KR102589892B1 - Novel hetero-cyclic compound and organic light emitting device comprising the same - Google Patents

Abstract

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

Description

Novel compound and organic light emitting device using the same {Novel hetero-cyclic compound and organic light emitting device comprising the same}

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

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

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

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

Meanwhile, recently, in order to reduce process costs, organic light-emitting devices have been developed using a solution process, especially an inkjet process, instead of the existing deposition process. In the early days, attempts were made to develop organic light emitting devices by coating all organic light emitting device layers using a solution process, but there are limitations to the current technology, so only HIL, HTL, and EML in the form of a fixed structure were performed using a solution process, and the subsequent processes were carried out using the existing deposition process. A hybrid process utilizing is being studied.

Accordingly, the present invention provides a novel organic light-emitting device material that can be used in organic light-emitting devices and can be deposited through a solution process.

Korean Patent Publication No. 10-2000-0051826

The present invention relates to novel heterocyclic compounds and organic light-emitting devices containing the same.

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

[Formula 1]

In Formula 1,

R ₁ and R ₂ are each independently hydrogen; or substituted or unsubstituted C _4-60 alkyl, where at least one of R ₁ and R ₂ is substituted or unsubstituted C _4-60 alkyl,

Ar ₁ and Ar ₂ are each independently substituted or unsubstituted C _6-60 aryl,

L ₁ and L ₂ are each independently directly bonded; Or substituted or unsubstituted C _6-60 arylene,

R ₃ to R ₆ are each independently deuterium; halogen; hydroxy; cyano; nitrile; nitro; Amino; Substituted or unsubstituted C _1-60 alkyl; Substituted or unsubstituted C _1-60 haloalkyl; Substituted or unsubstituted C _1-60 thioalkyl; Substituted or unsubstituted C _1-60 alkoxy; Substituted or unsubstituted C _1-60 haloalkoxy; Substituted or unsubstituted C _3-60 cycloalkyl; Substituted or unsubstituted C _1-60 alkenyl; Substituted or unsubstituted C _6-60 aryl; Substituted or unsubstituted C _6-60 aryloxy; or C _2-60 heteroaryl containing one or more of substituted or unsubstituted O, N, Si and S,

a, b, c and d are each independently integers from 0 to 4.

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. do.

The compound represented by the above-mentioned formula 1 can be used as a material for the organic layer of an organic light-emitting device, and can improve efficiency, low driving voltage, and/or lifespan characteristics of the organic light-emitting device. In particular, the compound represented by Formula 1 described above can be applied to a solution process and 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.
Figure 2 shows an example of an organic light emitting device consisting of a substrate (1), an anode (2), a hole injection layer (5), a hole transport layer (6), a light emitting layer (7), and a cathode (4).

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

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

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

As used herein, the term “substituted or unsubstituted” refers to deuterium; halogen group; Nitrile group; nitro group; hydroxyl group; carbonyl group; ester group; imide group; amino group; Phosphine oxide group; Alkoxy group; Aryloxy group; Alkylthioxy group; Arylthioxy group; Alkyl sulphoxy group; Aryl sulfoxy group; silyl group; boron group; Alkyl group; Cycloalkyl group; alkenyl group; Aryl group; Aralkyl group; Aralkenyl group; Alkylaryl group; Alkylamine group; Aralkylamine group; heteroarylamine group; Arylamine group; Arylphosphine group; or substituted or unsubstituted with one or more substituents selected from the group consisting of 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 the present specification, the boron group specifically includes trimethyl boron group, triethyl boron group, t-butyldimethyl boron group, triphenyl boron group, and phenyl boron group, but is not limited thereto.

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

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

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

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

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

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

In the present specification, the 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.

Preferably, Ar ₁ and Ar ₂ may each independently be selected from the group consisting of:

Preferably, L ₁ and L ₂ may each independently be a direct bond or any one selected from the group consisting of the following.

Preferably, a, b, c and d are 0.

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

The compound represented by Formula 1 can be prepared by the production method shown in Scheme 1 or 2 below. Scheme 1 below may be a production method when the compound is symmetric, and Scheme 2 below may be a production method when the compound is asymmetric. This manufacturing method can be further detailed in the manufacturing examples described later.

[Scheme 1]

[Scheme 2]

In Schemes 1 and 2, Ar ₁ , Ar ₂ , L ₁ , L ₂ , R ₁ to R ₆ , a, b, c and d are defined as previously defined.

