CN110869366A - Heterocyclic compound and organic light-emitting device comprising the same - Google Patents

Abstract

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

Description

Heterocyclic compound and organic light-emitting device comprising the same

technical field

Cross-reference with related applications

The present application claims priority based on Korean Patent Application No. 10-2018-0010013 filed on January 26, 2018, and the entire contents disclosed in the documents of the Korean Patent Application are incorporated as a part of this specification.

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

Background technique

In general, the organic light-emitting phenomenon refers to the phenomenon of using organic substances to convert electrical energy into light energy. Organic light-emitting devices utilizing the organic light-emitting phenomenon have wide viewing angles, excellent contrast ratios, fast response times, and are excellent in luminance, driving voltage, and response speed characteristics, and thus a great deal of research is being conducted.

The organic light emitting device generally has a structure including an anode and a cathode and an organic layer between the anode and the cathode. In order to improve the efficiency and stability of the organic light-emitting device, the above-mentioned organic layer is usually formed of a multilayer structure composed of different substances, for example, a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer , an electron injection layer, etc. are formed. For the structure of such an organic electroluminescence device, if a voltage is applied between two electrodes, holes are injected from the anode to the organic layer, and electrons are injected from the cathode to the organic layer. When the injected holes and electrons meet, they will An exciton is formed, and when the exciton re-transitions to the ground state, light is emitted.

For organic substances used in organic light-emitting devices as described above, development of new materials is continuously required.

prior art literature

Patent Literature

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

SUMMARY OF THE INVENTION

problem to be solved

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

Solution to the problem

The present invention provides a compound represented by the following Chemical Formula 1:

[Chemical formula 1]

In the above Chemical Formula 1,

Y is S, O or CR' ₂ ,

R' is each independently substituted or unsubstituted C _1-60 alkyl, substituted or unsubstituted C _1-60 alkoxy, substituted or unsubstituted C _3-60 cycloalkyl, substituted or unsubstituted C _6-60 aryl, substituted or unsubstituted C _6-60 aryloxy, or substituted or unsubstituted C _2-60 heteroaryl containing at least one of O, N, Si and S,

R ₁ to R ₇ are each independently 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 substituted or unsubstituted containing O, N, Si and more than 1 C _2-60 heteroaryl group in S,

a, e and g are each independently 0 to 4,

b, d, and f are each independently 0 to 3,

c is 0 to 5.

In addition, the present invention provides an organic light-emitting device including a first electrode, a second electrode provided opposite to the first electrode, and a layer provided between the first electrode and the second electrode In the above-mentioned organic material layer, one or more layers of the above-mentioned organic material layers contain the compound represented by the above-mentioned Chemical Formula 1.

Invention effect

The compound represented by the above-mentioned Chemical Formula 1 can be used as a material of an organic layer of an organic light emitting device, in which an improvement in efficiency, a lower driving voltage and/or an improvement in lifetime characteristics can be achieved. In particular, the compound represented by the above-mentioned Chemical Formula 1 can be used as a material for hole injection, hole transport, hole injection and transport, and light emission.

Description of drawings

FIG. 1 illustrates an example of an organic light-emitting device composed of a substrate 1 , an anode 2 , a light-emitting layer 3 , and a cathode 4 .

FIG. 2 illustrates an organic light emitting device composed of a substrate 1 , an anode 2 , a hole injection layer 5 , a hole transport layer 6 , an electron blocking layer 7 , a light emitting layer 8 , an electron transport layer 9 , an electron injection layer 10 and a cathode 4 example of.

3 illustrates an example of an organic light-emitting device composed of a substrate 1 , an anode 2 , a hole injection layer 5 , a hole transport layer 6 , a light-emitting layer 8 , an electron transport layer 9 , an electron injection and transport layer 11 , and a cathode 4 .

Detailed ways

Hereinafter, in order to help understanding of this invention, it demonstrates in detail.

The present invention provides the compound represented by the above-mentioned Chemical Formula 1.

和

是指与其它取代基连接的键。In this manual,

and

Refers to bonds to other substituents.

Alkyl thioxy)；芳基硫基(

Aryl thioxy)；烷基磺酰基(

Alkyl sulfoxy)；芳基磺酰基(

Aryl sulfoxy)；甲硅烷基；硼基；烷基；环烷基；烯基；芳基；芳烷基；芳烯基；烷基芳基；烷基胺基；芳烷基胺基；杂芳基胺基；芳基胺基；芳基膦基；或者包含N、O和S原子中的1个以上的杂环基中的1个以上的取代基取代或未取代，或者被上述例示的取代基中的2个以上的取代基连接而成的取代基取代或未取代。例如，“2个以上的取代基连接而成的取代基”可以为联苯基。即，联苯基可以为芳基，也可以被解释为2个苯基连接而成的取代基。In this specification, the term "substituted or unsubstituted" means a group selected from the group consisting of deuterium; halogen group; nitrile group; nitro group; hydroxyl group; carbonyl group; ester group; imide group; amino group; phosphine oxide group; alkane oxy; aryloxy; alkylthio (

Alkyl thioxy); Aryl thio (

Aryl thioxy); alkylsulfonyl (

Alkyl sulfoxy); Aryl sulfonyl (

Aryl sulfoxy);silyl;boron;alkyl;cycloalkyl;alkenyl;aryl;aralkyl;aralkenyl;alkylaryl;alkylamino;aralkylamino;heteroaryl arylamino group; arylamino group; arylphosphino group; or one or more substituents of heterocyclic groups containing one or more of N, O, and S atoms substituted or unsubstituted, or substituted by those exemplified above A substituent in which two or more substituents in the group are connected is substituted or unsubstituted. For example, "a substituent in which two or more substituents are connected" may be a biphenyl group. That is, the biphenyl group may be an aryl group, and 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 preferably 1 to 40 carbon atoms. Specifically, although it may be a compound of the following structure, it is not limited to this.

In the present specification, in the ester group, the oxygen of the ester group may be substituted with a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms. Specifically, although it may be a compound of the following structural formula, it is not limited to this.

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

In this specification, the silyl group specifically includes trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, A triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group, etc., are not limited thereto.

