KR102270475B1 - Multicyclic compound and organic light emitting device comprising the same - Google Patents

Abstract

The present specification provides a compound represented by Formula 1 and an organic light emitting device comprising the same.

Description

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

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 the exchange of holes and/or electrons between the electrode and the organic semiconductor material. The organic light emitting device can be roughly divided into two types as follows according to the principle of operation. First, excitons are formed in the organic material layer by photons flowing into the device from an external light source, the excitons are separated into electrons and holes, and these electrons and holes are transferred to different electrodes and used as a current source (voltage source). It is a type of light emitting device. The second is a light emitting device of a type that applies a voltage or current to two or more electrodes to inject holes and/or electrons into an organic semiconductor material layer forming an interface with the electrodes, and operates by the injected electrons and holes.

In general, the organic light emitting phenomenon refers to a phenomenon in which electric energy is converted into light energy using an organic material. An organic light emitting device using an organic light emitting phenomenon generally has a structure including an anode and a cathode and an organic material layer therebetween. Here, the organic material layer is often formed of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device, and may include, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. In the structure of such an organic light emitting device, when a voltage is applied between the two electrodes, holes are injected into the organic material layer from the anode and electrons from the cathode are injected into the organic material layer. When the injected holes and electrons meet, excitons are formed, and these excitons are When it falls back to the ground state, it lights up. Such an organic light emitting device is known to have characteristics such as self-luminescence, 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 may be classified into a light emitting material and a charge transport material, for example, a hole injection material, a hole transport material, an electron transport material, an electron injection material, and the like, according to functions. The light-emitting material includes blue, green, and red light-emitting materials depending on the light-emitting color, and yellow and orange light-emitting materials required to realize better natural colors.

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

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

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

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

[Formula 1]

In Formula 1,

Ar1 and Ar2 are each independently a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted anthracenyl group; a substituted or unsubstituted phenanthrenyl group; a substituted or unsubstituted pyrenyl group; a substituted or unsubstituted perylenyl group; a substituted or unsubstituted triphenylenyl group; a substituted or unsubstituted chrysenyl group; a substituted or unsubstituted fluorenyl group; Or a substituted or unsubstituted heterocyclic group,

L is a substituted or unsubstituted arylene group; A substituted or unsubstituted divalent dibenzofuran group; a substituted or unsubstituted divalent dibenzothiophene group; Or a substituted or unsubstituted divalent carbazole group,

a is an integer from 1 to 3,

When a is 2 or more, L in parentheses are the same as or different from each other,

Ar3 is the following formula (2),

n is an integer from 2 to 5,

When n is 2 or more, Ar3 in parentheses are the same as or different from each other,

[Formula 2]

In Formula 2,

Y is O; or S.

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

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

FIG. 1 shows an example of an organic light emitting device including a substrate 1 , an anode 2 , a light emitting layer 3 , and a cathode 4 .
2 shows an example of an organic light emitting device including 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 did it

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

The present specification provides a compound represented by Formula 1 above. When the compound represented by Formula 1 is used in the organic material layer of the organic light emitting device, the efficiency of the organic light emitting device is always improved.

In the present specification, when a part "includes" a certain component, this means that other components may be further included rather than excluding other components unless otherwise stated.

In the present specification, when a member is said to be located "on" another member, this includes not only a case in which a member is in contact with another member but also a case in which another member exists between the two members.

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

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

As used herein, the term "substituted or unsubstituted" refers to deuterium; halogen group; cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted arylamine group; a substituted or unsubstituted aryl group; And it means that it is substituted with one or two or more substituents selected from the group consisting of a substituted or unsubstituted heterocyclic group, is substituted with a substituent to which two or more of the above-exemplified substituents are connected, or does not have any substituents. For example, "a substituent in which two or more 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.

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, and the number of carbon atoms is not particularly limited, but is preferably 1 to 60. According to an exemplary embodiment, the number of carbon atoms in the alkyl group is 1 to 30. 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 a methyl group, an ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-ox There is a tyl group, and the like, but is not limited thereto.

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

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

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

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

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

,

등의 스피로플루오레닐기,

(9,9-디메틸플루오레닐기), 및

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

,

spirofluorenyl groups such as

(9,9-dimethyl fluorenyl group), and

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

In the present specification, the heterocyclic group is a cyclic group including at least one of N, O, P, S, Si and Se as a heteroatom, and the number of carbon atoms is not particularly limited, but it is preferably from 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 a pyridyl group, a pyrrole group, a pyrimidyl group, a pyridazinyl group, a furanyl group, a thiophenyl group, an imidazole group, a pyrazole group, a dibenzofuranyl group, a dibenzothiophenyl group, etc., but these is not limited to

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

As used herein, "adjacent" The group may mean a substituent substituted on an atom directly connected to the atom in which the substituent is substituted, a substituent sterically closest to the substituent, or another substituent substituted on the atom in which the substituent is substituted. For example, two substituents substituted at an ortho position in a benzene ring and two substituents substituted at the same carbon in an aliphatic ring may be interpreted as "adjacent" to each other.

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

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

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 atoms other than carbon and one or more heteroatoms, 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, Ar1 and Ar2 are each independently a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted anthracenyl group; a substituted or unsubstituted phenanthrenyl group; a substituted or unsubstituted pyrenyl group; a substituted or unsubstituted perylenyl group; a substituted or unsubstituted triphenylenyl group; a substituted or unsubstituted chrysenyl group; a substituted or unsubstituted fluorenyl group; Or a substituted or unsubstituted heterocyclic group.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are each independently a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted anthracenyl group; a substituted or unsubstituted phenanthrenyl group; Or a substituted or unsubstituted heterocyclic group.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are each independently a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted anthracenyl group; a substituted or unsubstituted phenanthrenyl group; A substituted or unsubstituted dibenzofuran group; a substituted or unsubstituted dibenzothiophene group; It is a substituted or unsubstituted carbazole group.

