KR20200053259A - Novel compound and organic light emitting device comprising the same - Google Patents

Abstract

The present invention provides a novel compound and an organic light emitting device comprising the same. The compound is represented by chemical formula 1.

Description

Novel compound and organic light emitting device comprising the same}

The present invention relates to a novel compound and an organic light emitting device comprising the same.

In general, the organic light emitting phenomenon refers to a phenomenon that converts electrical energy into light energy using an organic material. The organic light emitting device using the organic light emitting phenomenon has a wide viewing angle, excellent contrast, and a fast response time, and has excellent luminance, driving voltage, and response speed characteristics, and thus many studies have been conducted.

The organic light emitting device generally has a structure including an anode and a cathode and an organic material layer between the anode and the cathode. In order to increase the efficiency and stability of the organic light emitting device, the organic material layer is often formed of a multi-layered structure composed of different materials, for example, may be formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. When a voltage is applied between two electrodes in the structure of the organic light emitting device, holes are injected at the anode, and electrons are injected at the cathode, and an exciton is formed when the injected holes meet the electrons. When it falls to the ground again, it glows.

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

Meanwhile, an organic light emitting device using a solution process, particularly an inkjet process, has been developed instead of a conventional deposition process to reduce process cost. In the early days, all organic light-emitting device layers were coated with a solution process to develop an organic light-emitting device, but there are limitations in current technology, so only HIL, HTL, and EML are used as a solution process in the form of a regular structure, and the subsequent process is an existing deposition process A hybrid process that utilizes is being studied.

Accordingly, the present invention provides a novel organic light-emitting device material that can be used in an organic light-emitting device and can be used in a solution process at the same time.

Korean Patent Publication No. 10-2000-0051826

The present invention relates to a novel compound and an organic light emitting device comprising the same.

The present invention provides a compound represented by Formula 1:

[Formula 1]

In Chemical Formula 1,

Ar ₁ and Ar ₂ are each independently, substituted or unsubstituted C _6-60 aryl; Or C _2-60 heteroaryl including any one or more selected from the group consisting of substituted or unsubstituted N, O and S,

R ₁ and R ₂ are the same as or different from each other, and each independently hydrogen; Substituted or unsubstituted C _1-60 alkyl; Or substituted or unsubstituted C _3-60 cycloalkyl, provided that at least one of R ₁ and R ₂ is substituted or unsubstituted C _1-60 alkyl; Or substituted or unsubstituted C _3-60 cycloalkyl,

R ₃ is hydrogen; heavy hydrogen; halogen; Cyano; Nitro; Amino; Substituted or unsubstituted C _1-60 alkyl; Substituted or unsubstituted C _3-60 cycloalkyl; Substituted or unsubstituted C _2-60 alkenyl; Substituted or unsubstituted C _6-60 aryl; Or C _2-60 heteroaryl including any one or more selected from the group consisting of substituted or unsubstituted N, O and S,

a1 and a2 are each independently an integer of 0 to 4, a1 + a2 is 1 or more,

a3 is an integer of 0-6.

In addition, the present invention is a first electrode; A second electrode provided to face the first electrode; And an organic light emitting device including at least one layer of an organic material provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes a compound represented by Chemical Formula 1, and provides an organic light emitting device. .

The compound represented by Chemical Formula 1 may be used as a material for an organic material layer of an organic light emitting device, and may also be used in a solution process, and may improve efficiency, improve low driving voltage, and / or life characteristics in an organic light emitting device. have. In particular, the compound represented by Formula 1 may be used as a hole injection, hole transport, hole injection and transport, light emission, electron transport, or electron injection material

FIG. 1 shows an example of an organic light emitting device including a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4.
2 is composed of a substrate (1), an anode (2), a hole injection layer (5), a hole transport layer (6), a light emitting layer (3), an electron transport layer (7), an electron injection layer (8) and a cathode (4) An example of an organic light emitting device is shown.

Hereinafter, it will be described in more detail in order to help the understanding of the present invention.

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

는 다른 치환기에 연결되는 결합을 의미한다. In this specification,

Means a linkage to another substituent.