In the present specification, the boron group specifically includes trimethylboronyl, triethylboronyl, t-butyldimethylboronyl, triphenylboronyl, phenylboronyl and the like, but is not limited thereto.

In this specification, as examples of the halogen group, there are fluorine, chlorine, bromine or iodine.

In this specification, the above-mentioned alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but preferably 1 to 40. According to one embodiment, the above-mentioned alkyl group has 1 to 20 carbon atoms. According to another embodiment, the above-mentioned alkyl group has 1 to 10 carbon atoms. According to another embodiment, the above-mentioned alkyl group has 1 to 6 carbon atoms. As specific examples of the alkyl group, there 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 base, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl group, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, etc., but not limited thereto.

In this specification, the above-mentioned alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but preferably 2 to 40. According to one embodiment, the above-mentioned alkenyl group has 2 to 20 carbon atoms. According to another embodiment, the above-mentioned alkenyl group has 2 to 10 carbon atoms. According to another embodiment, the above-mentioned 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 Alkenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylethen-1-yl, 2-phenylethen-1-yl, 2,2 -Diphenylethen-1-yl, 2-phenyl-2-(naphthalen-1-yl)ethen-1-yl, 2,2-bis(diphenyl-1-yl)ethen-1-yl, stilbene group, styryl group, etc., but not limited to this.

In the present specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group having 3 to 60 carbon atoms. According to one embodiment, the number of carbon atoms in the cycloalkyl group is 3 to 30. According to another embodiment, the above-mentioned cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the above-mentioned cycloalkyl group has 3 to 6 carbon atoms. Specifically, there are cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methyl Cyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, etc., but not limited thereto.

基、芴基等，但并不限定于此。In the present specification, the aryl group is not particularly limited, but is preferably an aryl group having 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the above-mentioned aryl group has 6 to 30 carbon atoms. According to one embodiment, the above-mentioned aryl group has 6 to 20 carbon atoms. As for the above-mentioned aryl group, as a monocyclic aryl group, a phenyl group, a biphenyl group, a terphenyl group, or the like may be used, but it is not limited thereto. As the above-mentioned polycyclic aryl group, naphthyl, anthracenyl, phenanthryl, pyrenyl, perylene,

group, fluorene group, etc., but not limited to this.

等，但并不限定于此。In this specification, the fluorenyl group may be substituted, and two substituents may be combined with each other to form a spiro structure. In the case where the above-mentioned fluorenyl group is substituted, it may be

etc., but not limited to this.

唑基、

二唑基、三唑基、吡啶基、联吡啶基、嘧啶基、三嗪基、吖啶基、哒嗪基、吡嗪基、喹啉基、喹唑啉基、喹喔啉基、酞嗪基、吡啶并嘧啶基、吡啶并吡嗪基、吡嗪并吡嗪基、异喹啉基、吲哚基、咔唑基、苯并

唑基、苯并咪唑基、苯并噻唑基、苯并咔唑基、苯并噻吩基、二苯并噻吩基、苯并呋喃基、菲咯啉基(phenanthroline)、异

唑基、噻二唑基、吩噻嗪基和二苯并呋喃基等，但不仅限于此。In the present specification, the heterocyclic group is a heterocyclic group containing one or more of O, N, Si and S as a hetero atom, and the number of carbon atoms is not particularly limited, but preferably 2 to 60 carbon atoms. As examples of heterocyclic groups, there are thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl,

azolyl,

oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridine, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazine base, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzoyl

azolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, benzofuranyl, phenanthroline, iso

azolyl, thiadiazolyl, phenothiazinyl, dibenzofuranyl, etc., but not limited thereto.

In the present specification, the aryl group in the aralkyl group, the aralkenyl group, the alkylaryl group, and the arylamine group is the same as the above-mentioned examples of the aryl group. In the present specification, the alkyl group in the aralkyl group, the alkylaryl group, and the alkylamine group is the same as the above-mentioned examples of the alkyl group. In this specification, the above-mentioned description about the heterocyclic group can be applied to the heteroaryl group in the heteroarylamine. In this specification, the alkenyl group in the aralkenyl group is the same as the above-mentioned examples of the alkenyl group. In this specification, an arylene group is a divalent group, and other than that, the above-mentioned description about an aryl group can be applied. In the present specification, the heteroarylene group is a divalent group, and other than that, the above-mentioned description about the heterocyclic group can be applied. In the present specification, the hydrocarbon ring is not a monovalent group, but two substituents are bonded together, and the above-mentioned description about the aryl group or the cycloalkyl group can be applied. In this specification, the heterocyclic ring is not a monovalent group, but two substituents are bonded together, and the above-mentioned description about the heterocyclic group can be applied.

On the other hand, in the above Chemical Formula 1, the above R' is preferably a methyl group.

In the above Chemical Formula 1, a, b, c, d, e and f may be 0.

In the above Chemical Formula 1, at least one of R ₁ to R ₇ may be a cyano group.

The above-mentioned Chemical Formula 1 may be any one selected from the following compounds.

In the above 1-1 to 1-16, Y may be S, O or CR' ₂ .

The definition of the above R' is the same as mentioned above.

Preferably, the compound represented by the above Chemical Formula 1 may be any one selected from the following compounds.

The compound represented by the above-mentioned Chemical Formula 1 can be produced by the production method as shown in the following Reaction Formula 1. The above-mentioned manufacturing method can be more embodied in the manufacturing example mentioned later.

[Reaction 1]

In the above Reaction Formula 1, the description of Y is the same as the definition in the above Chemical Formula 1.

The compound represented by the above Chemical Formula 1 can be produced by referring to the above Reaction Formula 1 and appropriately substituting the starting materials corresponding to the structure of the compound to be produced.

In addition, the present invention provides an organic light-emitting device including the compound represented by the above-mentioned Chemical Formula 1. As an example, the present invention provides an organic light-emitting device comprising: a first electrode, a second electrode provided opposite to the first electrode, and an organic light-emitting device provided between the first electrode and the second electrode One or more organic substance layers, one or more of the organic substance layers including the compound represented by the above-mentioned Chemical Formula 1.

The organic material layer of the organic light-emitting device of the present invention may be formed of a single-layer structure, or may be formed of a multilayer 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, and the like as organic substance layers. However, the structure of the organic light-emitting device is not limited to this, and may include a smaller number of organic layers.

