl groups are connected.

Illustrative examples of such substituents are set forth below, but are not limited thereto.

In this 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, and the number of carbon atoms is not particularly limited, but is preferably 1 to 60. According to one embodiment, the alkyl group has 1 to 30 carbon atoms. According to another embodiment, the alkyl group has 1 to 20 carbon atoms. According to another embodiment, the alkyl group has 1 to 10 carbon atoms. Specific examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, a n-butyl group, an isobutyl group, a tert- And a til group, but are not limited thereto.

In this specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms. According to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specific examples thereof include, but are not limited to, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and a cyclooctyl group.

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 containing two or more aryl groups may contain 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, an anthracenylamine group, a 3-methylphenylamine group, a 4-methylnaphthylamine group, Group, a 9-methyl-anthracenylamine group, a diphenylamine group, a phenylnaphthylamine group, a biphenylphenylamine group, and the like, but the present invention is 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 one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a phenyl group, a biphenyl group, a terphenyl group or the like as the monocyclic aryl group, but is not limited thereto. Examples of the polycyclic aryl group include, but are not limited to, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a perylenyl group, a triphenyl group, a klycenyl group and a fluorenyl group.

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,

, A spirofluorenyl group

(9,9-dimethylfluorenyl group), and

(9,9-diphenylfluorenyl group), and the like. However, the present invention is not limited thereto.

In the present specification, the heterocyclic group is a heteroaromatic ring group containing at least one of N, O, P, S, Si and Se. The number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms. According to one embodiment, the number of carbon atoms of the heterocyclic group is 2 to 30. Examples of the heterocyclic group include a pyridyl group, a pyrrolyl group, a pyrimidyl group, a pyridazinyl group, a furanyl group, a thiophenyl group, an imidazole group, a pyrazole group, a dibenzofuranyl group and a dibenzothiophenyl group. The present invention is not limited thereto.

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

In this specification, "adjacent" The group may mean a substituent substituted on an atom directly connected to the substituted atom, a substituent stereostructically closest to the substituent, or another substituent substituted on the substituted atom of the substituent. 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 to each other.

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

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

In the present specification, the hetero ring includes one or more non-carbon atoms and hetero atoms. Specifically, the hetero atom includes at least one atom selected from the group consisting of N, O, P, S, Si and Se can do. The heterocyclic ring may be monocyclic or polycyclic, and may be an aromatic, aliphatic or aromatic and aliphatic condensed ring, and the aromatic heterocyclic ring may be selected from the examples of the heteroaryl group except that it is not monovalent.

According to one embodiment of the present invention, the formula (1) is represented by any one of the following formulas (3) to (6).

(3)

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

In formulas (3) to (6)

X1 to X3, Y1 to Y3, L1, R1, R2 and a are as defined above.

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

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

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

According to one embodiment of the present disclosure, X1 to X3 are N.

According to one embodiment of the present disclosure, Y1 and Y2 are N and Y3 is CR.

According to one embodiment of the present disclosure, Y1 and Y3 are N and Y2 is CR.

According to one embodiment of the present disclosure, Y2 and Y3 are N and Y1 is CR.

According to one embodiment of the present disclosure, Y1 to Y3 are N.

According to one embodiment of the present disclosure, X4 and X5 are N and X6 is CR.

According to one embodiment of the present disclosure, X4 and X6 are N and X5 is CR.

According to one embodiment of the present disclosure, X5 and X6 are N and X4 is CR.

According to one embodiment of the present disclosure, X4 to X6 are N.

According to one embodiment of the present disclosure, Y4 and Y5 are N and Y6 is CR.

According to one embodiment of the present disclosure, Y4 and Y6 are N and Y5 is CR.

According to one embodiment of the present disclosure, Y5 and Y6 are N and Y4 is CR.

According to one embodiment of the present disclosure, Y4 to Y6 are N.

According to one embodiment of the present disclosure, R is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted C6 to C30 aryl; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

According to one embodiment of the present disclosure, R is hydrogen; Or deuterium.

According to one embodiment of the present disclosure, L1 and L2 are each independently a direct bond; A substituted or unsubstituted arylene group having 6 to 30 carbon atoms or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

According to one embodiment of the present disclosure, L1 and L2 are each independently a direct bond; A substituted or unsubstituted arylene group having 6 to 15 carbon atoms or a substituted or unsubstituted heterocyclic group having 2 to 15 carbon atoms.