The term "substituted or unsubstituted" as used herein refers to deuterium; Halogen group; Nitrile group; Nitro group; Hydroxy group; Carbonyl group; Ester groups; Imide group; Amino group; Phosphine oxide group; Alkoxy groups; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy group; Aryl sulfoxyl group; Silyl group; Boron group; Alkyl groups; Cycloalkyl group; Alkenyl group; Aryl group; Aralkyl group; Ar alkenyl group; Alkyl aryl groups; Alkylamine groups; 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 substituents among the exemplified substituents above . For example, "a substituent having two or more substituents" may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent to which two phenyl groups are connected.

In this specification, the number of carbon atoms of the carbonyl group is not particularly limited, but is preferably 1 to 40 carbon atoms. Specifically, it may be a compound having 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 or cyclic 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 number of carbon atoms of the imide group is not particularly limited, but is preferably 1 to 25 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

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

In the present specification, the boron group is specifically a trimethyl boron group, a triethyl boron group, a t-butyl dimethyl boron group, a triphenyl boron group, a phenyl boron group, and the like, but is not limited thereto.

In the present specification, examples of the halogen group include fluorine, chlorine, bromine or iodine.

In the present specification, the alkyl group may be straight chain or branched chain, and carbon number is not particularly limited, but is preferably 1 to 40. According to an exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 8 carbon atoms. Specific examples of the alkyl group are 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, and the like, but is not limited thereto.

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

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

In the present specification, the aryl group is not particularly limited, but is preferably 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the carbon number of the aryl group is 6 to 30. According to one embodiment, the carbon number of the aryl group is 6 to 20. The aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc., as a monocyclic aryl 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, and the like, but is not limited thereto.

등이 될 수 있다. 다만, 이에 한정되는 것은 아니다.In the present specification, the fluorenyl group may be substituted, and two substituents may combine with each other to form a spiro structure. When the fluorenyl group is substituted,

It can be back. However, it is not limited thereto.

In the present specification, the heterocyclic group is a heterocyclic group containing one or more of O, N, Si and S as heterogeneous elements, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms. Examples of the heterocyclic group include thiophene group, furan group, pyrrol group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group, acridil 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, benzoxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, phenanthroline group, isooxazolyl group, tiadiia A sleepy group, a phenothiazinyl group, and a dibenzofuranyl group, but are not limited thereto.

In the present specification, an aryl group in an aralkyl group, an alkenyl group, an alkylaryl group, and an arylamine group is the same as the exemplified aryl group described above. In the present specification, the alkyl group among the aralkyl group, alkylaryl group, and alkylamine group is the same as the above-described example of the alkyl group. In the present specification, the description of the heteroaryl group among the heteroarylamines described above may be applied. In the present specification, the alkenyl group in the alkenyl group is the same as the exemplified alkenyl group. In the present specification, the description of the aryl group described above may be applied, except that the arylene is a divalent group. In the present specification, the description of the heterocyclic group described above may be applied, except that the heteroarylene is a divalent group. In the present specification, the hydrocarbon ring is not a monovalent group, and the description of the aryl group or cycloalkyl group described above may be applied, except that two substituents are formed by bonding. In this specification, the heterocycle is not a monovalent group, and the description of the aforementioned heterocyclic group may be applied, except that two substituents are formed by bonding.

(compound)

The compound of the present invention is represented by Formula 1 above.

The compound may be represented by any one of the following Chemical Formula 1-1 to Chemical Formula 1-3:

[Formula 1-1]

 [Formula 1-2]

[Formula 1-3]

In Chemical Formulas 1-1 to 1-3,

The description of Ar ₁ , Ar ₂ , R ₁ to R ₃ and a3 is as defined in Formula 1.