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

Additionally, the present invention provides an organic light-emitting device containing the compound represented by Formula 1 above. 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. do.

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

In addition, the organic material 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 represented by Formula 1 Contains the indicated compounds.

Additionally, the organic layer may include a light-emitting layer, and the light-emitting layer includes the compound represented by Chemical Formula 1.

Additionally, the organic material layer may include a hole transport layer or a hole injection layer, and the hole transport layer or the hole injection layer includes the compound represented by Formula 1 above.

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 the compound represented by Formula 1.

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

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

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

Figure 2 shows an example of an organic light emitting device consisting of a substrate (1), an anode (2), a hole injection layer (5), a hole transport layer (6), a light emitting layer (7), and a cathode (4). In this structure, the compound represented by Formula 1 may be included in one or more of the hole injection layer, hole transport layer, and 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 the compound represented by Formula 1 above. Additionally, when the organic light emitting device includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials.

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

In addition, the compound represented by Formula 1 may be formed as an organic layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light-emitting device. In particular, the compound represented by Formula 1 has excellent solubility in the solvent used in the solution application method, making it easy to apply the solution application method. 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.

Accordingly, the present invention provides a coating composition comprising the compound represented by Formula 1 and a solvent.

The solvent is not particularly limited as long as it is capable of dissolving or dispersing the compound according to the present invention, and examples include chloroform, methylene chloride, 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene, o -Chlorine-based solvents such as dichlorobenzene; Ether-based solvents such as tetrahydrofuran and dioxane; Aromatic hydrocarbon solvents such as toluene, xylene, trimethylbenzene, and mesitylene; Aliphatic hydrocarbon solvents such as cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane, and n-decane; Ketone-based solvents such as acetone, methyl ethyl ketone, and cyclohexanone; Ester solvents such as ethyl acetate, butyl acetate, and ethyl cellosolve acetate; Polyhydric acids such as ethylene glycol, ethylene glycol monobutyl ether, ethylene glycol monoethyl ether, ethylene glycol monomethyl ether, dimethoxyethane, propylene glycol, diethoxymethane, triethylene glycol monoethyl ether, glycerin, 1,2-hexanediol, etc. alcohol and its derivatives; Alcohol-based solvents such as methanol, ethanol, propanol, isopropanol, and cyclohexanol; Sulfoxide-based solvents such as dimethyl sulfoxide; and amide-based solvents such as N-methyl-2-pyrrolidone and N,N-dimethylformamide; Benzoate-based solvents such as butyl benzoate and methyl-2-methoxybenzoate; tetralin; Solvents such as 3-phenoxy-toluene may be mentioned. In addition, the above-mentioned solvents may be used individually or two or more types of solvents may be mixed.

Additionally, the viscosity of the coating composition is preferably 1 cP to 10 cP, and coating is easy within this range. In addition, the concentration of the compound according to the present invention in the coating composition is preferably 0.1 wt/v% to 20 wt/v%.

Additionally, the present invention provides a method of forming a functional layer using the above-described coating composition. Specifically, coating the coating composition according to the present invention described above by a solution process; and heat treating the coated coating composition.

In the heat treatment step, the heat treatment temperature is preferably 150 to 230°C. Additionally, the heat treatment time is 1 minute to 3 hours, and more preferably 10 minutes to 1 hour. Additionally, the heat treatment is preferably performed in an inert gas atmosphere such as argon or nitrogen.

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, but are not limited to, multi-layered materials such as LiF/Al or LiO ₂ /Al.

The hole injection material is a layer that injects holes from an electrode. The hole injection material has the ability to transport holes and has an excellent hole injection effect at the anode, a light-emitting layer or a light-emitting material, and is generated in the light-emitting layer. 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 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. Preferably, a compound according to the present invention is used as the host material. Additionally, the light-emitting layer may use two or more types of hosts, and the compound according to the present invention may be used as one of the hosts.

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 material 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 has high mobility for electrons. This is suitable. 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. These include, but are not limited to, complex compounds and nitrogen-containing five-membered ring derivatives.

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.

The organic light emitting device according to the present invention may be a front emitting type, a back emitting type, or a double-sided emitting type depending on the material used.

