KR102173642B1 - Hetero-cyclic compound and organic light emitting device comprising the same - Google Patents

Abstract

The present invention provides a novel heterocyclic compound and an organic light emitting device using the same.

Description

Hetero-cyclic compound and organic light emitting device comprising the same

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

In general, the organic light emission phenomenon refers to a phenomenon in which electrical energy is converted into light energy using an organic material. An organic light-emitting device using the organic light-emitting phenomenon has a wide viewing angle, excellent contrast, and fast response time, and has excellent luminance, driving voltage, and response speed characteristics, and thus many studies are being conducted.

The organic light emitting device generally has a structure including an anode and a cathode, and an organic material layer between the anode and the cathode. The organic material layer is often made of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device.For example, it may be formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. In the structure of such an organic light-emitting device, when a voltage is applied between the two electrodes, holes are injected from the anode and electrons from the cathode are injected into the organic material layer, and excitons are formed when the injected holes and electrons meet. It glows when it falls back to the ground.

Development of new materials for organic materials used in organic light emitting devices as described above is continuously required.

Korean Patent Publication No. 10-2000-0051826

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

The present invention provides a compound represented by the following formula (1).

[Formula 1]

In Formula 1,

Y is S, O, or CR' ₂ ,

Each R'is independently substituted or unsubstituted C _1-60 alkyl; Substituted or unsubstituted C _1-60 alkoxy; Substituted or unsubstituted C _3-60 cycloalkyl; Substituted or unsubstituted C _6-60 aryl; Substituted or unsubstituted C _6-60 aryloxy; Or a substituted or unsubstituted C _2-60 heteroaryl including at least one of O, N, Si and S,

R ₁ to R ₇ are each independently halogen; Hydroxy group; Cyano, nitrile; Nitro; Amino; Substituted or unsubstituted C _1-60 alkyl; Substituted or unsubstituted C _1-60 haloalkyl; Substituted or unsubstituted C _1-60 thioalkyl; Substituted or unsubstituted C _1-60 alkoxy; Substituted or unsubstituted C _1-60 haloalkoxy; Substituted or unsubstituted C _3-60 cycloalkyl; Substituted or unsubstituted C _1-60 alkenyl; Substituted or unsubstituted C _6-60 aryl; Substituted or unsubstituted C _6-60 aryloxy; Or a substituted or unsubstituted C _2-60 heteroaryl including at least one of O, N, Si and S,

a, e and g are each independently 0 to 4,

b, d and f are each independently 0 to 3,

c is from 0 to 5.

In addition, the present invention 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 a compound represented by Formula 1 do.

The compound represented by Chemical Formula 1 may be used as a material for an organic material layer of an organic light-emitting device, and may improve efficiency, low driving voltage, and/or lifetime characteristics in the organic light-emitting device. In particular, the compound represented by Formula 1 may be used as a hole injection, hole transport, hole injection and transport, and light emitting material.

FIG. 1 shows an example of an organic light-emitting device comprising a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4.
2 is a substrate (1), an anode (2), a hole injection layer (5), a hole transport layer (6), an electron blocking layer (7), a light emitting layer (8), an electron transport layer (9), an electron injection layer (10). And an example of an organic light-emitting device including the cathode 4 is shown.
3 is a substrate (1), an anode (2), a hole injection layer (5), a hole transport layer (6), a light emitting layer (8), an electron transport layer (9), an electron injection and transport layer (11), and a cathode (4). It shows an example of an organic light emitting device made of

Hereinafter, it will be described in more detail to aid the understanding of the present invention.

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

및

는 다른 치환기에 연결되는 결합을 의미한다. In this specification,

And

Means a bond connected to another substituent.

In the present specification, the term "substituted or unsubstituted" refers to deuterium; Halogen group; Nitrile group; Nitro group; Hydroxy group; Carbonyl group; Ester group; Imide group; Amino group; Phosphine oxide group; Alkoxy group; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy group; Arylsulfoxy group; Silyl group; Boron group; Alkyl group; Cycloalkyl group; Alkenyl group; Aryl group; Aralkyl group; Aralkenyl group; Alkylaryl group; Alkylamine group; Aralkylamine group; Heteroarylamine group; Arylamine group; Arylphosphine group; Or it means a substituted or unsubstituted substituted or unsubstituted with one or more substituents selected from the group consisting of a heterocyclic group containing one or more of N, O and S atoms, or linked with two or more substituents among the above-exemplified 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 to which two phenyl groups are connected.

In the present specification, the number of carbon atoms of the carbonyl group is not particularly limited, but it is preferably 1 to 40 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

In the present specification, the ester group may be substituted with an oxygen of the ester group with a straight chain, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.

In the present specification, the number of carbon atoms of the imide group is not particularly limited, but it is preferably 1 to 25 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

In the present specification, the silyl group is specifically trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, etc. However, it is not limited thereto.

In the present specification, the boron group specifically includes a trimethyl boron group, a triethyl boron group, a t-butyldimethyl boron group, a triphenyl boron group, and a phenyl boron group, but is not limited thereto.

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

In the present specification, the alkyl group may be a linear or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to an 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. According to another exemplary embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group 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, cycloheptylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2 -Dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like, but are not limited thereto.

In the present specification, the alkenyl group may be a linear or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to an exemplary embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-( Naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbenyl group, styrenyl group, and the like, but are not limited thereto.

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

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

등이 될 수 있다. 다만, 이에 한정되는 것은 아니다.In the present specification, the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure. When the fluorenyl group is substituted,

Etc. However, it is not limited thereto.

