KR102234159B1 - Compound and organic light emitting device comprising the same - Google Patents

Abstract

The present specification provides a compound of Formula 1 and an organic light emitting device including the same.

Description

A compound and an organic light-emitting device comprising the same TECHNICAL FIELD

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

This application claims the benefit of the filing date of Korean Patent Application No. 10-2018-0068168 filed with the Korean Intellectual Property Office on June 14, 2018, the entire contents of which are incorporated herein.

The organic light emitting device has a structure in which an organic thin film is disposed between two electrodes. When a voltage is applied to the organic light emitting device having such a structure, electrons and holes injected from the two electrodes are combined in the organic thin film to form a pair and then emit light while disappearing. The organic thin film may be composed of a single layer or multiple layers as necessary.

The material of the organic thin film may have a light emitting function as needed. For example, as the organic thin film material, a compound capable of constituting an emission layer by itself may be used, or a compound capable of serving as a host or a dopant of the host-dopant-based emission layer may be used. In addition, as a material of the organic thin film, a compound capable of performing a role of hole injection, hole transport, electron blocking, hole blocking, electron transport, or electron injection may be used.

In order to improve the performance, life, or efficiency of an organic light emitting device, the development of a material for an organic thin film is continuously required.

International Patent Application Publication No. 2003-012890

The present specification provides a compound and an organic light emitting device including the same.

An exemplary embodiment of the present specification provides a compound represented by Formula 1 below.

[Formula 1]

In Formula 1,

L1 and L2 are the same as or different from each other, and each independently a direct bond; Or an arylene group,

Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted indole group; A substituted or unsubstituted carbazole group; A substituted or unsubstituted benzocarbazole group; A substituted or unsubstituted dihydroindenocarbazole group; Substituted or unsubstituted dihydroindoloindole; A substituted or unsubstituted dihydroindenocarbazole group; A substituted or unsubstituted hexahydropyridoquinoline group; A substituted or unsubstituted triphenylsilyl group; Or a substituted or unsubstituted tetraphenylsilane group.

In addition, the present application is a first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the aforementioned compound.

The compound according to the exemplary embodiment of the present application is used in an organic light-emitting device to increase the luminance of the organic light-emitting device, increase the lifespan, lower the driving voltage, improve light efficiency, and improve the lifespan characteristics of the device by the thermal stability of the compound. Can be improved.

When a substituent is bonded to the 1,4 positions of triphenylene, the solubility is not good because it has a symmetrical structure on both sides of the flat triphenylene, and the sublimation temperature also tends to increase, resulting in thermal stability during device deposition. Falling problems arise. Therefore, when the compound according to the present invention binds a substituent at positions 1 and 3 of triphenylene, since it has an asymmetric structure, it gives a steric effect to increase solubility, and lowers the sublimation temperature to increase the solubility during device deposition. Improves thermal stability.

1 shows an example of an organic light emitting device in which a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4 are sequentially stacked.
2 is a substrate (1), an anode (2), a hole injection layer (5), a hole transport layer (6). An example of an organic light-emitting device in which the light emitting layer 3, the hole blocking layer 7, the electron transport layer 8, and the cathode 4 are sequentially stacked is shown.

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

The present specification provides a compound represented by Chemical Formula 1.

Since the compound of the present invention has a substituent bonded to the 1,3 position of triphenylene, compared to the compound at the 1,4 position, the solubility can be increased due to the steric effect and the sublimation temperature is lowered. I can. In addition, compared to the case where the substituent is bonded only to the 1st or 3rd position, the case of having a substituent at the 1st and 3rd positions at the same time has the advantage of being able to easily adjust the energy level by introducing more various substituents.

Examples of the substituent in the present specification 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 position to be substituted is not limited as long as the position where the hydrogen atom is substituted, that is, the position where the substituent can be substituted, and when two or more are substituted , Two or more substituents may be the same or different from each other.

In the present specification, the term "substituted or unsubstituted" refers to deuterium; Halogen group; Nitrile group; Alkyl group; Cycloalkyl group; Alkoxy group; Aryl group; And it is substituted with one or two or more substituents selected from the group consisting of a heterocyclic group, two or more of the substituents exemplified above are substituted with a connected substituent, or does not have any substituents. For example, "a substituent to 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 connected to two phenyl groups.

In the present specification, examples of the halogen group include fluorine, chlorine, bromine or iodine.

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 50. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl , Isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n -Heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethyl Heptyl, 1-ethylpropyl, 1,1-dimethylpropyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like, but are not limited thereto.