According to an exemplary embodiment of the present specification, L is a substituted or unsubstituted arylene group; A substituted or unsubstituted divalent dibenzofuran group; a substituted or unsubstituted divalent dibenzothiophene group; or a substituted or unsubstituted divalent carbazole group.

According to an exemplary embodiment of the present specification, L is a substituted or unsubstituted arylene group having 6 to 15 carbon atoms; substituted or unsubstituted divalent dibenzofuran; substituted or unsubstituted divalent dibenzothiophene; or a substituted or unsubstituted divalent carbazole.

According to an exemplary embodiment of the present specification, L is a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; a substituted or unsubstituted terphenylene group; a substituted or unsubstituted naphthylene group; a substituted or unsubstituted divalent phenanthrene group; a substituted or unsubstituted divalent anthracene group; A substituted or unsubstituted divalent dibenzofuran group; a substituted or unsubstituted divalent dibenzothiophene group; and a substituted or unsubstituted divalent carbazole group. Specifically, L may be two or more selected substituents connected to each other.

According to an exemplary embodiment of the present specification, L is a phenylene group; biphenylene group; terphenylene group; naphthylene group; a divalent phenanthrene group; a divalent anthracene group; a divalent dibenzofuran group; a substituted or unsubstituted divalent dibenzothiophene group; and a substituted or unsubstituted divalent carbazole group. Specifically, L may be two or more selected substituents connected to each other.

According to an exemplary embodiment of the present specification, a is an integer of 1 to 3.

According to an exemplary embodiment of the present specification, a is 1. In this case, L is a phenylene group; biphenylene group; terphenylene group; naphthylene group; a divalent phenanthrene group; a divalent anthracene group; a divalent dibenzofuran group; a substituted or unsubstituted divalent dibenzothiophene group; and a substituted or unsubstituted divalent carbazole group.

According to an exemplary embodiment of the present specification, a is 2. In this case, two Ls are connected, which can be expressed as L1-L2. L1 and L2 are each a phenylene group; biphenylene group; terphenylene group; naphthylene group; a divalent phenanthrene group; a divalent anthracene group; a divalent dibenzofuran group; a substituted or unsubstituted divalent dibenzothiophene group; and a substituted or unsubstituted divalent carbazole group. Specifically, L1-L2 is a phenylene group-phenylene group; naphthylene group-phenylene group; phenylene group-naphthylene group; a divalent anthracene group-phenylene group; a phenylene group-divalent anthracene group; phenylene-divalent carbazole; or a divalent carbazole-phenylene group.

According to an exemplary embodiment of the present specification, a is 3. In this case, two Ls are connected, which can be expressed as L1-L2-L3. L1 to L3 are each a phenylene group; biphenylene group; terphenylene group; naphthylene group; a divalent phenanthrene group; a divalent anthracene group; a divalent dibenzofuran group; a substituted or unsubstituted divalent dibenzothiophene group; and a substituted or unsubstituted divalent carbazole group. Specifically, L1-L2-L3 is a phenylene group-phenylene group-phenylene group; phenylene group-naphthylene group-phenylene group; phenylene group-phenylene group-naphthylene group; a phenylene group-divalent anthracene group-phenylene group; or a phenylene group-divalent carbazole-phenylene group.

According to an exemplary embodiment of the present specification, n is an integer of 2 to 5. Since the number of Ar3 substituted for L is determined according to n, specifically, L is (n+1).

According to an exemplary embodiment of the present specification, when a is 2, the number of Ar3 substituted in all two Ls is n, and specifically, when a is 2, when two Ls are expressed as L1-L2, L1 The sum of the number of Ar3 substituted in and the number of Ar3 substituted in L2 is n.

According to an exemplary embodiment of the present specification, when a is 3, the number of Ar3 substituted in all three Ls is n, and specifically, when a is 3, when the three Ls are expressed as L1-L2-L3 , the sum of the number of Ar3 substituted in L1, the number of Ar3 substituted in L2, and the number of Ar3 substituted in L3 is n.

According to an exemplary embodiment of the present specification, n is 2.

According to an exemplary embodiment of the present specification, n is 3.

According to an exemplary embodiment of the present specification, n is 4.

According to an exemplary embodiment of the present specification, n is 5.

According to an exemplary embodiment of the present specification, Ar3 is represented by the following formula (2).

[Formula 2]

In Formula 2, Y is O; or S;

는 결합되는 위치이다.

is the bonding position.

According to an exemplary embodiment of the present specification, Y is O.

According to an exemplary embodiment of the present specification, Y is S.

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

.

.

The compound of Formula 1 according to an exemplary embodiment of the present specification may be prepared by the method described below.

The conjugation length of a 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, compounds 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 can be controlled by introducing various substituents into the core structure of the structure as described above.

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

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

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 for forming one or more organic material layers using the above-described compound.

The compound may be formed into an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device. Here, the solution 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 multi-layer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, an electron transport layer, an electron injection layer, etc. as an organic material layer. However, the structure of the organic light emitting device is not limited 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 the compound represented by Formula 1 above.

In another exemplary embodiment, the organic material layer includes an emission layer, and the emission layer includes a compound represented by Formula 1 above.

