WO2024010336A1 - Novel compound and organic light-emitting device using same - Google Patents

Abstract

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

Description

Novel compounds and organic light-emitting devices using them

Cross-Citation with Related Application(s)

This application claims the benefit of priority based on Korean Patent Application No. 10-2022-0082051 dated July 4, 2022, and all contents disclosed in the documents of the Korean Patent Applications are included as part of this specification.

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

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

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

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

[Prior art literature]

[Patent Document]

(Patent Document 0001) Korean Patent Publication No. 10-2000-0051826

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

The present invention provides a compound represented by the following formula (1) or (2):

Compounds represented by Formula 1 or 2 below:

[Formula 1]

[Formula 2]

In Formula 1 or 2,

X is O or S,

R ₁ to R ₅ are each independently hydrogen,

R is substituted or unsubstituted C _6-60 aryl; or C _2-60 heteroaryl containing one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O, and S,

In Formula 3 above,

L is a direct bond; Substituted or unsubstituted C _6-60 arylene; or a C _2-60 heteroarylene containing one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O, and S,

Ar ₁ is substituted or unsubstituted C _6-60 aryl; or C _2-60 heteroaryl containing one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O, and S,

Ar ₂ is substituted or unsubstituted C _6-60 aryl; or C _2-60 heteroaryl containing one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O, and S.

In addition, the present invention includes a first electrode; a second electrode provided opposite to the first electrode; And an organic light-emitting device comprising at least one organic material layer provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes a compound represented by Formula 1 or 2. provides.

The compound represented by Formula 1 or 2 described above can be used as a material for the organic layer of an organic light-emitting device, and can improve efficiency, low driving voltage, and/or lifespan characteristics of the organic light-emitting device. In particular, the compound represented by Formula 1 or 2 can be used as a hole injection, hole transport, hole injection and transport, light emitting, electron transport, or electron injection material.

Figure 1 shows an example of an organic light emitting device consisting of a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4.

2 shows a substrate (1), an anode (2), a hole injection layer (5), a hole transport layer (6), an electron blocking layer (7), a light emitting layer (8), an electron injection and transport layer (9), and a cathode (4). It shows an example of an organic light emitting device made of.

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

In this specification,

or

means a bond connected to another substituent, and “D” means deuterium.

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

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

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

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

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

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

In the present specification, the alkyl group may be straight chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the carbon number of the alkyl group is 1 to 20. According to another embodiment, the carbon number of the alkyl group is 1 to 10. According to another embodiment, the carbon number of the alkyl group is 1 to 6. Specific examples of alkyl groups include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n. -pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl , n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2 -Dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, etc., but is not limited to these.

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

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

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

In the present specification, the fluorenyl group may be substituted, and two substituents may be combined with each other to form a spiro structure. When the fluorenyl group is substituted,

It can be etc. However, it is not limited to this.

In the present specification, the heterocyclic group is a heterocyclic group containing one or more of O, N, Si, and S as a heterogeneous element, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms. Examples of heterocyclic groups include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group, and acridyl group. , pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group, isoquinoline group, indole group , carbazole group, benzooxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, phenanthroline group, isoxazolyl group, thiadia These include, but are not limited to, a zolyl group, a phenothiazinyl group, and a dibenzofuranyl group.

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

As used herein, “deuterated or substituted with deuterium” means that at least one of the replaceable hydrogens in a compound, a divalent linking group, or a monovalent substituent is replaced with deuterium.

In addition, “unsubstituted or substituted with deuterium” or “unsubstituted or substituted with one or more deuterium” means “one to the maximum number of replaceable hydrogens is substituted or unsubstituted with deuterium” . For example, the term “naphthalene that is unsubstituted or substituted with one or more deuterium atoms” refers to “naphthalene that is unsubstituted or substituted with one to eight deuterium atoms,” considering that the maximum number of hydrogens that can be substituted with deuterium in the naphthalene structure is 8. It can be understood to mean “naphthalene.”

In addition, the meaning of “deuterated structure” refers to compounds of all structures in which at least one hydrogen is replaced with deuterium, a divalent linking group, or a monovalent substituent. For example, the deuterated structure of phenyl can be understood to refer to monovalent substituents of all structures in which at least one replaceable hydrogen in the phenyl group is replaced with deuterium, as follows.

