KR20200093358A - 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, wherein the compound is represented by chemical formula 1. The compound may improve life characteristics of the organic light emitting device.

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 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 excitons are formed when the injected holes meet the electrons. When it falls to the ground again, it will shine.

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

Meanwhile, in order to reduce process costs, an organic light emitting device using a solution process, particularly an inkjet process, has been developed instead of a conventional deposition process. 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 the 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,

n is an integer from 4 to 8,

Ar ₁ is 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,

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

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, 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 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 3, an electron injection and transport layer 7 and a cathode 4 It 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.

또는

는 다른 치환기에 연결되는 결합을 의미한다. In this specification,

or

Means a linkage to another substituent.

The term "substituted or unsubstituted" in this specification is 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; An 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-butyldimethyl 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 6 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, steelbenyl 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, pyridopyrimidinyl 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. In the present specification, the alkyl group among the aralkyl group, alkylaryl group, and alkylamine group is the same as the above-described alkyl group. In the present specification, heteroarylamine among heteroarylamines may be applied to the description of the aforementioned heterocyclic group. In the present specification, the alkenyl group among the alkenyl groups 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 a description of the aryl group or cycloalkyl group described above may be applied, except that two substituents are formed by bonding. In the present 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.

Preferably, n is 4.

Preferably, Ar ₁ is substituted or unsubstituted C _6-60 aryl,

More preferably, Ar ₁ is phenyl; Phenyl substituted with tertbutyl; Anthracenyl; Anthracenyl substituted with methyl phenyl; Anthracenyl substituted with tertbutyl phenyl; Anthracenyl substituted with diterbutyl phenyl; Anthracenyl substituted with 1 naphthyl; Or anthracenyl substituted with 2 naphthyl,

Most preferably, Ar ₁ is any one selected from the group consisting of:

Preferably, L is a single bond; Or substituted or unsubstituted C _6-20 arylene,

More preferably, L is a single bond, phenylene, biphenylylene, or terphenylylene,

Most preferably, L is a single bond, or any one selected from the group consisting of:

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, n, Ar ₁ , L and n are as defined in Chemical Formula 1, X is halogen, and preferably X is chloro or bromo.

Step 1 (step 1) and step 2 (step 2) of Reaction Scheme 1 are Suzuki coupling reactions, respectively, and it is preferable to perform in the presence of a palladium catalyst and a base, and reactors for Suzuki coupling reactions are known in the art. It can be changed accordingly. The manufacturing method may be more specific in the manufacturing examples to be described later.

Coating composition

The compound represented by Formula 1 according to the present invention may be included in the organic material layer of the organic light emitting device in a solution process. To this end, the present invention provides a coating composition comprising a compound represented by Formula 1 and a solvent 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 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 solvents such as dimethyl sulfoxide; And amide solvents such as N-methyl-2-pyrrolidone and N,N-dimethylformamide; Benzoate solvents such as butylbenzoate and methyl-2-methoxybenzoate; Tetralin; And solvents such as 3-phenoxy-toluene. In addition, the above-described solvents may be used alone or in combination of two or more solvents.

In addition, each coating composition may further include one or two or more additives selected from the group consisting of a thermal polymerization initiator and a photo polymerization initiator.

As the thermal polymerization initiator, methyl ethyl ketone peroxide, methyl isobutyl ketone peroxide, acetylacetone peroxide, methylcyclohexanone peroxide, cyclohexanone peroxide, isobutyryl peroxide, 2,4-dichlorobenzoyl per Peroxides such as oxide, bis-3,5,5-trimethyl hexanoyl peroxide, lauryl peroxide, benzoyl peroxide, or azobis isobutylnitrile, azobisdimethylvaleronitrile, and azobis cyclohexyl nitrile There are, but are not limited to, azo.