According to another exemplary embodiment, the organic material layer may include an emission layer, and the emission layer may include the compound represented by Formula 1 as a host of the emission layer.

In another exemplary embodiment, the organic material layer including the compound represented by Formula 1 includes the compound represented by Formula 1 as a host, a fluorescent host or a phosphorescent host, and another organic compound, metal or metal compound may be included as a dopant.

As another example, the organic material layer including the compound represented by Formula 1 includes the compound represented by Formula 1 as a host, includes a fluorescent host or a phosphorescent host, and can be used together with an iridium-based (Ir) dopant. have.

In the exemplary 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 organic light emitting device may have, for example, a stacked structure as follows, but is not limited thereto.

(1) anode/hole transport layer/light emitting layer/cathode

(2) anode / hole injection layer / hole transport layer / light emitting layer / cathode

(3) anode / hole injection layer / hole buffer layer / hole transport layer / light emitting layer / cathode

(4) anode / hole transport layer / light emitting layer / electron transport layer / cathode

(5) anode / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode

(6) anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / cathode

(7) anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode

(8) anode / hole injection layer / hole buffer layer / hole transport layer / light emitting layer / electron transport layer / cathode

(9) anode / hole injection layer / hole buffer layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode

(10) anode / hole transport layer / electron blocking layer / light emitting layer / electron transport layer / cathode

(11) anode / hole transport layer / electron blocking layer / light emitting layer / electron transport layer / electron injection layer / cathode

(12) anode / hole injection layer / hole transport layer / electron blocking layer / light emitting layer / electron transport layer / cathode

(13) anode / hole injection layer / hole transport layer / electron blocking layer / light emitting layer / electron transport layer / electron injection layer / cathode

(14) anode / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / cathode

(15) anode / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode

(16) anode / hole injection layer / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / cathode

(17) anode / hole injection layer / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode

(18) anode / hole injection layer / hole transport layer / light emitting layer / layer that simultaneously injects and transports electrons / cathode

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

For example, the organic light emitting device according to the present invention uses a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation, to form a metal or a conductive metal oxide or an alloy thereof on a substrate. It can be prepared by depositing an anode, forming an organic material layer including a hole injection layer, a hole transport layer, an electron blocking 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, an electron blocking 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 layer is formed using a variety of polymer materials in a smaller number by a solvent process rather than a deposition method, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer method. It can be made in layers.

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

The cathode material is preferably a material having a small work function to facilitate electron injection into 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; and a multilayer structure material such as LiF/Al or LiO ₂ /Al, but is not limited thereto.

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

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

An electron blocking layer may be provided between the hole transport layer and the light emitting layer. The electronic blocking layer may be the above-described compound or a material known in the art.

The light emitting layer may emit red, green, or blue light, and may be made of a phosphorescent material or a fluorescent material. The light emitting material is a material capable of emitting light in the visible ray region by receiving and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ); carbazole-based compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compounds; compounds of the benzoxazole, benzthiazole and benzimidazole series; Poly(p-phenylenevinylene) (PPV)-based polymers; spiro compounds; polyfluorene, rubrene, and the like, but is not limited thereto.

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

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

[Ir(piq) ₃ ] [Btp ₂ Ir(acac)]

[Ir(ppy) ₃ ] [Ir(ppy) ₂ (acac)]

[Ir(mpyp) ₃ ] [F ₂ Irpic]

[(F ₂ ppy) ₂ Ir(tmd)] [Ir(dfppz) ₃ ]

　　　

　　　

As the electron transport material, a material capable of receiving electrons from the cathode and transferring them to the light emitting layer is suitable, and a material having high electron mobility is suitable. Specific examples include Al complex of 8-hydroxyquinoline; complexes containing Alq _{3 ;} organic radical compounds; hydroxyflavone-metal complexes, and the like, but are not limited thereto.

The hole blocking layer is a layer that blocks the holes from reaching the cathode, and may be generally formed under the same conditions as the hole injection layer. Specifically, there are oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complex, and the like, but is not limited thereto.

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

Hereinafter, the present specification will be described in more detail through examples. However, the following examples are only for illustrating the present specification, and not for limiting the present specification.

[Production Example]

[Preparation Example 1] Preparation of compound A-2

1) Preparation of compound A-1

(5-chloro-1,3-phenylene) diboronic acid (30.0 g, 150.0 mmol) and 2-chlorobenzo [d] thiazole in a nitrogen atmosphere (2-chlorobenzo[d]thiazole) (50.7 g, 300.0 mmol) was added to 600 ml of tetrahydrofuran, stirred and refluxed. Thereafter, potassium carbonate (124.4 g, 899.9 mmol) was dissolved in 300 ml of water, and after sufficient stirring, tetrakistriphenyl-phosphinopalladium (10.4 g, 6 mol%) was added. After the reaction for 12 hours, the temperature was lowered to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled under reduced pressure. The distillate was extracted with chloroform and water, and the organic layer was dried over magnesium sulfate. The organic layer was dried and recrystallized from ethanol to prepare A-1 (25.5 g, 45%).

MS: [M+H]+ = 379

2) Preparation of compound A-2

Compound A-1 (25.5 g, 67.5 mmol), bis (pinacolato) diboron (18.8 g, 74.2 mmol) and potassium acetate (13.2 g, 134.9 mmol) were mixed in a nitrogen atmosphere and added to 200 ml of dioxane It was heated while stirring. Under reflux, bis(dibenzylideneacetone)palladium (0.6 g, 1.1 mmol) and tricyclohexylphosphine (0.6 g, 2.2 mmol) were added, and the mixture was stirred with heating for 3 hours. After completion of the reaction, the temperature was lowered to room temperature and then filtered. Water was poured into the filtrate, followed by extraction with chloroform, and the organic layer was dried over anhydrous magnesium sulfate. After distillation under reduced pressure, it was recrystallized from ethanol to prepare Compound A-2 (24.4 g, 77%).

