KR20200108161A - Novel organic compound and materials for organic electroluminescent devices comprising the same and organic electroluminescent devices comprising the same - Google Patents

Abstract

The present invention provides a novel organic compound represented by chemical formula 1, a material for an organic electroluminescent device including the organic compound, and an organic electroluminescent device. The present invention can improve color purity and device life.

Description

A novel organic compound, a material for an organic electroluminescent device containing the organic compound, and an organic electroluminescent device TECHNICAL FIELD [NOVEL ORGANIC COMPOUND AND MATERIALS FOR ORGANIC ELECTROLUMINESCENT DEVICES COMPRISING THE SAME AND ORGANIC ELECTROLUMINESCENT DEVICES COMPRISING THE SAME}

The present invention relates to a novel organic compound, a material for an organic electroluminescent device including the organic compound, and an organic electroluminescent device including the material.

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 electroluminescent device using an organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer therebetween. Here, 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 electroluminescent device, and may include, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer. .

Materials used as the organic material layer in the organic electroluminescent device can be classified into light-emitting materials and charge transport materials, such as hole injection materials, hole transport materials, electron transport materials, and electron injection materials, according to their functions.

Lifespan and efficiency are the most problematic in organic electroluminescent devices, and as displays become larger, these efficiency and lifetime issues must be resolved.

Efficiency, lifespan, and driving voltage are related to each other. As the efficiency increases, the driving voltage decreases relatively, and as the driving voltage decreases, the crystallization of organic materials by Joule heating generated during driving decreases. It shows a tendency to increase the lifespan.

However, simply improving the organic material layer cannot maximize efficiency. This is because the long life and high efficiency can be achieved at the same time when the optimum combination of the energy level and T1 value between each organic material layer and the intrinsic properties of the material (mobility, interfacial properties, etc.) is achieved.

The use of aromatic amines as a material for the hole transport layer in organic electroluminescent devices is because it was known that the utility of various classes of amines in improving the performance of organic electroluminescent devices in various conventional techniques was generally disclosed. . Improvements in hole transport material parameters include higher hole transport motility, more amorphous structure, higher glass transition temperature, and better electrochemical stability. The improvement in the organic electroluminescent device made using such an improved amine is that the luminous efficiency is higher, the operation and storage life are longer, and the heat resistance is better. For example, commonly assigned U.S. Patent No. 5,061,569 to Van Slicke et al. discloses an improved arylamine hole transport material. The commonly assigned US Pat. No. 5,554,450 to Shi et al. discloses a series of aromatic amines having a glass transition temperature as high as 165° C. designed for high temperature organic electroluminescent devices. U.S. Patent No. 5,374,489 to Shirota et al. discloses 4,4′,4″-tris(3-methylphenylamino), a novel π-conjugated starburst molecule that forms stable amorphous glass and acts as an excellent hole transport material. Triphenylamine (m-MTDATA) is disclosed.

Organic compounds other than aromatic amines are not usually used in the hole transport layer in the organic electroluminescent device, and it is well known that aromatic amines have hole transport properties. However, there is an important drawback in the case of using an aromatic amine as a hole transport layer in a two-layer organic electroluminescent device. Since amines are generally strong electron donors, they interact with the luminescent material used in the electron transport layer to form a fluorescence quenching center to reduce the luminous efficiency of the organic electroluminescent device.

In addition, in order to solve the problem of light emission in the hole transport layer in recent organic electroluminescent devices, a light emission auxiliary layer must exist between the hole transport layer and the light emitting layer, and different light emission assistance according to each light emitting layer (R, G, B) It is the time when layer development is necessary.

In general, electrons are transferred from the electron transport layer to the light emitting layer, and holes are transferred from the hole transport layer to the light emitting layer, thereby generating excitons through recombination.

However, in the case of a material used for the hole transport layer, since it must have a low HOMO value, most have a low T1 value, and this causes excitons generated in the emission layer to pass to the hole transport layer, resulting in charge unbalance in the emission layer. As a result, light is emitted in the hole transport layer or at the hole transport layer interface, resulting in a decrease in color purity, efficiency and lifetime of the organic electroluminescent device.

In addition, the driving voltage can be lowered by using a material having high hole mobility, but hole mobility is faster than electron mobility, causing charge unbalance in the light emitting layer. The color purity and efficiency of the electroluminescent device are deteriorated and the lifespan is shortened.

Therefore, development of a light emitting auxiliary layer having a high T1 value and having a HOMO level between the HOMO energy level of the hole transport layer and the HOMO energy level of the light emitting layer is urgently required.

On the other hand, while delaying penetration and diffusion of metal oxides from the anode electrode (ITO) into the organic layer, which is one of the causes of shortening the lifespan of organic electroluminescent devices, stable properties against Joule heating generated when the device is driven, that is, high glass There is a need to develop a material for a hole injection layer having a transition temperature. The low glass transition temperature of the hole transport layer material has a property of lowering the uniformity of the thin film surface when the device is driven, and it is reported that it has a great influence on the life of the device. In addition, organic electroluminescent devices are mainly formed by a vapor deposition method, and there is a need to develop a material that can withstand a long time during deposition, that is, a material having strong heat resistance.

In order for the organic electroluminescent device to fully exhibit the above-described excellent characteristics, materials that form the organic material layer in the device, such as hole injection material, hole transport material, light-emitting material, electron transport material, electron injection material, etc., must be stable and efficient materials. Until now, the development of stable and efficient organic materials for organic electroluminescent devices has not been sufficiently conducted. Therefore, in the related art, the development of new materials having low voltage driving, high efficiency and long life is continuously required.

U.S. Patent No. 5,061,569 U.S. Patent No. 5,554,450 U.S. Patent No. 5,374,489

The present invention has been derived to solve the problems of the prior art as described above, and can be applied to an organic electroluminescent device as a hole injection layer material or a light emitting layer material, and when applied to an organic electroluminescent device, the driving voltage can be lowered. , It is an object of the present invention to provide a novel organic compound that can improve luminous efficiency, luminance, thermal stability, color purity, and device life.

In addition, an object of the present invention is to provide a material for an organic electroluminescent device, which forms an organic electroluminescent device at least one of a hole injection layer and a light emitting layer including the organic compound.

In addition, an object of the present invention is to provide an organic electroluminescent device using the organic compound.

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

[Formula 1]

In addition, the present invention provides a material for an organic electroluminescent device, which forms an organic electroluminescent device at least one of a hole injection layer and an emission layer including the organic compound represented by Formula 1 above.

In addition, the present invention relates to an organic electroluminescent device in which an organic thin film layer comprising at least one or a plurality of layers including a light emitting layer is stacked between a cathode and an anode, wherein at least one layer of the organic thin film layer is represented by Formula 1 above. It provides an organic electroluminescent device characterized in that the compound is contained alone or in combination of two or more.

The organic compound according to the present invention can be applied to an organic electroluminescent device as an emission layer material such as a hole injection layer material or a phosphorescent dopant material, and when applied to an organic electroluminescent device, it lowers the driving voltage, luminous efficiency, luminance, and thermal stability. , Improve color purity and device life.

In addition, the organic electroluminescent device manufactured using the organic compound of the present invention has high efficiency and long life characteristics.