In the present specification, the heterocyclic group is a heterocyclic group including at least one of O, N, Si and S as a heterogeneous element, and the number of carbons is not particularly limited, but it is preferably 2 to 60 carbon atoms. Examples of the heterocyclic group include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group, acridyl group , Pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group, isoquinoline group, indole group , Carbazole group, benzoxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, phenanthroline group, isoxazolyl group, thiiadia There may be a zolyl group, a phenothiazinyl group, and a dibenzofuranyl group, but are not limited thereto.

In the present specification, the aryl group among the aralkyl group, aralkenyl group, alkylaryl group, and arylamine group is the same as the example of the aryl group described above. In the present specification, the alkyl group among the aralkyl group, the alkylaryl group and the alkylamine group is the same as the example of the aforementioned alkyl group. In the present specification, for heteroaryl among heteroarylamines, the description of the aforementioned heterocyclic group may be applied. In the present specification, the alkenyl group of the aralkenyl group is the same as the example of the alkenyl group described above. In the present specification, the description of the aryl group described above may be applied except that the arylene is a divalent group. In the present specification, the description of the aforementioned heterocyclic group may be applied except that the heteroarylene is a divalent group. In the present specification, the hydrocarbon ring is not a monovalent group, and the description of the aryl group or the cycloalkyl group described above may be applied except that the hydrocarbon ring is formed by bonding of two substituents. In the present specification, the heterocycle is not a monovalent group, and the description of the above-described heterocyclic group may be applied, except that two substituents are bonded to each other.

Meanwhile, in Formula 1, R'is preferably methyl.

In Formula 1, a, b, c, d, e, and f may be 0.

In Formula 1, at least one of R ₁ to R ₇ may be cyano.

Formula 1 may be any one selected from the group consisting of the following compounds.

In 1-1 to 1-16, Y may be S, O, or CR′ ₂ .

The definition of R'is as mentioned above.

Preferably, the compound represented by Formula 1 may be any one selected from the group consisting of the following.

The compound represented by Chemical Formula 1 can be prepared by a manufacturing method as shown in Scheme 1 below. The manufacturing method may be more specific in the manufacturing examples to be described later.

[Scheme 1]

In Reaction Scheme 1, the description of Y is as defined in Formula 1.

The compound represented by Formula 1 may be prepared by appropriately replacing the starting material according to the structure of the compound to be prepared by referring to Scheme 1 above.

In addition, the present invention provides an organic light-emitting device including the compound represented by Chemical Formula 1. For example, the present invention provides 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 a compound represented by Formula 1 do.

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

In addition, the organic material layer may include a hole injection layer, a hole transport layer, or a hole injection and transport layer (a layer that simultaneously injects and transports holes), and the hole injection layer, a hole transport layer, or a hole injection and transport layer is represented by the formula It includes the compound represented by 1.

In addition, the organic material layer may include an emission layer, and the emission layer includes the compound represented by Chemical Formula 1.

In addition, the emission layer includes two or more kinds of hosts, and one of the hosts includes the compound represented by Formula 1 above.

In addition, the organic material layer may include an electron transport layer, an electron injection layer, or an electron injection and transport layer (a layer that simultaneously injects and transports electrons), and the electron transport layer, an electron injection layer, or the electron injection and transport layer is represented by the formula It includes the compound represented by 1.

In addition, the electron transport layer, the electron injection layer, or the electron transport and injection layer includes the compound represented by Chemical Formula 1.

In addition, the organic material layer may include a light emitting layer and an electron transport layer, and the electron transport layer may include a compound represented by Formula 1 above.

In addition, the organic light emitting device according to the present invention may be an organic light emitting device having a structure (normal type) in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate. In addition, the organic light emitting device according to the present invention 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 embodiment of the present invention is illustrated in FIGS. 1 and 2.

1 shows an example of an organic light emitting device comprising a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4. In such a structure, the compound represented by Formula 1 may be included in the emission layer.

2 is a substrate (1), an anode (2), a hole injection layer (5), a hole transport layer (6), an electron blocking layer (7), a light emitting layer (8), an electron transport layer (9), an electron injection layer (10). And an example of an organic light-emitting device including the cathode 4 is shown. In such a structure, the compound represented by Formula 1 may be included in one or more of the hole injection layer, the hole transport layer, the electron blocking layer, the light emitting layer, the electron transport layer, and the electron injection layer.

3 is a substrate (1), an anode (2), a hole injection layer (5), a hole transport layer (6), a light emitting layer (8), an electron transport layer (9), an electron injection and transport layer (11), and a cathode (4). It shows an example of an organic light emitting device made of. In such a structure, the compound represented by Formula 1 may be included in one or more of the hole injection layer, the hole transport layer, the light emitting layer, the electron transport layer, and the electron injection and transport layer.

The organic light-emitting device according to the present invention may be manufactured by materials and methods known in the art, except that at least one of the organic material layers includes the compound represented by Chemical Formula 1. In addition, 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 according to the present invention may be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate. At this time, using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation, the anode is formed by depositing a metal or a conductive metal oxide or an alloy thereof on the substrate. 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 represented by 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, inkjet 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 (WO 2003/012890). However, the manufacturing method is not limited thereto.

For example, the first electrode is an anode, the second electrode is a cathode, or 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 cathode material 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 a metal and an 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 multi-layered materials such as LiF/Al or LiO ₂ /Al, but are not limited thereto.