In addition, the above-mentioned organic substance layer may include a hole injection layer, a hole transport layer, or a hole injection and transport layer (a layer that performs both hole injection and transport), the above-mentioned hole injection layer, hole transport layer or hole injection and transport layer. The transport layer contains the compound represented by Chemical Formula 1 above.

In addition, the organic substance layer may include a light-emitting layer, and the light-emitting layer may include the compound represented by Chemical Formula 1 above.

Moreover, the said light-emitting layer contains two or more types of hosts, and one of the said hosts contains the compound represented by the said Chemical Formula 1.

In addition, the above-mentioned organic substance layer may include an electron transport layer, an electron injection layer, or an electron injection and transport layer (a layer in which electron injection and transport are performed simultaneously), and the above-mentioned electron transport layer, electron injection layer, or electron injection and transport layer The compound represented by Chemical Formula 1.

In addition, the above-mentioned electron transport layer, electron injection layer, or electron transport and injection layer contains the compound represented by the above-mentioned Chemical Formula 1.

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

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

FIG. 1 illustrates an example of an organic light-emitting device composed of a substrate 1 , an anode 2 , a light-emitting layer 3 , and a cathode 4 . In the above-mentioned structure, the compound represented by the above-mentioned Chemical Formula 1 may be contained in the above-mentioned light-emitting layer.

FIG. 2 illustrates an organic light emitting device composed of a substrate 1 , an anode 2 , a hole injection layer 5 , a hole transport layer 6 , an electron blocking layer 7 , a light emitting layer 8 , an electron transport layer 9 , an electron injection layer 10 and a cathode 4 example of. In the above structure, the compound represented by the above Chemical Formula 1 may be contained in one or more of the above hole injection layer, hole transport layer, electron blocking layer, light emitting layer, electron transport layer and electron injection layer.

3 illustrates an example of an organic light-emitting device composed of a substrate 1 , an anode 2 , a hole injection layer 5 , a hole transport layer 6 , a light-emitting layer 8 , an electron transport layer 9 , an electron injection and transport layer 11 , and a cathode 4 . In the structure as described above, the compound represented by the above Chemical Formula 1 may be contained in one or more layers of the above hole injection layer, hole transport layer, light emitting layer, electron transport layer, and electron injection and transport layer.

The organic light-emitting device according to the present invention can be manufactured using materials and methods known in the technical field, except that one or more of the above-mentioned organic substance layers contain the compound represented by the above-mentioned Chemical Formula 1. In addition, when the above-mentioned organic light-emitting device includes a plurality of organic substance layers, the above-mentioned organic substance layers may be formed of the same substance or different substances.

For example, the organic light emitting device according to the present invention can be manufactured by sequentially stacking a first electrode, an organic layer, and a second electrode on a substrate. In this case, it can be produced by vapor-depositing a metal or a conductive material on a substrate by a PVD (physical Vapor Deposition) method such as sputtering or e-beam evaporation. Metal oxides or their alloys are used to form an anode, and then an organic layer including a hole injection layer, a hole transport layer, a light emitting layer and an electron transport layer is formed on the anode, and then vapor deposition on the organic layer can be used as a cathode. made of substances. In addition to this method, an organic light-emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

In addition, the compound represented by the above-mentioned Chemical Formula 1 can form an organic layer by not only a vacuum evaporation method but also a solution coating method when producing an organic light-emitting device. Here, the solution coating method refers to a spin coating method, a dip coating method, a blade coating method, an ink jet printing method, a screen printing method, a spray method, a roll coating method, or the like, but is not limited thereto.

In addition to these methods, an organic light-emitting device can be produced by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate (WO2003/012890). However, the manufacturing method is not limited to this.

As an 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.

As the anode material, generally, a material having a large work function is preferable in order to enable smooth injection of holes into the organic material 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); ZnO : Al or SNO ₂ : Combination of metals such as Sb and oxides; poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole and conductive polymers such as polyaniline, etc., but not limited to this.

As the above-mentioned cathode material, a material having a small work function is preferably used in order to easily inject electrons into the organic material layer. Specific examples of the above-mentioned cathode materials include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or their alloys; LiF/Al or LiO ₂ /Al, etc. Multilayer structure substances, etc., but not limited to this.

The hole-injecting substance is a layer that injects holes from an electrode, and the hole-injecting substance is preferably a compound that has the ability to transport holes, has a hole-injecting effect from an anode, and is excellent in a light-emitting layer or a light-emitting material The excellent hole injection effect prevents the excitons generated in the light-emitting layer from migrating to the electron injection layer or the electron injection material, and the film forming ability is excellent. Preferably, the HOMO (highest occupied molecular orbital) of the hole injecting material is between the work function of the anode material and the HOMO of the surrounding organic material layer. Specific examples of the hole-injecting substance include porphyrin, oligothiophene, arylamine-based organic matter, hexanitrile hexaazatriphenylene-based organic matter, quinacridone-based organic matter, perylene ( perylene) organic compounds, anthraquinone, polyaniline and polythiophene-based conductive polymers, etc., but not limited to this.

The above-mentioned hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light emitting layer, and as a hole transport material, is a layer capable of receiving holes from the anode or the hole injection layer and transferring them to the light emitting layer. As the material of the light-emitting layer, a material having a high mobility for holes is suitable. Specific examples include arylamine-based organic substances, conductive polymers, and block copolymers in which both a conjugated portion and a non-conjugated portion are present, but the present invention is not limited thereto.

唑、苯并噻唑及苯并咪唑系化合物；聚(对亚苯基亚乙烯基)(PPV)系高分子；螺环(spiro)化合物；聚芴；红荧烯等，但不仅限于此。The light-emitting substance is a substance capable of receiving holes and electrons from the hole transport layer and electron transport layer, respectively, and combining them to emit light in the visible light region, and preferably a substance having high quantum efficiency for fluorescence or phosphorescence. As specific examples, there are 8-hydroxyquinoline aluminum complex (Alq ₃ ); carbazole-based compound; dimerizedstylyl compound; BAlq; 10-hydroxybenzoquinoline-metal compound;

azoles, benzothiazoles, and benzimidazole-based compounds; poly(p-phenylene vinylene) (PPV)-based polymers; spiro compounds; polyfluorenes; rubrene, etc., but not limited thereto.

