KR20230157247A - 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 an organic compound represented by the following formula (1) and an organic electroluminescent device containing the same:
[Formula 1]

Description

Novel organic compounds, materials for organic electroluminescent devices containing the organic compounds, and organic electroluminescent devices

The present invention relates to the field of displays, and more specifically, to organic compounds that can be used in the manufacture of organic electroluminescent devices, which are a type of display, and organic electroluminescent devices containing the same.

In general, organic luminescence refers to a phenomenon that converts electrical energy into light energy using organic materials. Organic electroluminescent devices that utilize the organic light emission phenomenon usually have a structure including an anode, a cathode, and an organic material layer between them. Here, the organic material layer is often composed of a multi-layer structure composed of different materials to increase the efficiency and stability of the organic electroluminescent 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. .

Materials used as organic layers in organic electroluminescent devices 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, depending on their function.

The biggest issues with organic electroluminescent devices are lifespan and efficiency, and as displays become larger in area, these efficiency and lifespan issues must be resolved.

Efficiency, lifespan, driving voltage, etc. are related to each other. As efficiency increases, the driving voltage relatively decreases. As the driving voltage decreases, crystallization of organic materials due to Joule heating generated during driving decreases, resulting in less crystallization of organic substances. Life expectancy tends to increase.

However, efficiency cannot be maximized simply by improving the organic layer. This is because long lifespan and high efficiency can be achieved at the same time when the energy level and T1 value between each organic layer and the intrinsic properties of the material (mobility, interface properties, etc.) are optimally combined.

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

Organic compounds other than aromatic amines are generally not used in the hole transport layer of an organic electroluminescent device, and it is well known that aromatic amines have hole transport properties. However, there is a significant drawback when using aromatic amines as the 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, thereby reducing the luminous efficiency of the organic electroluminescent device.

In addition, in order to solve the problem of light emission from 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 auxiliaries are required for each light-emitting layer (R, G, B). It is time for layered development.

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, and excitons are generated by recombination.

However, the material used in the hole transport layer must have a low HOMO value, so most of them have a low T1 value. This causes the exciton generated in the light-emitting layer to pass to the hole transport layer, resulting in a charge unbalance in the light-emitting layer. As a result, light is emitted within the hole transport layer or at the interface of the hole transport layer, resulting in a decrease in color purity and a decrease in efficiency and lifespan of the organic electroluminescent device.

In addition, the driving voltage can be lowered by using a material with fast hole mobility, but the hole mobility is faster than the electron mobility, causing a charge unbalance in the light emitting layer, resulting in organic organic matter. Problems arise in which the color purity and efficiency of the electroluminescent device are reduced and its lifespan is shortened.

Therefore, there is an urgent need to develop a light-emitting auxiliary layer with a high T1 value and a HOMO level between the HOMO energy level of the hole transport layer and the HOMO energy level of the light-emitting layer.

Meanwhile, it delays the penetration and diffusion of metal oxides from the anode electrode (ITO) into the organic layer, which is one of the causes of shortened lifespan of organic electroluminescent devices, and provides stable characteristics against Joule heating generated during device operation, that is, high glass efficiency. There is a need to develop hole injection layer materials with a transition temperature. The low glass transition temperature of the hole transport layer material has the property of lowering the uniformity of the thin film surface when driving the device, and this is reported to have a significant impact on device lifespan. In addition, organic electroluminescent devices are mainly formed by deposition methods, and there is a need to develop materials that can withstand deposition for a long time, that is, materials with strong heat resistance properties.

In order for an organic electroluminescent device to fully demonstrate the above-mentioned excellent features, the materials that make up the organic layer within the device, such as hole injection materials, hole transport materials, light-emitting materials, electron transport materials, and electron injection materials, must be stable and efficient materials. Until now, the development of stable and efficient organic materials for organic electroluminescent devices has not been sufficiently developed. Therefore, in the technical field, there is a continued need for the development of new materials with low voltage operation, high efficiency, and long lifespan.