The hole injection material is a layer that injects holes from the electrode, and the hole injection material has the ability to transport holes, so it has a hole injection effect at the anode, an excellent hole injection effect for the light emitting layer or the light emitting material, and is generated in the light emitting layer. A compound that prevents the transfer of the excitons into the electron injection layer or the electron injection material and has excellent thin film formation ability 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, etc., 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 light emitting layer.As a hole transport material, a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer and having high mobility for holes This 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.

The light-emitting material is a material capable of emitting light in a visible light region by transporting and bonding 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 of 8-hydroxy-quinoline aluminum complex (Alq ₃ ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-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 carbazole derivatives, dibenzofuran derivatives, ladder type Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

Dopant materials include aromatic amine derivatives, strylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene, chrysene, and periflanthene having an arylamino group, and the styrylamine compound is substituted or unsubstituted As a compound in which at least one arylvinyl group is substituted on the arylamine, one or two or more substituents selected from the group consisting of an aryl group, silyl group, alkyl group, cycloalkyl group, and arylamino group are substituted or unsubstituted. Specifically, there are styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like, but are not limited thereto. In addition, the metal complex includes an iridium complex, a platinum complex, and the like, but is not limited thereto.

The electron transport material is a layer that receives electrons from the electron injection layer and transports electrons to the emission layer. The electron transport material is a material that can transfer electrons from the cathode to the emission layer and transfers them to the emission layer. This 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 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 the light emitting material, and hole injection of excitons generated in the light emitting layer A compound that prevents migration to the layer and has excellent thin film formation ability is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, and their derivatives, metals Complex compounds and nitrogen-containing 5-membered ring derivatives, but are not limited thereto.

Examples of the metal complex compound include lithium 8-hydroxyquinolinato, 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 organic light emitting device according to the present invention may be a top emission type, a bottom emission type, or a double-sided emission type depending on the material used.

In addition, the compound represented by Formula 1 may be included in an organic solar cell or an organic transistor in addition to the organic light emitting device.

Hereinafter, preferred embodiments are presented to aid understanding of the invention. However, the following examples are only for illustrating the present invention, and the present invention is not limited thereto.

[ Manufacturing example ]

Manufacturing example 1: Preparation of intermediate A1

2-chloro-4-(4-chlorophenyl)-6-phenyl-1,3,5-triazine (15.0g, 49.64mmol), dibenzo[b,d]thiophene in a 500ml round bottom flask in nitrogen atmosphere After completely dissolving -4-ylboronic acid (11.3g, 49.64mmol) in 210ml of tetrahydrofuran, 1M aqueous potassium carbonate solution (150ml) was added, and tetrakis-(triphenylphosphine)palladium (1.7g, 1.49mmol) was added. After adding, the mixture was heated and stirred for 6 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 250 ml of ethanol to prepare the compound A1 (21.1g, yield: 94%) (MS[M+H] ⁺ = 450). .

Manufacturing example 2: Preparation of intermediate A2

Intermediate A1 (21.1 g, 46.89mmol) in a 1L round bottom flask in a nitrogen atmosphere, bis(pinacolato)diboron (13.1g, 51.58mmol), Pd(dba) ₂ (0.8g, 1.41mmol), PCy ₃ ( 0.8g, 2.81mmol), KOAc (13.8g, 140.68mmol) was added to 300 mL of dioxane, refluxed, and stirred for 2 hours. After confirming the completion of the reaction through HPLC, the base was removed by filtering and the solution was concentrated under reduced pressure. This was dissolved in CHCl _3, washed completely with water, and the solution in which the product was dissolved was concentrated under reduced pressure and recrystallized using ethanol to prepare the compound A2 (21.1g, yield 83%) (MS[M+H] ⁺ = 542).

Manufacturing example 3: Preparation of intermediate A3

Compound A2 (21.1g, 38.97mmol) and 1-bromo-2-nitrobenzene (8.7g, 42.86mmol) were completely dissolved in 200ml of tetrahydrofuran in a 1L round bottom flask in a nitrogen atmosphere, and then 2M aqueous potassium carbonate solution (60ml). Was added, tetrakis-(triphenylphosphine)palladium (1.4g, 1.17mmol) was added, followed by heating and stirring for 24 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 250 ml of ethanol to prepare the compound A3 (17.4g, yield: 83%) (MS[M+H] ⁺ = 537).

Manufacturing example 4: Preparation of intermediate A4

Triethyl phosphite (100 mL, 580.3 mmol) was added to Compound A3 (17.4 g, 32.43 mmol) in a 1 L round bottom flask in a nitrogen atmosphere, followed by heating and stirring for 3 hours. Lower the temperature to room temperature and filter to obtain a solid and wash it with water. The obtained compound was dried to prepare compound A4 (11.3g, yield: 69%) (MS[M+H] ⁺ = 505).

[ Example ]

Example 1: Preparation of compound 1

Compound A4 (11.3g, 22.39mmol), 2-bromodibenzo[b,d]thiophene (6.1g, 23.51mmol), sodium tert-butoxide (4.3g, 44.79mmol) in a 1L round bottom flask in a nitrogen atmosphere After adding xylene 200mL, bis(tri-tert-butylphosphine)palladium(0) (0.1g, 0.22mmol) was added and heated and stirred for 1 hour. Lower the temperature to room temperature and filter to obtain a solid and wash it with water. The obtained compound was dried to prepare compound 1 (5.7 g, yield: 37%) (MS[M+H] ⁺ = 687).

