CN110494430B - Novel compound and organic light-emitting device using the same - Google Patents

Abstract

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

Description

Novel compounds and organic light-emitting devices using the same

technical field

Cross-reference with related applications

This application claims priority based on Korean Patent Application No. 10-2017-0135923 filed on October 19, 2017 and Korean Patent Application No. 10-2018-0062161 filed on May 30, 2018, and documents including the Korean Patent Application The entire content disclosed in is made a part of this specification.

The present invention relates to a novel amine compound and an organic light-emitting device including 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. An organic light-emitting element utilizing the organic light-emitting phenomenon has a wide viewing angle, excellent contrast ratio, fast response time, and excellent characteristics of luminance, driving voltage, and response speed, and thus a lot of research is being carried out.

An organic light-emitting element 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 element, the above-mentioned organic material 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. In the structure of such an organic light-emitting element, when a voltage is applied between the two electrodes, holes are injected from the anode to the organic layer, and electrons are injected from the cathode to the organic layer. excitons, and emit light when the excitons re-transition to the ground state.

The development of new materials has continued to be demanded for organic substances used in the above-mentioned organic light-emitting elements.

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 a novel amine compound and an organic light-emitting device including the same.

Solution to the problem

this invention

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

[Chemical formula 1]

In the above chemical formula 1,

Among X ₁ to X ₄ , X ₁ and X ₂ , X ₂ and X ₃ , or X ₃ and X ₄ are respectively connected to * of the following Chemical Formula 2, and the rest are hydrogen,

[Chemical formula 2]

a, c, d and e are integers from 0 to 3,

b is an integer from 0 to 2,

x is 1 or 2,

R ₁ to R ₅ are each independently hydrogen, deuterium, halogen group, cyano group, substituted or unsubstituted C _1-60 alkyl, substituted or unsubstituted C _1-60 alkoxy, substituted or unsubstituted C _1-60 thioalkyl, substituted or unsubstituted C _3-60 cycloalkyl, substituted or unsubstituted C _6-60 aryl, or tri(C _1-60 alkyl)silyl,

R is each independently represented by the following Chemical Formula 3,

[Chemical formula 3]

In the above chemical formula 3,

L ₁ , L ₂ and L ₃ are each independently a single bond; a substituted or unsubstituted C _6-60 arylene group; or a substituted or unsubstituted group containing any one or more selected from N, O and S C _2-60 heteroarylene of the heteroatom of the person,

Ar ₁ and Ar ₂ are each independently a substituted or unsubstituted C _6-60 aryl group; or a substituted or unsubstituted C ₂ containing a heteroatom selected from any one or more of N, O and S _-60 Heteroaryl.

In addition, the present invention provides an organic light-emitting element 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 organic layer, one or more of the organic layers contains 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 element, and can achieve improvement in efficiency, low driving voltage, and/or improvement in lifetime characteristics in the organic light-emitting element. In particular, the compound represented by the above-mentioned Chemical Formula 1 can be used as a hole injection, hole transport, hole injection and transport, light emission, electron transport, or electron injection material.

Description of drawings

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

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

Detailed ways

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

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

或者

表示与其他取代基连接的键。In this manual,

or

Represents 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原子中的一个以上的杂环基中的一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; arylamino; arylphosphino; or one or more substituents of heterocyclic groups containing one or more of N, O, and S atoms substituted or unsubstituted, or substituted or unsubstituted by the substituents exemplified above A substituent formed by connecting two or more substituents 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. As specific examples, there are 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, and according to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. 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. Regarding the above-mentioned aryl group, the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, or the like, but 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.

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

等。但并不限定于此。

Wait. But it is 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，但并不仅限于此。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 this 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 this 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 description about the above-mentioned heterocyclic group can be applied to the heteroaryl group in the heteroarylamine. In the present 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 this specification, the heteroarylene group is a divalent group, and 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 description about the heterocyclic group can be applied.