In the present specification, the cycloalkyl group is not particularly limited, but is preferably 3 to 30 carbon atoms, and specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, etc., but are limited thereto. It is not.

In the present specification, the alkoxy group may be a straight chain, branched chain, or cyclic chain. Although the number of carbon atoms of the alkoxy group is not particularly limited, it is preferably 1 to 30 carbon atoms. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, Isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, etc. May be, but is not limited thereto.

In the present specification, when the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but it is preferably 6 to 30 carbon atoms. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, or a terphenyl group, but is not limited thereto.

When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited. It is preferably 10 to 24 carbon atoms. Specifically, the polycyclic aryl group may be a naphthyl group, an anthracene group, a phenanthrene group, a pyrenyl group, a perylenyl group, a chrysene group, or a fluorene group, but is not limited thereto.

In the present specification, the heteroaryl group is an atom other than carbon and includes one or more heteroatoms, and specifically, the heteroatom may include one or more atoms selected from the group consisting of O, N, Se, Si, and S. have. The number of carbon atoms of the heteroaryl group is not particularly limited, but is preferably 2 to 60 carbon atoms or 2 to 30 carbon atoms. Examples of the heteroaryl group include thiophene group, furan group, pyrrole group, imidazolyl group, thiazolyl group, oxazolyl group, oxadiazolyl group, triazolyl group, pyridyl group, bipyridyl group, pyrimidyl group, tria Genyl group, acridyl group, pyridazinyl group, pyrazinyl group, quinolinyl group, quinazolinyl group, quinoxalinyl group, phthalazinyl group, pyridopyrimidinyl group, pyridopyrazinyl group, pyrazinopyrazinyl group , Isoquinolinyl group, indole group, carbazolyl group, benzoxazolyl group, benzimidazolyl group, benzothiazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, benzothiophene group, dibenzothiophene group , Benzofuran group, dibenzofuran group, benzosilol group, dibenzosilol group, phenanthrolinyl group, isoxazolyl group, thiadiazolyl group, phenothiazinyl group, phenoxazine group and their condensation structure, etc. However, it is not limited to these.

In the present specification, an arylene group means that the aryl group has two bonding positions, that is, a divalent group. Except that each of these is a divalent group, the description of the aryl group described above may be applied.

In the exemplary embodiment of the present specification, L1 and L2 are direct bonds.

In the exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently an indole group unsubstituted or substituted with one or more substituents selected from the group consisting of an alkyl group and an aryl group; A carbazole group unsubstituted or substituted with one or more substituents selected from the group consisting of an alkyl group and an aryl group; A benzocarbazole group unsubstituted or substituted with one or more substituents selected from the group consisting of an alkyl group and an aryl group; A dihydroindolocarbazole group unsubstituted or substituted with one or more substituents selected from the group consisting of an alkyl group and an aryl group; A dihydroindoloindole group unsubstituted or substituted with one or more substituents selected from the group consisting of an alkyl group and an aryl group; A dihydroindenocarbazole group unsubstituted or substituted with one or more substituents selected from the group consisting of an alkyl group and an aryl group; A hexahydropyridoquinoline group unsubstituted or substituted with one or more substituents selected from the group consisting of an alkyl group and an aryl group; A triphenylsilyl group unsubstituted or substituted with one or more substituents selected from the group consisting of an alkyl group and an aryl group; Or a tetraphenylsilane group unsubstituted or substituted with one or more substituents selected from the group consisting of an alkyl group and an aryl group.

In the exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently an indole group unsubstituted or substituted with an alkyl group or an aryl group; A carbazole group unsubstituted or substituted with an alkyl group or an aryl group; A benzocarbazole group unsubstituted or substituted with an alkyl group or an aryl group; Dihydroindolocarbazole group unsubstituted or substituted with an alkyl group or an aryl group; Dihydroindoloindole group unsubstituted or substituted with an alkyl group or an aryl group; Dihydroindenocarbazole group unsubstituted or substituted with an alkyl group or an aryl group; A hexahydropyridoquinoline group unsubstituted or substituted with an alkyl group or an aryl group; A triphenylsilyl group unsubstituted or substituted with an alkyl group or an aryl group; Or a tetraphenylsilane group unsubstituted or substituted with an alkyl group or an aryl group.

In the exemplary embodiment of the present specification, the alkyl group is an alkyl group having 1 to 20 carbon atoms.

In the exemplary embodiment of the present specification, the alkyl group is an alkyl group having 1 to 10 carbon atoms.

In the exemplary embodiment of the present specification, the aryl group is an aryl group having 1 to 20 carbon atoms.

In the exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and are each independently selected from the following structural formulas.