Example 2: Preparation of compound 2

Compound 2 was prepared in the same manner as in the method of preparing compound 1, except that 4-bromodibenzo[b,d]thiophene was used instead of 2-bromodibenzo[b,d]thiophene (MS[M+ H] ⁺ = 687).

Example 3: Preparation of compound 3

Compound 3 was prepared in the same manner as in the method of preparing compound 1, except that 1-bromodibenzo[b,d]thiophene was used instead of 2-bromodibenzo[b,d]thiophene (MS[M+ H] ⁺ = 687).

Example 4: Preparation of compound 4

1-(4-(dibenzo[b,d]thiophen-4-yl)-6-phenyl-1,3,5-triazine- instead of compound A4 and 2-bromodibenzo[b,d]thiophene 2-yl)-9H-carbazole and 3-bromodibenzo[b,d]thiophene were used to prepare compound 4 in the same manner as in the preparation of compound 1 (MS[M+H] ⁺ = 687).

Example 5: Preparation of compound 5

Compound 5 was prepared in the same manner as the method of preparing compound 4, except that 2-bromodibenzo[b,d]thiophene was used instead of 3-bromodibenzo[b,d]thiophene (MS[M+ H] ⁺ = 687).

Example 6: Preparation of compound 6

3-(4-(dibenzo[b,d]thiophen-4-yl)-6-phenyl-1,3,5-triazine- instead of compound A4 and 2-bromodibenzo[b,d]thiophene- 2-yl)-9H-carbazole and 4-bromodibenzo[b,d]thiophene were used to prepare compound 6 in the same manner as in the preparation of compound 1 (MS[M+H] ⁺ = 687).

Example 7: Preparation of compound 7

3-(4-(dibenzo[b,d]thiophen-4-yl)-6-phenyl-1,3,5-triazine- instead of compound A4 and 2-bromodibenzo[b,d]thiophene 2-yl)-9H-carbazole and 3-bromodibenzo[b,d]thiophene were used to prepare compound 7 in the same manner as in the preparation of compound 1 (MS[M+H] ⁺ = 687).

Example 8: Preparation of compound 8

3-(4-(dibenzo[b,d]thiophen-4-yl)-6-phenyl1,3,5-triazine-2 instead of compound A4 and 2-bromodibenzo[b,d]thiophene -Yl)-9H-carbazole and 1-bromodibenzo[b,d]thiophene were used, and compound 8 was prepared in the same manner as the method of preparing compound 1 (MS[M+H] ⁺ = 687).

Example 9: Preparation of compound 9

Compound A4 and 2-bromodibenzo[b,d]thiophene instead of 4-(4-(dibenzo[b,d]thiophen-4-yl)-6-phenyl-1,3,5-triazine- 2-yl)-9H-carbazole and 4-bromodibenzo[b,d]thiophene was used to prepare compound 9 in the same manner as in the preparation of compound 1 (MS[M+H] ⁺ = 687).

Example 10: Preparation of compound 10

Compound A4 and 2-bromodibenzo[b,d]thiophene instead of 4-(4-(dibenzo[b,d]thiophen-4-yl)-6-phenyl-1,3,5-triazine- 2-yl)-9H-carbazole and 2-bromodibenzo[b,d]thiophene were used to prepare compound 10 in the same manner as in the preparation of compound 1 (MS[M+H] ⁺ = 687).

Example 11: Preparation of compound 11

Compound A4 and 2-bromodibenzo[b,d]thiophene instead of 4-(4-(dibenzo[b,d]thiophen-4-yl)-6-phenyl-1,3,5-triazine- 2-yl)-9H-carbazole and 1-bromodibenzo[b,d]thiophene were used to prepare compound 11 in the same manner as in the preparation of compound 1 (MS[M+H] ⁺ = 687).

Example 12: Preparation of compound 12

1-(4-(dibenzo[b,d]thiophen-4-yl)-6-phenyl-1,3,5-triazine- instead of compound A4 and 2-bromodibenzo[b,d]thiophene 2-yl)-9H-carbazole and 4-bromodibenzo[b,d]furan was used to prepare compound 12 in the same manner as in the preparation of compound 1 (MS[M+H] ⁺ = 671).

Example 13: Preparation of compound 13

Compound A4 and 2-bromodibenzo[b,d]thiophene instead of 1-(4-(dibenzo[b,d]thiophen-4-yl)-6-phenyl-1,3,5-triazine Compound 13 was prepared in the same manner as in the method of preparing compound 1, except for using -2-yl)-9H-carbazole and 2-bromodibenzo[b,d]furan (MS[M+H] ⁺ = 671).

Example 14: Preparation of compound 14

2-(4-(dibenzo[b,d]thiophen-4-yl)-6-phenyl-1,3,5-triazine- instead of compound A4 and 2-bromodibenzo[b,d]thiophene 2-yl)-9H-carbazole and 3-bromodibenzo[b,d]furan was used to prepare compound 14 in the same manner as in the preparation of compound 1 (MS[M+H] ⁺ = 671).

Example 15: Preparation of compound 15

2-(4-(dibenzo[b,d]thiophen-4-yl)-6-phenyl-1,3,5-triazine- instead of compound A4 and 2-bromodibenzo[b,d]thiophene 2-yl)-9H-carbazole and 2-bromodibenzo[b,d]furan was used to prepare compound 15 in the same manner as in the preparation of compound 1 (MS[M+H] ⁺ = 671).