According to one embodiment of the present disclosure, L1 and L2 are each independently a direct bond; Or a substituted or unsubstituted arylene group having 6 to 15 carbon atoms.

According to one embodiment of the present disclosure, L1 and L2 are each independently a direct bond; Or a substituted or unsubstituted phenylene group.

According to one embodiment of the present disclosure, when L2 is a direct bond, R3 is selected from the group consisting of deuterium; A substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group, or adjacent R3's are bonded to each other to form a ring.

According to one embodiment of the present invention, when L2 is a direct bond, R3 is a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group, or adjacent R3 is bonded to each other to form a ring.

According to one embodiment of the present disclosure, when L2 is a direct bond, R3 is a substituted or unsubstituted aryl group, or adjacent R3 is bonded to each other to form a ring.

According to one embodiment of the present disclosure, when L2 is a direct bond, R3 is a substituted or unsubstituted aryl group, or adjacent R3 is bonded to each other to form a substituted or unsubstituted hydrocarbon ring.

According to one embodiment of the present disclosure, when L2 is a direct bond, R &lt; 3 &gt; is a substituted or unsubstituted phenyl group, or adjacent R &

. Here, A1 to A3 each independently represent hydrogen; heavy hydrogen; A 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 is an integer of 0 to 4, and * represents a substituted position.

According to one embodiment of the present disclosure, when L2 is a direct bond, R &lt; 3 &gt; is a phenyl group, or adjacent R &

. Herein, A1 is hydrogen, A2 and A3 are each independently a substituted or unsubstituted alkyl group, a1 is 4, and * indicates substitution position.

According to one embodiment of the present disclosure, A2 and A3 are methyl groups.

According to one embodiment of the present invention, R 1 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

According to one embodiment of the present invention, R 1 is a substituted or unsubstituted aryl group having 6 to 15 carbon atoms.

According to one embodiment of the present disclosure, R 1 is a substituted or unsubstituted phenyl group.

According to one embodiment of the present disclosure, R2 and R3 are each independently selected from the group consisting of hydrogen; heavy hydrogen; 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 one embodiment of the present disclosure, R2 and R3 are each independently selected from the group consisting of hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group having 6 to 15 carbon atoms or a substituted or unsubstituted heterocyclic group having 2 to 15 carbon atoms.

According to one embodiment of the present disclosure, R2 and R3 are each independently selected from the group consisting of hydrogen; Or deuterium.

According to one embodiment of the present disclosure, R2 and R3 are hydrogen.

According to one embodiment of the present invention, R 3 is a substituted or unsubstituted aryl group having 6 to 15 carbon atoms.

According to one embodiment of the present disclosure, R 3 is a substituted or unsubstituted phenyl group.

According to one embodiment of the present disclosure, a and b are 0 or 1.

According to one 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 an aromatic hydrocarbon ring.

According to one 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 an aromatic hydrocarbon ring having 4 to 30 carbon atoms.

According to one embodiment of the present invention, when a and b are each independently 2 or more, adjacent R2 or R3 may combine with each other to form an aromatic hydrocarbon ring having 4 to 15 carbon atoms.

According to one embodiment of the present invention, the formula (1) is represented by any one of the following structures.

According to one embodiment of the present invention, the formula (2) is represented by any one of the following structures.

Substituents of the compounds of formula (1) or (2) herein may be combined by methods known in the art, and the type, position and number of substituents may be varied 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 bandgap.

In the present invention, compounds having various energy bandgaps can be synthesized by introducing various substituents into the core structure as described above. Further, in the present invention, the HOMO and LUMO energy levels of the compound can be controlled by introducing various substituents to the core structure having the above structure.

Further, by introducing various substituents into the core structure having the above structure, it is possible to synthesize a compound having the intrinsic characteristics of the substituent introduced. For example, by introducing a substituent mainly used in a hole injecting layer material, a hole transporting material, a light emitting layer material, and an electron transporting layer material used in manufacturing an organic light emitting device into the core structure, a material meeting the requirements of each organic layer is synthesized .

Further, the organic light emitting device according to the present invention includes a first electrode; A second electrode facing the first electrode; And at least one organic compound layer disposed between the first electrode and the second electrode, wherein at least one of the organic compound layers includes the compound of Formula 1 or Formula 2.