The present invention relates to a novel organic compound represented by the following formula (1):

[Formula 1]

In Formula 1,

M is Ir, Os or Pt,

Y1 and Y2 are each independently oxygen, carbon or sulfur,

X1, X2, X3, X4, X5, X6, X7, X8, X9, X10, X11, X12 and X13 are each independently carbon or nitrogen,

R1, R2, R3, R4, R5, R6, R7, R8, R9 and R10 are each independently hydrogen, deuterium, F, Cl, Br, I, CN, Si(CH ₃ ) ₃ , B(OH) ₂ , pyridine, pyrimidine, pyrazine, 1,3,5-triazine, quinolone, isoquinoline, indolizine, 1-phenyl-1H-indole, 2-phenyl-2H-isoindole, benzofuran, benzo[b]thiophene, benzo[d]thiazole, 4H-quinolizine, cinnoline, furan, phthalazine, quinazoline, quinoxaline, 1,8-naphthyridine, pteridine, thiophene, oxazole, thiazole, isoxazole, isothiazole, 1,2,3-oxadiazole, 1,2,3-thiadiazole, 1, 3,4-thiadiazole, pyridazine, furo[2,3-b]pyridine, furo[2,3-c]pyridine, furo[3,2-c]pyridine furo[3,2-b]pyridine benzo[d] oxazole furo[2,3-d]pyrimidine, furo[3,2-d]pyrimidine, furo[2,3-b]pyrazine, thieno[2,3-b]pyridine, thieno[3,2-c]pyridine , thieno[3,2-b]pyridine, benzo[d]thiazole, thieno[2,3-d]pyrimidine, thieno[2,3-d]pyridazine, thieno[2,3-b]pyrazine, benzofuro[2 ,3-b]pyridine, benzofuro[2,3-c]pyridine, benzofuro[3,2-c]pyridine, benzofuro[3,2-b]pyridine, benzofuro[2,3-d]pyrimidine, benzofuro[2 ,3-b]pyrazine, benzo[4,5]thi eno[2,3-b]pyridine, benzo[4,5]thieno[3,2-c]pyridine, benzo[4,5]thieno[3,2-b]pyridine, benzo[4,5]thieno[ 3,2-b]pyridine, benzo[4,5]thieno[2,3-d]pyrimidine, benzo[4,5]thieno[2,3-b]pyrazine, furo[2,3-b:5, 4-b']dipyridine, furo[2,3-b:4,5-c']dipyridine, furo[2,3-b:5,4-c']dipyridine, furo[2,3-b:4 ,5-b']dipyridine, pyrido[3',2':4,5]furo[3,2-d]pyrimidine, thieno[2,3-b:5,4-b']dipyridine, thieno[2 ,3-b:5,4-c']dipyridine, thieno[2,3-b:4,5-c']dipyridine, thieno[2,3-b:4,5-b']dipyridine, pyrido[ 3',2':4,5]thieno[2,3-d]pyridazine, straight or branched chain alkyl having 1 to 40 carbon atoms, alkoxy having 1 to 40 carbon atoms, thioalkyl having 1 to 40 carbon atoms, or 3 to carbon atoms 40 cycloalkyl group, or

F, Cl, Br, I, CN, Si(CH ₃ ) ₃ , B(OH) ₂ , straight or branched chain alkyl having 1 to 40 carbon atoms, alkoxy having 1 to 40 carbon atoms, thioalkyl having 1 to 40 carbon atoms, carbon number 3 to 40 cycloalkyl, phenyl, biphenyl, naphthyl, anthracenyl, anthracenyl substituted with a phenyl group, phenanthrenyl, pyrenyl, 9,9-dimethylfluorenyl, carbazolyl, dibenzofuranyl, A pyrrole, triazole, pyridinyl, pyrazinyl, pyrimidinyl group, and an aromatic hydrocarbon group having 6 to 60 carbon atoms unsubstituted or substituted with one or more selected from the group consisting of a quinolinyl group,

F, Cl, Br, I, CN, Si(CH ₃ ) ₃ , B(OH) ₂ , straight or branched chain alkyl having 1 to 40 carbon atoms, alkoxy having 1 to 40 carbon atoms, thioalkyl having 1 to 40 carbon atoms, carbon number 3 to 40 cycloalkyl, phenyl, biphenyl, naphthyl, anthracenyl, anthracenyl substituted with a phenyl group, phenanthrenyl, pyrenyl, 9,9-dimethylfluorenyl, carbazolyl, dibenzofuranyl, One or more elements substituted or unsubstituted with one or more selected from the group consisting of pyrrole, triazole, pyridinyl, pyrazinyl, pyrimidinyl group, and quinolinyl group, and selected from the group consisting of S, O, N, and Si Or a heteroaromatic hydrocarbon group having 5 to 60 carbon atoms including,

F, Cl, Br, I, CN, Si(CH ₃ ) ₃ , B(OH) ₂ , straight or branched chain alkyl having 1 to 40 carbon atoms, alkoxy having 1 to 40 carbon atoms, thioalkyl having 1 to 40 carbon atoms, and Phenyl, biphenyl, naphthyl, anthracenyl, anthracenyl substituted with a phenyl group, 9,9 substituted or unsubstituted with one or more selected from the group consisting of a cycloalkyl group having 3 to 40 carbon atoms, phenanthrenyl, pyrenyl, 9,9 -It is an amino group substituted with one or more selected from the group consisting of dimethylfluorenyl, carbazolyl, quinolinyl, dibenzofuranyl, pyrrole, triazole, pyridinyl, pyrazinyl, and pyrimidinyl groups.

Preferably, in Formula 1,

M is Ir,

X13 is nitrogen,

R1, R2, R3, R4, R5, R6, R7, R8, R9 and R10 are each independently hydrogen, deuterium, F, CN, Si(CH3)3, pyridine, pyrimidine, pyrazine, 1,3,5-triazine , quinolone, isoquinoline, indolizine, 1-phenyl-1H-indole, 2-phenyl-2H-isoindole, benzofuran, benzo[b]thiophene, benzo[d]thiazole, 4H-quinolizine, cinnoline, furan, phthalazine, quinazoline, quinoxaline , 1,8-naphthyridine, pteridine, thiophene, oxazole, thiazole, isoxazole, isothiazole, 1,2,3-oxadiazole, 1,2,3-thiadiazole, 1,3,4-thiadiazole, pyridazine, furo[2,3 -b]pyridine, furo[2,3-c]pyridine, furo[3,2-c]pyridine furo[3,2-b]pyridine benzo[d]oxazole furo[2,3-d]pyrimidine, furo[ 3,2-d]pyrimidine, furo[2,3-b]pyrazine, thieno[2,3-b]pyridine, thieno[3,2-c]pyridine, thieno[3,2-b]pyridine, benzo[ d]thiazole, thieno[2,3-d]pyrimidine, thieno[2,3-d]pyridazine, thieno[2,3-b]pyrazine, benzofuro[2,3-b]pyridine, benzofuro[2,3- c]pyridine, benzofuro[3,2-c]pyridine, benzofuro[3,2-b]pyridine, benzofuro[2,3-d]pyrimidine, benzofuro[2,3-b]pyrazine, benzo[4,5] thieno[2,3-b]pyridine, benz o[4,5]thieno[3,2-c]pyridine, benzo[4,5]thieno[3,2-b]pyridine, benzo[4,5]thieno[3,2-b]pyridine, benzo[ 4,5]thieno[2,3-d]pyrimidine, benzo[4,5]thieno[2,3-b]pyrazine, furo[2,3-b:5,4-b']dipyridine, furo[2 ,3-b:4,5-c']dipyridine, furo[2,3-b:5,4-c']dipyridine, furo[2,3-b:4,5-b']dipyridine, pyrido[ 3',2':4,5]furo[3,2-d]pyrimidine, thieno[2,3-b:5,4-b']dipyridine, thieno[2,3-b:5,4-c ']dipyridine, thieno[2,3-b:4,5-c']dipyridine, thieno[2,3-b:4,5-b']dipyridine, pyrido[3',2':4,5] thieno[2,3-d]pyridazine, straight or branched chain alkyl having 1 to 40 carbon atoms, straight or branched chain alkyl having 1 to 25 carbon atoms substituted with deuterium, alkoxy having 1 to 25 carbon atoms, thioalkyl having 1 to 25 carbon atoms , Or a cycloalkyl group having 3 to 25 carbon atoms,

Deuterium, F, CN, Si(CH3)3, straight or branched chain alkyl having 1 to 25 carbon atoms, alkoxy having 1 to 25 carbon atoms, thioalkyl having 1 to 25 carbon atoms, cycloalkyl having 3 to 25 carbon atoms, phenyl, biphenyl , Naphthyl, anthracenyl, anthracenyl substituted with a phenyl group, phenanthrenyl, pyrenyl, 9,9-dimethylfluorenyl, carbazolyl, dibenzofuranyl, pyrrole, triazole, pyridinyl, pyrazinyl, A pyrimidinyl group and a substituted or unsubstituted C6-C60 aromatic hydrocarbon group selected from the group consisting of a quinolinyl group,