Republic of Korea Public Patent No. 1020110103141 Republic of Korea Patent No. 1022021710000 Republic of Korea Patent No. 1018256120000 Republic of Korea Patent No. 1012267000000

The present invention was derived to solve the problems of the prior art as described above, and can be applied to organic electroluminescent devices as a hole injection layer material, hole transport layer material, electron blocking layer material, or light emitting layer material, and can be applied to organic electroluminescent devices. The purpose is to provide a new organic compound that can lower the driving voltage when applied and improve luminous efficiency, luminance, thermal stability, color purity, and device lifespan.

In addition, the present invention aims to provide a material for an organic electroluminescent device that forms one or more of the hole injection layer, hole transport layer, electron blocking layer, and light emitting layer containing the organic compound.

Additionally, the present invention aims to provide an organic electroluminescent device using the above organic compound.

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

[Formula 1]

In the above equation

Z1, Z2, Z3 are each independently selected from tritium, deuterium, hydrogen, adamantane, halogen, CN, CF ₃ , straight or branched chain alkyl with 1 to 40 carbon atoms, alkoxy with 1 to 40 carbon atoms, and 1 to 40 carbon atoms. phenyl, naphthanyl, biphenyl, anthracenyl, phenanthrenyl, substituted or unsubstituted with one or more selected from the group consisting of thioalkyl, cycloalkyl having 3 to 40 carbon atoms, phenyl, biphenyl, naphthyl, and anthracenyl groups, Pyrenyl, phenylamine, biphenylamine, 9,9-dimethylfluorenyl, carbazolyl, dibenzofuranyl, pyrrole, triazole, pyridinyl, pyrazinyl, pyrimidinyl, quinolinyl, phenyl pyridinyl. , phenylamine, biphenylamine, phenyl pyrimidinyl, phenyl imidazole, imidazopyrazinyl, or phenyl triazinyl, or an aromatic hydrocarbon group having 6 to 60 carbon atoms that is substituted or unsubstituted, or

Tritium, deuterium, adamantane, halogen, CN, CF ₃ , straight or branched chain alkyl with 1 to 40 carbon atoms, alkoxy with 1 to 40 carbon atoms, thioalkyl with 1 to 40 carbon atoms, cycloalkyl with 3 to 40 carbon atoms, Anthracenyl, phenanthrenyl, pyrenyl, 9,9-dimethylfluorenyl, spirobifluorenyl, substituted or unsubstituted with one or more selected from the group consisting of phenyl, biphenyl, naphthyl, and anthracenyl groups. Carbazolyl, dibenzofuranyl, pyrrole, triazole, pyridinyl, pyrazinyl, pyrimidinyl, quinolinyl, phenyl pyridinyl, phenyl pyrimidinyl, phenyl imidazole, imidazopyrazinyl or phenyl triazinyl group. It is a heteroaromatic hydrocarbon group having 5 to 70 carbon atoms, which is substituted or unsubstituted with one or more elements selected from the group consisting of S, O, N, B, and Si;

a, b, and c are each independently 0 or 1, 2, or 3. If 0, it means that the combination does not exist, and a + b + C = 2 or 3 is satisfied;

M is Ir or Pt or Os or C or Si or Ge;

Y is oxygen or sulfur or selenium;

X1, X2, X3, and X4 are each independently carbon, nitrogen, or boron;

R1, R2, R3, R4, R5, R6, R7 and R8 are each independently tritium, hydrogen, deuterium, adamantane, F, Cl, Br, I, CN, Si(CH ₃ ) ₃ , and 1 to 1 carbon atom. It is a straight-chain or branched alkyl group of 40 carbon atoms, an alkoxyl group of 1 to 40 carbon atoms, a thioalkyl group of 1 to 40 carbon atoms, or a cycloalkyl group of 3 to 40 carbon atoms, or