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

The compound may be formed into an organic material layer by a solution coating method as well as a vacuum deposition method in the production of an organic light emitting device. Here, the solution coating method refers to spin coating, dip coating, inkjet printing, screen printing, spraying, 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 injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and an electron injecting layer 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 layers.

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

In another embodiment, the organic layer includes a light-emitting layer, and the light-emitting layer includes a compound represented by the general formula (1) or (2).

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

In another embodiment, the organic material layer containing the compound represented by the above formula (1) or (2) contains a compound represented by the above formula (1) or (2) as a dopant and includes a fluorescent host or a phosphorescent host. A compound, a metal or a metal compound as a dopant.

As another example, the organic material layer containing the compound represented by Formula 1 or Formula 2 includes a compound represented by Formula 1 or Formula 2 as a dopant and includes a fluorescent host or a phosphorescent host, and an iridium-based (Ir ) Dopants.

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

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

The structure of the organic light emitting device of the present invention may have a structure as shown in FIGS. 1 and 2, but the present invention 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 laminated on a substrate 1. In FIG. 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 injecting layer 5, a hole transporting layer 6, a light emitting layer 7, an electron transporting layer 8 and a cathode 4 are sequentially laminated on a substrate 1 Structure is illustrated. In such a structure, the compound may be included in the hole injecting layer 5, the hole transporting layer 6, the light emitting layer 7, or the electron transporting layer 8.

For example, the organic light emitting device according to the present invention may be formed by using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation to form a metal oxide or a metal oxide having conductivity on the substrate, To form an anode, an organic material layer including a hole injection layer, a hole transporting layer, a light emitting layer, and an electron transporting layer is formed on the anode, and a material which can be used as a cathode is deposited thereon. In addition to such a method, an organic light emitting device may be formed 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. The organic material layer may be formed using a variety of polymeric materials by a method such as a solvent process such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, Layer.

As the anode material, a material having a large work function is preferably used so that hole injection can be smoothly conducted into the organic material layer. Specific examples of the cathode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO: Al or SnO _2: a combination of a metal and an oxide such as Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole and polyaniline.

The negative electrode material is preferably 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; Layer structure materials such as LiF / Al or LiO ₂ / Al, but are not limited thereto.

As the hole injecting material, it is preferable that the highest 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 layer. Specific examples of the hole injecting material include metal porphyrine, oligothiophene, arylamine-based organic materials, hexanitrile hexaazatriphenylene-based organic materials, quinacridone-based organic materials, perylene , Anthraquinone, polyaniline and polythiophene-based conductive polymers, but the present invention is not limited thereto.

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

The light emitting layer may emit red, green or blue light, and may be formed of a phosphor or a fluorescent material. The light emitting material is preferably a material capable of emitting light in the visible light region by transporting and receiving holes and electrons from the hole transporting layer and the electron transporting layer, respectively, and 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-hydroxybenzoquinoline-metal compounds; Compounds of the benzoxazole, benzothiazole and benzimidazole series; Polymers of poly (p-phenylenevinylene) (PPV) series; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited thereto.

Examples of the host material of the light emitting layer include a condensed aromatic ring derivative or a heterocyclic compound. Specific examples of the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds. Examples of the heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

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

As the electron transporting material, a material capable of transferring electrons from the cathode well into the light emitting layer, which is suitable for electrons, is suitable. Specific examples include an Al complex of 8-hydroxyquinoline; Complexes containing 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 both-sided emission type, depending on the material used.

Hereinafter, the present invention will be described in detail by way of examples with reference to the drawings. However, the embodiments according to the present disclosure can be modified in various other forms, and the scope of the present application is not construed as being limited to the embodiments described below. The embodiments of the present application are provided to enable those skilled in the art to more fully understand the present invention.

[Synthesis Example]

end. Synthesis of intermediates 1A to 1K

[Preparation Example 1] Synthesis of intermediate 1A

2-chloro-4,6-diphenyl-1,3,5-triazine (50.0 g, 187.2 mmol) and (2-chlorophenyl) boronic acid (35.1 g, 224.7 mmol) were added to 400 ml of tetrahydrofuran in a nitrogen atmosphere Potassium carbonate (77.6 g, 561.8 mmol) was dissolved in water while stirring. Tetrakis (triphenylphosphine) palladium (0) (6.5 g, 3 mol%) was slowly added under heating at reflux. The reaction was then terminated after about 9 hours of reaction. When the reaction was completed, the temperature was lowered to room temperature (25 ° C), and the resulting solid was filtered. The filtered solid was dissolved in chloroform and washed twice with water. The organic layer was separated, and anhydrous magnesium sulfate was added thereto, followed by stirring, followed by filtration, and the filtrate was distilled under reduced pressure. The concentrate was purified through a silica column using chloroform and hexane to obtain an intermediate 1A (31.5 g, yield: 49%) as a white solid compound.