Deuterium, F, CN, Si(CH3)3, B(OH)2, straight or branched chain alkyl having 1 to 40 carbon atoms, alkoxy having 1 to 40 carbon atoms, thioalkyl having 1 to 40 carbon atoms, cyclo of 3 to 40 carbon atoms Alkyl, phenyl, biphenyl, naphthyl, anthracenyl, anthracenyl substituted with a phenyl group, phenanthrenyl, pyrenyl, 9,9-dimethylfluorenyl, carbazolyl, dibenzofuranyl, pyrrole, triazole, 5 carbon atoms substituted or unsubstituted with one or more selected from the group consisting of pyridinyl, pyrazinyl, pyrimidinyl group, and quinolinyl group, and containing at least one element selected from the group consisting of S, O, N, and Si Or a heteroaromatic hydrocarbon group of from to 60,

From the group consisting of deuterium, F, CN, Si(CH3)3, straight or branched chain alkyl having 1 to 25 carbon atoms, alkoxy having 1 to 25 carbon atoms, thioalkyl having 1 to 25 carbon atoms, and cycloalkyl groups having 3 to 25 carbon atoms Substituted or unsubstituted phenyl, biphenyl, naphthyl, anthracenyl, anthracenyl substituted with a phenyl group, phenanthrenyl, pyrenyl, 9,9-dimethylfluorenyl, carbazolyl, qui It is an amino group substituted with one or more selected from the group consisting of nolinyl, dibenzofuranyl, pyrrole, triazole, pyridinyl, pyrazinyl, and pyrimidinyl groups.

Specifically, the organic compound may be any one of compounds 1 to 120 below.

The organic compound of the present invention may be used as a material for a hole injection layer or a material for a light emitting layer among materials for an organic electroluminescent device. The emission layer material may be, for example, a phosphorescent dopant material.

In addition, the present invention relates to a material for an organic electroluminescent device, which forms an organic electroluminescent device at least one of a hole injection layer and an emission layer including the organic compound.

In the above, the material for forming the hole injection layer or the light-emitting layer may further include a material commonly added when preparing the organic compound in a form necessary for use in forming the hole injection layer or the light-emitting layer, such as a solvent.

In addition, the present invention relates to an organic electroluminescent device in which an organic thin film layer including at least one or a plurality of layers including a light emitting layer is stacked between a cathode and an anode, wherein at least one or more of the organic thin film layers contain an organic compound of Formula 1 It relates to an organic electroluminescent device characterized in that it is contained alone or in a combination of two or more.

In the organic electroluminescent device, the organic compound may be included as one or more of a hole injection layer material and a light emitting layer material.

The organic electroluminescent device may have a structure in which an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and a cathode are stacked, and an electron blocking layer, a hole blocking layer, etc. are additionally stacked as needed. Can be.

The organic thin film layer includes a hole injection layer, a hole transport layer, an emission layer, an electron transport layer, and an electron injection layer, and the organic compound of the present invention may be included in at least one of the hole injection layer and the emission layer.

In addition, the organic thin film layer includes a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron blocking layer, and an electron injection layer, and the organic compound of the present invention is included in one or more of the hole injection layer and the light emitting layer. Can have

Hereinafter, the organic electroluminescent device of the present invention will be described by way of example. However, the contents illustrated below do not limit the organic electroluminescent device of the present invention.

The organic electroluminescent device of the present invention may have a structure in which an anode (hole injection electrode), a hole injection layer (HIL), a hole transport layer (HTL), a light emitting layer (EML), and a cathode (electron injection electrode) are sequentially stacked, Preferably, an electron blocking layer (EBL) between the anode and the emission layer, and an electron transport layer (ETL) and an electron injection layer (EIL) between the cathode and the emission layer may be further included. In addition, a hole blocking layer (HBL) may be further included between the cathode and the emission layer.

In the method of manufacturing an organic electroluminescent device according to the present invention, first, an anode is formed by coating a material for an anode on a substrate surface in a conventional manner. At this time, the substrate to be used is preferably a glass substrate or a transparent plastic substrate having excellent transparency, surface smoothness, ease of handling and waterproofness. In addition, as a material for the anode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), and the like, which are transparent and have excellent conductivity, may be used.

Next, a hole injection layer is formed on the anode surface by vacuum thermal evaporation or spin coating with a hole injection layer (HIL) material in a conventional manner. Examples of the material for the hole injection layer include the organic compounds of the present invention, copper phthalocyanine (CuPc), 4,4',4"-tris(3-methylphenylamino)triphenylamine (m-MTDATA), 4,4',4" -Tris(3-methylphenylamino)phenoxybenzene (m-MTDAPB), starburst type amines 4,4',4"-tri(N-carbazolyl)triphenylamine (TCTA), 4,4 Examples are',4"-tris(N-(2-naphthyl)-N-phenylamino)-triphenylamine (2-TNATA) or IDE406, available from Idemitsu.

A hole transport layer is formed on the surface of the hole injection layer by vacuum thermal evaporation or spin coating with a hole transport layer (HTL) material in a conventional manner. At this time, as the material for the hole transport layer, the organic compound of the present invention, bis(N-(1-naphthyl-n-phenyl))benzidine (α-NPD), N,N'-di(naphthalen-1-yl)-N ,N'-biphenyl-benzidine (NPB) or N,N'-biphenyl-N,N'-bis(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD) For example.

An emission layer is formed by vacuum thermal evaporation or spin coating on the surface of the hole transport layer with an emission layer (EML) material in a conventional manner. In this case, as a single light-emitting material or a light-emitting dopant material among the light-emitting layer materials used, tris (8-hydroxyquinolinolato) aluminum (Alq3), etc. may be used for green, and Balq (8-hydroxyquinoline beryllium) for blue. Salt), DPVBi(4,4'-bis(2,2-biphenylethenyl)-1,1'-biphenyl) series, Spiro substance, Spiro-DPVBi (spiro-4,4'-bis (2,2-biphenylethenyl)-1,1'-biphenyl), LiPBO (2-(2-benzoxazolyl)-phenol lithium salt), bis(biphenylvinyl)benzene, aluminum-quinoline metal complex , A metal complex of imidazole, thiazole, and oxazole may be used, and in the case of red, the organic compound of the present invention may be used. The organic compound of the present invention may be used as a phosphorescent green dopant material.

In the case of a dopant that can be used together with a light-emitting dopant material among the light-emitting layer materials, IDE102 and IDE105 available from Idemitsu as a fluorescent dopant, and tris(2-phenylpyridine)iridium(III)(Ir( ppy)3), iridium(III)bis[(4,6-difluorophenyl)pyridinato-N,C-2′]picolinate (FIrpic) (Chihaya Adachi et al., Appl. Phys. Lett., 2001, 79, 3082-3084], platinum (II) octaethyl porphyrin (PtOEP), TBE002 (Cobion), and the like can be used.

Optionally, an electron blocking layer (EBL) may be additionally formed between the hole transport layer and the light emitting layer.

An electron transport layer is formed by vacuum thermal evaporation or spin coating of an electron transport layer (ETL) material on the surface of the light emitting layer in a conventional manner. In this case, the electron transport layer material to be used is not particularly limited, and preferably tris(8-hydroxyquinolinolato)aluminum (Alq3) may be used.

Optionally, by additionally forming a hole blocking layer (HBL) between the light emitting layer and the electron transport layer and using a phosphorescent dopant in the light emitting layer, it is possible to prevent a phenomenon in which triplet excitons or holes are diffused into the electron transport layer.

The hole blocking layer may be formed by vacuum thermal evaporation and spin coating of the hole blocking layer material in a conventional manner, and the hole blocking layer material is not particularly limited, but preferably the organic compound of the present invention, (8 -Hydroxyquinolinolato)lithium (Liq), bis(8-hydroxy-2-methylquinolinolnato)-aluminum biphenoxide (BAlq), bathocuproine (BCP) and LiF Can be used.

An electron injection layer is formed by vacuum thermal evaporation or spin coating of an electron injection layer (EIL) material on the surface of the electron transport layer in a conventional manner. In this case, materials such as LiF, Liq, Li ₂ O, BaO, NaCl, and CsF may be used as the electron injection layer material used.