Example 16: Preparation of compound 16

2-(4-(dibenzo[b,d]thiophen-4-yl)-6-phenyl-1,3,5-triazine- instead of compound A4 and 2-bromodibenzo[b,d]thiophene 2-yl)-9H-carbazole and 1-bromodibenzo[b,d]furan was used to prepare compound 16 in the same manner as in the preparation of compound 1 (MS[M+H] ⁺ = 671).

Example 17: Preparation of compound 17

3-(4-(dibenzo[b,d]thiophen-4-yl)-6-phenyl-1,3,5-triazine- instead of compound A4 and 2-bromodibenzo[b,d]thiophene 2-yl)-9H-carbazole and 4-bromodibenzo[b,d]furan was used to prepare compound 17 in the same manner as in the preparation of compound 1 (MS[M+H] ⁺ = 671).

Example 18: Preparation of compound 18

3-(4-(dibenzo[b,d]thiophen-4-yl)-6-phenyl-1,3,5-triazine- instead of compound A4 and 2-bromodibenzo[b,d]thiophene 2-yl)-9H-carbazole and 2-bromodibenzo[b,d]furan was used, and compound 18 was prepared in the same manner as in the preparation of compound 1 (MS[M+H] ⁺ = 671).

Example 19: Preparation of compound 19

Compound A4 and 2-bromodibenzo[b,d]thiophene instead of 4-(4-(dibenzo[b,d]thiophen-4-yl)-6-phenyl-1,3,5-triazine- 2-yl)-9H-carbazole and 4-bromodibenzo[b,d]furan was used to prepare compound 19 in the same manner as in the preparation of compound 1 (MS[M+H] ⁺ = 671).

Example 20: Preparation of compound 20

Compound A4 and 2-bromodibenzo[b,d]thiophene instead of 4-(4-(dibenzo[b,d]thiophen-4-yl)-6-phenyl-1,3,5-triazine- 2-yl)-9H-carbazole and 3-bromodibenzo[b,d]furan was used to prepare compound 20 in the same manner as in the preparation of compound 1 (MS[M+H] ⁺ = 671).

Example 21: Preparation of compound 21

Compound A4 and 2-bromodibenzo[b,d]thiophene instead of 4-(4-(dibenzo[b,d]thiophen-4-yl)-6-phenyl-1,3,5-triazine- 2-yl)-9H-carbazole and 1-bromodibenzo[b,d]furan was used to prepare compound 21 in the same manner as in the preparation of compound 1 (MS[M+H] ⁺ = 671).

Example 22: Preparation of compound 22

1-(4-(dibenzo[b,d]thiophen-4-yl)-6-phenyl-1,3,5-triazine- instead of compound A4 and 2-bromodibenzo[b,d]thiophene 2-yl)-9H-carbazole and 1-bromo-9,9-dimethyl-9H-fluorene was used to prepare compound 22 in the same manner as for preparing compound 1 (MS[M+ H] ⁺ = 697).

Example 23: Preparation of compound 23

1-(4-(dibenzo[b,d]thiophen-4-yl)-6-phenyl-1,3,5-triazine- instead of compound A4 and 2-bromodibenzo[b,d]thiophene 2-yl)-9H-carbazole and 3-bromo-9,9-dimethyl-9H-fluorene was used, and compound 23 was prepared in the same manner as in the method of preparing compound 1 (MS[M+ H] ⁺ = 697).

Example 24: Preparation of compound 24

2-(4-(dibenzo[b,d]thiophen-4-yl)-6-phenyl-1,3,5-triazine- instead of compound A4 and 2-bromodibenzo[b,d]thiophene 2-yl)-9H-carbazole and 1-bromo-9,9-dimethyl-9H-fluorene was used to prepare compound 24 in the same manner as for preparing compound 1 (MS[M+ H] ⁺ = 697).

Example 25: Preparation of compound 25

2-(4-(dibenzo[b,d]thiophen-4-yl)-6-phenyl-1,3,5-triazine- instead of compound A4 and 2-bromodibenzo[b,d]thiophene 2-yl)-9H-carbazole and 2-bromo-9,9-dimethyl-9H-fluorene was used to prepare compound 25 in the same manner as for preparing compound 1 (MS[M+ H] ⁺ = 697).

Example 26: Preparation of compound 26

2-(4-(dibenzo[b,d]thiophen-4-yl)-6-phenyl-1,3,5-triazine- instead of compound A4 and 2-bromodibenzo[b,d]thiophene 2-yl)-9H-carbazole and 4-bromo-9,9-dimethyl-9H-fluorene was used to prepare compound 26 in the same manner as in the preparation of compound 1 (MS[M+ H] ⁺ = 697).

Example 27: Preparation of compound 27

3-(4-(dibenzo[b,d]thiophen-4-yl)-6-phenyl-1,3,5-triazine- instead of compound A4 and 2-bromodibenzo[b,d]thiophene 2-yl)-9H-carbazole and 2-bromo-9,9-dimethyl-9H-fluorene was used to prepare compound 27 in the same manner as in the method of preparing compound 1 (MS[M+ H] ⁺ = 697).

Example 28: Preparation of compound 28

3-(4-(dibenzo[b,d]thiophen-4-yl)-6-phenyl-1,3,5-triazine- instead of compound A4 and 2-bromodibenzo[b,d]thiophene 2-yl)-9H-carbazole and 3-bromo-9,9-dimethyl-9H-fluorene was used to prepare compound 28 in the same manner as in the method of preparing compound 1 (MS[M+ H] ⁺ = 697).