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

Tritium, deuterium, adamantane, F, Cl, Br, I, CN, Si(CH ₃ ) ₃ , B(OH) ₂ , straight or branched chain alkyl with 1 to 40 carbon atoms, alkoxy with 1 to 40 carbon atoms, Anthracenyl, phenanthrenyl, pi substituted or unsubstituted with one or more selected from the group consisting of thioalkyl having 1 to 40 carbon atoms, cycloalkyl having 3 to 40 carbon atoms, phenyl, biphenyl, naphthyl, anthracenyl, and phenyl groups. From the group consisting of renyl, 9,9-dimethylfluorenyl, spirobifluorenyl, carbazolyl, dibenzofuranyl, pyrrole, triazole, pyridinyl, pyrazinyl, pyrimidinyl group, and quinolinyl group. It is a heteroaromatic hydrocarbon group having 5 to 70 carbon atoms that is substituted or unsubstituted with one or more selected elements and contains one or more elements selected from the group consisting of S, O, N, B, and Si, or

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

In addition, the present invention relates to an organic electroluminescent device in which an organic thin film layer consisting of one or multiple layers including at least a light-emitting layer is laminated between a cathode and an anode,

An organic electroluminescent device is provided, wherein the light-emitting layer contains the organic compound of the present invention alone or in combination of two or more types.

In the organic electroluminescent device, the organic thin film layer may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer,

The hole transport layer may contain one type of organic compound of the following formula (2) alone or in a combination of two or more types:

[Formula 2]

In the above equation,

R1, R2, R3 and R4 are each independently hydrogen; A straight-chain or branched-chain alkyl group having 1 to 20 carbon atoms; Aromatic hydrocarbon having 6 to 60 carbon atoms substituted or unsubstituted with one or more selected from the group consisting of C1 to C10 straight or branched alkyl, C1 to C10 alkoxy, halogen, CN, CF ₃ and Si(CH ₃ ) ₃ group energy; or substituted or unsubstituted with one or more selected from the group consisting of C1~C10 straight or branched alkyl, C1~C10 alkoxy, halogen, CN, CF ₃ and Si(CH ₃ ) ₃ groups, S, O, N and a heteroaromatic hydrocarbon group having 5 to 60 carbon atoms containing at least one element selected from the group consisting of Si;

R1, R2, R3, and R4 may each independently combine with the phenyl group of the basic structure to form an aromatic hydrocarbon or heteroaromatic hydrocarbon.

The organic compound according to the present invention can be applied to organic electroluminescent devices as a light-emitting layer material such as a hole injection layer material, hole transport layer material, electron blocking layer material, or phosphorescent host material. When applied to an organic electroluminescent device, the driving voltage is reduced. It improves luminous efficiency, brightness, thermal stability, color purity, and device lifespan.

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

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

[Formula 1]

In the above equation

Z1, Z2, Z3 are each independently selected from tritium, deuterium, hydrogen, adamantane, halogen, CN, CF ₃ , straight or branched chain alkyl with 1 to 40 carbon atoms, alkoxy with 1 to 40 carbon atoms, and 1 to 40 carbon atoms. phenyl, naphthanyl, biphenyl, anthracenyl, phenanthrenyl, substituted or unsubstituted with one or more selected from the group consisting of thioalkyl, cycloalkyl having 3 to 40 carbon atoms, phenyl, biphenyl, naphthyl, and anthracenyl groups, Pyrenyl, phenylamine, biphenylamine, 9,9-dimethylfluorenyl, carbazolyl, dibenzofuranyl, pyrrole, triazole, pyridinyl, pyrazinyl, pyrimidinyl, quinolinyl, phenyl pyridinyl. , phenylamine, biphenylamine, phenyl pyrimidinyl, phenyl imidazole, imidazopyrazinyl, or phenyl triazinyl, or an aromatic hydrocarbon group having 6 to 60 carbon atoms that is substituted or unsubstituted, or