A negative electrode is formed by vacuum thermal evaporation on the surface of the electron injection layer using a conventional method.

At this time, the negative electrode materials used are lithium (Li), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium (Mg), magnesium-indium (Mg-In), and magnesium-silver. (Mg-Ag) and the like can be used. In addition, in the case of a top emission organic electroluminescent device, indium tin oxide (ITO) or indium zinc oxide (IZO) may be used to form a transparent cathode through which light can pass.

A capping layer (CPL) may be formed on the surface of the negative electrode by the composition for forming a capping layer of the present invention.

Hereinafter, a method for synthesizing the compounds will be described below with a representative example. However, the method for synthesizing the compounds of the present invention is not limited to the methods illustrated below, and the compounds of the present invention may be prepared by the methods exemplified below and methods known in the art.

Preparation Example 1: Synthesis of Compound 22

<Synthesis of Intermediate 22-2>

[Scheme 1]

Intermediate 22-1 408.22g (1723.23mmol) was dissolved in THF 4000ml, maintained at -78℃ using a dryice-acetone bath, and 2.5M n-BuLi 690ml (1723.23mmol) was added dropwise. After 1 hour, 244.60 g (1723.23 mmol) of methyl iodide was slowly dropped. After completion of the reaction, the temperature was raised to room temperature, and after distillation of the solvent, extraction was performed with 5000 ml of water and 5000 ml of EA. The solvent was distilled and columned to obtain 225.29 g of Intermediate 22-2 in a yield of 76%.

<Synthesis of Intermediate 22-3>

[Scheme 2]

225.29g (1309.66mmol) of Intermediate 22-2 was dissolved in 2300ml of THF, maintained at -78°C using a dryice-acetone bath, and 576ml (1440.62mmol) of 2.5M n-BuLi was added dropwise. After 1 hour, 163.3g (1571.59mmol) of trimethylborate was slowly dropped. After completion of the reaction, the temperature was raised to room temperature, and after distillation of the solvent, extraction was performed with 5000 ml of water and 5000 ml of EA. The solvent was distilled and recrystallized from PE/MC to obtain 143.48 g of intermediate 22-3 in a yield of 80%.

<Synthesis of Intermediate 22-5>

[Scheme 3]

143.48g (1047.72mmol) of Intermediate 22-3 and 268.09g (1257.27mmol) of Intermediate 22-4 are dissolved in 30L of toluene, and then 2M K ₂ CO ₃ 1572ml (3143.17mmol), EtOH 300ml, Pd(PPh ₃ ) ₄ 60.54g (60.54g) 52.39 mmol) was added, followed by refluxing for 24 hours and stirring. After confirming the completion of the reaction, the water layer was removed and the solvent was distilled off. After the column, 180.96g of the intermediate 22-5 was obtained in a yield of 81%.

<Synthesis of Intermediate 22-6>

[Scheme 4]

After dissolving 180.96g (848.66mmol) of intermediate 22-5 in 540ml of MsOH, the mixture was heated to 80°C and stirred for 1 hour. After the reaction was completed, the mixture was cooled to room temperature, slowly added to ice water, and the resulting solid was washed with water, filtered, and then washed with a saturated NaHCO ₃ aqueous solution and filtered. The solid was dried, followed by column and recrystallized with MC/PE to obtain 69.58 g of intermediate 22-6 in a yield of 42%.

<Synthesis of Intermediate 22-9>

[Scheme 5]

After dissolving 75.25g (672.52mmol) of Intermediate 22-7 and 190.92g (672.52mmol) of Intermediate 22-8 in 2L of toluene, 2M K ₂ CO ₃ 1008ml (2017.56mmol), EtOH 200ml, Pd(PPh ₃ ) ₄ 38.86g (38.86g) 33.63mmol) was added and the mixture was refluxed for 24 hours and stirred. After confirming the completion of the reaction, the water layer was removed and the solvent was distilled off. After the column, 79.86 g of intermediate 22-9 was obtained in a yield of 53%.

<Synthesis of Intermediate 22-10>

[Scheme 6]

After dissolving 79.86g (356.44mmol) of intermediate 22-9 in 700ml of THF, 143ml (356.44mmol) of 2.5M n-BuLi was added at -78°C. After stirring for 1 hour, 69.58g (356.44mmol) of the intermediate 22-6 was slowly added. After confirming the completion of the reaction, sodium bicarbonate aqueous solution was added and extracted with EA. After the column, 89.78 g of intermediate 22-10 was obtained in a yield of 74%.

<Synthesis of Intermediate 22-11>

[Scheme 7]

After dissolving 89.78g (263.76mmol) of intermediate 22-10 in 270ml of MsOH, the mixture was heated to 80°C and stirred for 1 hour. After the reaction was completed, the mixture was cooled to room temperature, slowly added to ice water, and the resulting solid was washed with water, filtered, and then washed with a saturated NaHCO ₃ aqueous solution and filtered. The solid was dried, followed by column, and recrystallized with MC/PE to obtain 69.72 g of intermediate 22-11 in a yield of 82%.

<Synthesis of Intermediate 22-15>

[Scheme 8]

After dissolving 102.41g (655.54mmol) of Intermediate 22-13 and 82.73g (655.54mmol) of Intermediate 22-14 in 1L of DMF, an ice bath was installed to maintain 0℃, and NaH (60%) 26.22g (655.54mmol) was added dropwise. I did. After raising the temperature to room temperature and stirring for 12 hours, after confirming the reaction, 1L of 1N HCl was added and stirred. After extraction by adding 1 L of PE, distillation and column to obtain 69.72 g of intermediate 22-15 in a yield of 45%.

<Synthesis of Intermediate 22-12>

[Scheme 9]

After dissolving 69.72g (216.29mmol) of Intermediate 22-11 in 2.1L of 2-Ethoxyethanol, 700ml of water and 25.97g (72.10mmol) of IrCl3 were added and heated for 18 hours to reflux and stirred. After confirming the completion of the reaction, the mixture was cooled to room temperature, and the resulting solid was washed with MeOH, filtered, and dried to obtain 51.65 g of intermediate 22-12 with a yield of 81%.

<Synthesis of Compound 22>

[Scheme 10]

After dissolving 51.65g (29.20mmol) of Intermediate 22-12 and 69.01g (291.99mmol) of Intermediate 22-15 in 400ml of 2-ethoxyethanol, 40.36g (291.99mmol) of K ₂ CO ₃ was added and stirred at room temperature for 24 hours. After completion of the reaction, the reaction mixture was washed with MeOH and washed, and the resulting solid was columned and recrystallized with PE/MC and MeOH/MC to obtain 10 g of compound 22 in a yield of 32%.

¹ H NMR (DMSO, 300Hz): δ (ppm) = 9.12-8.85 (d, 2H), 8.81-8.68 (d, 2H), 8.25-8.09 (d, 2H), 8.06-7.96 (d, 2H), 7.84-7.16 (m, 10H), 6.54-6.38 (m, 2H), 4.41-4.22 (s, 2H), 3.12-2.81 (m, 6H), 2.75-2.46 (m, 2H), 1.96-1.38 (m , 20H)

MS(FAB): 1071(M ⁺ )

Preparation Example 2: Synthesis of Compound 46

<Synthesis of Intermediate 46-2>

[Scheme 11]

1213.58g (4911.48mmol) of Intermediate 46-1 was dissolved in 12L of THF, maintained at -78°C using a dryice-acetone bath, and 2161ml (5402.63mmol) of 2.5M n-BuLi was added dropwise. After 1 hour, 612.42g (5893.78mmol) of trimethylborate was slowly dropped. After the reaction was completed, the temperature was raised to room temperature, the solvent was distilled, and extracted with 10L of water and 10L of EA. The solvent was distilled and recrystallized from PE/MC to obtain 791.38 g of intermediate 46-2 in a yield of 76%.

