KR20230132258A - Novel compound and organic light emitting device comprising the same - Google Patents

Abstract

The present invention provides a novel compound and an organic light emitting device containing the same. The compound represented by the chemical formula 1 can be used as a material for an organic material layer of the organic light emitting device, and can improve efficiency, lower driving voltage, and/or improve lifespan characteristics of the organic light emitting device.

Description

Novel compound and organic light emitting device comprising the same}

The present invention relates to novel compounds and organic light-emitting devices containing them.

In general, organic luminescence refers to a phenomenon that converts electrical energy into light energy using organic materials. Organic light-emitting devices using the organic light-emitting phenomenon have a wide viewing angle, excellent contrast, fast response time, and excellent luminance, driving voltage, and response speed characteristics, so much research is being conducted.

Organic light emitting devices generally have a structure including an anode, a cathode, and an organic layer between the anode and the cathode. The organic material layer is often composed of a multi-layer structure made of different materials to increase the efficiency and stability of the organic light-emitting device, and may be composed of, for example, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer. In the structure of this organic light-emitting device, when a voltage is applied between the two electrodes, holes are injected from the anode and electrons from the cathode into the organic material layer. When the injected holes and electrons meet, an exciton is formed, and this exciton is When it falls back to the ground state, it glows.

The 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 novel organic light-emitting materials and organic light-emitting devices containing the same.

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

[Formula 1]

In Formula 1,

X is O or S,

One of A and B is -L-Ar ₁ , the other is -Ar ₂ ,

Wherein L is a single bond or substituted or unsubstituted C _6-60 arylene,

이고,Ar ₁ is

ego,

Here, X ₁ to X ₃ are each independently N, CH, or CD, but at least two of X ₁ to X ₃ are N,

R ₁ and R ₂ are each independently hydrogen, deuterium, phenyl, biphenylyl, naphthyl, phenanthrenyl, pyridinyl, dibenzofuranyl, dibenzothiophenyl, or dimethylfluorenyl, and R ₁ and R ₂ is each independently unsubstituted or C _2-60 hetero containing at least one selected from the group consisting of deuterium, cyano, C _1-20 alkyl, C _6-60 aryl, or N, O, and S. substituted with aryl,

Ar ₂ is phenyl, biphenylyl, or naphthyl.

In addition, the present invention includes a first electrode; a second electrode provided opposite to the first electrode; and an organic light-emitting device comprising at least one organic material layer provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes a compound represented by Formula 1. .

The compound represented by the above-described formula 1 can be used as a material for the organic layer of an organic light-emitting device, and can improve efficiency, low driving voltage, and/or lifespan characteristics of the organic light-emitting device. In particular, the compound represented by the above-mentioned formula 1 can be used as a hole injection, hole transport, light emission, electron transport, and/or electron injection material.

Figure 1 shows an example of an organic light-emitting device consisting of a substrate 1, an anode 2, a light-emitting layer 3, an electron injection and transport layer 4, and a cathode 5.
2 shows a substrate 1, an anode 2, a hole injection layer 6, a first hole transport layer 7, a second hole transport layer 8, a light emitting layer 3, an electron injection and transport layer 4, and a cathode. (5) shows an example of an organic light-emitting device.

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

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

In this specification, or means a bond connected to another substituent.

As used herein, the term “substituted or unsubstituted” refers to deuterium; halogen group; Nitrile group; nitro group; hydroxyl group; carbonyl group; ester group; imide group; amino group; Phosphine oxide group; Alkoxy group; Aryloxy group; Alkylthioxy group; Arylthioxy group; Alkyl sulphoxy group; Aryl sulfoxy 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 substituted or unsubstituted with one or more substituents selected from the group consisting of a heteroaryl group containing one or more of N, O and S atoms, or substituted or unsubstituted with two or more of the above-exemplified substituents linked. . For example, “a substituent group in which two or more substituents are connected” may be a biphenyl group. That is, the biphenyl group may be an aryl group, or it may be interpreted as a substituent in which two phenyl groups are connected.

In this specification, the carbon number of the carbonyl group is not particularly limited, but is preferably 1 to 40 carbon atoms. Specifically, the substituent may have the following structure, but is not limited thereto.

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

In this specification, the carbon number of the imide group is not particularly limited, but is preferably 1 to 25 carbon atoms. Specifically, the substituent may have the structure shown below, but is not limited thereto.