In the above structural formula, R4 is the same as or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group,

m is an integer of 1 to 8, n is an integer of 1 to 10,

When m and n are 2 or more, R4 in parentheses is the same as or different from each other.

In the exemplary embodiment of the present specification, R4 is hydrogen; A substituted or unsubstituted C1-C10 alkyl group; Or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

In the exemplary embodiment of the present specification, R4 is hydrogen; A substituted or unsubstituted methyl group; A substituted or unsubstituted butyl group; A substituted or unsubstituted phenyl group; Or a substituted or unsubstituted naphthyl group.

In the exemplary embodiment of the present specification, R4 is hydrogen; Methyl group; tert-butyl group; Phenyl group; Or a naphthyl group.

In the exemplary embodiment of the present specification, Ar1 and Ar2 are the same as each other.

In the exemplary embodiment of the present specification, Ar1 and Ar2 are different from each other.

In an exemplary embodiment of the present specification, the compound represented by Formula 1 is selected from the following structural formulas.

The compound according to an exemplary embodiment of the present application may be prepared by a manufacturing method described below.

For example, the compound of Formula 1 may have a core structure as shown in Scheme 1 below. Substituents may be bonded by methods known in the art, and the type, position, or number of substituents may be changed according to techniques known in the art.

[Scheme 1]

The manufacturing method of Chemical Formula 1 is as described above. A and B are halogen and may be the same or different. It can be synthesized through Suzuki or Buchwald reaction, which is usually used in the art.

In Reaction Scheme 1, L1, L2, Ar1, and Ar2 are as defined in Formula 1.

In the exemplary embodiment of the present application, the maximum emission wavelength of the compound is 400 to 700 nm.

In the exemplary embodiment of the present application, the maximum emission wavelength of the compound is 500 to 540m.

In the exemplary embodiment of the present application, the maximum emission wavelength of the compound is 510 to 525m.

In the exemplary embodiment of the present application, the maximum emission wavelength of the compound is 515 to 520m.

In addition, the present specification provides an organic light-emitting device including the above-described compound.

In the exemplary embodiment of the present application, 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 of the organic material layers includes the compound.

In this specification, when a member is positioned "on" another member, this 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.

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

The organic material layer of the organic light emitting device of the present application may have a single-layer structure, but may have a multilayer structure in which two or more organic material layers are stacked. For example, as a representative example of the organic light emitting device of the present invention, the organic light emitting device may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like as an organic material layer. However, the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers.

In the exemplary embodiment of the present application, the organic material layer includes an emission layer, and the emission layer includes the compound.

In the exemplary embodiment of the present application, the organic material layer includes an emission layer, the emission layer includes the compound, and the emission layer is a green emission layer.

In the exemplary embodiment of the present application, the organic material layer includes an emission layer, and the emission layer includes the compound as a host.

In the exemplary embodiment of the present specification, the organic material layer including the compound of Formula 1 may include the compound of Formula 1 as a host, and may include other organic compounds, metals, or metal compounds as a dopant.

In the exemplary embodiment of the present specification, the organic material layer including the compound of Formula 1 may include the compound of Formula 1 as a host, and may include an iridium-based dopant.

In the exemplary embodiment of the present specification, the organic material layer including the compound of Formula 1 may include the compound of Formula 1 as a host and may include a phosphorescent dopant.

In the exemplary embodiment of the present specification, the organic material layer including the compound of Formula 1 may include the compound of Formula 1 as a host, and may include a red or green phosphorescent dopant.

In the exemplary embodiment of the present specification, the organic material layer including the compound of Formula 1 may include the compound of Formula 1 as a host, and may include an iridium-based phosphorescent dopant.

According to the exemplary embodiment of the present specification, the emission layer includes the compound and the dopant in a weight ratio of 1:99 to 99:1.

According to the exemplary embodiment of the present specification, the emission layer includes the compound and the dopant in a weight ratio of 2:1 to 99:1.

In the exemplary embodiment of the present application, the organic material layer includes a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer includes the compound.

In the exemplary embodiment of the present application, the organic material layer includes a hole injection layer, a hole transport layer, or a hole injection and transport layer, and the hole injection layer, a hole transport layer, or the hole injection and transport layer includes the compound.

In the exemplary embodiment of the present application, 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.

In the exemplary embodiment of the present application, the organic material layer includes an electron injection layer, an electron transport layer, or an electron injection and transport layer, and the electron injection layer, the electron transport layer, or the electron injection and transport layer includes the compound.