MS: [M+H]+ = 471

[Preparation Example 2] Preparation of compound B-2

1) Preparation of compound B-1

(5-chloro-1,3-phenylene) diboronic acid (30.0 g, 150.0 mmol) and 2-chlorobenzo [d] oxazole in a nitrogen atmosphere (2-chlorobenzo[d]oxazole) (45.9 g, 300.0 mmol) was added to 600 ml of tetrahydrofuran, stirred and refluxed. Thereafter, potassium carbonate (124.4 g, 899.9 mmol) was dissolved in 300 ml of water, and after sufficient stirring, tetrakistriphenyl-phosphinopalladium (10.4 g, 6 mol%) was added. After the reaction for 12 hours, the temperature was lowered to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled under reduced pressure. The distillate was extracted with chloroform and water, and the organic layer was dried over magnesium sulfate. After drying the organic layer, it was recrystallized from ethanol to prepare B-1 (28.0 g, 54%).

MS: [M+H]+ = 346

2) Preparation of compound B-2

Compound B-1 (28.0 g, 80.9 mmol), bis (pinacolato) diboron (22.6 g, 89.0 mmol) and potassium acetate (15.9 g, 161.8 mmol) were mixed in a nitrogen atmosphere and added to 200 ml of dioxane It was heated while stirring. At reflux, bis(dibenzylideneacetone)palladium (1.4 g, 2.4 mmol) and tricyclohexylphosphine (1.4 g, 4.9 mmol) were added, and the mixture was stirred with heating for 3 hours. After completion of the reaction, the temperature was lowered to room temperature and then filtered. Water was poured into the filtrate, followed by extraction with chloroform, and the organic layer was dried over anhydrous magnesium sulfate. After distillation under reduced pressure, it was recrystallized from ethanol to prepare compound B-2 (28.7 g, 81%).

MS: [M+H]+ = 439

[Preparation Example 3] Preparation of Compound 1

Compound A-2 (20.0 g, 42.5 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (2-chloro-4,6-diphenyl-1,3,5) in a nitrogen atmosphere -triazine) (11.4 g, 42.5 mmol) was added to 200 ml of tetrahydrofuran, stirred and refluxed. Thereafter, potassium carbonate (17.6 g, 127.6 mmol) was dissolved in 40 ml of water, and after stirring sufficiently, tetrakistriphenyl-phosphinopalladium (1.5 g, 3 mol%) was added. After the reaction for 4 hours, the temperature was lowered to room temperature and filtered. The filtrate was dissolved in chloroform, extracted with water, and the organic layer was dried over magnesium sulfate. After drying the organic layer, it was recrystallized from ethyl acetate to prepare Compound 1 (10.8 g, 44%).

MS: [M+H]+ = 576

[Preparation Example 4] Preparation of Compound 2

Compound B-2 (20.0 g, 45.6 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (2-chloro-4,6-diphenyl-1,3,5) in a nitrogen atmosphere -triazine) (12.2 g, 45.6 mmol) was added to 200 ml of tetrahydrofuran, stirred and refluxed. Thereafter, potassium carbonate (18.9 g, 136.9 mmol) was dissolved in 40 ml of water, and after stirring sufficiently, tetrakistriphenyl-phosphinopalladium (1.6 g, 3 mol%) was added. After the reaction for 4 hours, the temperature was lowered to room temperature and filtered. The filtrate was dissolved in chloroform, extracted with water, and the organic layer was dried over magnesium sulfate. After drying the organic layer, it was recrystallized from ethyl acetate to prepare compound 2 (9.7 g, 39%).

MS: [M+H]+ = 544

[Preparation Example 5] Preparation of compound 3 (Compound 3)

Compound A-2 (20.0 g, 42.5 mmol) and 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine ( 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine) (14.6 g, 42.5 mmol) was added to 200 ml of tetrahydrofuran, stirred and refluxed. Thereafter, potassium carbonate (17.6 g, 127.6 mmol) was dissolved in 40 ml of water, and after stirring sufficiently, tetrakistriphenyl-phosphinopalladium (1.5 g, 3 mol%) was added. After the reaction for 4 hours, the temperature was lowered to room temperature and filtered. The filtrate was dissolved in chloroform, extracted with water, and the organic layer was dried over magnesium sulfate. After drying the organic layer, it was recrystallized from ethyl acetate to prepare compound 3 (14.7 g, 53%).

MS: [M+H]+ = 652

[Preparation Example 6] Preparation of Compound 4

Compound A-2 (20.0 g, 42.5 mmol) and 2-(4-chloro-6-phenyl-1,3,5-triazin-2-yl)-9-phenyl-9H-carbazole (2) in a nitrogen atmosphere -(4-chloro-6-phenyl-1,3,5-triazin-2-yl)-9-phenyl-9H-carbazole) (18.4 g, 42.5 mmol) was added to 200 ml of tetrahydrofuran, stirred and refluxed. . Thereafter, potassium carbonate (17.6 g, 127.6 mmol) was dissolved in 40 ml of water, and after stirring sufficiently, tetrakistriphenyl-phosphinopalladium (1.5 g, 3 mol%) was added. After the reaction for 4 hours, the temperature was lowered to room temperature and filtered. The filtrate was dissolved in chloroform, extracted with water, and the organic layer was dried over magnesium sulfate. After drying the organic layer, it was recrystallized from ethyl acetate to prepare compound 4 (20.2 g, 64%).