Tritium, deuterium, adamantane, halogen, CN, CF ₃ , straight or branched chain alkyl with 1 to 40 carbon atoms, alkoxy with 1 to 40 carbon atoms, thioalkyl with 1 to 40 carbon atoms, cycloalkyl with 3 to 40 carbon atoms, Anthracenyl, phenanthrenyl, pyrenyl, 9,9-dimethylfluorenyl, spirobifluorenyl, substituted or unsubstituted with one or more selected from the group consisting of phenyl, biphenyl, naphthyl, and anthracenyl groups. Carbazolyl, dibenzofuranyl, pyrrole, triazole, pyridinyl, pyrazinyl, pyrimidinyl, quinolinyl, phenyl pyridinyl, phenyl pyrimidinyl, phenyl imidazole, imidazopyrazinyl or phenyl triazinyl group. It is a heteroaromatic hydrocarbon group having 5 to 70 carbon atoms, which is substituted or unsubstituted with one or more elements selected from the group consisting of S, O, N, B, and Si;

a, b, and c are each independently 0 or 1, 2, or 3. If 0, it means that the combination does not exist, and a + b + C = 2 or 3 is satisfied;

M is Ir or Pt or Os or C or Si or Ge;

Y is oxygen or sulfur or selenium;

X1, X2, X3, and X4 are each independently carbon, nitrogen, or boron;

R1, R2, R3, R4, R5, R6, R7 and R8 are each independently tritium, hydrogen, deuterium, adamantane, F, Cl, Br, I, CN, Si(CH ₃ ) ₃ , and 1 to 1 carbon atom. It is a straight-chain or branched alkyl group of 40 carbon atoms, an alkoxyl group of 1 to 40 carbon atoms, a thioalkyl group of 1 to 40 carbon atoms, or a cycloalkyl group of 3 to 40 carbon atoms, or

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

Tritium, deuterium, adamantane, F, Cl, Br, I, CN, Si(CH ₃ ) ₃ , B(OH) ₂ , straight or branched chain alkyl with 1 to 40 carbon atoms, alkoxy with 1 to 40 carbon atoms, Anthracenyl, phenanthrenyl, pi substituted or unsubstituted with one or more selected from the group consisting of thioalkyl having 1 to 40 carbon atoms, cycloalkyl having 3 to 40 carbon atoms, phenyl, biphenyl, naphthyl, anthracenyl, and phenyl groups. From the group consisting of renyl, 9,9-dimethylfluorenyl, spirobifluorenyl, carbazolyl, dibenzofuranyl, pyrrole, triazole, pyridinyl, pyrazinyl, pyrimidinyl group, and quinolinyl group. It is a heteroaromatic hydrocarbon group having 5 to 70 carbon atoms that is substituted or unsubstituted with one or more selected elements and contains one or more elements selected from the group consisting of S, O, N, B, and Si, or

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

The present invention also,

In an organic electroluminescent device in which an organic thin film layer consisting of one or multiple layers including at least a light-emitting layer is laminated between the cathode and the anode,

It relates to an organic electroluminescent device, wherein the light-emitting layer contains the organic compound alone or in combination of two or more kinds.

The organic thin film layer may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer,

The hole transport layer may contain one type of organic compound of the following formula (2) alone or in a combination of two or more types:

[Formula 2]

In the above equation,

R1, R2, R3 and R4 are each independently hydrogen; A straight-chain or branched-chain alkyl group having 1 to 20 carbon atoms; Aromatic hydrocarbon having 6 to 60 carbon atoms substituted or unsubstituted with one or more selected from the group consisting of C1 to C10 straight or branched alkyl, C1 to C10 alkoxy, halogen, CN, CF ₃ and Si(CH ₃ ) ₃ group energy; or substituted or unsubstituted with one or more selected from the group consisting of C1~C10 straight or branched alkyl, C1~C10 alkoxy, halogen, CN, CF ₃ and Si(CH ₃ ) ₃ groups, S, O, N and a heteroaromatic hydrocarbon group having 5 to 60 carbon atoms containing at least one element selected from the group consisting of Si;

R1, R2, R3, and R4 may each independently combine with the phenyl group of the back bone to form an aromatic hydrocarbon or heteroaromatic hydrocarbon.