<Synthesis of Intermediate 46-4>

[Scheme 12]

After dissolving 791.38g (3732.73mmol) of Intermediate 46-2 and 1055.99g (3732.73mmol) of Intermediate 46-3 in 11L of toluene, 2M K ₂ CO ₃ 5600ml (11198.18mmol), EtOH 1L, Pd(PPh ₃ ) ₄ 215.67g ( 186.64mmol) was added and the mixture was refluxed for 24 hours and stirred. After confirming the completion of the reaction, the water layer was removed and the solvent was distilled off. After the column, 796.19g of the intermediate 46-4 was obtained in a yield of 66%.

<Synthesis of Intermediate 46-5>

[Scheme 13]

After dissolving 796.19g (2463.60mmol) of intermediate 46-4 in 8L of THF, maintaining -78°C using a dryice-acetone bath, and 108-4ml (2709.96mmol) of 2.5M n-BuLi intermediate were added dropwise. After 1 hour, 307.19 g (2956.32 mmol) of trimethylborate was slowly dropped. After the reaction was completed, the temperature was raised to room temperature, the solvent was distilled, and extracted with 10L of water and 10L of EA. The solvent was distilled and recrystallized from PE/MC to obtain 546.54 g of intermediate 46-5 in a yield of 77%.

<Synthesis of Intermediate 46-7>

[Scheme 14]

Intermediate 46-5 546.54g (1896.97mmol) and Intermediate 46-6 449.37g (1896.97mmol) were dissolved in 11L of toluene, 2M K ₂ CO ₃ 2846ml (5690.92mmol), EtOH 570ml, Pd(PPh ₃ ) ₄ 109.60g (109.60g) 94.85 mmol) was added, followed by refluxing for 24 hours and stirring. After confirming the completion of the reaction, the water layer was removed and the solvent was distilled off. After the column, 425.21 g of the intermediate 46-7 was obtained in a yield of 56%.

<Synthesis of Intermediate 46-8>

[Scheme 15]

Intermediate 46-7 425.21g (1062.30mmol) was dissolved in 4L of THF, maintained at -78°C using a dryice-acetone bath, and 467ml (1168.53mmol) of 2.5M n-BuLi was added dropwise. After 1 hour, while measuring the reaction degree by HPLC, CO ₂ (g) was slowly added. After completion of the reaction, the temperature was raised to room temperature, and after the solvent was distilled, 1 L of 1HCl was added, and a saturated NaHCO ₃ aqueous solution was added. After distilling THF, the resulting solid was washed with water and filtered. After drying, it was recrystallized with MC/PE to obtain 236.77 g of intermediate 46-8 in a yield of 61%.

<Synthesis of Intermediate 46-9>

[Scheme 16]

Intermediate 46-8 236.77g (648.01mmol) was dissolved in MsOH 700ml, heated to 80 ℃ and stirred for 1 hour. After the reaction was completed, the mixture was cooled to room temperature, slowly added to ice water, and the resulting solid was washed with water, filtered, and then washed with a saturated NaHCO ₃ aqueous solution and filtered. The solid was dried, column, and recrystallized with MC/PE to obtain 195.84 g of intermediate 46-9 in a yield of 87%.

<Synthesis of Intermediate 46-10>

[Scheme 17]

126.31g (563.76mmol) of Intermediate 22-9 was dissolved in 2L of THF and 226ml (563.76mmol) of 2.5M n-BuLi was added at -78°C. After stirring for 1 hour, 195.84g (563.76mmol) of the intermediate 46-9 was slowly added. After confirming the completion of the reaction, sodium bicarbonate aqueous solution was added and extracted with EA. After the column, 177.71 g of the intermediate 46-10 was obtained in a yield of 64%.

<Synthesis of Intermediate 46-11>

[Scheme 18]

Intermediate 46-10 177.71g (360.81mmol) was dissolved in 500ml of MsOH, heated to 80°C, and stirred for 1 hour. After the reaction was completed, the mixture was cooled to room temperature, slowly added to ice water, and the resulting solid was washed with water, filtered, and then washed with a saturated NaHCO ₃ aqueous solution and filtered. The solid was dried, column, and recrystallized with MC/PE to obtain 142.10 g of intermediate 46-11 in a yield of 83%.

<Synthesis of Intermediate 46-15>

[Scheme 19]

After dissolving 98.10g (653.28mmol) of Intermediate 46-13 and 78.49g (653.28mmol) of Intermediate 46-14 in 2L of xylene, 35.29g (653.28mmol) of NaOMe was added and heated to reflux for 12 hours and stirred. After completion of the reaction, the mixture was cooled to room temperature, 700 ml of 1N HCl was added, and the organic layer was extracted and distilled. After the column, 142.10 g of the intermediate 46-15 was obtained in a yield of 98%.

<Synthesis of Intermediate 46-11>

[Scheme 20]

After dissolving 142.10g (299.47mmol) of Intermediate 46-11 in 4.2L of 2-Ethoxyethanol, 1.4L of water and 35.95g (99.82mmol) of IrCl ₃ were added, heated for 18 hours to reflux and stirred. After confirming the completion of the reaction, the mixture was cooled to room temperature, and the resulting solid was washed with MeOH, filtered and dried to obtain 91.46g of intermediate 46-12 in a yield of 78%.

<Synthesis of compound 46>

[Scheme 21]

After dissolving 91.46g (38.93mmol) of Intermediate 46-12 and 87.30g (389.31mmol) of Intermediate 46-15 in 900ml of 2-ethoxyethanol, 53.81g (389.31mmol) of K ₂ CO ₃ was added and stirred at room temperature for 24 hours. After completion of the reaction, the mixture was washed with MeOH, and the resulting solid was columned and recrystallized with PE/MC and MeOH/MC to obtain 10 g of compound 46 in a yield of 24%.

¹ H NMR (DMSO, 300Hz): δ (ppm) = 8.87-8.65 (d, 2H), 8.43-8.26 (d, 2H), 8.12-7.92 (m, 8H), 7.88-7.76 (m, 4H), 7.72-7.18 (m, 24H), 6.85-6.71 (d, 2H), 6.52-6.37 (d, 2H), 4.41-4.22 (s, 2H)

MS(FAB): 1363 (M ⁺ )

Preparation Example 3: Synthesis of Compound 73

<Synthesis of Intermediate 73-2>

[Scheme 22]

87.89g (412.46mmol) of the intermediate 73-1 was dissolved in 800ml of THF, maintained at -78°C using a dryice-acetone bath, and 182ml (453.71mmol) of 2.5M n-BuLi was added dropwise. After 1 hour, 51.43g (494.95mmol) of trimethylborate was slowly dropped. After completion of the reaction, the temperature was raised to room temperature, and after distillation of the solvent, the mixture was extracted with 1L of water and 1L of EA. After distilling the solvent, it was recrystallized from PE/MC to obtain 63.15 g of intermediate 73-2 in a yield of 86%.

<Synthesis of Intermediate 73-4>

[Scheme 23]

After dissolving 63.15g (354.72mmol) of Intermediate 73-2 and 91.91g (354.72mmol) of Intermediate 73-3 in 1L of toluene, 2M K ₂ CO ₃ 532ml (1064.15mmol), EtOH 100ml, Pd(PPh ₃ ) ₄ 20.49g ( 17.74mmol) was added, and the mixture was refluxed for 24 hours and stirred. After confirming the completion of the reaction, the water layer was removed and the solvent was distilled off. After the column, 87.54 g of the intermediate 73-4 was obtained in a yield of 79%.

<Synthesis of Intermediate 73-5>

[Scheme 24]

After dissolving 62.78g (280.23mmol) of intermediate 22-9 in 800ml of THF, 112ml (280.23mmol) of 2.5M n-BuLi was added at -78°C. After stirring for 1 hour, 87.54g (280.23mmol) of the intermediate 73-4 was slowly added. After confirming the completion of the reaction, sodium bicarbonate aqueous solution was added and extracted with EA. After the column, 89.75 g of the intermediate 73-5 was obtained in a yield of 64%.

<Synthesis of Intermediate 73-6>

[Scheme 25]

After dissolving 89.75g (196.16mmol) of intermediate 73-5 in 300ml of MsOH, the mixture was heated to 80°C and stirred for 1 hour. After the reaction was completed, the mixture was cooled to room temperature, slowly added to ice water, and the resulting solid was washed with water, filtered, and then washed with a saturated NaHCO ₃ aqueous solution and filtered. The solid was dried, followed by column, and recrystallized with MC/PE to obtain 73.28 g of an intermediate 73-6 in a yield of 85%.