In the above chemical formula 1, the above chemical formula 1 is respectively represented by the following chemical formula 1-1, 1-2 or 1-3 according to the bonding position of the chemical formula 2.

[Chemical formula 1-1]

[Chemical formula 1-2]

[Chemical formula 1-3]

Preferably, a, b, c, d and e are zero. In addition, preferably, R ₁ to R ₅ are hydrogen.

Preferably, L ₁ is a single bond, phenylene, biphenylenediyl, terphenylenediyl, tetraphenylenediyl, naphthalenediyl, anthracenediyl, phenanthrenediyl, triphenylenediyl, pyrenediyl, Dimethylfluorenediyl, methylphenylfluorenediyl, diphenylfluorenediyl, dibenzofurandiyl, dibenzothiophenediyl, carbazolediyl, or 9-phenyl-9H-carboxy oxazolyl. More preferably, L ₁ is a single bond or phenylene.

Preferably, L ₂ and L ₃ are each independently a single bond, phenylene, biphenylenediyl, terphenylenediyl, tetraphenylenediyl, naphthalenediyl, anthracenediyl, phenanthrenediyl, triphenylenediyl base, pyrenediyl, dimethylfluorenediyl, methylphenylfluorenediyl, diphenylfluorenediyl, spirofluorenediyl, dibenzofurandiyl, dibenzothiophenediyl, carbazolediyl group, or 9-phenyl-9H-carbazolediyl.

Preferably, Ar ₁ and Ar ₂ are each independently phenyl, biphenyl, terphenyl, tetraphenyl, naphthyl, phenanthryl, dimethylfluorenyl, dibenzofluorenyl, spirofluorenyl, Dibenzofuranyl, dibenzothienyl, carbazolyl, or 9-phenyl-9Hcarbazolyl.

Representative examples of the compounds represented by the above-mentioned Chemical Formula 1 are as follows:

In addition, in the present invention, as an example, the compound represented by the above-mentioned chemical formula 1-1 can be produced by the production method as shown in the following reaction formula 1, and can also be applied to the other compounds represented by chemical formulas 1-2 and 1-3. .

[Reaction 1]

The above Reaction Formula 1 is an amine substitution reaction, which is a reaction for producing the compound represented by the above Chemical Formula 1-1 by reacting the compound represented by the above Chemical Formula 1-a with the compound represented by the above Chemical Formula 1-b. The above reaction is preferably carried out in the presence of a palladium catalyst and a base, and the reactive group used in the amine substitution reaction can be changed to a reactive group known in the art. Preferably, the above X is a halogen group (more preferably bromine or chlorine). The above-mentioned manufacturing method can be more embodied in the manufacturing example mentioned later.

In addition, the present invention provides an organic light-emitting element including the compound represented by the above-mentioned Chemical Formula 1. As an example, the present invention provides an organic light-emitting element including a first electrode, a second electrode provided opposite to the first electrode, and an organic light-emitting element 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 element 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 element 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 element is not limited to this, and a smaller number of organic layers may be included.

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

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. In particular, the compounds according to the invention can be used as dopants for light-emitting layers.

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

In addition, the above-mentioned electron transport layer, electron injection layer, or layer performing both electron transport and electron injection 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 element according to the present invention may be an organic light-emitting element 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 element according to the present invention may be an organic light emitting element having a reverse 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 element 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 element 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 example of an organic light-emitting element composed of a substrate 1 , an anode 2 , a hole injection layer 5 , a hole transport layer 6 , a light-emitting layer 7 , an electron transport layer 8 , and a cathode 4 . In the above structure, 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, and electron transport layer.

The organic light-emitting element according to the present invention can be manufactured using materials and methods well-known in the 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 element includes a plurality of organic material layers, the above-mentioned organic material layers may be formed of the same substance or different substances.