Additionally, the “deuterium substitution rate” or “deuteration degree” of a compound is the number of substituted deuteriums relative to the total number of hydrogens that can be present in the compound (the total sum of the number of hydrogens that can be replaced by deuterium and the number of substituted deuteriums in the compound). It means calculating the ratio as a percentage. Therefore, when the “deuterium substitution rate” or “deuteration degree” of a compound is “K%”, it means that K% of the hydrogen replaceable by deuterium in the compound has been replaced with deuterium.

At this time, the “deuterium substitution rate” or “deuteration degree” is determined by MALDI-TOF MS (Matrix-Assisted Laser Desorption/Ionization Time-of-Flight Mass Spectrometer), nuclear magnetic resonance spectroscopy ( ^1H NMR), TLC/MS (Thin -It can be measured according to commonly known methods using Layer Chromatography/Mass Spectrometry) or GC/MS (Gas Chromatography/Mass Spectrometry). More specifically, when using MALDI-TOF MS, the “deuterium substitution rate” or “deuteration degree” is calculated by calculating the number of deuterium substituted in the compound through MALDI-TOF MS analysis, and then comparing the total number of hydrogens that may exist in the compound. The ratio of the number of deuteriums formed can be calculated as a percentage.

(compound)

The present invention provides a compound represented by Formula 1 or 2 above.

X is O or S. Preferably, X is O.

R ₁ to R ₅ are each independently hydrogen or deuterium.

R is substituted or unsubstituted C _6-60 aryl; or C _2-60 heteroaryl containing one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O, and S.

Preferably, R is phenyl. Additionally, R may be unsubstituted or substituted with one or more deuterium.

L is a direct bond; Substituted or unsubstituted C _6-60 arylene; Or it is a C _2-60 heteroarylene containing one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O, and S.

Preferably, L is a direct bond.

Ar ₁ is substituted or unsubstituted C _6-60 aryl; or C _2-60 heteroaryl containing one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O, and S.

Preferably, Ar ₁ is phenyl; biphenylyl; naphthyl; or dibenzofuranyl. Additionally, Ar ₁ may be unsubstituted or substituted with one or more deuterium.

Ar ₂ is substituted or unsubstituted C _6-60 aryl; or C _2-60 heteroaryl containing one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O, and S.

Preferably, Ar ₂ is phenyl; biphenylyl; naphthyl; or dibenzofuranyl. Additionally, Ar ₂ may be unsubstituted or substituted with one or more deuterium.

The compound represented by Formula 1 or 2 is any one selected from the group consisting of:

.

The compounds may contain no deuterium or may contain one or more deuterium.

When the compound contains deuterium, the deuterium substitution rate of the compound may be 1% to 100%. Specifically, the deuterium substitution rate of the compound is 5% or more, 10% or more, 20% or more, 25% or more, 30% or more, 40% or more, or 50% or more, and is 100% or less, 90% or less, or 80% or less. It may be less than or equal to 70%.

As an example, the compound may not contain deuterium, or may contain 1 to 30 deuterium. Specifically, when the compound contains deuterium, the compound contains 1 or more, 3 or more, 5 or more, 6 or more, 7 or more, 8 or more, 10 or more, 11 or more, 12 or more. , 15 or more, or 18 or more, and may include 30 or less, 28 or less, 26 or less, 24 or less, 22 or less, or 20 or less deuterium.

Additionally, the present invention provides a method for producing a compound represented by Formula 1 or 2, as shown in Scheme 1 or 2 below.

[Scheme 1]

[Scheme 2]

In Scheme 1 or 2, the definitions of L, Ar ₁ , Ar ₂ , R ₁ to R ₅ , X and R are the same as Formula 1 or 2, and Z is halogen, preferably chloro.

Scheme 1 or 2 is a Suzuki coupling reaction, which is preferably carried out in the presence of a palladium catalyst, and the reactor for the Suzuki coupling reaction can be changed according to what is known in the art. The manufacturing method may be further detailed in manufacturing examples and synthesis examples that will be described later.

(Organic light emitting device)

Additionally, the present invention provides an organic light-emitting device containing the compound represented by Formula 1 or 2 above. In one example, the present invention includes a first electrode; a second electrode provided opposite to the first electrode; And an organic light-emitting device comprising at least one organic material layer provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes a compound represented by Formula 1 or 2. provides.

The organic material layer of the organic light emitting device of the present invention may have a single-layer structure, or may have a multi-layer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present invention may have a structure that includes a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, etc. as an organic material layer. However, the structure of the organic light emitting device is not limited to this and may include fewer organic layers.