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

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

In this specification, examples of halogen groups include fluorine, chlorine, bromine, or iodine.

In the present specification, the alkyl group may be straight chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the carbon number of the alkyl group is 1 to 20. According to another embodiment, the carbon number of the alkyl group is 1 to 10. According to another embodiment, the carbon number of the alkyl group is 1 to 6. Specific examples of alkyl groups 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 -Dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, etc., but is not limited to these.

In the present specification, the alkenyl group may be straight chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another 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, etc., but are not limited to these.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the carbon number of the cycloalkyl group is 3 to 20. According to another embodiment, the carbon number of the cycloalkyl group is 3 to 6. Specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3, Examples include, but are not limited to, 4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, and cyclooctyl.

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

In the present specification, the fluorenyl group may be substituted, and two substituents may be combined with each other to form a spiro structure. When the fluorenyl group is substituted, It can be etc. However, it is not limited to this.

In the present specification, the heteroaryl group is a heteroaryl group containing one or more of O, N, Si, and S as heterogeneous elements, and the number of carbon atoms is not particularly limited, but it is preferably 2 to 60 carbon atoms. According to one embodiment, the heteroaryl group has 6 to 30 carbon atoms. According to one embodiment, the heteroaryl group has 6 to 20 carbon atoms. Examples of heteroaryl groups 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, and 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, benzooxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, phenanthroline group, isoxazolyl group, thiadia These include, but are not limited to, a zolyl group, a phenothiazinyl group, and a dibenzofuranyl group.

In this 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 this specification, the aralkyl group, alkylaryl group, and alkylamine group are the same as the examples of the alkyl group described above. In the present specification, the description regarding the heteroaryl group described above may be applied to heteroaryl among heteroarylamines. In this specification, the alkenyl group among the aralkenyl groups is the same as the example of the alkenyl group described above. In the present specification, the description of the aryl group described above can be applied, except that arylene is a divalent group. In the present specification, the description of the heteroaryl group described above can be applied, except that heteroarylene is a divalent group. In the present specification, the description of the aryl group or cycloalkyl group described above can be applied, except that the hydrocarbon ring is not monovalent and is formed by combining two substituents. In the present specification, the description of the heteroaryl group described above can be applied, except that heteroaryl is not a monovalent group and is formed by combining two substituents.

Preferably, L may be a single bond, or substituted or unsubstituted C _6-20 arylene. More preferably, L may be a single bond, phenylene, phenylene substituted with one phenyl, biphenyldiyl, or naphthylene. Most preferably, L may be any one selected from the group consisting of:

.

.

Preferably, X ₁ to X ₃ may each be N.

Preferably, R ₁ and R ₂ may each independently be hydrogen, deuterium, phenyl, biphenylyl, naphthyl, phenanthrenyl, pyridinyl, dibenzofuranyl, dibenzothiophenyl, or dimethylfluorenyl; , R ₁ and R ₂ are each independently unsubstituted or contain at least one selected from the group consisting of deuterium, cyano, C _1-10 alkyl, C _6-20 aryl, or N, O and S. It may be substituted with C _2-20 heteroaryl. More preferably, R ₁ and R ₂ are each independently phenyl, phenyl substituted with 5 deuteriums, phenyl substituted with 2 methyls, phenyl substituted with 1 butyl, phenyl substituted with 1 dibenzofuran, Biphenylyl, biphenylyl substituted with 1 cyano, naphthyl, naphthyl substituted with 1 cyano, naphthyl substituted with 1 phenyl, phenanthrenyl, pyridinyl, dibenzofuranyl, dibenzothio It may be phenyl, or 9,9-dimethyl-9H-fluorenyl. Most preferably, R ₁ and R ₂ may each independently be selected from the group consisting of:

.

.

Preferably, Ar ₂ may be any one selected from the group consisting of:

.

.

Representative examples of compounds represented by Formula 1 are as follows:

.

.

The compound represented by Formula 1 above can be prepared by the method shown in Scheme 1 below, for example, when A is -L-Ar ₁ and B is -Ar ₂ , and the remaining compounds can be prepared similarly. You can.

[Scheme 1]

In Scheme 1 _, R _{1 ,} R _{2 ,} X,

Scheme 1 is a Suzuki coupling reaction, which is preferably carried out in the presence of a palladium catalyst and a base, and the reactor for the Suzuki coupling reaction can be changed according to what is known in the art. The manufacturing method may be further detailed in the manufacturing examples described later.