MS: [M + H] &lt; + &gt; = 344

[Manufacturing Example 2] Synthesis of Intermediate 1B

(30 g, 87.4 mmol), bis (pinacolato) diboron (24.4 g, 96.2 mmol) and potassium acetate (25.7 g, 262.3 mmol) were added to 300 ml of dioxane and heated with stirring in a nitrogen atmosphere . Bis (dibenzylidineacetone) palladium (1.5 g, 3 mol%) and tricyclohexylphosphine (2.2 g, 6 mol%) were added under reflux and heated and stirred for 13 hours. After completion of the reaction, the temperature was lowered to room temperature (25 캜) and then filtered. Water was poured into the filtrate, extracted with chloroform, and the organic layer was dried over anhydrous magnesium sulfate. After distillation under reduced pressure, recrystallization with ethanol gave Intermediate 1B (33.5 g, yield: 88%). [M + H] &lt; + &gt; = 436

[Manufacturing Example 3] Synthesis of Intermediate 1C

(50.0 g, 222.2 mmol) and (9-phenyl-9H-carbazol-1-yl) boronic acid (63.8 g, 222.2 mmol) Was added to 800 ml of tetrahydrofuran and potassium carbonate (61.4 g, 444.5 mmol) was dissolved in water and added with stirring. Tetrakis (triphenylphosphine) palladium (0) (2.6 g, 1 mol%) was slowly added under heating at reflux. The reaction was then terminated after about 9 hours of reaction. When the reaction was completed, the temperature was lowered to room temperature (25 ° C), and the resulting solid was filtered. The filtered solid was dissolved in chloroform and washed twice with water. The organic layer was separated, and anhydrous magnesium sulfate was added thereto, followed by stirring, followed by filtration, and the filtrate was distilled under reduced pressure. The concentrate was purified through a silica column using chloroform and ethyl acetate to obtain a white solid compound 1C (67.2 g, yield: 70%).

MS: [M + H] &lt; + &gt; = 433

[Preparation Example 4] Synthesis of Intermediate 1D

Synthesis of Intermediate 1C of Synthesis Example 1-3 was repeated except that 9-phenyl-9H-carbazol-2-yl) boronic acid was used instead of 9-phenyl-9H-carbazol- Intermediate 1D was synthesized in the same manner. (52.8 g, yield: 55%).

MS: [M + H] &lt; + &gt; = 433

[Manufacturing Example 5] Synthesis of Intermediate 1E

Synthesis of Intermediate 1C of Synthesis Example 1-3 was repeated except that (9-phenyl-9H-carbazol-3-yl) boronic acid was used instead of 9-phenyl-9H-carbazol- Intermediate 1E was synthesized in the same manner. (59.5 g, yield: 62%).

MS: [M + H] &lt; + &gt; = 433

[Manufacturing Example 6] Synthesis of Intermediate 1F

Synthesis of Intermediate 1C of Synthesis Example 1-3 was repeated except that (9-phenyl-9H-carbazol-3-yl) boronic acid was used instead of 9-phenyl-9H-carbazol- Intermediate 1F was synthesized in the same manner. (50.9 g, yield: 53%).

MS: [M + H] &lt; + &gt; = 433

[Manufacturing Example 7] Synthesis of Intermediate 1G

In a nitrogen atmosphere, 9H-carbazole (54.0 g, 222.2 mmol) was added to 500 mL of dimethyformamide, cooled to 0 ^° C and slowly added with sodium hydride (10.7 g, 444.6 mmol) with stirring. 2,4-dichloro-6-phenyl-1,3,5-triazine (50.0 g, 222.2 mmol) was slowly added. After the reaction proceeded for about 2 hours, the reaction was terminated. When the reaction was completed, 1.5 L of water was added dropwise, and the resulting solid was filtered. The filtered solid was dissolved in chloroform and washed twice with water. The organic layer was separated, and anhydrous magnesium sulfate was added thereto, followed by stirring, followed by filtration, and the filtrate was distilled under reduced pressure. The concentrate was purified through a silica column using chloroform and ethyl acetate to obtain 37.5 g (39%) of Intermediate 1G as a white solid compound.