In addition, the organic layer may include a hole injection layer, a hole transport layer, or a layer that simultaneously performs hole injection and transport, and the hole injection layer, the hole transport layer, or a layer that simultaneously performs hole injection and transport is Formula 1 or It may include a compound represented by 2.

Additionally, the organic layer may include a light-emitting layer, and the light-emitting layer includes a compound represented by Formula 1 or 2. In particular, the compound according to the present invention can be used as a host for a light-emitting layer. In particular, the compound according to the present invention can be used as a red host for a light-emitting layer.

In addition, the organic material layer may include a hole blocking layer, an electron transport layer, an electron injection layer, or a layer that simultaneously performs electron transport and electron injection, and the hole blocking layer, an electron transport layer, an electron injection layer, or an electron transport and electron injection layer. The layer that is simultaneously injected may include a compound represented by Formula 1 or 2 above.

Additionally, the organic layer may include a light-emitting layer and an electron injection and transport layer, and the light-emitting layer or the electron injection and transport layer may include a compound represented by Formula 1 or 2.

Additionally, the organic layer may include an electron transport layer or an electron injection layer, and the electron transport layer or electron injection layer includes a compound represented by Formula 1 or 2.

In addition, the electron transport layer, the electron injection layer, or the layer that simultaneously performs electron transport and electron injection includes a compound represented by Formula 1 or 2.

Additionally, the organic layer includes a light-emitting layer and an electron transport layer, and the electron transport layer may include a compound represented by Formula 1 or 2.

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

Figure 1 shows an example of an organic light emitting device consisting of a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4. In this structure, the compound represented by Formula 1 or 2 may be included in the light-emitting layer.

2 shows a substrate (1), an anode (2), a hole injection layer (5), a hole transport layer (6), an electron blocking layer (7), a light emitting layer (8), an electron injection and transport layer (9), and a cathode (4). It shows an example of an organic light emitting device made of. In this structure, the compound represented by Formula 1 or 2 may be included in the light-emitting layer.

The organic light emitting device according to the present invention can be manufactured using materials and methods known in the art, except that at least one of the organic layers includes a compound represented by Formula 1 or 2. Additionally, when the organic light emitting device includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials.

For example, the organic light emitting device according to the present invention can be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate. At this time, an anode is formed by depositing a metal or a conductive metal oxide or an alloy thereof on the substrate using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation. It can be manufactured by forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer thereon, and then depositing a material that can be used as a cathode thereon. In addition to this method, an organic light-emitting device can be made by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

In addition, the compound represented by Formula 1 or 2 may be formed as an organic layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light-emitting device. Here, the solution application method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited to these.

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

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

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

The cathode material is generally preferably a material with a small work function to facilitate electron injection into the organic layer. Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; There are multi-layer structure materials such as LiF/Al or LiO ₂ /Al, but they are not limited to these.

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

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

The electron blocking layer is a layer placed between the hole transport layer and the light emitting layer to prevent electrons injected from the cathode from being recombined in the light emitting layer and passing to the hole transport layer, and is also called an electron blocking layer. A material with lower electron affinity than the electron transport layer is preferred for the electron blocking layer. Preferably, the compound represented by Formula 1 or 2 may be included as a material for the electron blocking layer.

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

The light emitting layer may include a host material and a dopant material. Host materials include condensed aromatic ring derivatives or heterocyclic ring-containing compounds. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, and ladder-type compounds. These include, but are not limited to, furan compounds and pyrimidine derivatives.

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

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

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

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

Meanwhile, in the present invention, the “electron injection and transport layer” is a layer that performs the functions of both the electron injection layer and the electron transport layer. The materials that play the role of each layer can be used singly or in combination, but are limited thereto. It doesn't work. Preferably, the compound represented by Formula 1 or 2 may be included as a material for the electron injection and transport layer.

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

Additionally, the compound represented by Formula 1 or 2 may be included in an organic solar cell or an organic transistor in addition to an organic light-emitting device.

The preparation of the compound represented by Formula 1 or 2 and an organic light-emitting device containing the same will be described in detail in the Examples below. However, the following examples are for illustrating the present invention, and the scope of the present invention is not limited thereto.