Additionally, the present invention provides an organic light-emitting device containing the compound represented by Formula 1 above. For example, the present invention includes a first electrode; a second electrode provided opposite to the first electrode; and an organic light-emitting device comprising at least one organic material layer provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer 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, or may have a multi-layer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present invention may have a structure that includes a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, etc. as an organic material layer. However, the structure of the organic light emitting device is not limited to this and may include a smaller number of organic material layers.

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

Additionally, the organic light emitting device according to the present invention 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. Additionally, 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 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 Figures 1 and 2.

Figure 1 shows an example of an organic light-emitting device consisting of a substrate 1, an anode 2, a light-emitting layer 3, an electron injection and transport layer 4, and a cathode 5. 2 shows a substrate 1, an anode 2, a hole injection layer 6, a first hole transport layer 7, a second hole transport layer 8, a light emitting layer 3, an electron injection and transport layer 4, and a cathode. (5) shows an example of an organic light-emitting device. In this structure, the compound represented by Formula 1 may be included in the electron injection and transport layer.

The organic light emitting device according to the present invention can be manufactured using materials and methods known in the art, except that at least one of the organic layers includes the compound represented by Formula 1 above. Additionally, 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 can be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate. At this time, an anode is formed by depositing a metal or a conductive metal oxide or an alloy thereof on the substrate using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation. It can be manufactured by forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer thereon, and then depositing a material that can be used as a cathode thereon. In addition to this method, an organic light-emitting device can be made 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 layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light-emitting device. Here, the solution application method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited to these.

In addition to this method, an organic light-emitting device can be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate (WO 2003/012890). However, the manufacturing method is not limited to this.

In one example, the first electrode is an anode and the second electrode is a cathode, or the first electrode is a cathode and the second electrode is an anode.

The anode material is generally preferably a material with a large work function to facilitate hole injection into the organic layer. Specific examples of the anode 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); Combinations of metals and oxides such as ZnO:Al or SnO ₂ :Sb; Conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline are included, but are not limited to these.

The cathode material is generally preferably a material with a small work function to facilitate electron injection into the organic 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-layer structure materials such as LiF/Al or LiO ₂ /Al, but they are not limited to these.

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

The hole transport layer is a layer that receives holes from the hole injection layer and transports holes to the light-emitting layer. It is a hole transport material that can receive holes from the anode or hole injection layer and transfer them to the light-emitting layer, and is a material with high mobility for holes. This is suitable. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers with both conjugated and non-conjugated portions, but are not limited to these. Additionally, two or more hole transport layers can be introduced into the organic light emitting device.

The light-emitting material is a material that can emit light in the visible range by receiving and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and is preferably a material with good quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ); Carbazole-based compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compound; Compounds of the benzoxazole, benzthiazole and benzimidazole series; Poly(p-phenylenevinylene) (PPV) series polymer; Spiro compounds; Polyfluorene, rubrene, etc., but are not limited to these.

The light emitting layer may include a host material and a dopant material. Host materials include condensed aromatic ring derivatives or heterocyclic ring-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, and ladder-type compounds. These include, but are not limited to, furan compounds and pyrimidine derivatives.

Dopant materials include aromatic amine derivatives, strylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, aromatic amine derivatives include condensed aromatic ring derivatives having a substituted or unsubstituted arylamino group, such as pyrene, anthracene, chrysene, and periplanthene, and styrylamine compounds include substituted or unsubstituted arylamino groups. It is a compound in which at least one arylvinyl group is substituted on the arylamine, and is substituted or unsubstituted with one or two or more substituents selected from the group consisting of aryl group, silyl group, alkyl group, cycloalkyl group, and arylamino group. Specifically, styrylamine, styryldiamine, styryltriamine, styryltetraamine, etc. are included, but are not limited thereto. Additionally, metal complexes include, but are not limited to, iridium complexes and platinum complexes.

The electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the light-emitting layer. The electron transport material is a material that can easily inject electrons from the cathode and transfer them to the light-emitting layer, and a material with high electron mobility is suitable. do. Specific examples include Al complex of 8-hydroxyquinoline; Complex containing Alq ₃ ; organic radical compounds; Hydroxyflavone-metal complexes, etc., but are not limited to these. 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 with a low work function followed by an aluminum or silver layer. Specifically, cesium, barium, calcium, ytterbium and samarium, in each case followed by an aluminum layer or a silver layer. Preferably, the compound represented by Formula 1 may be included as a material for the electron transport layer.

The electron injection layer is a layer that injects electrons from the electrode, has the ability to transport electrons, has an excellent electron injection effect from the cathode, a light-emitting layer or a light-emitting material, and hole injection of excitons generated in the light-emitting layer. A compound that prevents movement to the layer and has excellent thin film forming ability is preferred. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, etc. and their derivatives, metals. Complex compounds and nitrogen-containing five-membered ring derivatives are included, but are not limited thereto. Preferably, the compound represented by Formula 1 may be included as a material for the electron injection layer.

Examples of the metal complex compounds 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-naphtolato) aluminum, bis(2-methyl-8-quinolinato)(2-naphtolato) gallium, etc. It is not limited to this.

Meanwhile, in the present invention, the “electron injection and transport layer” is a layer that performs the functions of both the electron injection layer and the electron transport layer. The materials that play the role of each layer can be used singly or in combination, but are limited thereto. It doesn't work. Preferably, the compound represented by Formula 1 may be included as a material for the electron injection and transport layer.

The organic light-emitting device according to the present invention may be a bottom-emitting device, a top-emitting device, or a double-sided light-emitting device. In particular, it may be a bottom-emitting device that requires relatively high luminous efficiency.

Additionally, the compound represented by Formula 1 may be included in organic solar cells or organic transistors in addition to organic light-emitting devices.

Hereinafter, the present invention will be described in more detail to aid understanding. However, the following examples only illustrate the present invention, and the content of the present invention is not limited by the following examples.

[Manufacturing example]

Preparation Example 1-1: Preparation of Compound E1

In a nitrogen atmosphere, compound E1-A (20 g, 62.5 mmol) and compound E1-B (21.5 g, 62.5 mmol) were added to 400 ml of tetrahydrofuran, stirred, and refluxed. Afterwards, potassium carbonate (25.9 g, 187.4 mmol) was dissolved in 26 ml of water, stirred sufficiently, and then tetrakistriphenyl-phosphinopalladium (2.2 g, 1.9 mmol) was added. After reacting for 2 hours, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in 629 mL of chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized with chloroform and ethyl acetate to prepare white solid compound E1 (24.9 g, yield 79%).

MS: [M+H] ⁺ = 504

Preparation Example 1-2: Preparation of Compound E2

Compound E2 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was used according to the above reaction scheme.

MS: [M+H] ⁺ = 654

Preparation Example 1-3: Preparation of Compound E3

Compound E3 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was prepared according to the above reaction scheme.

MS: [M+H] ⁺ = 578

Preparation Example 1-4: Preparation of Compound E4

Compound E4 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was prepared according to the above reaction scheme.

MS: [M+H] ⁺ = 527

Preparation Example 1-5: Preparation of Compound E5

Compound E5 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was used according to the above reaction scheme.

MS: [M+H] ⁺ = 512

Preparation Example 1-6: Preparation of Compound E6

Compound E6 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was used according to the above reaction scheme.

MS: [M+H] ⁺ = 654

Preparation Example 1-7: Preparation of Compound E7

Compound E7 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was prepared according to the above reaction scheme.

MS: [M+H] ⁺ = 578

Preparation Example 1-8: Preparation of compound E8

Compound E8 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was prepared according to the above reaction scheme.

MS: [M+H] ⁺ = 552

Preparation Example 1-9: Preparation of Compound E9

Compound E9 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was prepared according to the above reaction scheme.

MS: [M+H] ⁺ = 608

Preparation Example 1-10: Preparation of compound E10

Compound E10 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was used according to the above reaction formula.

MS: [M+H] ⁺ = 574

Preparation Example 1-11: Preparation of compound E11

Compound E11 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was used according to the above reaction scheme.

MS: [M+H] ⁺ = 594

Preparation Example 1-12: Preparation of compound E12

Compound E12 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was used according to the above reaction scheme.

MS: [M+H] ⁺ = 568

Preparation Example 1-13: Preparation of compound E13

Compound E13 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was prepared according to the above reaction scheme.