MS: [M+H]+ = 741

[Preparation Example 7] Preparation of Compound 5 (Compound 5)

Compound A-2 (20.0 g, 42.5 mmol) and 2-chloro-4- (dibenzo [b,d] furan-4-yl) -6-phenyl-1,3,5-triazine (2) in a nitrogen atmosphere -chloro-4-(dibenzo[b,d]furan-4-yl)-6-phenyl-1,3,5-triazine) (18.4 g, 42.5 mmol) was added to 200 ml of tetrahydrofuran, stirred and refluxed. . Thereafter, potassium carbonate (17.6 g, 127.6 mmol) was dissolved in 40 ml of water, and after stirring sufficiently, tetrakistriphenyl-phosphinopalladium (1.5 g, 3 mol%) was added. After the reaction for 4 hours, the temperature was lowered to room temperature and filtered. The filtrate was dissolved in chloroform, extracted with water, and the organic layer was dried over magnesium sulfate. After drying the organic layer, it was recrystallized from ethyl acetate to prepare compound 5 (15.5 g, 55%).

MS: [M+H]+ = 666

[Preparation Example 8] Preparation of Compound 6

Compound A-2 (20.0 g, 42.5 mmol) and 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine (2-(4-bromophenyl)-4 in nitrogen atmosphere ,6-diphenyl-1,3,5-triazine) (18.4 g, 42.5 mmol) was added to 200 ml of tetrahydrofuran, stirred and refluxed. Thereafter, potassium carbonate (17.6 g, 127.6 mmol) was dissolved in 40 ml of water, and after stirring sufficiently, tetrakistriphenyl-phosphinopalladium (1.5 g, 3 mol%) was added. After the reaction for 4 hours, the temperature was lowered to room temperature and filtered. The filtrate was dissolved in chloroform, extracted with water, and the organic layer was dried over magnesium sulfate. After drying the organic layer, it was recrystallized from ethyl acetate to prepare compound 6 (20.5 g, 74%).

MS: [M+H]+ = 652

[Preparation Example 9] Preparation of Compound 7

1) Preparation of compound C-1

2-chloro-4,6-diphenyl-1,3,5-triazine (30.0 g, 112.3 mmol) and ( 3,5-dichlorophenyl)boronic acid ((3,5-dichlorophenyl)boronic acid) (21.3 g, 112.3 mmol) was added to 300 ml of tetrahydrofuran, stirred and refluxed. Thereafter, potassium carbonate (46.6 g, 337.0 mmol) was dissolved in 100 ml of water, and after sufficient stirring, tetrakistriphenyl-phosphinopalladium (3.9 g, 3 mol%) was added. After the reaction for 12 hours, the temperature was lowered to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled under reduced pressure. The distillate was extracted with chloroform and water, and the organic layer was dried over magnesium sulfate. After drying the organic layer, it was recrystallized from ethyl acetate to prepare C-1 (32.6 g, 77%).

MS: [M+H]+ = 378

2) Preparation of compound C-2

Compound C-1 (31.6 g, 83.8 mmol), bis (pinacolato) diboron (46.8 g, 184.4 mmol) and potassium acetate (32.9 g, 335.2 mmol) were mixed in a nitrogen atmosphere, and added to 200 ml of dioxane It was heated while stirring. Under reflux, bis(dibenzylideneacetone)palladium (1.4 g, 2.5 mmol) and tricyclohexylphosphine (1.4 g, 5.0 mmol) were added, and the mixture was heated and stirred for 3 hours. After completion of the reaction, the temperature was lowered to room temperature and then filtered. Water was poured into the filtrate, followed by extraction with chloroform, and the organic layer was dried over anhydrous magnesium sulfate. After distillation under reduced pressure, it was recrystallized from ethanol to prepare compound C-2 (38.1 g, 81%).

MS: [M+H]+ = 562

3) Preparation of compound C-3

In a nitrogen atmosphere, 2-chlorobenzo [d] thiazole (30.0 g, 177.5 mmol) and (4-chlorophenyl) boronic acid ((4-chlorophenyl) boronic acid) (27.7 g, 177.5 mmol) was added to 300 ml of tetrahydrofuran, stirred and refluxed. Thereafter, potassium carbonate (73.6 g, 532.6 mmol) was dissolved in 100 ml of water, and after sufficient stirring, tetrakistriphenyl-phosphinopalladium (6.2 g, 3 mol%) was added. After the reaction for 12 hours, the temperature was lowered to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled under reduced pressure. The distillate was extracted with chloroform and water, and the organic layer was dried over magnesium sulfate. After drying the organic layer, it was recrystallized from ethyl acetate to prepare C-3 (26.5 g, 61%).

MS: [M+H]+ = 246

4) Preparation of compound 7

In a nitrogen atmosphere, compound C-2 (30.0 g, 35.6 mmol) and compound C-3 (17.5 g, 71.6 mmol) were added to 300 ml of tetrahydrofuran, stirred and refluxed. Thereafter, potassium carbonate (29.5 g, 213.8 mmol) was dissolved in 100 ml of water, and after stirring sufficiently, tetrakistriphenyl-phosphinopalladium (2.5 g, 6 mol%) was added. After the reaction for 12 hours, the temperature was lowered to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled under reduced pressure. The distillate was extracted with chloroform and water, and the organic layer was dried over magnesium sulfate. After drying the organic layer, it was recrystallized from ethyl acetate to prepare compound 7 (12.7 g, 49%).