Preferably, Ar ₁ and Ar ₂ are each independently, substituted or unsubstituted C _6-20 aryl; Or C _6-20 heteroaryl including any one or more selected from the group consisting of substituted or unsubstituted N, O and S,

More preferably, Ar ₁ and Ar ₂ are each independently, substituted or unsubstituted C _6-20 aryl,

More preferably, Ar ₁ and Ar ₂ are each independently deuterium, halogen, cyano, amino, nitro, C _1-30 alkyl, C _2-30 alkenyl, C _2-30 alkynyl, C _1-30 Alkoxy, C _6-30 aryloxy, or C _6-20 aryl unsubstituted or substituted with C _6-30 aryl,

More preferably, Ar ₁ and Ar ₂ are each independently deuterium, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tertbutyl, methoxy, ethoxy, propoxy, butoxy, isobutoxy, or C _6-20 aryl unsubstituted or substituted with _neobutoxy ,

More preferably, Ar ₁ and Ar ₂ are each independently phenyl, biphenylyl, terphenylyl, naphthyl, anthracenyl, phenanthrenyl, triphenylenyl, pyrenyl, perylenyl, chrysenyl, di Benzofuranyl and fluorenyl; Wherein Ar ₁ and Ar ₂ are each independently unsubstituted, or deuterium, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tertbutyl, methoxy, ethoxy, propoxy, butoxy, isobutoxy, Or substituted or unsubstituted with neobutoxy,

Most preferably, Ar ₁ and Ar ₂ are each independently phenyl, phenyl substituted with 5 deuterium, biphenylyl, terphenylyl, naphthyl, anthracenyl, phenanthrenyl, triphenylenyl, pyrenyl, Perylenyl, chrysenyl, dibenzofuranyl, or fluorenyl.

Preferably, R ₁ and R ₂ are each independently hydrogen; Or substituted or unsubstituted C _1-20 alkyl,

More preferably, R ₁ and R ₂ are each independently hydrogen; Or unsubstituted C _1-20 alkyl,

More preferably, R ₁ and R ₂ are each independently hydrogen, tertbutyl, butyl, octyl, octan-2-yl, or octan-3-yl,

Most preferably, R ₁ and R ₂ are each independently hydrogen, tertbutyl, butyl, octyl, or octan-3-yl.

Preferably, R ₃ is hydrogen, deuterium, or C _1-4 alkyl,

More preferably, R ₃ is hydrogen, deuterium, or methyl.

Representative examples of the compound represented by Formula 1 are as follows:

Meanwhile, the compound represented by Chemical Formula 1 may be prepared in the same manner as in Scheme 1 below.

[Scheme 1]

In Reaction Scheme 1, Ar ₁ , Ar ₂ , R ₁ to R ₃ and a1 to a3 are as defined in Chemical Formula 1, X is halogen, and preferably X is chloro or bromo.

Reaction Scheme 1 is a Suzuki coupling reaction, preferably performed in the presence of a palladium catalyst and a base, and the reactor for the Suzuki coupling reaction can be changed as known in the art. The manufacturing method may be more specific in the manufacturing examples to be described later.

 (Coating composition)

The compound represented by Chemical Formula 1 according to the present invention may be included in the organic material layer of the organic light emitting device by a solution process. To this end, the present invention provides a coating composition comprising a compound and a solvent represented by Formula 1 according to the present invention described above.

The solvent is not particularly limited as long as it is a solvent capable of dissolving or dispersing the compound represented by Chemical Formula 1, for example, chloroform, methylene chloride, 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene , chlorine-based solvents such as o-dichlorobenzene; Ether-based solvents such as tetrahydrofuran and dioxane; Aromatic hydrocarbon-based solvents such as toluene, xylene, trimethylbenzene, and mesitylene; Aliphatic hydrocarbon-based solvents such as cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane, and n-decane; Ketone solvents such as acetone, methyl ethyl ketone, and cyclohexanone; Ester solvents such as ethyl acetate, butyl acetate, and ethyl cellosolve acetate; Polyvalent values of 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. Alcohols and derivatives thereof; Alcohol solvents such as methanol, ethanol, propanol, isopropanol, and cyclohexanol; Sulfoxide-based solvents such as dimethyl sulfoxide; And amide solvents such as N-methyl-2-pyrrolidone and N, N-dimethylformamide; Benzoate solvents such as isoamyl benzoate, methyl benzoate, ethyl benzoate, butyl benzoate and methyl-2-methoxybenzoate; Tetralin; And solvents such as 3-phenoxy-toluene. In addition, the above-described solvent may be used alone or in combination of two or more solvents.