MS: [M + H] &lt; + &gt; = 433

[Preparation Example 8] Synthesis of intermediate 1H

2,4-dichloro-6-phenyl-1,3,5-triazine (50.0 g, 222.2 mmol) and (4-chlorophenyl) boronic acid (35.1 g, 224.7 mmol) were added to 400 ml of tetrahydrofuran in a nitrogen atmosphere Potassium carbonate (77.6 g, 561.7 mmol) was dissolved in water and added with stirring. Tetrakis (triphenylphosphine) palladium (0) (6.5 g, 3 mol%) was slowly added under heating at reflux. The reaction was then terminated after about 9 hours of reaction. When the reaction was completed, the temperature was lowered to room temperature (25 ° C), and the resulting solid was filtered. The filtered solid was dissolved in chloroform and washed twice with water. The organic layer was separated, and anhydrous magnesium sulfate was added thereto, followed by stirring, followed by filtration, and the filtrate was distilled under reduced pressure. The concentrate was purified through a silica column using chloroform and ethyl acetate to obtain an intermediate 1H (46.3 2, yield: 69%) as a white solid compound.

MS: [M + H] &lt; + &gt; = 303

[Manufacturing Example 9] Synthesis of Intermediate 1I

(30.0 g, 99.7 mmol) and 1B (43.4 g, 99.7 mmol) were added to 400 ml of tetrahydrofuran in a nitrogen atmosphere and potassium carbonate (27.5 g, 199.3 mmol) was dissolved in water while stirring. After heating, tetrakis (triphenylphosphine) palladium (0) (3.5 g, 3 mol%) was slowly added under reflux. After the reaction was completed for about 4 hours, the reaction was terminated. When the reaction was completed, the temperature was lowered to room temperature (25 ° C), and the resulting solid was filtered. The filtered solid was dissolved in chloroform and washed twice with water. The organic layer was separated, and anhydrous magnesium sulfate was added thereto, followed by stirring, followed by filtration, and the filtrate was distilled under reduced pressure. The concentrate was purified through a silica column using chloroform and ethyl acetate to obtain 36.1 g (yield: 64%) of a white solid, Intermediate 1I.

MS: [M + H] &lt; + &gt; = 576

[Production Example 10] Synthesis of intermediate 1J

Except that 4,6-dichloro-2-phenylpyrimidine was used instead of 2,4-dichloro-6-phenyl-1,3,5-triazine in the same manner as in the synthesis of Intermediate 1H of Synthesis Example 1-8 1J was synthesized (30.7 g, yield: 46%).

MS: [M + H] &lt; + &gt; = 302

[Manufacturing Example 11] Synthesis of Intermediate 1K

Intermediate 1K was synthesized in the same manner as Intermediate 1I of Preparation Example 9, except that 1J was used instead of 1H. (31.5 g, yield: 55%).

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

I. Synthesis of compounds 1 to 8

[Synthesis Example 1] Synthesis of Compound 1

To a solution of Intermediate 1C (15.0 g, 34.7 mmol) and Intermediate 1B (18.1 g, 41.7 mmol) in 400 ml of tetrahydrofuran was added potassium carbonate (14.4 g, 104.1 mmol) dissolved in water under stirring. Then, by heating, tetrakis (triphenylphosphine) palladium (0) (1.2 g, 3 mol%) was slowly added under reflux. After the reaction was completed for about 6 hours, the reaction was terminated. When the reaction was completed, the temperature was lowered to room temperature (25 ° C), and the resulting solid was filtered. The filtered solid was dissolved in chloroform and washed twice with water. The organic layer was separated, and anhydrous magnesium sulfate was added thereto, followed by stirring, followed by filtration, and the filtrate was distilled under reduced pressure. The concentrate was purified through a silica column using chloroform and ethyl acetate to give Compound 1 (8.1 g, yield: 33%) as a white solid compound.

MS: [M + H] &lt; + &gt; = 706

[Synthesis Example 2] Synthesis of Compound 2

Compound 2 was synthesized in the same manner as Compound 1 of Synthesis Example 1 except that 1D was used instead of 1C. (9.0 g, yield: 38%).