In the exemplary embodiment of the present application, the organic light emitting device includes a first electrode; A second electrode provided to face the first electrode; And a light emitting layer provided between the first electrode and the second electrode. Two or more organic material layers are provided between the light-emitting layer and the first electrode, or between the light-emitting layer and the second electrode, and at least one of the two or more organic material layers includes the compound.

In another exemplary embodiment, the organic light-emitting device may be a normal type organic light-emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.

In another exemplary embodiment, the organic light-emitting device may be an inverted type organic light-emitting device in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate.

For example, the structure of an organic light-emitting device according to an exemplary embodiment of the present application is illustrated in FIGS. 1 and 2.

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

2 is a substrate (1), an anode (2), a hole injection layer (5), a hole transport layer (6). An example of an organic light-emitting device in which the light emitting layer 3, the hole blocking layer 7, the electron transport layer 8, and the cathode 4 are sequentially stacked is shown.

The organic light-emitting device of the present application may be manufactured by materials and methods known in the art, except that at least one of the organic material layers includes the compound of the present application, that is, the compound.

When the organic light-emitting device includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials.

For example, the organic light emitting device of the present application may be manufactured by sequentially laminating a first electrode, an organic material layer, and a second electrode on a substrate. At this time, by using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation, a metal or conductive metal oxide or alloy thereof is deposited on the substrate to form an anode. And, after forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer thereon, it can be prepared by depositing a material that can be used as a cathode thereon. In addition to this 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.

In addition, the compound of Formula 1 may be formed as an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device. Here, the solution coating method refers to spin coating, dip coating, doctor blading, ink jet printing, screen printing, spray method, roll coating, and the like, but is not limited thereto.

In addition to such a method, an organic light-emitting device may be manufactured by sequentially depositing an organic material layer and an anode material from a cathode material on a substrate (International Patent Application Publication No. 2003/012890). However, the manufacturing method is not limited thereto.

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

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

As the anode material, a material having a large work function is preferable so that holes can be smoothly injected 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, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); A combination of metal and oxide such as ZnO:Al or SnO _{2 :Sb;} Poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), conductive polymers such as polypyrrole and polyaniline, and the like, but are not limited thereto.

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

The hole injection layer is a layer that injects holes from an electrode, and has the ability to transport holes as a hole injection material, so that it has a hole injection effect at the anode, an excellent hole injection effect for a light emitting layer or a light emitting material, and is generated from the light emitting layer. A compound that prevents the movement of excitons to the electron injection layer or the electron injection material and has excellent ability to form a thin film is preferable. It is preferable that the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer. Specific examples of hole injection materials include metal porphyrin, oligothiophene, arylamine-based organic substances, hexanitrile hexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based organic substances. Organic substances, anthraquinone, polyaniline, and polythiophene-based conductive polymers, but are not limited thereto.

The hole transport layer is a layer that receives holes from the hole injection layer and transports holes to the emission layer.The hole transport material is a material capable of transporting holes from the anode or the hole injection layer to the emission layer, and has high mobility for holes. The material is suitable. Specific examples include an arylamine-based organic material, a conductive polymer, and a block copolymer including a conjugated portion and a non-conjugated portion, but are not limited thereto.

As the light-emitting material, a material capable of emitting light in a visible light region by transporting 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-hydroxybenzoquinoline-metal compound; Benzoxazole, benzthiazole, and benzimidazole-based compounds; Poly(p-phenylenevinylene) (PPV)-based polymer; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited thereto.

The emission layer may include a host material and a dopant material. Host materials include condensed aromatic ring derivatives or heterocyclic-containing compounds. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and heterocycle-containing compounds include compounds, dibenzofuran derivatives, and ladder furan compounds. , Pyrimidine derivatives, and the like, but are not limited thereto.

The electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the emission layer. As an electron transport material, a material capable of receiving electrons from the cathode and transferring them to the emission layer. 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 electron transport layer can be used with any desired cathode material as used according to the prior art. In particular, examples of suitable cathode materials are conventional materials that have a low work function and are followed by an aluminum layer or a silver layer. Specifically, they are cesium, barium, calcium, ytterbium, and samarium, and in each case an aluminum layer or a silver layer follows.

The electron injection layer is a layer that injects electrons from the electrode, has the ability to transport electrons, has an electron injection effect from the cathode, an excellent electron injection effect on the light emitting layer or light emitting material, and injects holes of excitons generated from the light emitting layer. A compound that prevents migration to the layer and is excellent in thin film forming ability is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, preorenylidene methane, anthrone, etc. Complex compounds and nitrogen-containing 5-membered ring derivatives, but are not limited thereto.

Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, Tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h] Quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)( o-cresolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtholato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtholato)gallium, etc. It is not limited to this.

The hole blocking layer is a layer that prevents 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 complexes, etc., but are not limited thereto.

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

The preparation of the compound represented by Formula 1 and the organic light-emitting device including the same will be described in detail in the following examples. However, the following examples are for illustrative purposes only, and the scope of the present specification is not limited thereto.

<Production Example>

Synthesis of compound 1

After completely dissolving the compound 1-bromo-3-chlorotriphenylene (10g, 29.41mmol) and 9H-carbazole (9.8g, 58.83mmol) in 90ml of xylene, sodium-tert-butoxide (6.7 g, 70.58mmol) was added and stirred while raising the temperature until refluxed. When reflux started, 2 mol% of bis(tri-tert-butylphosphine)palladium was slowly dropped and added. After 5 hours, the reaction was terminated, the temperature was lowered to room temperature, concentrated under reduced pressure, and purified by column to obtain 10.1 g (yield 61%) of Compound 1.

MS[M+H] ⁺ = 559

Synthesis of compound 2

After completely dissolving the compound 1-bromo-3-chlorotriphenylene (10g, 29.41mmol) and 3,6-diphenyl-9H-carbazole (18.8g, 58.83mmol) in 90ml of xylene, sodium -tert-butoxide (6.7g, 70.58mmol) was added and stirred while raising the temperature until reflux. When reflux started, 2 mol% of bis(tri-tert-butylphosphine)palladium was slowly dropped and added. After 7 hours, the reaction was completed, the temperature was lowered to room temperature, concentrated under reduced pressure, and purified by column to give 13.4 g (yield 53%) of compound 2.

MS[M+H] ⁺ = 863

Synthesis of compound 3

The compound 1-bromo-3-chlorotriphenylene (10g, 29.41mmol), (9-phenyl-9H-carbazol-3-yl) boronic acid (16.9g, 29.41mmol) and tetrakistriphenylphosphine Palladium (Tetrakis (triphenylphosphine) palladium) 4 mol% was added to 60 ml of dioxane, potassium carbonate (24.4 g, 40.86 mmol) was dissolved in 30 ml of water and mixed. After stirring at 100° C. for 12 hours, the reaction was terminated, cooled to room temperature, and water and an organic layer were separated. Only the organic layer was received, anhydrous magnesium sulfate was added thereto, stirred, filtered with a silica pad, and the solution was concentrated under reduced pressure for column purification, and 14.2 g (yield 68%) of Compound 3 was obtained.

MS: [M+H] ⁺ = 711

Synthesis of compound 4

The compound 1-bromo-3-chlorotriphenylene (10g, 29.41mmol), bis(pinacolato)diborone (9.7g, 38.23mmol), potassium acetate (5.8g, 58.83mmol), bis(dibenzyl) Ideneacetone) palladium (Bis (dibenzylideneacetone) palladium) 4 mol% and tricyclohexylphosphine 8 mol% were added to 80 ml dioxane and stirred at 100° C. for 12 hours. After the reaction was completed, the mixture was cooled to room temperature, anhydrous magnesium sulfate was added thereto, stirred, filtered with a silica pad, and concentrated under reduced pressure. After column purification, 9.3g (66% yield) of Intermediate 4-1 was obtained.

The intermediate 4-1 (9.3g, 19.36mmol), bromotriphenylsilane (13.1g, 38.731mmol) and tetrakistriphenylphosphine palladium (Tetrakis (triphenylphosphine) palladium) 4mol% was added to dioxane 50ml potassium carbonate (16.1g, 116.16mmol) was dissolved in 25ml of water and mixed. After stirring at 100° C. for 12 hours, the reaction was terminated, cooled to room temperature, and water and an organic layer were separated. Take only the organic layer, add anhydrous magnesium sulfate and stir. After filtration with a silica pad, the solution was concentrated under reduced pressure, followed by column purification, and 10.4 g (72% yield) of compound 4 was obtained.

MS: [M+H] ⁺ = 745

Synthesis of compound 5

After completely dissolving the compound 1-bromo-3-chlorotriphenylene (10g, 29.41mmol) and 9H-carbazole (4.9g, 29.41mmol) in 90ml of xylene, sodium-tert-butoxide (3.4 g, 35.29mmol) was added and stirred while increasing the temperature until refluxed. When reflux started, 2 mol% of bis(tri-tert-butylphosphine)palladium was slowly dropped and added. After 2 hours, the reaction was completed, the temperature was lowered to room temperature, concentrated under reduced pressure, and purified by column to obtain 9.5 g (yield 76%) of Intermediate 5-1.