[Manufacturing example]

Preparation Example 1: Preparation of Compound 1

In a nitrogen atmosphere, Compound 1-1 (50 g, 139.7 mmol) and Compound 1-2 (60.3 g, 146.7 mmol) were added to THF (750 ml), stirred, and refluxed. Afterwards, potassium carbonate (57.9 g, 419.2 mmol) was dissolved in water (290 ml), stirred sufficiently, and then Pd(dppf)Cl ₂ (1.6 g, 1.4 mmol) was added. After reaction for 2 hours, it was cooled to room temperature, the organic layer was separated using chloroform and water, and the organic layer was distilled. This was again dissolved in dichlorobenzene, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by recrystallization alone in dichlorobenzene, and then compound 1 (75.4 g) was prepared through sublimation purification. (Yield: 89%, MS:[M+H] ⁺ =608)

Preparation Example 2: Preparation of Compound 2

In a nitrogen atmosphere, Compound 2-1 (50 g, 186.8 mmol) and Compound 2-2 (80.6 g, 196.1 mmol) were added to THF (750 ml), stirred, and refluxed. Afterwards, potassium carbonate (77.4 g, 560.3 mmol) was dissolved in water (387 ml), stirred sufficiently, and then Pd(dppf)Cl ₂ (2.2 g, 1.9 mmol) was added. After reaction for 2 hours, it was cooled to room temperature, the organic layer was separated using chloroform and water, and the organic layer was distilled. This was again dissolved in dichlorobenzene, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by recrystallizing dichlorobenzene, and then compound 2 (84.9 g) was prepared through sublimation purification. (Yield: 88%, MS:[M+H] ⁺ =518)

Preparation Example 3: Preparation of Compound 3

In a nitrogen atmosphere, Compound 3-1 (50 g, 145.4 mmol) and Compound 3-2 (62.8 g, 152.7 mmol) were added to THF (750 ml), stirred, and refluxed. Afterwards, potassium carbonate (60.3 g, 436.3 mmol) was dissolved in water (301 ml), stirred sufficiently, and then Pd(dppf)Cl ₂ (1.7 g, 1.5 mmol) was added. After reaction for 2 hours, it was cooled to room temperature, the organic layer was separated using chloroform and water, and the organic layer was distilled. This was again dissolved in dichlorobenzene, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by recrystallizing dichlorobenzene, and then compound 3 (75.8 g) was prepared through sublimation purification. (Yield: 88%, MS:[M+H] ⁺ =594)

Preparation Example 4: Preparation of Compound 4

Compound 4 (82 g) was prepared using the same method as Preparation Example 2, except that 4-2 was used instead of Compound 2-2. (Yield: 85%, MS:[M+H] ⁺ =518)

[Experimental example]

Experimental Example 1

A glass substrate coated with a thin film of ITO (Indium Tin Oxide) with a thickness of 1,400 Å was placed in distilled water dissolved in detergent and washed ultrasonically. At this time, Decon ^TM CON705 from Fischer Co. was used as detergent, and distilled water filtered secondarily with a 0.22 ㎛ sterilizing filter from Millipore Co. was used as distilled water. After washing the ITO for 30 minutes, ultrasonic washing was repeated twice with distilled water for 10 minutes. After washing with distilled water, it was ultrasonic washed with solvents of isopropyl alcohol, acetone, and methanol for 10 minutes each, dried, and then transported to a plasma cleaner. Additionally, the substrate was cleaned for 5 minutes using oxygen plasma, and then transported to a vacuum evaporator.

On the ITO transparent electrode prepared in this way, the following compound HI-A and compound LG-101 were sequentially thermally vacuum deposited to a thickness of 800 Å and 50 Å, respectively, to form a hole injection layer. On top of this, the following compound HT-A was vacuum deposited to a thickness of 800 Å as a hole transport layer, and then the following compound EB-A was thermally vacuum deposited to a thickness of 600 Å as an electron blocking layer.

Next, on the EB-A deposition film, a mixture of Compound 1 prepared in Preparation Example 1 and the following compound pRH at a weight ratio of 50:50 as the light emitting layer host, and the following compound RD-A as a dopant were applied, and the host and the dopant were applied. A red light-emitting layer was formed by vacuum deposition to a thickness of 400 Å at a weight ratio of 98:2.

Next, as an electron injection and transport layer, the following compound ET-A and compound Liq were thermally vacuum deposited at a ratio of 1:1 to a thickness of 360 Å, and then the following compound Liq was vacuum deposited to a thickness of 5 Å. On the electron injection and transport layer, magnesium and silver were sequentially deposited at a ratio of 10:1 to a thickness of 220 Å, and aluminum was deposited to a thickness of 1000 Å to form a cathode.