The boiling point of the solvent may be 40 to 350 ° C, preferably 80 to 330 ° C.

In addition, the viscosity of the coating composition is 1 cP to 10 cP, preferably 3 to 8 cP, and coating is easy in the above range. In addition, the concentration of the polymer according to the present invention in the coating composition is 0.1 wt / v% to 20 wt / v%, preferably 0.5 to 10 wt%.

In addition, the present invention provides a method of forming a light emitting layer using the above-described coating composition. Specifically, coating the coating composition according to the present invention as described above on the positive electrode or on the hole transport layer formed on the positive electrode in a solution process; And drying the coated coating composition.

The solution process refers to the use of the coating composition according to the present invention described above, which means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited thereto.

The drying step may be performed in nitrogen, argon atmosphere or air, but is not limited thereto.

The drying step may be performed through heat treatment, and the heat treatment temperature is 80 to 230 ° C, preferably 100 to 150 ° C. In addition, the heat treatment time is 1 minute to 2 hours, preferably 1 minute to 30 minutes. In addition, the heat treatment is preferably performed in an inert gas atmosphere such as argon and nitrogen.

(Organic light emitting element)

In addition, the present invention provides an organic light emitting device comprising the compound represented by the formula (1). In one example, the present invention is a first electrode; A second electrode provided to face the first electrode; And an organic light emitting device including at least one layer of an organic material provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes a compound represented by Chemical Formula 1, and an organic light emitting device is provided. do.

The organic material layer of the organic light emitting device of the present invention may have a single-layer structure, but 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 including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer 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 light emitting layer, and the light emitting layer includes a compound represented by Chemical Formula 1. In particular, the compound according to the present invention can be used as a host for a light emitting layer.

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

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

In addition, the organic material layer includes a light emitting layer and an electron transport layer, and the light emitting layer may include a compound represented by Chemical Formula 1.

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

1 shows an example of an organic light emitting device including a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4. In such a structure, the compound represented by Chemical Formula 1 may be included in the light emitting layer.

2 is composed of a substrate (1), an anode (2), a hole injection layer (5), a hole transport layer (6), a light emitting layer (3), an electron transport layer (7), an electron injection layer (8) and a cathode (4) An example of an organic light emitting device is shown. In such a structure, the compound represented by Chemical Formula 1 may be included in one or more of the hole injection layer, the hole transport layer, the light emitting layer, and the electron transport layer.

The organic light emitting device according to the present invention may be manufactured by materials and methods known in the art, except that at least one layer of the organic material layer includes the compound represented by Chemical Formula 1. In addition, 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, a positive electrode is formed by depositing a metal or conductive metal oxide or an alloy thereof on a substrate using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation. Then, an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer is formed thereon, and a material that can be used as a cathode is deposited thereon. In addition to this method, an organic light emitting device may be formed by sequentially depositing a cathode material, an organic material layer, and a cathode material on a substrate.

In addition, the compound represented by Chemical Formula 1 may be formed as an organic material 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 means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited to these.

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

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

The positive electrode material is preferably a material having a large work function so that hole injection into the organic material layer is smooth. Specific examples of the positive electrode 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); Metal and oxide combinations 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, but are not limited thereto.

The cathode material is preferably a material having a small work function to facilitate electron injection into the organic material 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 is a multilayer structure material such as LiF / Al or LiO ₂ / Al, but is not limited thereto.

The hole injection layer is a layer for injecting holes from an electrode, and has the ability to transport holes as a hole injection material, and thus has a hole injection effect at an anode, an excellent hole injection effect for a light emitting layer or a light emitting material, and is produced in the light emitting layer. A compound that prevents migration of the excitons to the electron injection layer or the electron injection material and has excellent thin film formation ability is preferred. It is preferred that the high occupied molecular orbital (HOMO) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic layer. Specific examples of the hole injection material include metal porphyrin, oligothiophene, arylamine-based organic matter, hexanitrile hexaazatriphenylene-based organic matter, quinacridone-based organic matter, and perylene-based Organic materials, anthraquinones, polyaniline and polythiophene-based conductive polymers, and the like, but are not limited thereto.