MS: [M+H]+ = 728

[Preparation Example 10] Preparation of Compound 8 (Compound 8)

1) Preparation of compound D-1

(9H-carbazole-3,6-diyl) diboronic acid (30.0 g, 117.6 mmol) and 2-chlorobenzo [d] thiazole in a nitrogen atmosphere (2-chlorobenzo[d]thiazole) (38.7 g, 235.2 mmol) was added to 600 ml of tetrahydrofuran, stirred and refluxed. Thereafter, potassium carbonate (124.4 g, 899.9 mmol) was dissolved in 300 ml of water, and after sufficient stirring, tetrakistriphenyl-phosphinopalladium (10.4 g, 6 mol%) was added. After the reaction for 12 hours, the temperature was lowered to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled under reduced pressure. The distillate was extracted with chloroform and water, and the organic layer was dried over magnesium sulfate. After drying the organic layer, it was recrystallized from ethanol to prepare D-1 (31.1 g, 61%).

MS: [M+H]+ = 434

2) Preparation of compound 8

Compound D-1 (20.0 g, 46.2 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (2-chloro-4,6-diphenyl-1,3,5-triazine) (12.3 g, 46.2 mmol) was dissolved in 200 mL of xylene, and sodium tert-butoxide (12.8 g, 46.2 mmol) was added and heated. Bis (tri-tertiary-butylphosphine) palladium (1.0 g, 3 mol%) was added and stirred while refluxing 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, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by recrystallization using chloroform and ethyl acetate to prepare a pale green solid compound 8 (20.2 g, 66%).

MS: [M+H]+ = 665

[Preparation Example 11] Preparation of Compound 9

Compound D-1 (20.0 g, 46.2 mmol) and 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine (2- (3-bromophenyl) -4,6- diphenyl-1,3,5-triazine) (17.9 g, 46.2 mmol) was dissolved in 200 mL of xylene, and sodium tert-butoxide (12.8 g, 46.2 mmol) was added and heated. Bis (tri-tertiary-butylphosphine) palladium (1.0 g, 3 mol%) was added and stirred while refluxing 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, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by recrystallization using chloroform and ethyl acetate to prepare a pale green solid compound 9 (9.9 g, 21%).

MS: [M+H]+ = 741

[Preparation Example 12] Preparation of Compound 10

1) Synthesis of compound E-1

2-bromophenol (49.4 g, 287.3 mmol), (2-chloro-6-fluorophenyl) boronic acid ((2-chloro-6-fluorophenyl) boronic acid) (50.0 g, 287.3 mmol) in tetrahydrofuran (THF) was dissolved in 500 ml. Sodium carbonate (Na ₂ CO ₃ ) 2 M solution (430 mL), tetrakis (triphenylphosphine) palladium (0) [Pd(PPh ₃ ) ₄ ] (10.0 g, 8.6 mmol) was added thereto, and refluxed for 12 hours. did it After the reaction was completed, the mixture was cooled to room temperature, and the resulting mixture was extracted three times with water and toluene. The toluene layer was separated, dried over magnesium sulfate, and the filtered filtrate was distilled under reduced pressure. The resulting mixture was purified by column chromatography using chloroform and hexane to obtain compound E-1 (34.4 g, yield 54%; MS: [M+H]+=223) was obtained.

2) Synthesis of compound E-2

Compound E-1 (30 g, 135.1 mmol) is dissolved in 300 ml of chloroform. N-bromosuccinimide (160.3 g, 270.25 mmol) was added thereto, and the mixture was stirred at room temperature for 4 hours. After the reaction is complete, water is added. After layer separation, the layers were separated after stirring twice with sodium thiosulfate solution. After distillation, compound E-2 (51.1 g, yield 100%; MS:[M+H]+=379) was obtained.

3) Synthesis of compound E-3

Compound E-2 (51.1 g, 135.1 mmol) was dissolved in distilled dimethylformamide (DMF) (400 ml). It was cooled to 0 °C, and sodium hydride (3.5 g, 145.9 mmol) was slowly added dropwise thereto. After stirring for 20 minutes, the mixture was stirred at 100° C. for 1 hour. After the reaction was completed, it was cooled to room temperature, and 100 ml of ethanol was slowly added thereto. The mixture obtained by distillation under reduced pressure was recrystallized from chloroform and ethyl acetate to obtain compound E-3 (32.9 g, yield 68%; MS:[M+H]+=359).

4) Synthesis of compound E-4

Compound E-3 (20.8 g, 58.7 mmol) and bis(pinacolato)diborone) (25.0 g, 70.6 mmol) potassium acetate (16.9 g, 176.2 mmol), bis( Dibenzylideneacetone)palladium (1.0 g, 1.8 mmol) and tricyclohexylphosphine (1.0 g, 3.5 mmol) were added to dioxane (300 ml) and refluxed for 12 hours. After the reaction was completed, the solvent was removed by distillation under reduced pressure after cooling to room temperature. This was dissolved in chloroform, washed three times with water, and the organic layer was separated and dried over magnesium sulfate. This was distilled under reduced pressure to prepare compound E-4 (25.0 g, yield 77%; MS:[M+H]+=447).