For example, the organic light-emitting element according to the present invention can be manufactured by sequentially stacking a first electrode, an organic layer, and a second electrode on a substrate. At this time, it can be produced as follows: using a PVD (physical Va por Deposition) method such as sputtering or e-beam evaporation, vapor deposition of metal or a conductive material on the substrate metal oxides or their alloys to form an anode, and then an organic layer comprising a hole injection layer, a hole transport layer, a light emitting layer and an electron transport layer is formed on the anode, and then the organic layer is evaporated on the organic layer. Manufactured as a cathode material. In addition to this method, an organic light-emitting element 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 be used to form an organic substance layer not only by a vacuum deposition method but also by a solution coating method when producing an organic light-emitting element. 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 element 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 above anode materials include metals such as vanadium, chromium, copper, zinc, and gold or their alloys; 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), poly Conductive polymers such as pyrrole and polyaniline, etc., are not limited thereto.

As the above-mentioned cathode material, generally, in order to facilitate electron injection into the organic substance layer, a material having a small work function is preferable. 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; for example, LiF/Al or LiO ₂ /Al and other multi-layer structure substances, etc., but not limited to this.

The above-mentioned hole injection layer is a layer that injects holes from an electrode, and the hole injection material is preferably a compound that has the ability to transport holes, has a hole injection effect from an anode, and is excellent for a light-emitting layer or a light-emitting material The excellent hole injection effect prevents 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. The material of the light-emitting layer is suitable for a material with high hole mobility. 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，但并不仅限于此。The above-mentioned light-emitting substance is a substance that can receive holes and electrons from the hole transport layer and the electron transport layer, respectively, and combine them to emit light in the visible light region, and is preferably a substance with 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;

azole, benzothiazole and benzimidazole-based compounds; poly(p-phenylene vinylene) (PPV)-based polymers; spiro compounds; polyfluorene, 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 fused ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and examples of the heterocyclic-containing compound include carbazole derivatives , dibenzofuran derivatives, ladder furan compounds

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

二茚并芘(Periflanthene)等，作为苯乙烯基胺化合物，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一个或两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, as the aromatic amine derivatives, there are aromatic fused ring derivatives having a substituted or unsubstituted arylamino group, such as pyrene, anthracene,

Diindenopyrene (Periflanthene), etc., as styrylamine compounds, are compounds in which at least one arylvinyl group is substituted on a substituted or unsubstituted arylamine, and are selected from aryl, silyl, alkyl , cycloalkyl and arylamino are substituted or unsubstituted with one or two or more substituents. Specifically, although styrylamine, styryl diamine, styryl triamine, styryl tetraamine, etc. are mentioned, it is not limited to these. Further, as the metal complex, there are iridium complexes, platinum complexes, and the like, but are not limited to these.

The above-mentioned electron transport layer is a layer that receives electrons from the electron injection layer and transports the electrons to the light-emitting layer. The electron-transporting material is a material that can inject electrons from the cathode well and transfer them to the light-emitting layer, and has a high electron mobility. is appropriate. Specific examples include, but are not limited to, Al complexes of 8-hydroxyquinoline, complexes containing Alq ₃ , organic radical compounds, and hydroxyflavone-metal complexes. 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 the emission of electrons 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, anthraqui nodimethane, diphenoquinone, thiopyran dioxide,

azole,

But not limited to, oxadiazoles, triazoles, imidazoles, perylenetetracarboxylic acids, fluorenylene methanes, anthrone, and the like and their derivatives, metal complexes, nitrogen-containing five-membered ring derivatives, and the like.

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.

The organic light-emitting element according to the present invention may be of a top emission type, a bottom emission type, or a bidirectional emission type, depending on the material used.

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

Production of the compound represented by the above-mentioned Chemical Formula 1 and the organic light-emitting element including the same will be specifically described in the following examples. However, the following examples are intended to illustrate the present invention, and the scope of the present invention is not limited thereto.