嘧啶衍生物等，但并不限定于此。The above-mentioned light-emitting layer may contain a host material and a dopant material. The host material includes aromatic condensed ring derivatives or heterocyclic compounds. Specifically, the aromatic condensed ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and the heterocyclic-containing compounds include carbazole derivatives , dibenzofuran derivatives, ladder furan compounds

Pyrimidine derivatives and the like, but are not limited thereto.

二茚并芘(Periflanthene)等，苯乙烯基胺化合物是在取代或未取代的芳基胺上取代有至少一个芳基乙烯基的化合物，被选自芳基、甲硅烷基、烷基、环烷基和芳基氨基中的1个或2个以上的取代基取代或未取代。具体而言，有苯乙烯基胺、苯乙烯基二胺、苯乙烯基三胺、苯乙烯基四胺等，但并不限定于此。此外，作为金属配合物，有铱配合物、铂配合物等，但并不限定于此。As the dopant material, there are aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, and the like. Specifically, the aromatic amine derivative is an aromatic fused ring derivative having a substituted or unsubstituted arylamino group, and there are pyrene, anthracene,

Diindenopyrene (Periflanthene), etc., styrylamine compounds are compounds substituted with at least one arylvinyl group on substituted or unsubstituted arylamines, and are selected from aryl, silyl, alkyl, cyclic One or more substituents in the alkyl group and the arylamino group are substituted or unsubstituted. Specifically, although styrylamine, styryl diamine, styryl triamine, styryl tetraamine, etc. are mentioned, it is not limited to these. Moreover, as a metal complex, although there exist iridium complex, a platinum complex, etc., it is not limited to these.

The electron-transporting material is a layer that receives electrons from the electron injection layer and transmits the electrons to the light-emitting layer. The electron-transporting material is a material that can favorably receive electrons from the cathode and transfer them to the light-emitting layer, and has high mobility for electrons. substance is suitable. Specific examples include, but are not limited to, Al complexes of 8-hydroxyquinoline, complexes containing Alq ₃ , organic radical compounds, hydroxybrass-metal complexes, and the like. The electron transport layer can be used with any desired cathode material as used in the prior art. In particular, examples of suitable cathode materials are the usual materials with a low work function accompanied by an aluminum or silver layer. Specifically cesium, barium, calcium, ytterbium and samarium, in each case accompanied by an aluminum or silver layer.

唑、

二唑、三唑、咪唑、苝四羧酸、亚芴基甲烷、蒽酮等和它们的衍生物、金属配位化合物以及含氮五元环衍生物等，但并不限定于此。The above-mentioned electron injection layer is a layer that injects electrons from an electrode, and is preferably a compound that has the ability to transport electrons, has an electron injection effect from a cathode, has an excellent electron injection effect to a light-emitting layer or a light-emitting material, and prevents all substances contained in the light-emitting layer. The generated excitons migrate to the hole injection layer, and the film forming ability is excellent. Specifically, there are fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide,

azole,

Diazoles, triazoles, imidazoles, perylenetetracarboxylic acids, fluorenylene methanes, anthrone, etc. and their derivatives, metal complexes, nitrogen-containing five-membered ring derivatives, etc., but not limited thereto.

Examples of the aforementioned metal complex include lithium 8-quinolinate, bis(8-quinolinolato)zinc, bis(8-quinolinolato)copper, bis(8-quinolinolato)manganese, tris(8-hydroxyquinoline) Quinoline)aluminum, tris(2-methyl-8-hydroxyquinoline)aluminum, tris(8-hydroxyquinoline)gallium, bis(10-hydroxybenzo[h]quinoline)beryllium, bis(10-hydroxyl) Benzo[h]quinoline)zinc, bis(2-methyl-8-quinoline)gallium chloride, bis(2-methyl-8-quinoline)(o-cresol)gallium, bis(2-methyl) yl-8-quinoline)(1-naphthol)aluminum, bis(2-methyl-8-quinoline)(2-naphthol)gallium, etc., but not limited thereto.

Depending on the materials used, the organic light emitting device according to the present invention may be of a top emission type, a bottom emission type or a bidirectional emission type.

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

Hereinafter, in order to help understanding of the invention, preferred embodiments are presented. However, the following examples are only for illustrating the present invention, and the present invention is not limited thereto.

[Production example]

Production Example 1: Production of Intermediate A1

Under nitrogen atmosphere, in a 500 ml round bottom flask, combine 2-chloro-4-(4-chlorophenyl)-6-phenyl-1,3,5-triazine (15.0 g, 49.64 mmol), bis Benzo[b,d]thiophen-4-ylboronic acid (11.3g, 49.64mmol) was completely dissolved in 210ml of tetrahydrofuran, 1M potassium carbonate solution (150ml) was added, tetrakis(triphenylphosphine)palladium (1.7g) was added , 1.49 mmol), heated and stirred for 6 hours. The temperature was lowered to room temperature, the aqueous layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 250 ml of ethanol to produce the above-mentioned compound A1 (21.1 g, yield: 94%) (MS [M] +H] ⁺ =450).

Production Example 2: Production of Intermediate A2

烷中，进行回流，搅拌2小时。通过HPLC确认反应结束后，过滤而去除碱(base)，将溶液减压浓缩。将其溶解于CHCl₃，用水完全洗涤，将溶解有生成物的溶液减压浓缩，用乙醇重结晶，从而制造了上述化合物A2(21.1g，收率83％)(MS[M+H]⁺＝542)。In a 1 L round bottom flask under nitrogen atmosphere, intermediate A1 (21.1 g, 46.89 mmol), bis(pinacol)diboron (13.1 g, 51.58 mmol), Pd(dba) ₂ (0.8 g) were combined , 1.41 mmol), PCy ₃ (0.8 g, 2.81 mmol), KOAc (13.8 g, 140.68 mmol) were added to 300 mL of two

alkane, refluxed, and stirred for 2 hours. After the completion of the reaction was confirmed by HPLC, the base was removed by filtration, and the solution was concentrated under reduced pressure. This was dissolved in CHCl ₃ , washed completely with water, the solution in which the product was dissolved was concentrated under reduced pressure, and recrystallized from ethanol to produce the above-mentioned compound A2 (21.1 g, yield 83%) (MS [M+H] ⁺ = 542).