MS: [M+H] ⁺ = 568

Preparation Example 1-14: Preparation of compound E14

Compound E14 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was used according to the above reaction scheme.

MS: [M+H] ⁺ = 582

Preparation Example 1-15: Preparation of compound E15

Compound E15 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was prepared according to the above reaction scheme.

MS: [M+H] ⁺ = 493

[Example]

Example 1-1

A glass substrate coated with a thin film of ITO (indium tin oxide) to a thickness of 1000 Å was placed in distilled water with a detergent dissolved in it and washed ultrasonically. At this time, a detergent from Fischer Co. was used, and distilled water filtered secondarily using a filter from Millipore Co. was used as distilled water. After washing the ITO for 30 minutes, ultrasonic cleaning was repeated twice with distilled water for 10 minutes. After washing with distilled water, it was ultrasonic washed with solvents of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. Additionally, the substrate was cleaned for 5 minutes using oxygen plasma and then transported to a vacuum evaporator.

On the ITO transparent electrode prepared in this way, the following compound HI-A was thermally vacuum deposited to a thickness of 600 Å to form a hole injection layer. On the hole injection layer, 50 Å of the following compound HAT and 60 Å of the following compound HT-A were sequentially vacuum deposited to form a first hole transport layer and a second hole transport layer.

Next, the following compound BH and compound BD were vacuum deposited on the second hole transport layer to a film thickness of 200 Å at a weight ratio of 25:1 to form a light emitting layer.

On the emitting layer, the previously prepared compound E1 and the following compound LiQ were vacuum deposited at a weight ratio of 1:1 to form an electron injection and transport layer with a thickness of 350 Å. A cathode was formed by sequentially depositing lithium fluoride (LiF) to a thickness of 10 Å and aluminum to a thickness of 1000 Å on the electron injection and transport layer.

In the above process, the deposition rate of organic materials was maintained at 0.4 Å/sec to 0.9 Å/sec, the deposition rate of lithium fluoride of the cathode was maintained at 0.3 Å/sec, and aluminum was maintained at 2 Å/sec, and the vacuum level during deposition was An organic light emitting device was manufactured by maintaining 1 * 10 ^-7 torr to 5 * 10 ^-5 torr.

Examples 1-2 to 1-15

An organic light emitting device was manufactured in the same manner as in Example 1-1, except that compounds E2 to E15 shown in Table 1 below were used instead of compound E1 in Example 1-1.

Comparative Examples 1-1 to 1-4

An organic light emitting device was manufactured in the same manner as in Example 1-1, except that compounds ET-1 to ET-4 shown in Table 1 below were used instead of compound E1 in Example 1-1. The compounds ET-1 to ET-4 are as follows.

[Experimental example]

Experimental Example 1

For the organic light-emitting devices manufactured in Examples 1-1 to 1-15 and Comparative Examples 1-1 to 1-4, the driving voltage and luminous efficiency were measured at a current density of 10 mA/cm ² and 20 mA/cm. The time (T90) to reach 90% of the initial luminance at a current density of ² was measured. The results are shown in Table 1 below.

division compound Voltage (V)
(@10 mA/cm ² ) Efficiency (cd/A)
(@10 mA/cm ² ) Color coordinates (x, y) Lifespan (hr)
(T90 @20 mA/cm ² ) Example 1-1 E1 4.04 5.40 (0.140, 0.092) 165 Example 1-2 E2 4.12 5.45 (0.140, 0.093) 157 Example 1-3 E3 4.12 5.51 (0.140, 0.093) 149 Example 1-4 E4 4.16 5.29 (0.141, 0.092) 215 Examples 1-5 E5 4.08 5.45 (0.140, 0.092) 182 Example 1-6 E6 4.16 5.51 (0.140, 0.093) 150 Example 1-7 E7 4.00 5.48 (0.140, 0.093) 162 Examples 1-8 E8 4.10 5.51 (0.141, 0.092) 153 Example 1-9 E9 4.12 5.24 (0.140, 0.092) 173 Examples 1-10 E10 4.16 5.43 (0.140, 0.093) 160 Example 1-11 E11 4.12 5.56 (0.140, 0.093) 147 Examples 1-12 E12 4.08 5.35 (0.140, 0.092) 170 Example 1-13 E13 4.08 5.54 (0.140, 0.093) 153 Example 1-14 E14 4.18 5.63 (0.140, 0.093) 137 Example 1-15 E15 4.12 5.29 (0.140, 0.092) 185 Comparative Example 1-1 ET-1 4.85 3.78 (0.140, 0.093) 83 Comparative Example 1-2 ET-2 4.45 3.34 (0.140, 0.092) 125 Comparative Example 1-3 ET-3 4.41 3.21 (0.140, 0.093) 133 Comparative Example 1-4 ET-4 4.99 3.70 (0.140, 0.092) 86