[Manufacturing example]

Production Example 1: Production of Compounds A-1-1 to A-1-3

Step 1) Production of Compound A-1-1

9,9'-spirobis[fluorene]-2-ol (150 g, 465 mmol) was added and dissolved in DMF (400 ml), NBS (83.5 g, 469 mmol) was slowly added dropwise at 0°C, and the mixture was stirred at room temperature for 3 Hour. After extraction with water and chloroform at room temperature, the white solid was recrystallized from hexane to produce the above-mentioned compound A-1-1 (162 g, yield 85%).

MS[M+H] ⁺ = 412.30

Step 2) Production of Compound A-1-2

烷(300ml)边搅拌边加热。在回流状态下，加入双(二亚苄基丙酮)钯(840mg，0.02mol％)和三环己基膦(820mg，0.04mol％)加热并搅拌3小时。反应结束后，将温度降至常温后过滤。在过滤液中倒入水，用氯仿萃取，有机层用无水硫酸镁干燥。减压蒸馏后用乙酸乙酯和己烷重结晶而制造了上述化合物A-1-2(28.4g，85％)。The above compound A-1-1 (30 g, 72.9 mmol), bis(pinacol)diboron (22.23 g, 87.5 mmol) and potassium acetate (25.06 g, 255.2 mmol) were mixed under nitrogen atmosphere, and two

Alkane (300 mL) was heated with stirring. Under reflux, bis(dibenzylideneacetone)palladium (840 mg, 0.02 mol %) and tricyclohexylphosphine (820 mg, 0.04 mol %) were added and heated and stirred for 3 hours. After the reaction was completed, the temperature was lowered to normal temperature and filtered. Water was poured into the filtrate, extracted with chloroform, and the organic layer was dried over anhydrous magnesium sulfate. After distillation under reduced pressure, the compound A-1-2 (28.4 g, 85%) was produced by recrystallization from ethyl acetate and hexane.

MS[M+H] ⁺ = 459.36

Step 3) Production of Compound A-1-3

The above-mentioned compound A-1-2 (30 g, 65.5 mmol) was put into a 2M sodium hydroxide solution, and after stabilization treatment at 0°C, hydrogen peroxide (25 ml, 131.18 mmol) was added with stirring to complete the reaction. After completion of the reaction, water was poured into the mixture and stirred for 30 minutes, and then the temperature was lowered to normal temperature, thereby producing the above-mentioned compound A-1-3 (18.28 g, yield 80%).

MS[M+H] ⁺ = 349.30

Production Example 2: Production of Compounds B-1-1 to B-1-6

Production Example 2-1: Production of Compound B-1-1

To DMF (300 ml) were added 3,4-dihydroxy-9H-fluoren-9-one (30 g, 141.3 mmol), 4-bromo-1,2-difluorobenzene (40.93 g, 212.06 mmol) and potassium carbonate ( 82.06 g, 593.7 mmol) was refluxed and stirred. After the reaction was completed, the temperature was lowered to normal temperature and filtered. After extraction with water and chloroform at room temperature, the white solid was subjected to column chromatography with ethyl acetate and hexane to produce the above-mentioned compound B-1-1 (18.06 g, yield 35%).

MS[M+H] ⁺ = 366.18

Production Example 2-2: Production of Compound B-1-2

In the production of the above-mentioned B-1-1, the compound B-1-2 was produced by separation by column chromatography.

MS[M+H] ⁺ = 366.18

Production Example 2-3: Production of Compound B-1-3

B was produced by the same method as the production method of compound B-1-1 except that 1-bromo-2,3-difluorobenzene was used instead of 4-bromo-1,2-difluorobenzene -1-3.

MS[M+H] ⁺ = 366.18

Production Example 2-4: Production of Compound B-1-4

In the production of the above-mentioned B-1-3, the compound B-1-4 was separated and produced by column chromatography.

MS[M+H] ⁺ = 366.18

Production Example 2-5: Production of Compound B-1-5

Except having used 1,2-dichloro-4,5-difluorobenzene instead of 4-bromo-1,2-difluorobenzene, it was produced by the same method as the production method of compound B-1-1, thereby Made the B-1-5.