More preferably in the above formula,

R1, R2, R3 and R4 may each independently be a phenyl, biphenyl, naphthyl, anthracenyl, phenanthrenyl, fluorenyl carbazole or pyrenyl group,

R1, R2, R3, and R4 may each independently combine with a phenyl group in the basic structure to form naphthalene, anthracene, or phenanthrene.

Specific examples of the organic compounds include any one of the following compounds 2-1 to 2-15.

Below, the organic electroluminescent device of the present invention will be described as an example. However, the contents illustrated below do not limit the organic electroluminescent device of the present invention.

The organic compound of the present invention can be used as a hole injection layer material, hole transport layer material, electron blocking layer material, or light emitting layer material among materials for organic electroluminescent devices. The light-emitting layer material may be, for example, a phosphorescent dopant material.

Additionally, the present invention relates to a material for an organic electroluminescent device, which forms an organic electroluminescent device containing at least one of a hole injection layer, a hole transport layer, an electron blocking layer, and a light emitting layer containing the organic compound.

In the above, the material for forming the hole injection layer, hole transport layer, electron blocking layer or light emitting layer is usually added when manufacturing the organic compound in the form required for use in forming the hole injection layer, hole transport layer, electron blocking layer or light emitting layer. It may further include substances such as solvents.

In addition, the present invention relates to an organic electroluminescent device in which an organic thin film layer consisting of one or multiple layers including at least a light emitting layer is laminated between a cathode and an anode, wherein at least one of the organic thin film layers contains the organic compound of Formula 1. It relates to an organic electroluminescent device characterized by containing the species singly or in combination of two or more species.

In the organic electroluminescent device, the organic compound may be included as one or more of a hole injection layer material, a hole transport layer material, an electron blocking 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 if necessary, an electron blocking layer, a hole blocking layer, etc. are further stacked. It can be.

The organic thin film layer includes a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer, and the organic compound of the present invention may be included in one or more of the hole injection layer, the hole transport layer, and the light-emitting layer. there is.

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 used in any of the hole injection layer, the hole transport layer, the electron blocking layer, and the light emitting layer. It may have features included in more than one layer.

Hereinafter, the organic electroluminescent device of the present invention will be described as an 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), an emission layer (EML), and a cathode (electron injection electrode) are sequentially stacked, Preferably, an electron blocking layer (EBL) may be further included between the anode and the emission layer, and an electron transport layer (ETL) and an electron injection layer (EIL) may be further included between the cathode and the emission layer. Additionally, a hole blocking layer (HBL) may be further included between the cathode and the light emitting layer.

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

Next, a hole injection layer (HIL) material is vacuum thermally deposited or spin coated on the surface of the anode using a conventional method to form a hole injection layer. Such hole injection layer materials 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), 4,4',4"-tri(N-carbazolyl)triphenylamine (TCTA), a starburst type amine, 4,4 Examples include ',4"-tris(N-(2-naphthyl)-N-phenylamino)-triphenylamine (2-TNATA) or IDE406 available from Idemitsu.

A hole transport layer (HTL) material is vacuum thermally deposited or spin coated on the surface of the hole injection layer using a conventional method to form a hole transport layer. At this time, the hole transport layer material is an 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) Examples include:

An emitting layer (EML) material is formed on the surface of the hole transport layer by vacuum thermal evaporation or spin coating using a conventional method. At this time, the single light-emitting material or light-emitting host material among the light-emitting layer materials used may be an organic compound of the present invention, tris(8-hydroxyquinolinolato)aluminum (Alq3), etc. in the case of green, and in the case of blue, the light-emitting host material of the present invention may be used. Organic compounds, Balq (8-hydroxyquinoline beryllium salt), DPVBi (4,4'-bis(2,2-biphenylethenyl)-1,1'-biphenyl) series, Spiro materials, Spiro-DPVBi (spiro-4,4'-bis(2,2-biphenylethenyl)-1,1'-biphenyl), LiPBO (2-(2-benzooxazolyl)-phenol lithium salt), bis (Biphenylvinyl)benzene, aluminum-quinoline metal complex, imidazole, thiazole, and oxazole metal complex can be used. Additionally, the organic compound of the present invention can be used as a phosphorescent red host material.