The hole transport layer is a layer that receives holes from the hole injection layer and transports holes from the hole injection layer to the light emitting layer. It is a material that transports holes from the anode or the hole injection layer as a hole transport material and transfers them to the light emitting layer. This is suitable. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers having a conjugated portion and a non-conjugated portion, but are not limited thereto.

As the light-emitting material, a material capable of emitting light in the visible region by receiving and bonding holes and electrons from the hole transport layer and the electron transport layer, respectively, is preferably a material having 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-hydroxybenzo quinoline-metal compound; Benzoxazole, benzthiazole and benzimidazole compounds; Poly (p-phenylenevinylene) (PPV) polymers; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited to these.

The light emitting layer may include a host material and a dopant material. The host material may be a condensed aromatic ring derivative or a heterocyclic compound. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, and ladder types Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

Examples of the dopant material include aromatic amine derivatives, strylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene, chrysene, periplanene, etc. having an arylamino group, and substituted or unsubstituted as a styrylamine compound. A compound in which at least one arylvinyl group is substituted with the arylamine, a substituent selected from 1 or 2 or more from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamino group is substituted or unsubstituted. Specifically, styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like, but are not limited thereto. Further, examples of the metal complex include an iridium complex, a platinum complex, and the like, but are not limited thereto.

The electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer. As the electron transport material, a material capable of receiving electrons from the cathode and transferring them to the light emitting layer is suitable. Do. Specific examples include the Al complex of 8-hydroxyquinoline; Complexes including Alq ₃ ; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited thereto. 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 that have a low work function and are followed by an aluminum or silver layer. Specifically, cesium, barium, calcium, ytterbium and samarium, followed by an aluminum layer or a silver layer in each case.

The electron injection layer is a layer that injects electrons from an electrode, has the ability to transport electrons, has an electron injection effect from a cathode, has an excellent electron injection effect on a light emitting layer or a light emitting material, and injects holes generated in the light emitting layer A compound that prevents migration 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 and the like and their derivatives, metal Complex compounds, nitrogen-containing 5-membered ring derivatives, and the like, but are not limited thereto.

Examples of the metal complex compound 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) ( There are o-cresolato) gallium, bis (2-methyl-8-quinolinato) (1-naphtholato) aluminum, bis (2-methyl-8-quinolinato) (2-naphtholato) gallium, It is not limited to this.

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

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

Hereinafter, preferred embodiments are provided to help understanding of the present invention. However, the following examples are only provided to more easily understand the present invention, and the contents of the present invention are not limited thereby.

Preparation Example 1 Preparation of Compound 1

Intermediate a-1 (1.5 g, 3.3 mmol, 1.1 eq), intermediate a-2 (0.52 g, 3.0 mmol, 1.0 eq), Pd (PPh ₃ ) ₄ (0.14 g, 0.1 mmol, 0.03 eq), K ₂ CO ₃ (1.25 g, 9.0 mmol, 3.0 eq) was added to 250 mL two-neck RB and nitrogen was added. Then, THF (100 mL) and H ₂ O (10 mL) were added, stirred, heated to 80 ° C., reacted overnight, extracted with DCM / H ₂ O, and the organic layer was separated, and MgSO ₄ and charcoal were added and stirred for 30 minutes. Was passed through a silica pad. The solvent of filtrate was removed and the column was purified by DCM / Hx to obtain intermediate a.

Obtained intermediate a (0.7 g, 1.4 mmol, 1.0 eq), intermediate b (0.86 g, 1.7 mmol, 1.2 eq), Pd (PPh ₃ ) ₄ (0.06 g, 0.05 mmol, 0.04 eq), K ₂ CO ₃ (0.6 g, 4.3 mmol, 3.0 eq) into 250 mL two-neck RB and nitrogen. Then, THF (120 mL) and H ₂ O (10 mL) were added, stirred, heated to 80 ° C., reacted overnight, extracted with DCM / H ₂ O, and the organic layer was separated. MgSO ₄ and charcoal were added and stirred for 30 minutes. Was passed through a silica pad. After removing the solvent of the filtrate and column purification with DCM / Hx, THF / EtOH precipitated to obtain compound 1.