Example 29: Preparation of compound 29

Compound A4 and 2-bromodibenzo[b,d]thiophene instead of 4-(4-(dibenzo[b,d]thiophen-4-yl)-6-phenyl-1,3,5-triazine- 2-yl)-9H-carbazole and 2-bromo-9,9-dimethyl-9H-fluorene was used to prepare compound 29 in the same manner as the method of preparing compound 1 (MS[M+ H] ⁺ = 697).

Example 30: Preparation of compound 30

Compound A4 and 2-bromodibenzo[b,d]thiophene instead of 4-(4-(dibenzo[b,d]thiophen-4-yl)-6-phenyl-1,3,5-triazine- 2-yl)-9H-carbazole and 4-bromo-9,9-dimethyl-9H-fluorene was used to prepare compound 30 in the same manner as in the method of preparing compound 1 (MS[M+ H] ⁺ = 697).

Example 31: Preparation of compound 31

Compound 31 was prepared in the same manner as for preparing compound 1, except that compound A4-1 was used instead of compound A4 (MS[M+H] ⁺ = 712).

Example 32: Preparation of compound 32

3-(4-(dibenzo[b,d]thiophen-4-yl)-6-phenyl-1,3,5-triazine- instead of compound A4 and 2-bromodibenzo[b,d]thiophene 2-yl)-9H-carbazole and 8-bromodibenzo[b,d]thiophene-2-carbonitrile was used to prepare compound 32 in the same manner as in the method of preparing compound 1 (MS[ M+H] ⁺ = 712).

Example 33: Preparation of compound 33

3-(4-(dibenzo[b,d]thiophen-4-yl)-6-phenyl-1,3,5-triazine- instead of compound A4 and 2-bromodibenzo[b,d]thiophene 2-yl)-9H-carbazole and 6-bromodibenzo[b,d]thiophene-3-carbonitrile was used to prepare compound 33 in the same manner as in the method of preparing compound 1 (MS[ M+H] ⁺ = 712).

Example 34: Preparation of compound 34

Compound 34 was prepared in the same manner as the method for preparing compound 21, except that compound A4-2 was used instead of compound A4 (MS[M+H] ⁺ = 696).

Example 35: Preparation of compound 35

3-(4-(dibenzo[b,d]thiophen-4-yl)-6-phenyl-1,3,5-triazine- instead of compound A4 and 2-bromodibenzo[b,d]thiophene 2-yl)-9H-carbazole and 7-bromodibenzo[b,d]furan-2-carbonitrile was used to prepare compound 35 in the same manner as in the method of preparing compound 1 (MS[M +H] ⁺ = 696).

Example 36: Preparation of compound 36

3-(4-(dibenzo[b,d]thiophen-4-yl)-6-phenyl-1,3,5-triazine- instead of compound A4 and 2-bromodibenzo[b,d]thiophene 2-yl)-9H-carbazole and 8-bromodibenzo[b,d]furan-2-carbonitrile was used to prepare compound 36 in the same manner as in the method of preparing compound 1 (MS[M +H] ⁺ = 696).

[ Experimental example ]

Experimental example 1-1

A glass substrate coated with a thin film of ITO (indium tin oxide) to a thickness of 1,300Å was placed in distilled water dissolved in a detergent and washed with ultrasonic waves. At this time, a product made by Fischer Co. was used as a detergent, and distilled water secondarily filtered with a filter manufactured 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 cleaning 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 ITO transparent electrode prepared as described above, the following HI-1 compound was thermally vacuum deposited to a thickness of 50 Å to form a hole injection layer. The following HT-1 compound was thermally vacuum deposited on the hole injection layer to a thickness of 250 Å to form a hole transport layer, and the following HT-2 compound was vacuum deposited on the HT-1 evaporated film to a thickness of 50 Å to form an electron blocking layer. A light emitting layer having a thickness of 400 Å was formed on the HT-2 deposited film by co-depositing Compound 1 prepared in Example 1, the following YGH-1 compound, and a phosphorescent dopant YGD-1 at a weight ratio of 44:44:12 as a light emitting layer. The following ET-1 compound was vacuum-deposited on the light emitting layer to a thickness of 250Å to form an electron transport layer, and the following ET-2 compound and Li were co-deposited on the electron transport layer in a weight ratio of 98:2 to form an electron injection layer. 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 organic materials was maintained at 0.4 ~ 0.7 Å/sec, and the deposition rate of aluminum was maintained at 2 Å/sec, and the vacuum degree during deposition was maintained at 1 × 10 ^-7 ~ 5 × 10 ^-8 torr. I did.

Experimental example 1-1 to 1-36

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

Comparative Experimental Example 1-1 and 1-2

In Experimental Example 1, an organic light-emitting device was manufactured in the same manner as in Experimental Example 1-1, except that the compound shown in Table 1 was used instead of the compound 1 of Example 1. Meanwhile, the compounds of CE1 and CE2 in Table 1 are as follows.