5) Synthesis of compound E-5

Compound E-4 (25.0 g, 55.0 mmol) and 2-chlorobenzo[d]thiazole (18.6 g, 110.1 mmol) were dissolved in 300 ml of tetrahydrofuran (THF). Potassium carbonate (K ₂ CO ₃ ) 2 M solution (165 mL) and tetrakis (triphenylphosphine) palladium (0) [Pd(PPh ₃ ) ₄ ] (3.8 g, 3 mol%) were added thereto, and 6 hours refluxed while After the reaction was completed, the mixture was cooled to room temperature, and the resulting mixture was extracted three times with water and toluene. The toluene layer was separated, dried over magnesium sulfate, and the filtered filtrate was distilled under reduced pressure. The resulting mixture was recrystallized using chloroform and ethyl acetate to obtain compound E-5 (18.5 g, yield 72%; MS: [M+) H] + = 469) was obtained.

6) Synthesis of compound E-6

Compound E-5 (18.5 g, 39.5 mmol) and bis(pinacolato)diborone (12.1 g, 47.3 mmol) potassium acetate (15.5 g, 158.1 mmol), bis( Dibenzylideneacetone)palladium (0.7 g, 1.2 mmol) and tricyclohexylphosphine (0.7 g, 2.4 mmol) were added to dioxane (300 ml) and refluxed for 12 hours. After the reaction was completed, the solvent was removed by distillation under reduced pressure after cooling to room temperature. This was dissolved in chloroform, washed three times with water, and the organic layer was separated and dried over magnesium sulfate. This was distilled under reduced pressure to prepare compound E-6 (20.4 g, yield 92%; MS:[M+H]+=561).

7) Synthesis of compound 10

Compound E-6 (20.0 g, 35.7 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (2-chloro-4,6-diphenyl-1,3,5-triazine) (9.5 g, 35.7 mmol) was dissolved in 200 ml of tetrahydrofuran (THF). Potassium carbonate (K ₂ CO ₃ ) 2 M solution (165 mL), tetrakis (triphenylphosphine) palladium (0) [Pd(PPh ₃ ) ₄ ] (3.8 g, 3 mol%) was added thereto, and 6 hours refluxed while After the reaction was completed, the mixture was cooled to room temperature, and the resulting mixture was extracted three times with water and toluene. After separating the toluene layer, the filtrate was dried over magnesium sulfate and filtered under reduced pressure. A mixture obtained by distillation under reduced pressure was recrystallized using chloroform and ethyl acetate to obtain compound 10 (11.8 g, yield 50%; MS: [M+H] +=666) was obtained.

[Preparation Example 13] Preparation of compound 11 (Compound 11)

1) Preparation of compound F-1

2-chloro-4,6-diphenyl-1,3,5-triazine 2-chlorobenzo [d] thiazole (30.0 g, 112.3 mmol) and (2 ,4,6-trichlorophenyl)boronic acid ((2,4,6-trichlorophenyl)boronic acid) (25.2 g, 112.3 mmol) was added to 300 ml of tetrahydrofuran, stirred and refluxed. Thereafter, potassium carbonate (46.6 g, 337.0 mmol) was dissolved in 100 ml of water, and after sufficient stirring, tetrakistriphenyl-phosphinopalladium (3.9 g, 3 mol%) was added. After the reaction for 12 hours, the temperature was lowered to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled under reduced pressure. The distillate was extracted with chloroform and water, and the organic layer was dried over magnesium sulfate. After drying the organic layer, it was recrystallized from ethyl acetate to prepare F-1 (27.7 g, 77%).

MS: [M+H]+ = 378

2) Preparation of compound F-2

Compound F-1 (27.7 g, 67.4 mmol), bis (pinacolato) diboron (56.5 g, 222.4 mmol) and potassium acetate (39.7 g, 404.4 mmol) were mixed in a nitrogen atmosphere and added to 300 ml of dioxane It was heated while stirring. At reflux, bis(dibenzylideneacetone)palladium (1.2 g, 2.0 mmol) and tricyclohexylphosphine (1.2 g, 4.0 mmol) were added, and the mixture was heated and stirred for 3 hours. After completion of the reaction, the temperature was lowered to room temperature and then filtered. Water was poured into the filtrate, followed by extraction with chloroform, and the organic layer was dried over anhydrous magnesium sulfate. After distillation under reduced pressure, it was recrystallized from ethanol to prepare compound F-2 (23.2 g, 51%).

MS: [M+H]+ = 688

3) Synthesis of compound 11

In a nitrogen atmosphere, compound F-2 (20.0 g, 29.1 mmol) and 2-chlorobenzo[d]thiazole (14.7 g, 87.3 mmol) were added to 300 ml of tetrahydrofuran, stirred and refluxed. Thereafter, potassium carbonate (24.1 g, 174.6 mmol) was dissolved in 100 ml of water, and after stirring sufficiently, tetrakistriphenyl-phosphinopalladium (2.0 g, 6 mol%) was added. After the reaction for 12 hours, the temperature was lowered to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled under reduced pressure. The distillate was extracted with chloroform and water, and the organic layer was dried over magnesium sulfate. After drying the organic layer, it was recrystallized from ethyl acetate to prepare compound 11 (9.2 g, 45%).

MS: [M+H]+ = 709

[Experimental example]

<Experimental Example 1>

A glass substrate coated with indium tin oxide (ITO) to a thickness of 1,300 Å was placed in distilled water in which detergent was dissolved and washed with ultrasonic waves. In this case, a product manufactured by Fischer Co. was used as the detergent, and distilled water that was secondarily filtered with a filter manufactured by Millipore Co. was used as the distilled water. After washing ITO for 30 minutes, ultrasonic cleaning was performed for 10 minutes by repeating twice with distilled water. After washing with distilled water, ultrasonic washing was performed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. In addition, after cleaning the substrate for 5 minutes using oxygen plasma, the substrate was transported to a vacuum evaporator.