Production Example 3: Production of Intermediate A3

Under nitrogen atmosphere, in a 1L round-bottom flask, compound A2 (21.1 g, 38.97 mmol) and 1-bromo-2-nitrobenzene (8.7 g, 42.86 mmol) were completely dissolved in 200 ml of tetrahydrofuran, and then 2M of tetrahydrofuran was added. An aqueous potassium carbonate solution (60 ml) was added with tetrakis(triphenylphosphine)palladium (1.4 g, 1.17 mmol), followed by stirring with heating for 24 hours. The temperature was lowered to normal temperature, the aqueous layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 250 ml of ethanol to produce the above-mentioned compound A3 (17.4 g, yield: 83%) (MS [M] +H] ⁺ =537).

Production Example 4: Production of Intermediate A4

Under a nitrogen atmosphere, triethyl phosphite (100 mL, 580.3 mmol) was added to Compound A3 (17.4 g, 32.43 mmol) in a 1 L round-bottomed flask, followed by stirring with heating for 3 hours. The temperature was lowered to normal temperature, and a solid was obtained by filtration, which was washed with water. The obtained compound was dried to produce compound A4 (11.3 g, yield: 69%) (MS [M+H] ⁺ =505).

[Example]

Example 1: Production of Compound 1

In a 1 L round bottom flask under nitrogen atmosphere, compound A4 (11.3 g, 22.39 mmol), 2-bromodibenzo[b,d]thiophene (6.1 g, 23.51 mmol), sodium tert-butoxide (4.3 mmol) g, 44.79 mmol), 200 mL of xylene was added, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.22 mmol) was added, and the mixture was heated and stirred for 1 hour. The temperature was lowered to normal temperature, and a solid was obtained by filtration, which was washed with water. The obtained compound was dried to produce Compound 1 (5.7 g, yield: 37%) (MS [M+H] ⁺ =687).

Example 2: Production of Compound 2

Compound 2 (MS[M+ H] ⁺ =687).

Example 3: Production of Compound 3

Compound 3 (MS[M+ H] ⁺ =687).

Example 4: Production of Compound 4

Using 1-(4-(Dibenzo[b,d]thiophen-4-yl)-6-phenyl-1,3,5-triazin-2-yl)-9H-carbazole and 3-bromobis Compound 4 (MS[M+H] was prepared by the same method as that of compound 1, except that benzo[b,d]thiophene was used instead of compound A4 and 2-bromodibenzo[b,d]thiophene. ⁺ = 687).

Example 5: Production of Compound 5

Compound 5 (MS[M+ H] ⁺ =687).

Example 6: Production of Compound 6

Using 3-(4-(dibenzo[b,d]thiophen-4-yl)-6-phenyl-1,3,5-triazin-2-yl)-9H-carbazole and 4-bromobis Compound 6 (MS[M+H] was prepared by the same method as that of compound 1, except that benzo[b,d]thiophene was used instead of compound A4 and 2-bromodibenzo[b,d]thiophene. ⁺ = 687).

Example 7: Production of Compound 7

Using 3-(4-(Dibenzo[b,d]thiophen-4-yl)-6-phenyl-1,3,5-triazin-2-yl)-9H-carbazole and 3-bromobis Compound 7 (MS[M+H] was prepared by the same method as that of compound 1, except that benzo[b,d]thiophene was used instead of compound A4 and 2-bromodibenzo[b,d]thiophene. ⁺ = 687).

Example 8: Production of Compound 8

Using 3-(4-(Dibenzo[b,d]thiophen-4-yl)-6-phenyl 1,3,5-triazin-2-yl)-9H-carbazole and 1-bromodiphenyl Compound 8 (MS[M+H] ⁺ = 687).

Example 9: Preparation of Compound 9

Using 4-(4-(dibenzo[b,d]thiophen-4-yl)-6-phenyl-1,3,5-triazin-2-yl)-9H-carbazole and 4-bromobis Compound 9 (MS[M+H] was prepared by the same method as that of compound 1, except that benzo[b,d]thiophene was used instead of compound A4 and 2-bromodibenzo[b,d]thiophene. ⁺ = 687).

Example 10: Preparation of Compound 10

Using 4-(4-(dibenzo[b,d]thiophen-4-yl)-6-phenyl-1,3,5-triazin-2-yl)-9H-carbazole and 2-bromobis Compound 10 (MS[M+H] was prepared by the same method as that of compound 1, except that benzo[b,d]thiophene was used instead of compound A4 and 2-bromodibenzo[b,d]thiophene. ⁺ = 687).

Example 11: Production of Compound 11

Using 4-(4-(dibenzo[b,d]thiophen-4-yl)-6-phenyl-1,3,5-triazin-2-yl)-9H-carbazole and 1-bromobis Compound 11 (MS[M+H] was prepared by the same method as that of compound 1, except that benzo[b,d]thiophene was used instead of compound A4 and 2-bromodibenzo[b,d]thiophene. ⁺ = 687).

Example 12: Preparation of Compound 12

Using 1-(4-(Dibenzo[b,d]thiophen-4-yl)-6-phenyl-1,3,5-triazin-2-yl)-9H-carbazole and 4-bromobis Compound 12 (MS[M+H] was prepared by the same method as that of compound 1, except that benzo[b,d]furan was used instead of compound A4 and 2-bromodibenzo[b,d]thiophene. ⁺ = 671).

Example 13: Production of Compound 13

Using 1-(4-(Dibenzo[b,d]thiophen-4-yl)-6-phenyl-1,3,5-triazin-2-yl)-9H-carbazole and 2-bromobis Compound 13 (MS[M+H] was prepared by the same method as that of compound 1, except that benzo[b,d]furan was used instead of compound A4 and 2-bromodibenzo[b,d]thiophene. ⁺ = 671).

Example 14: Production of Compound 14

Using 2-(4-(Dibenzo[b,d]thiophen-4-yl)-6-phenyl-1,3,5-triazin-2-yl)-9H-carbazole and 3-bromobis Compound 14 (MS[M+H] was prepared by the same method as that of compound 1, except that benzo[b,d]furan was used in place of compound A4 and 2-bromodibenzo[b,d]thiophene. ⁺ = 671).