As shown in Table 1, the compound represented by Formula 1 according to the present specification can be used in an organic material layer capable of simultaneously injecting and transporting electrons in an organic light-emitting device.

Comparing Examples 1-1 to 1-15 of Table 1 and Comparative Example 1-1, the organic light-emitting device containing the heterocyclic compound of Formula 1 according to the present specification is a compound in which triazinyl is substituted with oxadiazole. It was confirmed that it showed significantly superior characteristics in terms of efficiency and lifespan than the organic light emitting device containing it.

Comparing Examples 1-1 to 1-15 of Table 1 and Comparative Examples 1-2 and 1-3, the organic light-emitting device containing the heterocyclic compound of Formula 1 according to the present specification is substituted with triphenylenyl. It was confirmed that it showed significantly superior characteristics in terms of efficiency compared to organic light-emitting devices containing compounds containing triazinyl.

Comparing Examples 1-1 to 1-15 of Table 1 and Comparative Example 1-4, the organic light-emitting device containing the heterocyclic compound of Formula 1 according to the present specification includes a compound containing a substituted linker L. It was confirmed that it showed significantly superior characteristics in terms of efficiency and lifespan compared to organic light-emitting devices.

1: Substrate 2: Anode
3: Light-emitting layer 4: Electron injection and transport layer
5: cathode 6: hole injection layer
7: first hole transport layer 8: second hole transport layer

Claims (10)

Compound represented by Formula 1:
[Formula 1]

In Formula 1,
X is O or S,
One of A and B is -L-Ar ₁ , the other is -Ar ₂ ,
Wherein L is a single bond or substituted or unsubstituted C _6-60 arylene,
Ar ₁ is

ego,
Here, X ₁ to X ₃ are each independently N, CH, or CD, but at least two of X ₁ to X ₃ are N,
R ₁ and R ₂ are each independently hydrogen, deuterium, phenyl, biphenylyl, naphthyl, phenanthrenyl, pyridinyl, dibenzofuranyl, dibenzothiophenyl, or dimethylfluorenyl, and R ₁ and R ₂ is each independently unsubstituted or C _2-60 hetero containing at least one selected from the group consisting of deuterium, cyano, C _1-20 alkyl, C _6-60 aryl, or N, O, and S. substituted with aryl,
Ar ₂ is phenyl, biphenylyl, or naphthyl.
According to paragraph 1,
L is a single bond, phenylene, phenylene substituted with one phenyl, biphenyldiyl, or naphthylene,
compound.
According to paragraph 1,
L is any one selected from the group consisting of:
compound:

.
According to paragraph 1,
X ₁ to X ₃ are each N,
compound.
According to paragraph 1,
R ₁ and R ₂ are each independently phenyl, phenyl substituted with 5 deuteriums, phenyl substituted with 2 methyls, phenyl substituted with 1 butyl, phenyl substituted with 1 dibenzofuran, biphenylyl, 1 biphenylyl, naphthyl substituted with 1 cyano, naphthyl substituted with 1 cyano, naphthyl with 1 phenyl, phenanthrenyl, pyridinyl, dibenzofuranyl, dibenzothiophenyl, or 9, 9-dimethyl-9H-fluorenyl,
compound.
According to paragraph 1,
R ₁ and R ₂ are each independently selected from the group consisting of:
compound:

.
According to paragraph 1,
Ar ₂ is any one selected from the group consisting of:
compound:

.
According to paragraph 1,
The compound represented by Formula 1 is any one selected from the group consisting of:
compound:

.
first electrode; a second electrode provided opposite to the first electrode; And an organic light-emitting device comprising at least one organic material layer provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes the compound according to any one of claims 1 to 8. doing,
Organic light emitting device.
According to clause 9,
The organic material layer is an electron transport layer, an electron injection layer, or an electron injection and transport layer,
Organic light emitting device.