The intermediate 5-1 (9.5g, 22.24mmol) and 2-phenyl-9H-carbazole (5.4g, 22.24mmol) were completely dissolved in 60ml of xylene, and sodium-tert-butoxide (2.6g, 26.69). mmol) and stirred while increasing the temperature until reflux. When reflux started, 2 mol% of bis(tri-tert-butylphosphine)palladium was slowly dropped and added. After 5 hours, the reaction was completed, the temperature was lowered to room temperature, concentrated under reduced pressure, and purified by column to obtain 8.3 g (59% yield) of compound 5.

MS: [M+H] ⁺ = 635

Synthesis of compound 6

The intermediate 5-1 (9.5g, 22.24mmol), bis (pinacolato) diboron (7.3g, 28.91mmol), potassium acetate (4.4g, 44.48mmol), bis (dibenzylideneacetone) palladium (Bis (dibenzylideneacetone)palladium) 4 mol% and tricyclohexylphosphine 8 mol% were added to 50 ml dioxane and stirred at 100° C. for 12 hours. After the reaction was completed, the mixture was cooled to room temperature, anhydrous magnesium sulfate was added thereto, stirred, filtered with a silica pad, and concentrated under reduced pressure. Column purification was performed to obtain 7.7 g (67% yield) of Intermediate 6-1.

Intermediate 6-1 (7.7g, 14.9mmol), (4-bromophenyl) triphenylsilane (6.2g, 14.9mmol) and tetrakistriphenylphosphine palladium (Tetrakis (triphenylphosphine) palladium) 2 mol% in tetrahydro Put in 50ml of furan, potassium carbonate (6.2g, 44.7mmol) was dissolved in 25ml of water and mixed. After stirring at 80° C. for 12 hours, the reaction was terminated, cooled to room temperature, and water and an organic layer were separated. Take only the organic layer, add anhydrous magnesium sulfate and stir. After filtration with a silica pad, the solution was concentrated under reduced pressure, followed by column purification, and 7.6 g (yield 70%) of compound 6 was obtained.

MS: [M+H] ⁺ = 728

Synthesis of compound 7

The compound 1-bromo-3-chlorotriphenylene (10g, 29.41mmol), (9-phenyl-9H-carbazol-2-yl) boronic acid (8.4g, 29.41mmol) and tetrakistriphenylphosphine Palladium (Tetrakis (triphenylphosphine) palladium) 2 mol% was added to 60 ml of tetrahydrofuran, potassium carbonate (8.1 g, 58.82 mmol) was dissolved in 30 ml of water and mixed. After stirring at 80° C. for 12 hours, the reaction was terminated, cooled to room temperature, and water and an organic layer were separated. Take only the organic layer, add anhydrous magnesium sulfate and stir. After filtration with a silica pad, the solution was concentrated under reduced pressure, followed by column purification, and 10.9 g (74% yield) of Intermediate 7-1 was obtained.

Intermediate 7-1 (10.9g, 21.66mmol) and 2-phenyl-9H-carbazole (5.3g, 21.66mmol) were completely dissolved in 60ml of xylene and sodium-tert-butoxide (2.5g, 25.99). mmol) and stirred while increasing the temperature until reflux. When reflux started, 1 mol% of bis(tri-tert-butylphosphine)palladium was slowly dropped and added. After 6 hours, the reaction was completed, the temperature was lowered to room temperature, concentrated under reduced pressure, and purified by column to give 8.9 g (yield 58%) of compound 7.

MS: [M+H] ⁺ = 711

Synthesis of compound 8

Intermediate 7-1 (10.9g, 21.66mmol) and 7,7-dimethyl-5,7-dihydroindeno [2,1-b] carbazole (6.1g, 21.66mmol) xylene (Xylene) 60ml After completely dissolved in sodium-tert-butoxide (2.5g, 25.99mmol) was added and stirred while raising the temperature until reflux. When reflux started, 1 mol% of bis(tri-tert-butylphosphine)palladium was slowly dropped and added. After 8 hours, the reaction was completed, the temperature was lowered to room temperature, concentrated under reduced pressure, and purified by column to obtain 8.8 g (yield 54%) of compound 8.