MS: [M + H] ⁺ = 796

Preparation Example 2: Preparation of compound 2

It was prepared in the same manner as in Production Example 1 except for using the compound e as an intermediate instead of the intermediate b to obtain compound 2.

MS: [M + H] ⁺ = 846

Preparation Example 3: Preparation of compound 3

Compound 3 was obtained by the same method as Preparation Example 1, except that compound f-1 was used as an intermediate instead of intermediate a-1, and then intermediate f was prepared.

MS: [M + H] ⁺ = 795

Comparative Preparation Example 1: Preparation of Compound A

Intermediate c (2.0 g, 7.0 mmol, 1.0 eq), Intermediate d (5.35 g, 15.4 mmol, 2.2 eq), Pd (PPh ₃ ) ₄ (0.65 g, 0.56 mmol, 0.08 eq), K ₂ CO ₃ (5.8 g , 42 mmol, 6.0 eq) into 500 mL two-neck RB and nitrogen. Subsequently, Toluene (200 mL) and H ₂ O (25 mL) were added, stirred, heated to 110 ° C., reacted overnight, extracted with DCM / H ₂ O, and the solid of the organic layer was filtered and washed to obtain Compound A.

MS: [M + H] ⁺ = 734

Comparative Production Example 2: Preparation of compound B

It was prepared in the same manner as in Comparative Production Example 1 except for using the compound g as an intermediate instead of the intermediate c to obtain compound B.

MS: [M + H] ⁺ = 734

Example 1

The glass substrate on which ITO (indium tin oxide) was thinly deposited to a thickness of 500 에 was placed in distilled water in which detergent was dissolved and washed with ultrasonic waves. At this time, Fischer (Fisher Co.) was used as the detergent, and distilled water filtered secondarily by a filter of Millipore Co. was used as the distilled water. After washing the ITO for 30 minutes, ultrasonic cleaning was repeated for 2 minutes with distilled water twice. After washing with distilled water, ultrasonic cleaning was performed with acetone, distilled water, and isopropyl alcohol and dried to prepare a cleaned ITO glass substrate.

The composition in which the ratio of the following compound Z-1 and the following compound Z-2 was mixed in a weight ratio of 8: 2 on the ITO transparent electrode was spin-coated and cured at 220 ° C. for 30 minutes in a hot plate under a nitrogen atmosphere to obtain a thickness of 400 Å. A hole injection layer was formed.

On the hole injection layer, a composition in which the following compound Z-3 was dissolved in toluene in a weight ratio of 1% was spin-coated and heat-treated at 200 ° C. for 30 minutes on a hot plate to form a hole transport layer having a thickness of 200 mm 2.

On the hole transport layer, a composition obtained by dissolving Compound 1 according to Preparation Example 1 and Compound Z-4 below in a weight ratio of 94: 6 in toluene at a weight ratio of 0.5% is spin-coated to form a light emitting layer having a thickness of 200 200, and hot in an N ₂ atmosphere. The coating composition was dried on the plate at 120 ° C for 10 minutes.

Then, the following compounds Z-5 (350 Å), LiF (10 Å), and Al (1000 Å) were sequentially deposited on a vacuum evaporator to produce an organic light emitting device. In the process, the deposition rate of the cathode LiF was 0.1 0.1 / sec, and 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 2 and Example 3

The organic light emitting devices of Examples 2 and 3 were manufactured in the same manner as in Example 1, except that the compound shown in Table 2 below was used instead of Compound 1 according to Preparation Example 1.

Comparative Example 1 and Comparative Example 2

The organic light emitting devices of Comparative Examples 1 and 2 were manufactured in the same manner as in Example 1, except that the compound shown in Table 2 below was used instead of Compound 1 according to Preparation Example 1.