Example 15: Production of Compound 15

Using 2-(4-(Dibenzo[b,d]thiophen-4-yl)-6-phenyl-1,3,5-triazin-2-yl)-9H-carbazole and 2-bromobis Compound 15 (MS[M+H] was prepared by the same method as that of compound 1, except that benzo[b,d]furan was used instead of compound A4 and 2-bromodibenzo[b,d]thiophene. ⁺ = 671).

Example 16: Production of Compound 16

Using 2-(4-(Dibenzo[b,d]thiophen-4-yl)-6-phenyl-1,3,5-triazin-2-yl)-9H-carbazole and 1-bromobis Compound 16 (MS[M+H] was prepared by the same method as that of compound 1, except that benzo[b,d]furan was used instead of compound A4 and 2-bromodibenzo[b,d]thiophene. ⁺ = 671).

Example 17: Production of Compound 17

Using 3-(4-(dibenzo[b,d]thiophen-4-yl)-6-phenyl-1,3,5-triazin-2-yl)-9H-carbazole and 4-bromobis Compound 17 (MS[M+H] was prepared by the same method as that of compound 1, except that benzo[b,d]furan was used instead of compound A4 and 2-bromodibenzo[b,d]thiophene. ⁺ = 671).

Example 18: Production of Compound 18

Using 3-(4-(dibenzo[b,d]thiophen-4-yl)-6-phenyl-1,3,5-triazin-2-yl)-9H-carbazole and 2-bromobis Compound 18 (MS[M+H] was prepared by the same method as that of compound 1, except that benzo[b,d]furan was used in place of compound A4 and 2-bromodibenzo[b,d]thiophene. ⁺ = 671).

Example 19: Preparation of Compound 19

Using 4-(4-(dibenzo[b,d]thiophen-4-yl)-6-phenyl-1,3,5-triazin-2-yl)-9H-carbazole and 4-bromobis Compound 19 (MS[M+H] was prepared by the same method as that of compound 1, except that benzo[b,d]furan was used in place of compound A4 and 2-bromodibenzo[b,d]thiophene. ⁺ = 671).

Example 20: Preparation of Compound 20

Using 4-(4-(dibenzo[b,d]thiophen-4-yl)-6-phenyl-1,3,5-triazin-2-yl)-9H-carbazole and 3-bromobis Compound 20 (MS[M+H] was prepared by the same method as that of compound 1, except that benzo[b,d]furan was used in place of compound A4 and 2-bromodibenzo[b,d]thiophene. ⁺ = 671).

Example 21: Production of Compound 21

Using 4-(4-(dibenzo[b,d]thiophen-4-yl)-6-phenyl-1,3,5-triazin-2-yl)-9H-carbazole and 1-bromobis Compound 21 (MS[M+H] was prepared by the same method as that of compound 1, except that benzo[b,d]furan was used in place of compound A4 and 2-bromodibenzo[b,d]thiophene. ⁺ = 671).

Example 22: Preparation of Compound 22

Using 1-(4-(Dibenzo[b,d]thiophen-4-yl)-6-phenyl-1,3,5-triazin-2-yl)-9H-carbazole and 1-bromo- Compound 22 (MS[M +H] ⁺ =697).

Example 23: Production of Compound 23

Using 1-(4-(dibenzo[b,d]thiophen-4-yl)-6-phenyl-1,3,5-triazin-2-yl)-9H-carbazole and 3-bromo- Compound 23 (MS[M +H] ⁺ =697).

Example 24: Preparation of Compound 24

Using 2-(4-(dibenzo[b,d]thiophen-4-yl)-6-phenyl-1,3,5-triazin-2-yl)-9H-carbazole and 1-bromo- Compound 24 (MS[M +H] ⁺ =697).

Example 25: Preparation of Compound 25

Using 2-(4-(dibenzo[b,d]thiophen-4-yl)-6-phenyl-1,3,5-triazin-2-yl)-9H-carbazole and 2-bromo- Compound 25 (MS[M +H] ⁺ =697).

Example 26: Production of Compound 26

2-(4-(Dibenzo[b,d]thiophen-4-yl)-6-phenyl-1,3,5-triazin-2-yl)-9H-carbazole and 4-bromo- Compound 26 (MS[M +H] ⁺ =697).

Example 27: Production of Compound 27

Using 3-(4-(dibenzo[b,d]thiophen-4-yl)-6-phenyl-1,3,5-triazin-2-yl)-9H-carbazole and 2-bromo- Compound 27 (MS[M +H] ⁺ =697).

Example 28: Preparation of Compound 28

Using 3-(4-(dibenzo[b,d]thiophen-4-yl)-6-phenyl-1,3,5-triazin-2-yl)-9H-carbazole and 3-bromo- Compound 28 (MS[M +H] ⁺ =697).

Example 29: Preparation of Compound 29

Using 4-(4-(dibenzo[b,d]thiophen-4-yl)-6-phenyl-1,3,5-triazin-2-yl)-9H-carbazole and 2-bromo- Compound 29 (MS[M +H] ⁺ =697).

Example 30: Preparation of Compound 30

Using 4-(4-(dibenzo[b,d]thiophen-4-yl)-6-phenyl-1,3,5-triazin-2-yl)-9H-carbazole and 4-bromo- Compound 30 (MS[M +H] ⁺ =697).

Example 31: Preparation of Compound 31

Compound 31 (MS [M+H] ⁺ =712) was produced by the same method as that for producing Compound 1, except that Compound A4-1 was used instead of Compound A4.

Example 32: Preparation of Compound 32

Using 3-(4-(dibenzo[b,d]thiophen-4-yl)-6-phenyl-1,3,5-triazin-2-yl)-9H-carbazole and 8-bromobis Compound 32 (MS [M+H] ⁺ =712).

Example 33: Preparation of Compound 33

Using 3-(4-(Dibenzo[b,d]thiophen-4-yl)-6-phenyl-1,3,5-triazin-2-yl)-9H-carbazole and 6-bromobis Compound 33 (MS [M+H] ⁺ =712).

Example 34: Preparation of Compound 34

Compound 34 (MS [M+H] ⁺ =696) was produced by the same method as that for producing compound 21 except that compound A4-2 was used instead of compound A4.