<Synthesis of Intermediate 73-10>

[Scheme 26]

After dissolving 47.12g (235.34mmol) of Intermediate 73-8 and 40.06g (253.34mmol) of Intermediate 73-9 in 2L of xylene, 12.71g (253.34mmol) of NaOMe was added, followed by heating for 12 hours to reflux and stirring. After completion of the reaction, the mixture was cooled to room temperature, 300 ml of 1N HCl was added, and the organic layer was extracted and distilled. After the column, 73.28g of the intermediate 73-10 was obtained in 96% yield.

<Synthesis of Intermediate 73-7>

[Scheme 27]

73.28g (166.73mmol) of Intermediate 73-6 was dissolved in 2.2L of 2-Ethoxyethanol, 730ml of water and 20.02g (55.58mmol) of IrCl ₃ were added and heated for 18 hours to reflux and stirred. After confirming the completion of the reaction, the mixture was cooled to room temperature, and the resulting solid was washed with MeOH, filtered, and dried to obtain 46.66 g of intermediate 73-6 with a yield of 76%.

<Synthesis of Compound 73>

[Scheme 28]

After dissolving 46.66g (21.12mmol) of Intermediate 73-7 and 68.51g (211.20mmol) of Intermediate 73-10 in 500ml of 2-ethoxyethanol, 29.19g (211.20mmol) of K ₂ CO ₃ was added and stirred at room temperature for 24 hours. After completion of the reaction, the mixture was washed with MeOH and washed, and the resulting solid was recrystallized with PE/MC and MeOH/MC to obtain 10 g of compound 73 in a yield of 34%.

¹ H NMR (DMSO, 300Hz): δ (ppm) = 8.88-8.51 (m, 4H), 8.34-7.95 (m, 16H), 7.92-7.55 (m, 14H), 7.51-7.28 6 (m, 6H) , 7.24-6.96 (m, 4H), 6.52-6.37 (d, 2H), 4.41-4.22 (s, 2H)

MS (FAB): 1393 (M ⁺ )

Preparation Example 3: Synthesis of Compound 97

<Synthesis of Intermediate 97-2>

[Scheme 29]

After dissolving 53.43g (238.49mmol) of Intermediate 22-9 in 400ml of THF, 95ml (238.49mmol) of 2.5M n-BuLi was added at -78°C. After stirring for 1 hour, 42.98g (238.49mmol) of the intermediate 97-1 was slowly added. After confirming the completion of the reaction, sodium bicarbonate aqueous solution was added and extracted with EA. After the column, 72.31g of the intermediate 97-2 was obtained in a yield of 75%.

<Synthesis of Intermediate 97-3>

[Scheme 30]

Intermediate 97-2 72.31g (178.86mmol) was dissolved in 200ml MsOH, heated to 80 degrees and stirred for 1 hour. After the reaction was completed, the mixture was cooled to room temperature, slowly added to ice water, and the resulting solid was washed with water, filtered, and then washed with a saturated NaHCO ₃ aqueous solution and filtered. The solid was dried, followed by column, and recrystallized with MC/PE to obtain 59.41 g of intermediate 97-3 in a yield of 86%.

<Synthesis of Intermediate 97-4>

[Scheme 31]

Intermediate 97-3 59.41g (153.82mmol) was dissolved in THF 600ml, maintained at -78°C using a dryice-acetone bath, and 2.5M n-BuLi 68ml (169-21mmol) was added dropwise. After 1 hour, 26.76 g (184.59 mmol) of methyl(3d) iodide was slowly dropped. After completion of the reaction, the temperature was raised to room temperature, and the solvent was distilled and extracted with 500 ml of water and 500 ml of EA. After distilling the solvent, the column was performed to obtain 44.91 g of the intermediate 97-4 in a yield of 90%.

<Synthesis of Intermediate 97-5>

[Scheme 32]

After dissolving 44.91g (138.44mmol) of Intermediate 97-4 in 1.3L of 2-Ethoxyethanol, 450ml of water and 16.62g (46.15mmol) of IrCl ₃ were added, heated to reflux for 18 hours, and stirred. After confirming the completion of the reaction, the mixture was cooled to room temperature, and the resulting solid was washed with MeOH, filtered, and dried to obtain 33.9 g of Intermediate 97-5 with a yield of 84%.

<Synthesis of compound 97>

[Scheme 33]

After dissolving 33.90g (19.38mmol) of Intermediate 97-5 and 19.40g (193.82mmol) of Intermediate 97-6 in 300ml of 2-ethoxyethanol, 26.79g (193.82mmol) of K ₂ CO ₃ was added and stirred at room temperature for 24 hours. After completion of the reaction, the reaction mixture was washed with MeOH and washed, and the resulting solid was recrystallized with PE/MC and MeOH/MC to obtain 10 g of compound 97 in a yield of 55%.

¹ H NMR (DMSO, 300Hz): δ(ppm)= )= 8.86-8.62 (d, 2H), 8.16-7.84 (m, 6H), 7.77-7.57 (d, 2H), 7.48-6.95 (m, 10H) ), 6.54-6.38 (m, 2H), 4.41-4.22 (s, 2H), 2.45-2.21 (m, 6H)

MS (FAB): 939 (M ⁺ )

Preparation Example 4: Synthesis of Compound 108

<Synthesis of Intermediate 108-2>

[Scheme 34]

53.98g (240.93mmol) of Intermediate 22-9 was dissolved in 400ml of THF, and then 96ml (240.93mmol) of 2.5M n-BuLi was added at -78°C. After stirring for 1 hour, 62.42g (240.93mmol) of the intermediate 108-1 was slowly added. After confirming the completion of the reaction, sodium bicarbonate aqueous solution was added and extracted with EA. After the column, 74.02g of intermediate 108-2 was obtained in a yield of 76%.

<Synthesis of Intermediate 108-3>

[Scheme 35]

Intermediate 108-2 74.02g (183.10mmol) was dissolved in 200ml MsOH, heated to 80 ℃ and stirred for 1 hour. After the reaction was completed, the mixture was cooled to room temperature, slowly added to ice water, and the resulting solid was washed with water, filtered, and then washed with a saturated NaHCO ₃ aqueous solution and filtered. The solid was dried, followed by column, and recrystallized with MC/PE to obtain 65.77 g of intermediate 108-3 in a yield of 93%.

<Synthesis of Intermediate 108-5>

[Scheme 36]

88.57g (224.06mmol) of the intermediate 108-4 was dissolved in 900ml of THF, maintained at -78℃ using a dryice-acetone bath, and 99ml (246.47mmol) of 2.5M n-BuLi was added dropwise. After 1 hour, 27.94g (268.87mmol) of trimethylborate was slowly dropped. After completion of the reaction, the temperature was raised to room temperature, and after distillation of the solvent, the mixture was extracted with 1L of water and 1L of EA. The solvent was distilled and recrystallized from PE/MC to obtain 61.34 g of intermediate 108-5 in a yield of 76%.

<Synthesis of Intermediate 108-6>

[Scheme 37]

After dissolving 65.77g (170.29mmol) of intermediate 108-3 and 61.34g (170.29mmol) of intermediate 108-5 in 500ml of toluene, 2M K ₂ CO ₃ 255ml (510.86mmol), EtOH 50ml, Pd(PPh ₃ ) ₄ 9.84g ( 8.51 mmol) was added, and the mixture was refluxed for 24 hours and stirred. After confirming the completion of the reaction, the water layer was removed and the solvent was distilled off. After the column, 87.54 g of the intermediate 108-6 was obtained in a yield of 44%.

<Synthesis of Intermediate 108-7>

[Scheme 38]

After dissolving 46.58g (74.93mmol) of intermediate 108-6 in 1.4L of 2-Ethoxyethanol, 450ml of water and 9.00g (24.98mmol) of IrCl3 were added, heated for 18 hours to reflux and stirred. After confirming the completion of the reaction, the mixture was cooled to room temperature, and the resulting solid was washed with MeOH, filtered, and dried to obtain 30.82 g of intermediate 108-7 in a yield of 84%.