In the above process, the deposition rate of organic materials was maintained at 0.4 Å/sec to 0.7 Å/sec, the deposition rate of lithium fluoride of the cathode was maintained at 0.3 Å/sec, and aluminum was maintained at 2 Å/sec, and the vacuum level during deposition was An organic light emitting device was manufactured by maintaining 2x10 ^-7 to 5x10 ^-6 torr.

Examples 2 to 4

An organic light-emitting device was manufactured in the same manner as in Example 1, except that the compounds listed in Table 1 below were used instead of Compound 1 prepared in Preparation Example 1.

Comparative Examples 1 to 3

An organic light-emitting device was manufactured in the same manner as in Example 1, except that the compounds listed in Table 1 below were used instead of Compound 1 prepared in Preparation Example 1. At this time, the structures of comparative compounds A-1, B-1, and C-1 are as follows.

Experiment example

Current was applied to the organic light-emitting devices manufactured in Examples 1 to 4 and Comparative Examples 1 to 3, and the voltage, efficiency, and lifespan were measured, and the results are shown in Table 1 below. At this time, voltage and efficiency were measured by applying a current density of 10 mA/cm ² , and the time (hr) for LT97 until the initial luminance (4000 nit) drops to 97% at a current density of 50 mA/cm ² is measured. it means.

	luminous layer host	@10mA/ cm2		@ 50mA/ cm2
		Driving voltage (V)	Efficiency (cd/A)	LT97(hr)
Example 1	Compound 1:pRH (50:50)	3.80	40.2	250
Example 2	Compound 2:pRH (50:50)	3.85	39.6	270
Example 3	Compound 3:pRH (50:50)	3.95	40.3	303
Example 4	Compound 4:pRH (50:50)	3.88	38.5	260
Comparative Example 1	Compound A-1: pRH (50:50)	4.32	31.1	152
Comparative Example 2	Compound B-1: pRH (50:50)	4.27	29.3	205
Comparative Example 3	Compound C-1: pRH (50:50)	4.43	32.2	133

From the results in Table 1, it can be confirmed that when compounds having the structure of Formula 1 or 2 are applied to the light-emitting layer of an organic electroluminescent device, a device with high efficiency and long lifespan can be obtained.

[Explanation of symbols]

1: Substrate 2: Anode

3: light emitting layer 4: cathode

5: hole injection layer 6: hole transport layer

7: electron blocking layer 8: light emitting layer

9: Electron injection and transport layer

Claims (9)

1. Compounds represented by the following formula 1 or 2:

   [Formula 1]

   

   [Formula 2]

   

   In Formula 1 or 2,

   X is O or S,

   R ₁ to R ₅ are each independently hydrogen or deuterium,

   R is substituted or unsubstituted C _6-60 aryl; or C _2-60 heteroaryl containing one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O, and S,

   L is a direct bond; Substituted or unsubstituted C _6-60 arylene; or a C _2-60 heteroarylene containing one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O, and S,

   Ar ₁ is substituted or unsubstituted C _6-60 aryl; or C _2-60 heteroaryl containing one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O, and S,

   Ar ₂ is substituted or unsubstituted C _6-60 aryl; or C _2-60 heteroaryl containing one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O, and S.
2. According to paragraph 1,

   X is O,

   compound
3. According to paragraph 1,

   R is phenyl,

   R is unsubstituted or substituted with one or more deuterium,

   compound.
4. According to paragraph 1,

   L is a direct bond

   compound.
5. According to paragraph 1,

   Ar ₁ is phenyl; biphenylyl; naphthyl; or dibenzofuranyl;

   Ar ₁ is unsubstituted or substituted with one or more deuterium,

   compound.
6. According to paragraph 1,

   Ar ₂ is phenyl; biphenylyl; naphthyl; or dibenzofuranyl;

   Ar ₂ is unsubstituted or substituted with one or more deuterium,

   compound.
7. According to paragraph 1,

   The compound represented by Formula 1 or 2 is any one selected from the group consisting of:

   compound:

   

   

   .
8. first electrode; a second electrode provided opposite to the first electrode; And an organic light-emitting device comprising at least one organic material layer provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes the compound according to any one of claims 1 to 7. An organic light-emitting device.
9. According to clause 8,

   The organic layer containing the compound is a light-emitting layer,

   Organic light emitting device.

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