Example 35: Preparation of Compound 35

Using 3-(4-(dibenzo[b,d]thiophen-4-yl)-6-phenyl-1,3,5-triazin-2-yl)-9H-carbazole and 7-bromobis Compound 35 (MS [M+H] ⁺ =696).

Example 36: Preparation of Compound 36

Using 3-(4-(dibenzo[b,d]thiophen-4-yl)-6-phenyl-1,3,5-triazin-2-yl)-9H-carbazole and 8-bromobis Compound 36 (MS [M+H] ⁺ =696).

[Experimental example]

Experimental Example 1-1

的厚度涂布成薄膜的玻璃基板放入溶解有洗涤剂的蒸馏水中，利用超声波进行洗涤。这时，洗涤剂使用菲希尔公司(FischerCo.)制品，蒸馏水使用了利用密理博公司(Millipore Co.)制造的过滤器(Filter)过滤两次的蒸馏水。将ITO洗涤30分钟后，用蒸馏水重复两次而进行10分钟超声波洗涤。在蒸馏水洗涤结束后，用异丙醇、丙酮、甲醇的溶剂进行超声波洗涤并干燥后，输送至等离子体清洗机。此外，利用氧等离子体，将上述基板清洗5分钟后，将基板输送至真空蒸镀机。ITO (indium tin oxide, indium tin oxide) with

The glass substrate coated into a thin film with a thickness of 100 is placed in distilled water in which detergent is dissolved, and washed with ultrasonic waves. At this time, a Fischer Co. product was used as the detergent, and distilled water filtered twice by a Millipore Co. filter was used for the distilled water. After washing with ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After washing with distilled water, ultrasonic washing was performed with a solvent of isopropanol, acetone, and methanol, followed by drying, and then transported to a plasma cleaning machine. Moreover, after the said board|substrate was wash|cleaned for 5 minutes by oxygen plasma, the board|substrate was conveyed to a vacuum vapor deposition machine.

的厚度进行热真空蒸镀而形成空穴注入层。在上述空穴注入层上，将下述HT-1化合物以

的厚度进行热真空蒸镀而形成空穴传输层，在HT-1蒸镀膜上，将下述HT-2化合物以

的厚度进行真空蒸镀而形成电子阻挡层。在上述HT-2蒸镀膜上，作为发光层，将在上述实施例1中制造的化合物1、下述YGH-1化合物、以及磷光掺杂剂YGD-1以44:44:12的重量比进行共蒸镀而形成

厚度的发光层。在上述发光层上，将下述ET-1化合物以

的厚度进行真空蒸镀而形成电子传输层，在上述电子传输层上以98:2的重量比将下述ET-2化合物和Li进行共蒸镀而形成电子注入层。在上述电子注入层上，将铝以

厚度进行蒸镀，从而形成阴极。On the ITO transparent electrode prepared in this way, the following HI-1 compound was mixed with

A hole injection layer was formed by thermal vacuum evaporation. On the above hole injection layer, the following HT-1 compound was mixed with

A hole transport layer was formed by thermal vacuum evaporation with a thickness of

The thickness of the electron blocking layer was formed by vacuum evaporation. On the above-mentioned HT-2 vapor-deposited film, as a light-emitting layer, compound 1 produced in the above-mentioned Example 1, the following YGH-1 compound, and phosphorescent dopant YGD-1 were prepared in a weight ratio of 44:44:12. formed by co-evaporation

thickness of the light-emitting layer. On the above-mentioned light-emitting layer, the following ET-1 compound was mixed with

An electron transport layer was formed by vacuum evaporation with a thickness of 100 Å, and an electron injection layer was formed by co-evaporating the following ET-2 compound and Li at a weight ratio of 98:2 on the electron transport layer. On the above electron injection layer, aluminum is

Thickness is evaporated to form a cathode.

铝维持

的蒸镀速度，在蒸镀时，真空度维持1×10^-7～5×10^-8托。During the above process, the evaporation rate of organic substances is maintained

Aluminum maintenance

The vapor deposition rate of 1×10 ^-7 to 5×10 ^-8 Torr is maintained during vapor deposition.

Experimental Examples 1-1 to 1-36

An organic light-emitting device was produced by the same method as in the above-mentioned Experimental Example 1-1, except that the compound described in the following Table 1 was used instead of the compound 1 of Example 1 in the above-mentioned Experimental Example 1-1.

Comparative Experimental Examples 1-1 and 1-2

In the above-mentioned Experimental Example 1, an organic light-emitting device was produced by the same method as in the above-mentioned Experimental Example 1-1, except that the compound described in the following Table 1 was used instead of the compound 1 of Example 1. On the other hand, the compounds of CE1 and CE2 in Table 1 below are shown below.

In the above-mentioned experimental examples and comparative experimental examples, the driving voltage and luminous efficiency of the organic light-emitting device were measured at a current density of 10 mA/cm ² , and at a current density of 50 mA/cm ² , the required amount of luminance to achieve 95% of the initial brightness was measured. time (LT ₉₅ ). The results are shown in Table 1 below.

【Table 1】

As shown in Table 1 above, it was confirmed that when the compound of the present invention was used as a material for a light-emitting layer, it exhibited characteristics excellent in efficiency and lifespan as compared with the comparative experimental examples.

Experimental example 2-1

的厚度涂布成薄膜的玻璃基板(康宁7059玻璃)放入溶解有分散剂的蒸馏水中，利用超声波进行洗涤。洗涤剂使用菲希尔公司制品，蒸馏水使用了利用密理博公司制造的过滤器过滤两次的蒸馏水。将ITO洗涤30分钟后，用蒸馏水重复两次而进行10分钟超声波洗涤。在蒸馏水洗涤结束后，用异丙醇、丙酮、甲醇的溶剂顺序进行超声波洗涤并干燥。ITO (Indium Tin Oxide)

A glass substrate (Corning 7059 glass) coated into a thin film with a thickness of 100 Å was placed in distilled water in which a dispersant was dissolved, and washed with ultrasonic waves. As the detergent, a product made by Fischer Co., Ltd. was used, and as the distilled water, distilled water filtered twice by a filter made by Millipore Co., Ltd. was used. After washing with ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After the washing with distilled water was completed, ultrasonic washing was performed sequentially with a solvent of isopropanol, acetone, and methanol, and then dried.