<Synthesis of compound 108>

[Scheme 39]

After dissolving 30.82g (10.49mmol) of Intermediate 108-7 and 16.39g (104.90mmol) of Intermediate 108-8 in 300ml of 2-ethoxyethanol, 14.50g (104.90mmol) of K ₂ CO ₃ was added and stirred at room temperature for 24 hours. After completion of the reaction, the mixture was washed with MeOH and washed, and the resulting solid was recrystallized with PE/MC and MeOH/MC to obtain 10 g of compound 108 in a yield of 60%.

¹ H NMR (DMSO, 300Hz): δ(ppm)= 8.89-8.63 (d, 2H), 8.16-7.97 (m, 6H), 7.94-7.53 (m, 20H), 7.49-6.96 (m, 22H), 6.54-6.38 (m, 2H), 4.41-4.22 (s, 2H), 2.95-2.65 (m, 2H), 1.43-1.06 (d, 12H)

MS(FAB): 1589 (M ⁺ )

Hereinafter, the present invention will be described in more detail through examples. However, the following examples are for explaining the present invention more specifically, and the scope of the present invention is not limited by the following examples. The following examples can be appropriately modified and changed by those skilled in the art within the scope of the present invention.

Fabrication of organic electroluminescent devices according to Examples and Comparative Examples

An anode was formed with ITO on the substrate on which the reflective layer was formed, and the surface was treated with N ₂ plasma. HAT-CN was deposited to a thickness of 10 nm as a hole injection layer (HIL) thereon. Subsequently, NPD was deposited to a thickness of 120 nm as a hole transport layer (HTL). Among the organic compounds represented by Formula 1 of the present invention, compounds 3, 18, 22, 36, 46, 55, 61, 73 as a dopant while depositing 40 nm of Host-1 capable of forming an emission layer (EML) on the hole transport layer. , 85, 97, 105 and 117 were doped about 8%, respectively. An electron transport layer (ETL) was deposited to a thickness of 35 nm by mixing ETM and LiQ at 1:1, and LiQ was deposited as an electron injection layer (EIL) to a thickness of 2 nm on it. Thereafter, a mixture of 9:1 magnesium and silver (Ag) as a cathode was deposited to a thickness of 15 nm, and N4,N4′-bis[4-[bis(3-methylphenyl)] as a capping layer on the cathode. Amino]phenyl]-N4,N4'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (DNTPD) was deposited to a thickness of 65 nm. The organic electroluminescent device according to Examples 1 to 12 and Comparative Example 1 can be protected from O ₂ or moisture in the atmosphere by bonding a seal cap containing a desiccant with a UV curable adhesive thereon. An electroluminescent device was manufactured.

Test Example 1: Evaluation of characteristics of an organic electroluminescent device

The characteristics of the organic electroluminescent devices according to Examples 1 to 12 and Comparative Example 1 were measured at a current density of 10 mA/cm ² , and the results are shown in Table 1 below.

Material Name Current Density
(mA/cm ² ) Voltage
(V) Efficiency
(Cd/A) CIE (X Y) Comparative Example 1 Comparative compound 1 10 4.6 31 (0.671, 0.334) Example 1 Compound 3 10 3.9 38 (0.664, 0.329) Example 2 Compound 18 10 3.7 36 (0.665, 0.327) Example 3 Compound 22 10 3.8 39 (0.667, 0.324) Example 4 Compound 36 10 3.9 40 (0.666, 0.325) Example 5 Compound 46 10 3.4 36 (0.667, 0.323) Example 6 Compound 55 10 3.8 38 (0.666, 0.324) Example 7 Compound 61 10 3.3 36 (0.668, 0.321) Example 8 Compound 73 10 3.9 41 (0.665, 0.326) Example 9 Compound 85 10 3.3 37 (0.668, 0.323) Example 10 Compound 97 10 3.3 36 (0.667, 0.321) Example 11 Compound 105 10 3.4 42 (0.666, 0.323) Example 12 Compound 117 10 3.3 41 (0.667, 0.320)

Referring to Table 1, the organic electroluminescent device according to Examples 1 to 12 including the organic compound represented by Chemical Formula 1 of the present invention as a dopant in the emission layer was compared with the organic electroluminescent device according to Comparative Example 1 by voltage ( It can be seen that it shows remarkably excellent characteristics in voltage) and efficiency characteristics.

Therefore, the organic electroluminescent device including the organic compound represented by Formula 1 of the present invention as a dopant in the emission layer has excellent voltage and efficiency characteristics, enabling low-power driving of the device and reducing power consumption. In addition, the light emission life of the organic electroluminescent device can be improved by low power driving.

Claims (8)