As the photopolymerization initiator, diethoxy acetophenone, 2,2-dimethoxy-1,2-diphenylethan-1-one, 1-hydroxy-cyclohexyl-phenyl-ketone, 4-(2-hydroxyethoxy )Phenyl-(2-hydroxy-2-propyl) ketone, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl) butanone-1,2-hydroxy-2-methyl-1- Phenyl propan-1-one, 2-methyl-2-morpholino(4-methyl thiophenyl) propan-1-one, 1-phenyl-1,2-propanedione-2-(o-ethoxycarbonyl) Acetophenone-based or ketal-based photopolymerization initiators such as oxime; Benzoin ether-based photopolymerization initiators such as benzoin, benzoin methyl ether, and benzoin ethyl ether; Benzophenone-based photopolymerization initiators such as benzophenone, 4-hydroxybenzophenone, 2-benzoylnaphthalene, 4-benzoylbiphenyl, and 4-benzoyl phenyl ether; Thioxanthone-based photopolymerization initiators such as 2-isopropyl thioxanthone, 2-chlorothioxanthone, 2,4-dimethyl thioxanthone, 2,4-diethyl thioxanthone and 2,4-dichlorothioxanthone; And ethyl anthraquinone, 2,4,6-trimethylbenzoyl diphenyl phosphine oxide, 2,4,6-trimethylbenzoyl phenyl ethoxy phosphine oxide, bis(2,4,6-trimethylbenzoyl) phenyl phosphine oxide, Other photopolymerization initiators such as bis(2,4-dimethoxy benzoyl)-2,4,4-trimethyl pentylphosphine oxide, but are not limited thereto.

Moreover, what has a photopolymerization promoting effect can also be used individually or in combination with the said photoinitiator. Examples include triethanolamine, methyldiethanolamine, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, ethyl benzoate(2-dimethylamino), 4,4'-dimethylaminobenzophenone, and the like. It is not limited.

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

In addition, the present invention provides a method of forming a light emitting layer using the above-described coating composition. Specifically, on the anode; On the hole injection layer formed on the anode; Or coating the coating composition according to the present invention as described above on the hole transport layer formed on the hole injection layer formed on the anode in a solution process; And heat-treating or photo-treating 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.

In the heat treatment step, the heat treatment temperature is preferably 150 to 230°C. Further, the heat treatment time is 1 minute to 3 hours, more preferably 10 minutes to 1 hour. In addition, the heat treatment is preferably performed in an inert gas atmosphere such as argon or nitrogen. In addition, a step of evaporating the solvent between the coating step and the heat treatment or light treatment step may be further included.

Organic light emitting device

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

In addition, 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 may include a compound represented by Chemical Formula 1.

Further, the electron transport layer, the electron injection layer, or the layer that simultaneously performs electron transport and electron injection may include a compound represented by Chemical Formula 1.

In addition, the organic material layer includes a light emitting layer and a hole transport layer, and the hole transport 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.

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. In such a structure, the compound represented by Chemical Formula 1 may be included in the light emitting layer.

2 is 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 3, an electron injection and transport layer 7 and a cathode 4 It 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. Further, 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 may 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 such a 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); A combination of metal and oxide 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 an 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 which prevents migration of the excitons to the electron injection layer or the electron injection material, and has excellent thin film formation ability is preferable. It is preferable that the highest 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 material layer. Specific examples of the hole injection material include metal porphyrin, oligothiophene, arylamine-based organic substances, hexanitrile hexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based substances. Organic materials, anthraquinones, and polyaniline and polythiophene-based conductive polymers, 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. A material capable of transporting holes from the anode or the hole injection layer to the light emitting layer as a hole transport material and having high mobility for holes 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 light region by transporting and combining holes and electrons from the hole transport layer and the electron transport layer, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable. 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)-based 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. In addition, metal complexes include, but are not limited to, iridium complexes, platinum complexes, and the like.

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, 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 provided only for easier understanding of the present invention, and the contents of the present invention are not limited thereby.