The experimental examples and comparative experimental examples were measured drive voltage and luminous efficiency of the organic light emitting devices at a current density of 10 mA / cm ² at, 50 mA / cm ² the time of 95% compared to the initial luminance at a current density (LT ₉₅ ) Was measured. The results are shown in Table 1 below.

compound Voltage(V)
(@10mA/cm ² ) Efficiency (Cd/A)
(@10mA/cm ² ) Color coordinates
(x,y) Life (hr)
(LT ₉₅ at 50mA/cm ² ) Experimental Example 1-1 Compound 1 3.39 66 0.134, 0.133 120 Experimental Example 1-2 Compound 2 3.42 60 0.133, 0.133 180 Experimental Example 1-3 Compound 3 3.45 62 0.134, 0.132 220 Experimental Example 1-4 Compound 4 3.66 71 0.134, 0.132 265 Experimental Example 1-5 Compound 5 3.82 72 0.134, 0.132 170 Experimental Example 1-6 Compound 6 3.24 69 0.134, 0.133 170 Experimental Example 1-7 Compound 7 3.49 68 0.133, 0.133 160 Experimental Example 1-8 Compound 8 3.85 71 0.134, 0.132 140 Experimental Example 1-9 Compound 9 3.77 67 0.134, 0.132 277 Experimental Example 1-10 Compound 10 3.72 72 0.134, 0.132 290 Experimental Example 1-11 Compound 11 3.44 70 0.134, 0.133 220 Experimental Example 1-12 Compound 12 3.46 70 0.132, 0.134 115 Experimental Example 1-13 Compound 13 3.40 68 0.133, 0.135 160 Experimental Example 1-14 Compound 14 3.38 80 0.134, 0.132 150 Experimental Example 1-15 Compound 15 3.39 60 0.134, 0.132 145 Experimental Example 1-16 Compound 16 3.44 50 0.134, 0.133 100 Experimental Example 1-17 Compound 17 3.52 80 0.133, 0.133 120 Experimental Example 1-18 Compound 18 3.33 70 0.134, 0.132 135 Experimental Example 1-19 Compound 19 3.47 90 0.134, 0.132 110 Experimental Example 1-20 Compound 20 3.40 77 0.134, 0.132 100 Experimental Example 1-21 Compound 21 3.98 74 0.134, 0.132 100 Experimental Example 1-22 Compound 22 3.85 66 0.134, 0.132 100 Experimental Example 1-23 Compound 23 3.70 76 0.134, 0.132 130 Experimental Example 1-24 Compound 24 3.92 78 0.134, 0.133 140 Experimental Example 1-25 Compound 25 3.55 75 0.132, 0.134 180 Experimental Example 1-26 Compound 26 3.42 70 0.133, 0.135 190 Experimental Example 1-27 Compound 27 3.39 64 0.134, 0.132 200 Experimental Example 1-28 Compound 28 3.46 68 0.133, 0.133 220 Experimental Example 1-29 Compound 29 3.58 53 0.134, 0.132 150 Experimental Example 1-30 Compound 30 3.64 70 0.134, 0.132 100 Experimental Example 1-31 Compound 31 3.79 82 0.133, 0.135 100 Experimental Example 1-32 Compound 32 3.76 88 0.131, 0.130 95 Experimental Example 1-33 Compound 33 3.59 70 0.133, 0.132 95 Experimental Example 1-34 Compound 34 3.75 80 0.134, 0.135 80 Experimental Example 1-35 Compound 35 3.54 77 0.132, 0.133 80 Experimental Example 1-36 Compound 36 3.52 80 0.133, 0.135 90 Comparative Experimental Example 1-1 CE 1 4.00 70 0.46, 0.53 90 Comparative Experimental Example 1-2 CE 2 4.50 60 0.44, 0.55 15

As shown in Table 1, when the compound of the present invention was used as the light emitting layer material, it was confirmed that the compound of the present invention exhibited excellent characteristics in terms of efficiency and lifespan compared to the Comparative Experimental Example.

Experimental example 2-1

A glass substrate (corning 7059 glass) coated with a thin film of ITO (indium tin oxide) to a thickness of 1,000 Å was placed in distilled water dissolved in a dispersant and washed with ultrasonic waves. The detergent was manufactured by Fischer Co., and the distilled water was Millipore Co. Distilled water filtered secondarily with the product's filter was used. After washing the ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After washing with distilled water, ultrasonic washing was performed in the order of isopropyl alcohol, acetone, and methanol, followed by drying.

The following HI-1 compound was thermally vacuum deposited to a thickness of 500 Å on the prepared ITO transparent electrode to form a hole injection layer. The following HT-1 compound was vacuum deposited on the hole injection layer to a thickness of 400 Å to form a hole transport layer, and the host H1 and the dopant D1 compound were vacuum-deposited on the hole transport layer to a thickness of 300 Å at a weight ratio of 97.5:2.5 to emit light. Formed. An electron transport layer was formed by vacuum depositing the following compound ET-A to a thickness of 50Å on the emission layer. On the electron transport layer, compound 1 prepared in Example 1 and LiQ (Lithium Quinolate) were vacuum-deposited at a weight ratio of 1:1 to form an electron injection and transport layer with a thickness of 350 Å. Lithium fluoride (LiF) in a thickness of 12 Å and aluminum in a thickness of 2,000 Å were sequentially deposited on the electron injection and transport layer to form a negative electrode.

In the above process, the deposition rate of the organic material was maintained at 0.4 ~ 0.7Å/sec, the deposition rate of lithium fluoride at the cathode was 0.3Å/sec, and the deposition rate of aluminum was 2Å/sec, and the vacuum degree during deposition was 2×10 ^{− 7} By maintaining ~ 5 × 10 ^-6 torr, an organic light emitting device was manufactured.