MS[M+H] ⁺ = 356.17

Production Example 2-6: Production of Compound B-1-6

Except having used 1,4-dichloro-2,3-difluorobenzene instead of 4-bromo-1,2-difluorobenzene, it was produced by the same method as the production method of compound B-1-1, thereby B-1-6 was made.

MS[M+H] ⁺ = 356.17

Production Example 3: Production of Compounds A1 to A6

Production Example 3-1: Production of Compound A1

The compound A1 was produced by the same method as the production method of the compound B-1-1 except that the compound A-1-3 was used instead of 3,4-dihydroxy-9H-fluoren-9-one.

MS[M+H] ⁺ = 502.38

Production Example 3-2: Production of Compound A2

The compound A1 was produced by the same method as the production method of the compound B-1-2 except that the compound A-1-3 was used instead of 3,4-dihydroxy-9H-fluoren-9-one.

MS[M+H] ⁺ = 502.38

Production Example 3-3: Production of Compound A3

The compound A1 was produced by the same method as the production method of the compound B-1-3 except that the compound A-1-3 was used instead of 3,4-dihydroxy-9H-fluoren-9-one.

MS[M+H] ⁺ = 502.38

Production Example 3-4: Production of Compound A4

The compound A4 was produced by the same method as the production method of the compound B-1-4 except that the compound A-1-3 was used instead of 3,4-dihydroxy-9H-fluoren-9-one.

MS[M+H] ⁺ = 502.38

Production Example 3-5: Production of Compound A5

The compound A5 was produced by the same method as the production method of the compound B-1-5 except that the compound A-1-3 was used instead of 3,4-dihydroxy-9H-fluoren-9-one.

MS[M+H] ⁺ = 492.37

Production Example 3-6: Production of Compound A6

The compound A6 was produced by the same method as the production method of the compound B-1-6 except that the compound A-1-3 was used instead of 3,4-dihydroxy-9H-fluoren-9-one.

MS[M+H] ⁺ = 492.37

Production Example 4: Production of Compounds B1 to B6

Production Example 4-1: Production of Compound B1

After dissolving 2-aminobiphenyl (80.2 mmol) in THF (250 ml), the temperature was lowered to -78°C, then 2.5 M n-butyllithium (n-BuLi) (9 ml) was added dropwise, stirred for 30 minutes, and then added Compound B-1-1 (80.2 mmol) was raised to normal temperature and stirred for 1 hour. 1N HCl (100 ml) was added, and after stirring for 30 minutes, the layers were separated to remove the solvent, followed by column chromatography with ethyl acetate and hexane, recrystallization from ethyl acetate, filtration and drying. Then, the dried solid was added to acetic acid (300 ml), heated and stirred, and after dropwise addition of sulfuric acid (1 ml), the mixture was refluxed for 3 hours. After completion of the reaction, the compound B1 was produced by filtration and recrystallization.

MS[M+H] ⁺ = 502.38

Production Example 4-2: Production of Compound B2

The compound B2 was produced by the same method as the production method of the compound B1 except that B-1-2 was used instead of the compound B-1-1.

MS[M+H] ⁺ = 502.38

Production Example 4-3: Production of Compound B3

The compound B3 was produced by the same method as the production method of the compound B1 except that B-1-3 was used instead of the compound B-1-1.

MS[M+H] ⁺ = 502.38

Production Example 4-4: Production of Compound B4

The compound B4 was produced by the same method as the production method of the compound B1 except that B-1-4 was used instead of the compound B-1-1.

MS[M+H] ⁺ = 502.38

Production Example 4-5: Production of Compound B5

The compound B5 was produced by the same method as the production method of the compound B1 except that B-1-5 was used instead of the compound B-1-1.

MS[M+H] ⁺ = 492.37

Production Example 4-6: Production of Compound B6

The compound B6 was produced by the same method as the production method of the compound B1 except that B-1-6 was used instead of the compound B-1-1.