Preparation Example 1 Synthesis of Compound 1

(Synthesis of Intermediate B)

1,4-Dibromo-2,5-dihexylbenzene (15.2 g, 1.0 eq.) and intermediate A (25.1 g, 1.2 eq.) were placed in a round bottom flask and dissolved in anhydrous tetrahydrofuran (0.3 M). . After filling with nitrogen gas for 10 minutes and stirring at room temperature, 2 MK ₂ CO ₃ (aq) (56.4 mL, 3.0 eq.) was injected, and the oil container temperature was raised from room temperature to 80°C. When the solvent started to boil, Pd(PPh ₃ ) ₄ was added dropwise, followed by stirring overnight. After the reaction, the organic layer was separated by washing with dichloromethane and water. Thereafter, water was removed with MgSO ₄ and acidic clay and palladium charcoal were adsorbed and then passed through a celite pad. The passed solution was concentrated under reduced pressure, and then purified through column chromatography to obtain intermediate B (27 g, yield 95%).

MS[M+H] ⁺ = 754

(Synthesis of Compound 1)

Intermediate B (3.73 g, 1.0 eq.) and Intermediate A (3.85 g, 1.2 eq.) were placed in a round bottom flask and mixed anhydrous tetrahydrofuran and toluene solution (anhydrous tetrahydrofuran: toluene = 1:2 volume ratio) (0.3 M). After filling with nitrogen gas for 10 minutes and stirring at room temperature, 2 MK ₂ CO ₃ (aq) (20.0 mL, 3.0 eq.) was injected, and the oil container temperature was raised from room temperature to 120°C. When the solvent started to boil, Pd(PPh ₃ ) ₄ was added dropwise, followed by stirring overnight. After the reaction, the organic layer was separated by washing with dichloromethane and water. Thereafter, water was removed with MgSO ₄ and palladium was adsorbed with palladium charcoal, and then passed through a celite pad. The passed solution was concentrated under reduced pressure, and then purified through column chromatography to obtain compound 1 (5 g, yield 92%).

MS[M+H] ⁺ = 1104

Preparation Example 2: Synthesis of Compound 2

Compound 2 was synthesized in the same manner as Compound 1, except that Intermediate C was used instead of Intermediate A.

MS[M+H] ⁺ = 752

Preparation Example 3: Synthesis of Compound 3

Compound 3 was synthesized in the same manner as in Compound 1, except that Intermediate D was used instead of Intermediate A.

MS[M+H] ⁺ = 808

Preparation Example 4 Synthesis of Compound 4

Compound 4 was synthesized in the same manner as in Compound 1, except that Intermediate E was used instead of Intermediate A.

MS[M+H] ⁺ = 1054

Example 1

A glass substrate coated with a thin film of ITO (indium tin oxide) of 500 에 was placed in distilled water in which detergent was dissolved and washed with ultrasonic waves. At this time, Fischer (Fischer Co.) was used as a detergent, and distilled water filtered secondarily by a filter of Millipore Co. was used as distilled water. After washing the ITO for 30 minutes, ultrasonic washing was repeated for 10 minutes by repeating it twice with distilled water. After washing with distilled water, ultrasonic cleaning was performed with a solvent of isopropyl and acetone, followed by drying, and then the substrate was washed for 5 minutes before transporting the substrate to a glove box.

On the ITO transparent electrode, 2 wt/v% toluene coating composition of the following compound H and compound G (8:2 weight ratio) was spin-coated (4000 rpm) and heat-treated (cured) at 200°C for 30 minutes (cured) to a thickness of 400 mm 2 A hole injection layer was formed. Spin coating (4000 rpm) of a 6 wt/v% toluene coating composition of the following compound F (Mn: 27,900; Mw: 35,600; measured by GPC using a PC standard using an Agilent 1200 series) on the hole injection layer And heat-treated at 200° C. for 30 minutes to form a hole transport layer having a thickness of 200 mm 2. 400 Å thick by spin-coating (4000 rpm) a 10 wt/v% cyclohexanone coating composition of Compound 1 and the following Compound I (weight ratio of 92:8) prepared above on the hole transport layer and heating at 180° C. for 30 minutes. A light emitting layer was formed. After transferring to a vacuum evaporator, the following compound J was vacuum-deposited to a thickness of 350 Pa on the light emitting layer to form an electron injection and transport layer. A cathode was formed by sequentially depositing 10 mm thick LiF and 1000 mm thick aluminum on the electron injection and transport layer.