Among the light-emitting layer materials, the dopant that can be used with the light-emitting host material includes the organic compound of the present invention as a fluorescent dopant, IDE102 and IDE105 available from Idemitsu, and the organic compound of the present invention, Tris ( 2-phenylpyridine)iridium(III)(Ir(ppy)3), iridium(III)bis[(4,6-difluorophenyl)pyridinato-N,C-2']picolinate (FIrpic) (Reference [Chihaya Adachi et al., Appl. Phys. Lett., 2001, 79, 3082-3084]), platinum (II) octaethylporphyrin (PtOEP), TBE002 (Covion), etc. 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 (ETL) material is vacuum thermally deposited or spin coated on the surface of the light emitting layer using a conventional method to form an electron transport layer. At this time, the electron transport layer material used is not particularly limited, and tris(8-hydroxyquinolinolato)aluminum (Alq3) is preferably 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, diffusion of triplet excitons or holes into the electron transport layer can be prevented.

The formation of the hole blocking layer can be performed by vacuum thermal evaporation and spin coating of the hole blocking layer material by conventional methods. The hole blocking layer material is not particularly limited, but is preferably the organic compound of the present invention, (8 -Hydroxyquinolinolato)lithium (Liq), bis(8-hydroxy-2-methylquinolinolnato)-aluminum biphenoxide (BAlq), bathocuproine (BCP) and LiF, etc. You can use it.

An electron injection layer (EIL) material is vacuum thermally deposited or spin coated on the surface of the electron transport layer using a conventional method to form an electron injection layer. At this time, materials such as LiF, Liq, Li ₂ O, BaO, NaCl, and CsF may be used as the electron injection layer material.

A cathode is formed by vacuum thermal deposition of a cathode material on the surface of the electron injection layer using a conventional method.

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

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

The organic electroluminescent device according to the present invention may be manufactured in the order described above, that is, anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode, and vice versa, cathode/electron injection layer/cathode. It may be manufactured in the following order: electron transport layer/light emitting layer/hole transport layer/hole injection layer/anode.

Claims (1)