Experimental Example 1: Solubility measurement

The compounds 1 to 3, compound A and compound B were respectively added to toluene and stirred at room temperature (25 ° C) at 1500 rpm for 30 minutes. Thereafter, the amount of dissolution was measured by passing a laser through the solution to confirm whether a precipitate was formed through the tindall effect, and the results are shown in Table 1 below.

solute Solubility (wt%) Example 1 Compound 1 7 Example 2 Compound 2 8 Example 3 Compound 3 10 Comparative Example 1 Compound A <1 Comparative Example 2 Compound B One

Referring to Table 1, it can be seen that the compounds 1 to 3 have significantly higher solubility in toluene than the compounds A to B.

Experimental Example 2: Evaluation of characteristics of organic light emitting device

When a current was applied to the organic light emitting devices according to Examples 1 to 3 and Comparative Examples 1 and 2, driving voltage, current efficiency, power efficiency, and lifetime (T90) were measured. The results are shown in Table 2 below.

The lifetime T90 refers to the time required for the luminance to decrease from the initial luminance to 90%.

Emitting layer
Host Driving voltage
(V @ 10mA / cm ² ) Current efficiency
(cd / A @ 10mA / cm ² ) Power efficiency
(lm / W) T90
(hr @ 20mA / cm ² ) Example 1 Compound 1 4.75 7.35 4.86 36 Example 2 Compound 2 4.69 7.41 4.96 37 Example 3 Compound 3 4.61 6.97 4.75 41 Comparative Example 1 Compound A 5.48 3.25 1.86 13 Comparative Example 2 Compound B 5.29 3.36 2.00 16

Referring to Table 2, the organic light emitting device using the compounds 1 to 3 as a host of the light emitting layer shows excellent properties in terms of driving voltage, current efficiency, and lifetime compared to using the compounds A to B as a host of the light emitting layer. Did.

1: substrate 2: anode
3: light emitting layer 4: cathode
5: hole injection layer 6: hole transport layer
7: electron transport layer 8: electron injection layer

Claims (7)

Compound represented by the formula (1):
[Formula 1]

In Chemical Formula 1,
Ar ₁ and Ar ₂ are each independently, substituted or unsubstituted C _6-60 aryl; Or C _2-60 heteroaryl including any one or more selected from the group consisting of substituted or unsubstituted N, O and S,
R ₁ and R ₂ are the same as or different from each other, and each independently hydrogen; Substituted or unsubstituted C _1-60 alkyl; Or substituted or unsubstituted C _3-60 cycloalkyl, provided that at least one of R ₁ and R ₂ is substituted or unsubstituted C _1-60 alkyl; Or substituted or unsubstituted C _3-60 cycloalkyl,
R ₃ is hydrogen; heavy hydrogen; halogen; Cyano; Nitro; Amino; Substituted or unsubstituted C _1-60 alkyl; Substituted or unsubstituted C _3-60 cycloalkyl; Substituted or unsubstituted C _2-60 alkenyl; Substituted or unsubstituted C _6-60 aryl; Or C _2-60 heteroaryl including any one or more selected from the group consisting of substituted or unsubstituted N, O and S,
a1 and a2 are each independently an integer of 0 to 4, a1 + a2 is 1 or more,
a3 is an integer of 0-6.
According to claim 1,
Formula 1 is represented by the following Formula 1-1 to Formula 1-3,
compound:
[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

In Chemical Formulas 1-1 to 1-3,
The description of Ar ₁ , Ar ₂ , R ₁ to R ₃ and a3 is as defined in claim 1.
According to claim 1,
Ar ₁ and Ar ₂ are each independently phenyl, phenyl substituted with 5 deuterium, biphenylyl, terphenylyl, naphthyl, anthracenyl, phenanthrenyl, triphenylenyl, pyrenyl, perenylenyl, cry Senyl, dibenzofuranyl, or fluorenyl,
compound.
According to claim 1,
R ₁ and R ₂ are each independently hydrogen, tertbutyl, butyl, octyl, octan-2-yl, or octan-3-yl,
compound.
According to claim 1,
R ₃ is hydrogen, deuterium, or C _1-4 alkyl,
compound.
According to claim 1,
The compound represented by Formula 1 is any one selected from the group consisting of,
compound:

.
A first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer contains the compound according to any one of claims 1 to 6. To do,
Organic light emitting device.

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