MS: [M+H] ⁺ = 751

Synthesis of compound 9

The compound 1-bromo-3-chlorotriphenylene (10g, 29.41mmol), (9-phenyl-9H-carbazol-3-yl) boronic acid (8.4g, 29.41mmol) and tetrakistriphenylphosphine Palladium (Tetrakis (triphenylphosphine) palladium) 2 mol% was added to 60 ml of tetrahydrofuran, potassium carbonate (8.1 g, 58.82 mmol) was dissolved in 30 ml of water and mixed. After stirring at 80° C. for 10 hours, the reaction was terminated, cooled to room temperature, and water and an organic layer were separated. Take only the organic layer, add anhydrous magnesium sulfate and stir. After filtration with a silica pad, the solution was concentrated under reduced pressure, followed by column purification, and 10.2 g (69% yield) of Intermediate 9-1 was obtained.

Intermediate 9-1 (10.2g, 20.27mmol) and 3-phenyl-9H-carbazole (4.9g, 20.27mmol) were completely dissolved in 60ml of xylene and sodium-tert-butoxide (2.3g, 24.32mmol). mmol) and stirred while increasing the temperature until reflux. When reflux started, 1 mol% of bis(tri-tert-butylphosphine)palladium was slowly dropped and added. After 6 hours, the reaction was completed, the temperature was lowered to room temperature, concentrated under reduced pressure, and purified by column to give 10.2 g (71% yield) of compound 9.

MS: [M+H] ⁺ = 711

<Experimental Example 1>

A glass substrate coated with a thin film of ITO (Indium tin oxide) to a thickness of 1,000Å was put in distilled water dissolved in a detergent and washed with ultrasonic waves. In this case, Fischer Co. product was used as a detergent, and distilled water secondarily filtered with a filter made by Millipore Co. was used as distilled water. After washing the ITO for 30 minutes, it was repeated twice with distilled water to perform ultrasonic cleaning for 10 minutes. 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.

On the prepared ITO transparent electrode m-MTDATA(60nm) / TCTA(80 nm) / Host + 10% by weight Ir(ppy) ₃ (300nm)/ BCP(10 nm)/ Alq ₃ (30 nm) / LiF(1 nm) ) / Al (200nm) to configure the light emitting device in the order. The structures of m-MTDATA, TCTA, Ir(ppy) ₃ and BCP are as follows, respectively.

<Experimental Example 1-1>

In Experimental Example 1, a light emitting device was manufactured using Compound 1 as a host.

<Experimental Example 1-2>

An organic light-emitting device was manufactured in the same manner as in Experimental Example 1-1, except that Compound 2 was used instead of Compound 1 in Experimental Example 1-1.

<Experimental Example 1-3>

An organic light-emitting device was manufactured in the same manner as in Experimental Example 1-1, except that Compound 3 was used instead of Compound 1 in Experimental Example 1-1.

<Experimental Example 1-4>

An organic light-emitting device was manufactured in the same manner as in Experimental Example 1-1, except that Compound 4 was used instead of Compound 1 in Experimental Example 1-1.

<Experimental Example 1-5>

An organic light-emitting device was manufactured in the same manner as in Experimental Example 1-1, except that Compound 5 was used instead of Compound 1 in Experimental Example 1-1.

<Experimental Example 1-6>

An organic light-emitting device was manufactured in the same manner as in Experimental Example 1-1, except that Compound 6 was used instead of Compound 1 in Experimental Example 1-1.

<Experimental Example 1-7>

An organic light-emitting device was manufactured in the same manner as in Experimental Example 1-1, except that Compound 7 was used instead of Compound 1 in Experimental Example 1-1.

<Experimental Example 1-8>

An organic light-emitting device was manufactured in the same manner as in Experimental Example 1-1, except that Compound 8 was used instead of Compound 1 in Experimental Example 1-1.

<Experimental Example 1-9>

An organic light-emitting device was manufactured in the same manner as in Experimental Example 1-1, except that Compound 9 was used instead of Compound 1 in Experimental Example 1-1.

<Comparative Example 1-1>

An organic light-emitting device was manufactured in the same manner as in Experimental Example 1-1, except that GH 1 was used instead of Compound 1 in Experimental Example 1-1.

<Comparative Example 1-2>

An organic light-emitting device was manufactured in the same manner as in Experimental Example 1-1, except that GH 2 was used instead of Compound 1 in Experimental Example 1-1.

<Comparative Example 1-3>

An organic light-emitting device was manufactured in the same manner as in Experimental Example 1-1, except that GH 3 was used instead of Compound 1 in Experimental Example 1-1.

<Comparative Example 1-4>

An organic light-emitting device was manufactured in the same manner as in Experimental Example 1-1, except that GH 4 was used instead of Compound 1 in Experimental Example 1-1.