Experimental example 2-2 to 2-36

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

Comparative Experimental Example 2-1 and 2-2

An organic light-emitting device was manufactured in the same manner as in Experimental Example 2-1, except that the compound shown in Table 2 below was used instead of Compound 1 of Example 1 in Experimental Example 2-1. The compounds of CE3 and CE4 in Table 2 are as follows.

In the above Experimental Examples and Comparative Experimental Examples, the driving voltage and luminous efficiency of the organic light-emitting device were measured at a current density of 10 mA/cm ² , and the time (LT ₉₅ ) was 95% of the initial luminance at a current density of 50 mA/cm ² Measured. The results are shown in Table 1 below.

compound Voltage(V)
(@10mA/cm ² ) Efficiency (Cd/A)
(@10mA/cm ² ) Color coordinates
(x,y) Life (hr)
(LT95 at 50mA/cm ² ) Experimental Example 2-1 Compound 1 3.39 67 0.134, 0.133 100 Experimental Example 2-2 Compound 2 3.52 60 0.133, 0.133 80 Experimental Example 2-3 Compound 3 3.50 90 0.134, 0.132 95 Experimental Example 2-4 Compound 4 3.60 75 0.134, 0.132 100 Experimental Example 2-5 Compound 5 3.90 82 0.134, 0.132 100 Experimental Example 2-6 Compound 6 3.60 73 0.134, 0.133 150 Experimental Example 2-7 Compound 7 3.55 70 0.133, 0.133 120 Experimental Example 2-8 Compound 8 3.66 72 0.134, 0.132 135 Experimental Example 2-9 Compound 9 3.77 75 0.133, 0.133 140 Experimental Example 2-10 Compound 10 3.82 66 0.133, 0.135 100 Experimental Example 2-11 Compound 11 3.66 80 0.134, 0.132 80 Experimental Example 2-12 Compound 12 3.42 70 0.134, 0.132 70 Experimental Example 2-13 Compound 13 3.34 75 0.133, 0.135 75 Experimental Example 2-14 Compound 14 3.60 74 0.135, 0.133 80 Experimental Example 2-15 Compound 15 3.63 68 0.134, 0.132 85 Experimental Example 2-16 Compound 16 3.66 70 0.134, 0.133 100 Experimental Example 2-17 Compound 17 3.58 78 0.133, 0.133 160 Experimental Example 2-18 Compound 18 3.48 80 0.134, 0.132 115 Experimental Example 2-19 Compound 19 3.67 85 0.134, 0.132 90 Experimental Example 2-20 Compound 20 3.86 84 0.134, 0.133 95 Experimental Example 2-21 Compound 21 3.83 73 0.132, 0.134 85 Experimental Example 2-22 Compound 22 3.80 82 0.133, 0.135 70 Experimental Example 2-23 Compound 23 3.75 78 0.133, 0.135 75 Experimental Example 2-24 Compound 24 3.77 85 0.135, 0.133 60 Experimental Example 2-25 Compound 25 3.73 70 0.134, 0.132 95 Experimental Example 2-26 Compound 26 3.66 83 0.134, 0.133 130 Experimental Example 2-27 Compound 27 3.62 84 0.133, 0.133 135 Experimental Example 2-28 Compound 28 3.60 68 0.134, 0.132 140 Experimental Example 2-29 Compound 29 3.58 77 0.134, 0.132 135 Experimental Example 2-30 Compound 30 3.74 75 0.134, 0.132 100 Experimental Example 2-31 Compound 31 3.82 80 0.133, 0.135 100 Experimental Example 2-32 Compound 32 3.73 90 0.131, 0.130 100 Experimental Example 2-33 Compound 33 3.65 80 0.133, 0.132 95 Experimental Example 2-34 Compound 34 3.70 85 0.134, 0.135 80 Experimental Example 2-35 Compound 35 3.50 90 0.132, 0.133 70 Experimental Example 2-36 Compound 36 3.52 80 0.133, 0.135 90 Comparative Experimental Example 2-1 CE3 3.90 58 0.133, 0.133 60 Comparative Experimental Example 2-2 CE4 4.10 66 0.134, 0.132 40 Comparative Experimental Example 2-3 CE5 3.90 75 0.132, 0.135 70

As shown in Table 2, when the compound of the present invention was used as an electron transport layer material, it was confirmed that the compound of the present invention exhibited excellent characteristics in terms of efficiency and lifetime compared to the comparative experimental example.

1: substrate 2: anode
3: light emitting layer 4: cathode
5: hole injection layer 6: hole transport layer
7: electron blocking layer 8: emitting layer
9: electron transport layer 10: electron injection layer
11: Electron injection and transport layer

Claims (9)

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

In Formula 1,
Y is S, O, or CR' ₂ ,
R'is unsubstituted C _1-60 alkyl,
R ₁ to R ₇ are cyano,
a and g are each independently 0 or 1,
b, c, d, e and f are 0.
The method of claim 1,
R'is methyl.
The method of claim 1,
a is 0, the compound.
delete The method of claim 1,
Formula 1 is a compound represented by any one selected from the group consisting of:

The description of Y is as defined in paragraph 1.
The method of claim 1,
The compound represented by Formula 1 is any one selected from the group consisting of the following compounds:

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 is any one of claims 1 to 3, 5, and 6 An organic light-emitting device comprising the compound according to claim one.
The method of claim 7,
The organic material layer containing the compound may include an electron injection layer; Electron transport layer; Electron injection and transport layer; Or an organic light emitting device which is a light emitting layer.
The method of claim 8,
The light emitting layer includes two or more types of hosts, and one of the hosts is the compound.

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