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

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

Manufacturing example 1: Preparation of Compound 1

Intermediate a1 (2.0 g, 12.3 mmol) and Ni(dppp)Cl ₂ (70 mg, 0.123 mmol) were added to RB, filled with nitrogen, and then 14 mL of diethyl ether was added. Intermediate a2 (1.0M in Et ₂ O, 16 mL, 16.0 mmol) was slowly injected at 0°C. After stirring overnight at room temperature, 1N HCl was added to terminate the reaction. The organic layer was extracted with DCM/H ₂ O, MgSO ₄ was added, stirred for 30 minutes, and then passed through a celite/silica pad. After concentration under reduced pressure, column purification was performed with Hx to obtain intermediate a3.

The obtained intermediate a3 (2.4 g, 12.3 mmol) was dissolved in 30 mL of DCM, then NBS (4.4 g, 24.6 mmol) was added and stirred at room temperature for 6 hours. The organic layer was extracted with DCM/H ₂ O, MgSO ₄ was added, stirred for 30 minutes, and then passed through a celite/silica pad. After concentration under reduced pressure, column purification was performed using Hx to obtain intermediate a.

The obtained intermediate a (1.0 g, 2.8 mmol), intermediate b (2.9 g, 5.7 mmol), Pd(PPh ₃ ) ₄ (0.16 g, 0.14 mmol), and K ₂ CO ₃ (1.2 g, 8.5 mmol) were dissolved in 250mL two- It was placed in the neck RB and filled with nitrogen. Afterwards, THF (55 mL) and H ₂ O (10 mL) were added, the temperature was raised to 70°C, and the mixture was stirred overnight. The organic layer was extracted with DCM/H ₂ O, MgSO ₄ and charcoal were added, stirred for 30 minutes, and then passed through a celite/silica pad. After concentration under reduced pressure, column purification with DCM/Hx and precipitation with THF/EtOH, Compound 1 was obtained. (MS: [M+H] ⁺ =953)

Manufacturing example 2: Preparation of Compound 2

Compound 2 was prepared in the same manner as Preparation Example 1, except that Intermediate c was used instead of Intermediate b. (MS: [M+H] ⁺ =953)

Manufacturing example 3: Preparation of Compound 3

Compound 3 was prepared in the same manner as Preparation Example 1, except that Intermediate d was used instead of Intermediate a. (MS: [M+H] ⁺ =1009)

Manufacturing example 4: Preparation of Compound 4

Compound 4 was prepared in the same manner as Preparation Example 3, except that Intermediate e was used instead of Intermediate b. (MS: [M+H] ⁺ =757)

Manufacturing example 5: Preparation of Compound 5

Compound 5 was prepared in the same manner as Preparation Example 1, except that Intermediate f was used instead of Intermediate b. (MS: [M+H] ⁺ =801)

Comparative manufacturing example 1: Preparation of Compound A

Compound A was prepared in the same manner as Preparation Example 4, except that intermediate g was used instead of intermediate d. (MS: [M+H] ⁺ =589)

Comparative manufacturing example 2: Preparation of Compound B

Compound B was prepared in the same manner as Preparation Example 1, except that Intermediate g was used instead of Intermediate a. (MS: [M+H] ⁺ =841)

Example 1 to 5 and Comparative example 1 to 2: Solubility evaluation

The compounds 1 to 5 and A to B were each added to toluene and stirred at 1500 rpm for 30 minutes at room temperature (25°C). Afterwards, the formation of precipitates was checked to determine the solubility of each compound, and the results are shown in Table 1 below.

solute Solubility (wt.%) Example 1 Compound 1 3 Example 2 compound 2 4 Example 3 Compound 3 2 Example 4 Compound 4 2 Example 5 Compound 5 3 Comparative Example 1 Compound A < 1 Comparative Example 2 Compound B < 1

Referring to Table 1, it was confirmed that Compounds 1 to 5 had significantly higher solubility in toluene than Compounds A to B.

Example 6: Manufacturing of organic light emitting device

A glass substrate on which ITO (indium tin oxide) was deposited as a thin film to a thickness of 500 Å was placed in distilled water with a detergent dissolved in it and washed ultrasonically. At this time, a product from Fisher Co. was used as a detergent, and distilled water filtered twice through a filter from Millipore Co. was used as distilled water. After washing the ITO for 30 minutes, ultrasonic cleaning was repeated twice with distilled water for 10 minutes. After washing with distilled water, the washed ITO glass substrate with a thickness of 500 Å was prepared by ultrasonic cleaning with acetone, distilled water, and isopropyl alcohol solvent and drying.