MS: [M + H] &lt; + &gt; = 706

[Synthesis Example 3] Synthesis of Compound 3

Compound 3 was synthesized in the same manner as Compound 1 of Synthesis Example 1 except that 1E was used instead of 1C. (10.8 g, yield: 44%).

MS: [M + H] &lt; + &gt; = 706

[Synthesis Example 4] Synthesis of Compound 4

Compound 4 was synthesized in the same manner as Compound 1 of Synthesis Example 1 except that 1F was used instead of 1C. (9.5 g, yield: 39%).

MS: [M + H] &lt; + &gt; = 706

[Synthesis Example 5] Synthesis of Compound 5

Compound 5 was synthesized in the same manner as Compound 1 of Synthesis Example 1 except that 1G was used instead of 1C. (15.1 g, yield: 65%).

MS: [M + H] &lt; + &gt; = 706

[Synthesis Example 6] Synthesis of Compound 6

Intermediate 1I (15.0 g, 26.1 mmol) and 9H-carbazole (4.7 g, 26.1 mmol) were dissolved in 100 mL of xylene, and sodium tert-butoxide (5.0 g, 52.3 mmol) was added and warmed. (Tris (tert-butylphosphine) palladium (0.1 g, 1 mol%) was added thereto, and the mixture was stirred under 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 washed twice with water. The organic layer was separated, and anhydrous magnesium sulfate was added thereto, followed by stirring, followed by filtration, and 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 pale green solid compound 6 (10.1 g, 55%).

MS: [M + H] &lt; + &gt; = 706

[Synthesis Example 7] Synthesis of Compound 7

Compound 7 was synthesized in the same manner as Compound 6 of Synthesis Example 6 except that 1K was used instead of 1I. (9.0 g, yield: 49%).

MS: [M + H] &lt; + &gt; = 705

[Synthesis Example 8] Synthesis of Compound 8

(7.4 g, 26.1 mmol) of 7,7-dimethyl-5,7-dihydroindeno [2,1-b] carbazole was dissolved in 100 mL of xylene to dissolve the mixture, and sodium tert- Side (5.0 g, 52.3 mmol) was added and warmed. (Tris (tert-butylphosphine) palladium (0.1 g, 1 mol%) was added thereto, and the mixture was stirred under 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 washed twice with water. The organic layer was separated, and anhydrous magnesium sulfate was added thereto, followed by stirring, followed by filtration, and the filtrate was distilled under reduced pressure. The concentrated compound was purified through a silica column using chloroform and ethyl acetate to give pale green solid compound 8 (6.0 g, 28%).

MS: [M + H] &lt; + &gt; = 822

[Experimental Example]

<Experimental Example 1>

A thin glass substrate coated with ITO (indium tin oxide) at a thickness of 1,300 Å was immersed in distilled water containing detergent and washed with ultrasonic waves. At this time, a Fischer Co. product was used as a detergent, and distilled water, which was filtered with a filter of Millipore Co., was used as distilled water. The ITO was washed for 30 minutes and then washed twice with distilled water and ultrasonically cleaned for 10 minutes. After the distilled water was washed, it was ultrasonically washed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. Further, the substrate was cleaned using oxygen plasma for 5 minutes, and then the substrate was transported by a vacuum evaporator.

The following HI-1 compound was thermally vacuum deposited on the ITO transparent electrode prepared above to a thickness of 50 Å to form a hole injection layer. The following HT-1 compound was thermally vacuum deposited on the hole injection layer to form a hole transport layer, and HT-2 compound was vacuum deposited on the HT-1 vapor deposition layer to a thickness of 50 Å to form an electron blocking layer. Compound 1, the following YGH-1 compound, and phosphorescent dopant YGD-1 prepared in Preparation Example 1 were co-deposited as a light emitting layer on the HT-2 deposited film at a weight ratio of 44:44:12 to form a 400Å thick light emitting layer. On the light emitting layer, the following ET-1 compound was vacuum deposited to a thickness of 250 ANGSTROM to form an electron transporting layer. On the electron transporting layer, the following ET-2 compound and Li were vacuum deposited at a weight ratio of 98: . Aluminum was deposited on the electron injecting layer to a thickness of 1000 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, the deposition rate of aluminum was maintained at 2 Å / sec, and the vacuum degree during deposition was maintained at 1 × 10 ^-7 to 5 × 10 ^-8 torr Respectively.

&Lt; Experimental Examples 2 to 8 &

An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that the compound shown in the following Table 1 was used instead of the Compound 1 of Synthesis Example 1 in Experimental Example 1.