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

In Formula 1
M is Ir, Os or Pt,
Y1 and Y2 are each independently oxygen, carbon or sulfur,
X1, X2, X3, X4, X5, X6, X7, X8, X9, X10, X11, X12 and X13 are each independently carbon or nitrogen,
R1, R2, R3, R4, R5, R6, R7, R8, R9 and R10 are each independently hydrogen, deuterium, F, Cl, Br, I, CN, Si(CH ₃ ) ₃ , B(OH) ₂ , pyridine, pyrimidine, pyrazine, 1,3,5-triazine, quinolone, isoquinoline, indolizine, 1-phenyl-1H-indole, 2-phenyl-2H-isoindole, benzofuran, benzo[b]thiophene, benzo[d]thiazole, 4H-quinolizine, cinnoline, furan, phthalazine, quinazoline, quinoxaline, 1,8-naphthyridine, pteridine, thiophene, oxazole, thiazole, isoxazole, isothiazole, 1,2,3-oxadiazole, 1,2,3-thiadiazole, 1, 3,4-thiadiazole, pyridazine, furo[2,3-b]pyridine, furo[2,3-c]pyridine, furo[3,2-c]pyridine furo[3,2-b]pyridine benzo[d] oxazole furo[2,3-d]pyrimidine, furo[3,2-d]pyrimidine, furo[2,3-b]pyrazine, thieno[2,3-b]pyridine, thieno[3,2-c]pyridine , thieno[3,2-b]pyridine, benzo[d]thiazole, thieno[2,3-d]pyrimidine, thieno[2,3-d]pyridazine, thieno[2,3-b]pyrazine, benzofuro[2 ,3-b]pyridine, benzofuro[2,3-c]pyridine, benzofuro[3,2-c]pyridine, benzofuro[3,2-b]pyridine, benzofuro[2,3-d]pyrimidine, benzofuro[2 ,3-b]pyrazine, benzo[4,5]thi eno[2,3-b]pyridine, benzo[4,5]thieno[3,2-c]pyridine, benzo[4,5]thieno[3,2-b]pyridine, benzo[4,5]thieno[ 3,2-b]pyridine, benzo[4,5]thieno[2,3-d]pyrimidine, benzo[4,5]thieno[2,3-b]pyrazine, furo[2,3-b:5, 4-b']dipyridine, furo[2,3-b:4,5-c']dipyridine, furo[2,3-b:5,4-c']dipyridine, furo[2,3-b:4 ,5-b']dipyridine, pyrido[3',2':4,5]furo[3,2-d]pyrimidine, thieno[2,3-b:5,4-b']dipyridine, thieno[2 ,3-b:5,4-c']dipyridine, thieno[2,3-b:4,5-c']dipyridine, thieno[2,3-b:4,5-b']dipyridine, pyrido[ 3',2':4,5]thieno[2,3-d]pyridazine, straight or branched chain alkyl having 1 to 40 carbon atoms, alkoxy having 1 to 40 carbon atoms, thioalkyl having 1 to 40 carbon atoms, or 3 to carbon atoms 40 cycloalkyl group, or
F, Cl, Br, I, CN, Si(CH ₃ ) ₃ , B(OH) ₂ , straight or branched chain alkyl having 1 to 40 carbon atoms, alkoxy having 1 to 40 carbon atoms, thioalkyl having 1 to 40 carbon atoms, carbon number 3 to 40 cycloalkyl, phenyl, biphenyl, naphthyl, anthracenyl, anthracenyl substituted with a phenyl group, phenanthrenyl, pyrenyl, 9,9-dimethylfluorenyl, carbazolyl, dibenzofuranyl, A pyrrole, triazole, pyridinyl, pyrazinyl, pyrimidinyl group, and an aromatic hydrocarbon group having 6 to 60 carbon atoms unsubstituted or substituted with one or more selected from the group consisting of a quinolinyl group,
F, Cl, Br, I, CN, Si(CH ₃ ) ₃ , B(OH) ₂ , straight or branched chain alkyl having 1 to 40 carbon atoms, alkoxy having 1 to 40 carbon atoms, thioalkyl having 1 to 40 carbon atoms, carbon number 3 to 40 cycloalkyl, phenyl, biphenyl, naphthyl, anthracenyl, anthracenyl substituted with a phenyl group, phenanthrenyl, pyrenyl, 9,9-dimethylfluorenyl, carbazolyl, dibenzofuranyl, One or more elements substituted or unsubstituted with one or more selected from the group consisting of pyrrole, triazole, pyridinyl, pyrazinyl, pyrimidinyl group, and quinolinyl group, and selected from the group consisting of S, O, N, and Si Or a heteroaromatic hydrocarbon group having 5 to 60 carbon atoms including,
F, Cl, Br, I, CN, Si(CH ₃ ) ₃ , B(OH) ₂ , straight or branched chain alkyl having 1 to 40 carbon atoms, alkoxy having 1 to 40 carbon atoms, thioalkyl having 1 to 40 carbon atoms, and Phenyl, biphenyl, naphthyl, anthracenyl, anthracenyl substituted with a phenyl group, 9,9 substituted or unsubstituted with one or more selected from the group consisting of a cycloalkyl group having 3 to 40 carbon atoms -It is an amino group substituted with one or more selected from the group consisting of dimethylfluorenyl, carbazolyl, quinolinyl, dibenzofuranyl, pyrrole, triazole, pyridinyl, pyrazinyl, and pyrimidinyl groups,
The method according to claim 1
In Formula 1,
M is Ir,
X13 is nitrogen,
R1, R2, R3, R4, R5, R6, R7, R8, R9 and R10 are each independently hydrogen, deuterium, F, CN, Si(CH3)3, pyridine, pyrimidine, pyrazine, 1,3,5-triazine , quinolone, isoquinoline, indolizine, 1-phenyl-1H-indole, 2-phenyl-2H-isoindole, benzofuran, benzo[b]thiophene, benzo[d]thiazole, 4H-quinolizine, cinnoline, furan, phthalazine, quinazoline, quinoxaline , 1,8-naphthyridine, pteridine, thiophene, oxazole, thiazole, isoxazole, isothiazole, 1,2,3-oxadiazole, 1,2,3-thiadiazole, 1,3,4-thiadiazole, pyridazine, furo[2,3 -b]pyridine, furo[2,3-c]pyridine, furo[3,2-c]pyridine furo[3,2-b]pyridine benzo[d]oxazole furo[2,3-d]pyrimidine, furo[ 3,2-d]pyrimidine, furo[2,3-b]pyrazine, thieno[2,3-b]pyridine, thieno[3,2-c]pyridine, thieno[3,2-b]pyridine, benzo[ d]thiazole, thieno[2,3-d]pyrimidine, thieno[2,3-d]pyridazine, thieno[2,3-b]pyrazine, benzofuro[2,3-b]pyridine, benzofuro[2,3- c]pyridine, benzofuro[3,2-c]pyridine, benzofuro[3,2-b]pyridine, benzofuro[2,3-d]pyrimidine, benzofuro[2,3-b]pyrazine, benzo[4,5] thieno[2,3-b]pyridine, benzo [4,5]thieno[3,2-c]pyridine, benzo[4,5]thieno[3,2-b]pyridine, benzo[4,5]thieno[3,2-b]pyridine, benzo[4 ,5]thieno[2,3-d]pyrimidine, benzo[4,5]thieno[2,3-b]pyrazine, furo[2,3-b:5,4-b']dipyridine, furo[2, 3-b:4,5-c']dipyridine, furo[2,3-b:5,4-c']dipyridine, furo[2,3-b:4,5-b']dipyridine, pyrido[3 ',2':4,5]furo[3,2-d]pyrimidine, thieno[2,3-b:5,4-b']dipyridine, thieno[2,3-b:5,4-c' ]dipyridine, thieno[2,3-b:4,5-c']dipyridine, thieno[2,3-b:4,5-b']dipyridine, pyrido[3',2':4,5]thieno [2,3-d]pyridazine, straight or branched chain alkyl having 1 to 40 carbon atoms, straight or branched chain alkyl having 1 to 25 carbon atoms substituted with deuterium, alkoxy having 1 to 25 carbon atoms, thioalkyl having 1 to 25 carbon atoms, Or a cycloalkyl group having 3 to 25 carbon atoms,
Deuterium, F, CN, Si(CH ₃ ) ₃ , straight or branched chain alkyl having 1 to 25 carbon atoms, alkoxy having 1 to 25 carbon atoms, thioalkyl having 1 to 25 carbon atoms, cycloalkyl having 3 to 25 carbon atoms, phenyl, bi Phenyl, naphthyl, anthracenyl, anthracenyl substituted with a phenyl group, phenanthrenyl, pyrenyl, 9,9-dimethylfluorenyl, carbazolyl, dibenzofuranyl, pyrrole, triazole, pyridinyl, pyrazinyl , A pyrimidinyl group, and one or more substituted or unsubstituted C6-C60 aromatic hydrocarbon groups selected from the group consisting of a quinolinyl group,
Deuterium, F, CN, Si(CH ₃ ) ₃ , B(OH) ₂ , C 1 to C 40 straight or branched chain alkyl, C 1 to C 40 alkoxy, C 1 to C 40 thioalkyl, C 3 to C 40 Cycloalkyl, phenyl, biphenyl, naphthyl, anthracenyl, anthracenyl substituted with a phenyl group, phenanthrenyl, pyrenyl, 9,9-dimethylfluorenyl, carbazolyl, dibenzofuranyl, pyrrole, triazole , Pyridinyl, pyrazinyl, pyrimidinyl group, and substituted or unsubstituted with one or more selected from the group consisting of a quinolinyl group, and carbon number containing at least one element selected from the group consisting of S, O, N and Si 5 to 60 heteroaromatic hydrocarbon groups, or
The group consisting of deuterium, F, CN, Si(CH ₃ ) ₃ , straight or branched chain alkyl having 1 to 25 carbon atoms, alkoxy having 1 to 25 carbon atoms, thioalkyl having 1 to 25 carbon atoms, and cycloalkyl groups having 3 to 25 carbon atoms Substituted or unsubstituted phenyl, biphenyl, naphthyl, anthracenyl, anthracenyl substituted with a phenyl group, phenanthrenyl, pyrenyl, 9,9-dimethylfluorenyl, carbazolyl, An organic compound, characterized in that it is an amino group substituted with at least one selected from the group consisting of quinolinyl, dibenzofuranyl, pyrrole, triazole, pyridinyl, pyrazinyl, and pyrimidinyl groups.
The method according to claim 1,
The organic compound is an organic compound, characterized in that any one of the following compounds 1 to 120:

The method according to claim 1,
The organic compound is an organic compound, characterized in that used as a material for a hole injection layer or a light emitting layer among materials for an organic electroluminescent device.
A material for an organic electroluminescent device for forming at least one of a hole injection layer and an emission layer comprising the organic compound of claim 1.
In an organic electroluminescent device in which an organic thin film layer consisting of one or more layers including at least a light emitting layer is stacked between a cathode and an anode,
An organic electroluminescent device, characterized in that at least one of the organic thin film layers contains the organic compound of claim 1 alone or in combination of two or more.
The method of claim 6,
The organic thin film layer includes a hole injection layer, a hole transport layer, an emission layer, an electron transport layer, and an electron injection layer, and the organic compound of claim 1 is included in at least one of the hole injection layer and the emission layer. device.
The method of claim 6,
The organic thin film layer includes a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer, and the organic compound of claim 1 is applied to any one or more of the hole injection layer and the emission layer. Organic electroluminescent device, characterized in that included.