When a current was applied to the organic light-emitting devices manufactured according to Experimental Examples 1-1 to 1-9 and Comparative Examples 1-1 to 1-4, the results of Table 1 were obtained.

compound
(Host) Voltage
(V@10mA/cm ² ) efficiency
(cd/A@10mA/cm ² ) EL peak
(nm) Experimental Example 1-1 Compound 1 3.79 43.81 517 Experimental Example 1-2 Compound 2 3.77 44.29 516 Experimental Example 1-3 Compound 3 3.68 45.26 518 Experimental Example 1-4 Compound 4 3.88 43.14 517 Experimental Example 1-5 Compound 5 3.81 42.38 515 Experimental Example 1-6 Compound 6 3.68 44.93 516 Experimental Example 1-7 Compound 7 3.90 42.64 516 Experimental Example 1-8 Compound 8 3.81 43.62 517 Experimental Example 1-9 Compound 9 3.72 42.75 518 Comparative Example 1-1 GH 1 5.61 39.08 517 Comparative Example 1-2 GH 2 5.45 38.93 517 Comparative Example 1-3 GH 3 5.09 37.11 517 Comparative Example 1-4 GH 4 5.47 38.14 517

In Table 1, the EL peak means the maximum emission wavelength (λmax), and the measurement method is as follows. The photoluminescence spectrum in a solution state was measured using an LS-55 manufactured by Perkin Elmer, and the emission spectrum at an excitation wavelength of 300 nm is 400 to 700 nm. As a solvent, high performance liquid chromatography grade (HPLC grade) tetrahydrofuran (THF) was used.

As a result of the experiment, the green organic light emitting devices of Experimental Examples 1-1 to 1-9 using the compounds represented by compounds 1 to 9 according to the present invention as a host material of the emission layer were Comparative Example 1-1 using conventional GH1 to GH4. It exhibited superior performance in terms of current efficiency and driving voltage than the green organic light emitting devices of 1-4.

In Comparative Example 1-1, GH 1 in which an aryl group different from the definition of Ar1 and Ar of the present invention was bonded to triphenylene at positions 1 and 3 was used, and in this case, it was confirmed that high voltage and low efficiency appeared.

GH 2 used in Comparative Example 1-2 is a compound in which Ar1 is bonded at the 3rd position of triphenylene, compared to Examples 1-1 to 1-9 in which Ar1 and Ar2 are bonded at the 1st and 3rd positions It was confirmed that the efficiency appeared.

In Comparative Example 1-3, a compound GH 3 in which an aryl group was bonded to position 1 of triphenylene and a substituent corresponding to the definition of Ar1 and Ar2 of the present invention was bonded at position 4 was used, and Comparative Example 1-4 Compound GH 4 in which a substituent corresponding to the definition of Ar1 and Ar2 of the present invention is bonded to position 2 and 11 of triphenylene was used. Through this, it was confirmed that the compounds of Examples 1-1 to 1-9 in which Ar1 and Ar2 are combined at positions 1 and 3 of the present invention have characteristics of low voltage and high efficiency.

1: substrate
2: anode
3: light-emitting layer
4: cathode
5: hole injection layer
6: hole transport layer
7: hole block
8: electron transport layer

Claims (8)

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

In Formula 1,
L1 and L2 are the same as or different from each other, and each independently a direct bond; Or an arylene group,
Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted indole group; A substituted or unsubstituted carbazole group; A substituted or unsubstituted benzocarbazole group; A substituted or unsubstituted dihydroindolocarbazole group; Substituted or unsubstituted dihydroindoloindole; A substituted or unsubstituted dihydroindenocarbazole group; A substituted or unsubstituted hexahydropyridoquinoline group; A substituted or unsubstituted triphenylsilyl group; Or a substituted or unsubstituted tetraphenylsilane group. The compound of claim 1, wherein Ar1 and Ar2 are the same as or different from each other, and each independently selected from the following structural formulas:

In the above structural formula, R4 is the same as or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group,
m is an integer of 1 to 8, n is an integer of 1 to 10,
When m and n are 2 or more, R4 in parentheses is the same as or different from each other. The compound of claim 1, wherein Ar1 and Ar2 are the same as each other. The compound of claim 1, wherein Ar1 and Ar2 are different from each other. The compound of claim 1, wherein the compound represented by Formula 1 is selected from the following structural formulas:

A first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers comprises the compound according to any one of claims 1 to 5 device. The organic light-emitting device of claim 6, wherein the organic material layer includes an emission layer, and the emission layer includes the compound. The organic light-emitting device of claim 6, wherein the organic material layer comprises a hole injection layer, a hole transport layer, or a hole injection and transport layer, and the hole injection layer, a hole transport layer, or a hole injection and transport layer comprises the compound.

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