&Lt; Comparative Experimental Examples 1 to 7 &

An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that the compound shown in the following Table 1 was used instead of the Compound 1 of Synthesis Example 1 in Experimental Example 1. The compounds of CE1 to CE7 in the following Table 1 are as follows.

Experimental Example and Comparative an organic light-emitting device of Experimental Example were measured and a voltage efficiency at a current density of 10mA / cm ^2, to measure the lifetime at a current density of 50mA / cm ² and the results are shown in Table 1. In this case, LT ₉₅ means the time to reach 95% of the initial luminance.

	compound	Voltage (V) (@ 10 mA / cm 2 )	Efficiency (Cd / A) (@ 10 mA / cm 2 )	The color coordinates (x, y)	Lifetime (h) (LT 95 at 50 mA / cm 2 )
Experimental Example 1	Compound 1	3.7	82	0.46, 0.54	140
Experimental Example 2	Compound 2	3.6	83	0.46, 0.54	185
Experimental Example 3	Compound 3	3.7	82	0.46, 0.53	180
Experimental Example 4	Compound 4	3.7	84	0.46, 0.54	190
Experimental Example 5	Compound 5	3.8	81	0.46, 0.54	135
Experimental Example 6	Compound 6	3.8	82	0.46, 0.53	160
Experimental Example 7	Compound 7	3.7	83	0.46, 0.54	115
Experimental Example 8	Compound 8	3.8	85	0.46, 0.54	175
Comparative Experimental Example 1	CE1	4.1	78	0.46, 0.53	100
Comparative Experimental Example 2	CE2	5.0	21	0.46, 0.55	11
Comparative Experimental Example 3	CE3	4.2	80	0.44, 0.55	75
Comparative Experimental Example 4	CE4	7.0	5	0.60, 0.60	One
Comparative Experiment Example 5	CE5	7.5	6.5	0.58, 0.61	One
Comparative Experimental Example 6	CE6	4.5	38	0.46, 0.53	60
Comparative Example 7	CE7	4.5	38	0.46, 0.53	80

As shown in Table 1, when the compound of the present invention was used as a light emitting layer material, it was confirmed that the compound exhibited better efficiency and longer lifetime than the comparative example. This is because the combination of an o-phenyltriazine unit and a carbazole group in the triazine unit is excellent in stability of the material, and is excellent in the efficiency and lifetime of the device.

Claims (9)

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

   [Chemical Formula 1]

   

   (2)

   

   In formulas (1) and (2)

   X1 to X6 and Y1 to Y6 each independently represent N or CR,

   At least two of X1 to X3, at least two of X4 to X6, at least two of Y1 to Y3 and at least two of Y4 to Y6 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 and L2 are each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heterocyclic group,

   R1 is a substituted or unsubstituted aryl group,

   R2 and R3 are each independently selected from the group consisting of hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

   a is an integer of 0 to 7,

   b is an integer of 1 to 8,

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

   Provided that when L2 is a direct bond, R &lt; 3 &gt; is deuterium; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or adjacent R3's are bonded to each other to form a ring.
2. The method according to claim 1,

   (1) is represented by any one of the following formulas (3) to (6):

   (3)

   

   [Chemical Formula 4]

   

   [Chemical Formula 5]

   

   [Chemical Formula 6]

   

   In formulas (3) to (6)

   X1 to X3, Y1 to Y3, L1, R1, R2 and a are as defined in claim 1.
3. The method according to claim 1,

   R2 and R3 are each independently selected from the group consisting of hydrogen; Or deuterium.
4. The method according to claim 1,

   (1) is represented by any one of the following structures:

   

   .
5. The method according to claim 1,

   Wherein the compound of formula (2) is represented by any one of the structures:

   

   

   .
6. A first electrode; A second electrode facing the first electrode; And at least one organic compound layer disposed between the first electrode and the second electrode, wherein at least one of the organic compound layers includes a compound according to any one of claims 1 to 5. The organic light- Light emitting element.
7. The method of claim 6,

   Wherein the organic material layer includes a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer comprises the compound of Formula 1 or Formula 2.
8. The method of claim 6,

   Wherein the organic material layer comprises an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer comprises a compound represented by the formula (1) or (2).
9. The method of claim 6,

   Wherein the organic layer includes a light emitting layer, and the light emitting layer comprises a compound represented by Formula 1 or Formula 2.

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