In the above process, the deposition rate of organic matter was maintained at 0.4 to 0.7 Å/sec, LiF was maintained at 0.3 Å/sec, and aluminum was maintained at a deposition rate of 2 Å/sec, and the vacuum degree during deposition was 2 × 10 ^-7 to 5 X 10 ^-8 torr was maintained.

Examples 2 to 4

An organic light-emitting device was manufactured in the same manner as in Example 1, except for using the compounds described in Table 2 below instead of Compound 1.

Comparative Example 1

An organic light emitting diode was manufactured according to the same method as Example 1 except for using Compound 5 instead of Compound 1.

Experimental Example 1: Solubility evaluation

Solubility of the solvents Toluene, Cyclohexanone, Methyl benzoate, Ethyl benzoate, and Isoamyl benzoate was measured at room temperature and normal pressure, respectively, using Compound 1 to Compound 4 prepared in Preparation Examples 1 to 4 and Compound 5 of Comparative Example 1 as solutes. The results are shown in Table 1 below.

compound Solubility by solvent (wt%) Toluene Cyclo-hexanone Methyl benzoate Ethyl benzoate Isoamyl benzoate Compound 1 1.5 1.5 1.5 1.2 1.2 Compound 2 2 2 2 2 2 Compound 3 2 2 2 2 2 Compound 4 1.8 1.8 1.6 1.5 1.5 Compound 5 0.9 1.5 1.1 1.1 1.1

Experimental Example 2: Evaluation of organic light emitting device

The results of measuring the driving voltage, external quantum efficiency (EQE), luminance and lifetime of the organic light-emitting devices prepared in Examples 1 to 4 and Comparative Example 1 at a current density of 10 mA/cm ² It is shown in Table 1 below. The external quantum efficiency was calculated as (number of emitted photons)/(number of injected charge carriers)*100. T90 means the time required for the luminance to decrease from the initial luminance (500 nit) to 90%.

Emitting layer Current density
(mA/cm ² ) Driving voltage (V) EQE (%) Life (hr)
(T90 at 500 nit) Example 1 Compound 1 10 4.30 7.91 85 Example 2 Compound 2 10 4.25 7.83 81 Example 3 Compound 3 10 4.34 7.34 83 Example 4 Compound 4 10 4.27 7.86 85 Comparative Example 1 Compound 5 10 4.24 7.55 50

As shown in Table 1, Compound 1 to Compound 4 according to an exemplary embodiment of the present specification was found to be excellent in solubility in an organic solvent, and thus easy to prepare a coating composition.

In addition, as shown in Table 2, the organic light emitting device according to the exemplary embodiment of the present specification includes a compound having a dialkyl group, so that the driving voltage and efficiency are equivalent compared to the organic light emitting device containing the compound 5 that is not. It was confirmed that the life was improved while showing the effect.

As a result of Table 1 and Table 2, it was confirmed that a uniform coating layer can be formed using the coating composition, and the stability of the film is also excellent, so that it shows better performance in an organic light emitting device.

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

Claims (7)

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

In Chemical Formula 1,
n is an integer from 4 to 8,
Ar ₁ is 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,
L is a single bond; Substituted or unsubstituted C _6-60 arylene; Or C _2-60 heteroarylene comprising any one or more selected from the group consisting of substituted or unsubstituted N, O and S.
According to claim 1,
Ar ₁ is phenyl; Phenyl substituted with tertbutyl; Anthracenyl; Anthracenyl substituted with methyl phenyl; Anthracenyl substituted with tertbutyl phenyl; Anthracenyl substituted with diterbutyl phenyl; Anthracenyl substituted with 1 naphthyl; Or anthracenyl substituted with two naphthyl,
compound.
According to claim 1,
Ar ₁ is any one selected from the group consisting of,
compound:

.
According to claim 1,
L is a single bond, phenylene, biphenylylene, or terphenylylene,
compound.
According to claim 1,
L is a single bond; Or any one selected from the group consisting of,
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 includes the compound according to any one of claims 1 to 6. To do,
Organic light emitting device.

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