A composition of the following compound Z-1 and the following compound Z-2 mixed at a weight ratio of 8:2 was spin coated on the ITO transparent electrode and cured at 220°C for 30 minutes on a hot plate under a nitrogen atmosphere to inject holes with a thickness of 400 Å. A layer was formed. On the hole injection layer, a composition containing 1% by weight of the following compound Z-3 dissolved in toluene was spin-coated and heat-treated on a hot plate at 200°C for 30 minutes to form a hole transport layer with a thickness of 200Å. On the hole transport layer, a composition obtained by dissolving Compound 1 according to Preparation Example 1 and the following Compound Z-4 (weight ratio 94:6) at 0.5% by weight in toluene was spin-coated to form a 550Å-thick light-emitting layer, followed by hot plate under N ₂ atmosphere. The coating composition was dried at 120°C for 10 minutes.

Afterwards, it was transferred to a vacuum evaporator and sequentially deposited LiF (10 Å) and Al (1000 Å) to produce an organic light-emitting device. In the above process, the deposition rate of LiF was maintained at 0.3 Å/sec, the deposition rate of aluminum (Al) was maintained at 2 Å/sec, and the vacuum degree during deposition was maintained at 2x10 ^-7 to 5x10 ^-8 torr.

Example 7 to 10 and Comparative example 3 to 4

An organic light-emitting device was manufactured in the same manner as Example 6, except that the compounds listed in Table 2 below were used instead of Compound 1.

The driving voltage, luminous efficiency, power efficiency, quantum efficiency, and lifespan (T ₉₀ ) of the organic light-emitting devices manufactured in Examples 6 to 10 and Comparative Examples 3 to 4 were measured at a current density of 10 mA/cm ² and measured. The results are shown in Table 2 below. Lifespan (T ₉₀ ) refers to the time it takes for luminance to decrease to 90% from the initial luminance.

luminous layer host driving voltage
(V) Luminous efficiency
(cd/A) power efficiency
(lm/W) quantum efficiency
(%) _T90
(hr) Example 6 Compound 1 4.45 8.05 5.67 7.97 56 Example 7 compound 2 4.32 8.21 5.92 8.06 96 Example 8 Compound 3 4.41 8.52 6.09 8.26 79 Example 9 Compound 4 4.36 8.09 5.81 7.98 40 Example 10 Compound 5 4.42 7.53 5.40 7.54 71 Comparative Example 3 Compound A 4.58 7.39 5.22 7.57 15 Comparative Example 4 Compound B 4.66 6.91 4.57 6.50 6

According to Table 2, it was confirmed that Examples 6 to 10 had lower driving voltage and were superior in luminous efficiency, power efficiency, quantum efficiency, and lifespan characteristics compared to Comparative Examples 3 and 4.

1: Substrate 2: Anode
3: light emitting layer 4: cathode
5: hole injection layer 6: hole transport layer
7: Light-emitting layer

Claims (8)

Compound represented by Formula 1:
[Formula 1]

In Formula 1,
R ₁ and R ₂ are each independently hydrogen; or C _4-60 alkyl, where at least one of R ₁ and R ₂ is C _4-60 alkyl,
Ar ₁ and Ar ₂ are each independently deuterium-substituted or unsubstituted C _6-60 aryl,
L ₁ and L ₂ are each independently directly bonded; or C _6-60 arylene,
R ₃ to R ₆ are each independently deuterium; halogen; hydroxy; cyano; nitrile; nitro; Amino; C _1-60 alkyl; C _1-60 haloalkyl; C _1-60 thioalkyl; C _1-60 alkoxy; C _1-60 haloalkoxy; C _3-60 cycloalkyl; C _1-60 alkenyl; C _6-60 aryl; C _6-60 aryloxy; or C _2-60 heteroaryl containing one or more of O, N, Si and S,
a, b, c and d are each independently integers from 0 to 4.
According to paragraph 1,
Ar ₁ and Ar ₂ are each independently any one selected from the group consisting of:

According to paragraph 1,
L ₁ and L ₂ are each independently a direct bond or any one selected from the group consisting of:

According to paragraph 1,
a, b, c and d are 0.
According to paragraph 1,
The compound represented by Formula 1 is characterized in that it is selected from the group consisting of the following compounds:

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 5. An organic light-emitting device.
According to clause 6,
The organic material layer containing the above compound is a light emitting layer; Hole transport layer; Or an organic light-emitting device, characterized in that it is a hole injection layer.
In clause 7,
The light-emitting layer may use two or more types of hosts, and one of the hosts includes the compound.