的厚度进行热真空蒸镀而形成空穴注入层。在上述空穴注入层上，将下述HT-1化合物以

的厚度进行真空蒸镀而形成空穴传输层，在上述空穴传输层上，将主体H1和掺杂剂D1化合物以97.5:2.5的重量比并以

的厚度进行真空蒸镀而形成发光层。在上述发光层上，将下述化合物ET-A以

的厚度进行真空蒸镀而形成电子传输层。在上述电子传输层上，将实施例1中制造的化合物1和LiQ(Lithium Quinolate，8-羟基喹啉锂)以1:1的重量比进行真空蒸镀而以

的厚度形成电子注入和传输层。在上述电子注入和传输层上，依次将氟化锂(LiF)以

的厚度、将铝以

的厚度进行蒸镀，从而形成阴极。On the ITO transparent electrode prepared in this way, the following HI-1 compound was mixed with

A hole injection layer was formed by thermal vacuum evaporation. On the above hole injection layer, the following HT-1 compound was mixed with

A hole transport layer is formed by vacuum evaporation with a thickness of 97.5:2.5 on the above hole transport layer, the host H1 and the dopant D1 compound are mixed with

A light-emitting layer was formed by vacuum evaporation. On the above-mentioned light-emitting layer, the following compound ET-A was mixed with

The thickness of the electron transport layer was formed by vacuum evaporation. On the above electron transport layer, compound 1 prepared in Example 1 and LiQ (Lithium Quinolate, lithium 8-quinolate) were vacuum-evaporated at a weight ratio of 1:1 to obtain a

The thickness of the electron injection and transport layer is formed. On the above electron injection and transport layer, lithium fluoride (LiF) was sequentially

thickness, aluminum to

The thickness is evaporated to form a cathode.

阴极的氟化锂维持

的蒸镀速度，铝维持

的蒸镀速度，在蒸镀时，真空度维持2×10^-7～5×10^-6托，从而制作了有机发光器件。During the above process, the evaporation rate of organic substances is maintained

Lithium fluoride maintenance of the cathode

The evaporation rate of aluminum maintains

The vapor deposition rate was 2×10 −7 to 5×10 −6 Torr, and the vacuum degree was maintained at 2×10 ⁻⁷ to 5×10 ⁻⁶ Torr during the vapor deposition, thereby producing an organic light-emitting device.

Experimental Examples 2-2 to 2-36

In the above Experimental Example 2-1, an organic light-emitting device was produced by the same method as in the above Experimental Example 2-1, except that the compound described in the following Table 2 was used instead of the compound 1 of Example 1.

Comparative Experimental Examples 2-1 and 2-2

In the above Experimental Example 2-1, an organic light-emitting device was produced by the same method as in the above Experimental Example 2-1, except that the compound described in the following Table 2 was used instead of the compound 1 of Example 1. The compounds of CE3 and CE4 in Table 2 below are shown below.

In the above-mentioned experimental examples and comparative experimental examples, the driving voltage and luminous efficiency of the organic light-emitting device were measured at a current density of 10 mA/cm ² , and at a current density of 50 mA/cm ² , the required amount of luminance to achieve 95% of the initial brightness was measured. time (LT ₉₅ ). The results are shown in Table 1 below.

【Table 2】

As shown in Table 2 above, it was confirmed that when the compound of the present invention was used as a material for an electron transport layer, it exhibited characteristics excellent in efficiency and lifetime as compared with the comparative experimental example.

【Symbol Description】

1: Substrate 2: Anode

3: Light-emitting layer 4: Cathode

5: Hole injection layer 6: Hole transport layer

7: Electron blocking layer 8: Light emitting layer

9: Electron transport layer 10: Electron injection layer

11: Electron injection and transport layers.

Claims (9)

1. A compound represented by the following chemical formula 1:

chemical formula 1

Wherein, in the chemical formula 1,

y is S, O or CR'₂，

R' is each independently substituted or unsubstituted C_1-60Alkyl, substituted or unsubstituted C_1-60Alkoxy, substituted or unsubstituted C_3-60Cycloalkyl, substituted or unsubstituted C_6-60Aryl, substituted or unsubstituted C_6-60Aryloxy group, or substituted or unsubstituted C containing 1 or more of O, N, Si and S_2-60(ii) a heteroaryl group, wherein,

R₁to R₇Each independently is halogenElements, hydroxy, cyano, nitrile, nitro, amino, substituted or unsubstituted C_1-60Alkyl, substituted or unsubstituted C_1-60Haloalkyl, substituted or unsubstituted C_1-60Thioalkyl, substituted or unsubstituted C_1-60Alkoxy, substituted or unsubstituted C_1-60Haloalkoxy, substituted or unsubstituted C_3-60Cycloalkyl, substituted or unsubstituted C_1-60Alkenyl, substituted or unsubstituted C_6-60Aryl, substituted or unsubstituted C_6-60Aryloxy group, or substituted or unsubstituted C containing 1 or more of O, N, Si and S_2-60(ii) a heteroaryl group, wherein,

a. e and g are each independently 0 to 4,

b. d and f are each independently 0 to 3,

c is 0 to 5.

2. The compound of claim 1, wherein R' is methyl.

3. The compound of claim 1, wherein a, b, c, d, e, and f are 0.

4. The compound of claim 1, wherein R₁To R₇At least 1 of which is cyano.

5. The compound according to claim 1, wherein the compound represented by the chemical formula 1 is represented by any one selected from the group consisting of:

the description of Y is the same as defined in claim 1.

6. The compound according to claim 1, wherein the compound represented by the chemical formula 1 is any one selected from the group consisting of:

7. an organic light emitting device, comprising: a first electrode, a second electrode provided so as to face the first electrode, and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers contain the compound according to any one of claims 1 to 6.

8. The organic light emitting device according to claim 7, wherein the organic layer containing the compound is an electron injection layer, an electron transport layer, an electron injection and transport layer, or a light emitting layer.

9. The organic light-emitting device according to claim 8, wherein the light-emitting layer contains 2 or more kinds of hosts, and 1 of the hosts is the compound.

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