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

In the above equation
Z1, Z2, Z3 are each independently selected from tritium, deuterium, hydrogen, adamantane, halogen, CN, CF ₃ , straight or branched chain alkyl with 1 to 40 carbon atoms, alkoxy with 1 to 40 carbon atoms, and 1 to 40 carbon atoms. phenyl, naphthanyl, biphenyl, anthracenyl, phenanthrenyl, substituted or unsubstituted with one or more selected from the group consisting of thioalkyl, cycloalkyl having 3 to 40 carbon atoms, phenyl, biphenyl, naphthyl, and anthracenyl groups, Pyrenyl, phenylamine, biphenylamine, 9,9-dimethylfluorenyl, carbazolyl, dibenzofuranyl, pyrrole, triazole, pyridinyl, pyrazinyl, pyrimidinyl, quinolinyl, phenyl pyridinyl. , phenylamine, biphenylamine, phenyl pyrimidinyl, phenyl imidazole, imidazopyrazinyl, or phenyl triazinyl, or an aromatic hydrocarbon group having 6 to 60 carbon atoms that is substituted or unsubstituted, or
Tritium, deuterium, adamantane, halogen, CN, CF ₃ , straight or branched chain alkyl with 1 to 40 carbon atoms, alkoxy with 1 to 40 carbon atoms, thioalkyl with 1 to 40 carbon atoms, cycloalkyl with 3 to 40 carbon atoms, Anthracenyl, phenanthrenyl, pyrenyl, 9,9-dimethylfluorenyl, spirobifluorenyl, substituted or unsubstituted with one or more selected from the group consisting of phenyl, biphenyl, naphthyl, and anthracenyl groups. Carbazolyl, dibenzofuranyl, pyrrole, triazole, pyridinyl, pyrazinyl, pyrimidinyl, quinolinyl, phenyl pyridinyl, phenyl pyrimidinyl, phenyl imidazole, imidazopyrazinyl or phenyl triazinyl group. It is a heteroaromatic hydrocarbon group having 5 to 70 carbon atoms, which is substituted or unsubstituted with one or more elements selected from the group consisting of S, O, N, B, and Si;
a, b, and c are each independently 0 or 1, 2, or 3. If 0, it means that the combination does not exist, and a + b + C = 2 or 3 is satisfied;
M is Ir or Pt or Os or C or Si or Ge;
Y is oxygen or sulfur or selenium;
X1, X2, X3, and X4 are each independently carbon, nitrogen, or boron;
R1, R2, R3, R4, R5, R6, R7 and R8 are each independently tritium, hydrogen, deuterium, adamantane, F, Cl, Br, I, CN, Si(CH ₃ ) ₃ , and 1 to 1 carbon atom. It is a straight-chain or branched alkyl group of 40 carbon atoms, an alkoxyl group of 1 to 40 carbon atoms, a thioalkyl group of 1 to 40 carbon atoms, or a cycloalkyl group of 3 to 40 carbon atoms, or
Tritium, deuterium, adamantane, F, Cl, Br, I, CN, Si(CH ₃ ) ₃ , B(OH) ₂ , straight or branched chain alkyl with 1 to 40 carbon atoms, alkoxy with 1 to 40 carbon atoms, Anthracenyl, phenanthrenyl, pi substituted or unsubstituted with one or more selected from the group consisting of thioalkyl having 1 to 40 carbon atoms, cycloalkyl having 3 to 40 carbon atoms, phenyl, biphenyl, naphthyl, anthracenyl, and phenyl groups. Substituted with one or more selected from the group consisting of renyl, 9,9-dimethylfluorenyl, carbazolyl, dibenzofuranyl, pyrrole, triazole, pyridinyl, pyrazinyl, pyrimidinyl group, and quinolinyl group, or It is an unsubstituted aromatic hydrocarbon group with 6 to 60 carbon atoms, or
Tritium, deuterium, adamantane, F, Cl, Br, I, CN, Si(CH ₃ ) ₃ , B(OH) ₂ , straight or branched chain alkyl with 1 to 40 carbon atoms, alkoxy with 1 to 40 carbon atoms, Anthracenyl, phenanthrenyl, pi substituted or unsubstituted with one or more selected from the group consisting of thioalkyl having 1 to 40 carbon atoms, cycloalkyl having 3 to 40 carbon atoms, phenyl, biphenyl, naphthyl, anthracenyl, and phenyl groups. From the group consisting of renyl, 9,9-dimethylfluorenyl, spirobifluorenyl, carbazolyl, dibenzofuranyl, pyrrole, triazole, pyridinyl, pyrazinyl, pyrimidinyl group, and quinolinyl group. It is a heteroaromatic hydrocarbon group having 5 to 70 carbon atoms that is substituted or unsubstituted with one or more selected elements and contains one or more elements selected from the group consisting of S, O, N, B, and Si, or
Tritium, deuterium, adamantane, F, Cl, Br, I, CN, Si(CH ₃ ) ₃ , B(OH) ₂ , straight or branched chain alkyl with 1 to 40 carbon atoms, alkoxy with 1 to 40 carbon atoms, phenyl, biphenyl, naphthyl, anthracenyl, anthracenyl substituted with a phenyl group, substituted or unsubstituted with one or more types selected from the group consisting of thioalkyl groups having 1 to 40 carbon atoms, and cycloalkyl groups having 3 to 40 carbon atoms, 1 selected from the group consisting of nathrenyl, pyrenyl, 9,9-dimethylfluorenyl, carbazolyl, quinolinyl, dibenzofuranyl, pyrrole, triazole, pyridinyl, pyrazinyl, and pyrimidinyl groups It is an amino group substituted in more than one species.