A hole injection layer was formed by thermal vacuum deposition of the following HI-1 compound to a thickness of 50 Å on the ITO transparent electrode prepared as described above. On the hole injection layer, the following HT-1 compound was thermally vacuum deposited to a thickness of 250 Å to form a hole transport layer, and the following HT-2 compound was vacuum deposited to a thickness of 50 Å on the HT-1 deposited film to form an electron blocking layer. Compound 1 prepared in Preparation Example 3, the following YGH-1 compound, and phosphorescent dopant YGD-1 were co-deposited on the HT-2 deposited film in a weight ratio of 44:44:12 as a light-emitting layer to form a light-emitting layer having a thickness of 400 Å. On the light emitting layer, the following ET-1 compound was vacuum deposited to a thickness of 250 Å to form an electron transport layer, and the following ET-2 compound and Li were vacuum deposited at a weight ratio of 98:2 on the electron transport layer to form an electron injection layer with a thickness of 100 Å. formed. A cathode was formed by depositing aluminum to a thickness of 1000 Å on the electron injection layer.

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

<Experimental Examples 2 to 11>

An organic light emitting diode was manufactured in the same manner as in Experimental Example 1, except that the compound shown in Table 1 was used instead of Compound 1 of Preparation Example 3 in Experimental Example 1.

<Comparative Experimental Examples 1 to 11>

An organic light emitting diode was manufactured in the same manner as in Experimental Example 1, except that the compound shown in Table 1 was used instead of Compound 1 of Preparation Example 3 in Experimental Example 1. The compounds of CE1 to CE11 in Table 1 below are as follows.

In the Experimental Examples and Comparative Experimental Examples, voltage and efficiency were measured ^{for the organic light emitting device at a current density of 10 mA/cm 2 , and lifetimes were measured at a current density of 50 mA/cm 2} The results are shown in Table 1 below. In this case, LT ₉₅ means a time at which 95% of the initial luminance is obtained.

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 8 compound 8 4.3 79 0.46, 0.54 152 Experimental Example 9 compound 9 4.2 80 0.46, 0.53 130 Comparative Experimental Example 1 CE1 4.5 75 0.46, 0.54 85 Comparative Experimental Example 2 CE2 4.2 65 0.47, 0.54 25 Comparative Experiment Example 3 CE3 4.8 50 0.48, 0.59 10 Comparative Experimental Example 4 CE4 4.7 71 0.46, 0.54 85 Comparative Experiment Example 5 CE5 4.2 50 0.47, 0.54 75 Comparative Experiment Example 6 CE6 4.6 54 0.48, 0.59 61 Comparative Experimental Example 7 CE7 4.5 65 0.46, 0.54 54 Comparative Experimental Example 8 CE8 4.4 69 0.47, 0.54 38 Comparative Experimental Example 9 CE9 4.6 57 0.48, 0.59 25 Comparative Experimental Example 10 CE10 4.5 74 0.46, 0.54 55 Comparative Experimental Example 11 CE11 4.4 77 0.47, 0.54 5

As shown in Table 1, when the compound of the present invention was used as a material for the light emitting layer, it was confirmed that the efficiency and lifespan were superior to those of Comparative Experimental Examples. It is seen that the electronic stability is increased as benzoxazole or benzothiazole is substituted with two or more.

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

Claims (6)

A compound represented by the following formula (1):
[Formula 1]

In Formula 1,
Ar1 and Ar2 are each independently a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted anthracenyl group; a substituted or unsubstituted phenanthrenyl group; a substituted or unsubstituted pyrenyl group; a substituted or unsubstituted perylenyl group; a substituted or unsubstituted triphenylenyl group; a substituted or unsubstituted chrysenyl group; a substituted or unsubstituted fluorenyl group; Or a substituted or unsubstituted heterocyclic group,
L is a substituted or unsubstituted arylene group; a substituted or unsubstituted divalent dibenzothiophene group; Or a substituted or unsubstituted divalent carbazole group,
a is an integer from 1 to 3,
When a is 1, L is a substituted or unsubstituted divalent dibenzothiophene group; Or a substituted or unsubstituted divalent carbazole group,
When a is 2, any one of L is a substituted or unsubstituted arylene group; a substituted or unsubstituted divalent dibenzothiophene group; or a substituted or unsubstituted divalent carbazole group, and the remaining L is a substituted or unsubstituted divalent dibenzothiophene group; Or a substituted or unsubstituted divalent carbazole group,
When a is 3, any one of L is a substituted or unsubstituted arylene group; a substituted or unsubstituted divalent dibenzothiophene group; Or a substituted or unsubstituted divalent carbazole group, the remaining L is each independently a substituted or unsubstituted divalent dibenzothiophene group; Or a substituted or unsubstituted divalent carbazole group,
When a is 2 or more, L in parentheses are different from each other,
Ar3 is the following formula (2),
n is an integer from 2 to 5,
When n is 2 or more, Ar3 in parentheses are the same as or different from each other,
[Formula 2]

In Formula 2,
Y is O; or S. The method according to claim 1,
Ar1 and Ar2 are each independently a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted anthracenyl group; a substituted or unsubstituted phenanthrenyl group; Or a compound that is a substituted or unsubstituted heterocyclic group. The method according to claim 1,
The compound of Formula 1 is represented by any one of the following structures:

. 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 organic material layer of the organic material layer comprises the compound according to any one of claims 1 to 3 light emitting element. 5. The method according to claim 4,
The organic material layer includes an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer includes the compound represented by Formula 1 above. 5. The method according to claim 4,
The organic material layer includes an emission layer, and the emission layer includes the compound represented by Formula 1 above.

Images