MS[M+H] ⁺ = 492.37

[Example]

Example 1: Production of Compound 1

Compound A1 (15 g, 29.9 mmol), bis([1,1'-biphenyl]-4-yl)amine (9.81 g, 30.5 mmol) and sodium tert-butoxide (4.03 g, 41.8 mol) were added to xylene , heated and stirred and refluxed, and [bis(tri-tert-butylphosphine)]palladium (170 mg, 1 mol%) was added. The temperature was lowered to normal temperature, and after completion of the reaction, compound 1 (16.4 g, yield 74%) was produced by recrystallization from tetrahydrofuran and ethyl acetate.

MS[M+H] ⁺ = 742.89

Example 2: Production of Compound 2

Use compound A2 instead of compound A1, use 9,9-dimethyl-N-phenyl-9H-fluoren-2-amine instead of bis([1,1'-biphenyl]-4-yl)amine, except , and the compound 2 was produced by the same method as the production method of the compound 1.

MS[M+H] ⁺ = 706.86

Example 3: Production of Compound 3

Use compound A3 instead of compound A1, use N-([1,1'-diphenyl]-2-yl)-9,9-dimethyl-9H-fluoren-2-amine instead of bis([1,1' -biphenyl]-4-yl)amine, except for this, it was manufactured by the same method as the manufacturing method of compound 1, and compound 3 was manufactured.

MS[M+H] ⁺ = 782.96

Example 4: Production of Compound 4

Use compound A4 instead of compound A1 and use N-([1,1'-biphenyl]-4-yl)-(1,1';4',1'-terphenyl)-4-amine instead of bis([ 1,1'-biphenyl]-4-yl)amine was produced by the same method as the production method of compound 1 except that, compound 4 was produced.

MS[M+H] ⁺ = 818.99

Example 5: Production of Compound 5

Step 1) Fabrication of compound int.1

It was carried out by the same method as the production method of compound A-3-1 except that compound A2 was used instead of compound A-2-1 and 3-chlorobenzeneboronic acid was used instead of 2-bromo-4-chloro-1-iodobenzene produced, thereby producing compound int.1.

MS[M+H] ⁺ =534.02

Step 2) Production of Compound 5

In the preparation of the above compound 1, compound int.1 was used in place of compound A1, and N-phenyl-[1,1'-biphenyl]-2-amine was used in place of bis([1,1'-biphenyl]-4 The compound 5 was produced by the same method as the production method of the compound 1 except for the production of the compound 1.

MS[M+H] ⁺ = 756.87

Example 6: Production of Compound 6

Step 1) Fabrication of compound int.4

In the production of the above-mentioned compound int.1, except that compound A3 was used instead of compound A2, and (4'-chloro-[1,1'-biphenyl]-3-yl)boronic acid was used instead of 3-chlorophenylboronic acid, The compound int.4 was produced by the same method as the production method of the compound int.1.

MS[M+H] ⁺ = 610.12

Step 2) Production of Compound 6

In the production of the above-mentioned compound 1, in addition to using compound int.4 in place of compound A1 and using diphenylamine in place of bis([1,1'-biphenyl]-4-yl)amine, the production method of compound 1 Production was carried out in the same manner, whereby Compound 6 was produced.

MS[M+H] ⁺ = 742.89

Example 7: Production of Compound 7

In the production of the above-mentioned compound 1, except that compound A5 was used instead of compound A1 and diphenylamine was used instead of bis([1,1'-biphenyl]-4-yl)amine, the same method as in the production of compound 1 was carried out. method to produce compound 7.

MS[M+H] ⁺ = 757.91

Example 8: Production of Compound 8

In the production of the above-mentioned compound 1, except that compound A6 was used in place of compound A1 and diphenylamine was used in place of bis([1,1'-biphenyl]-4-yl)amine, the same method as in the production of compound 1 was carried out. method to produce compound 8.

MS[M+H] ⁺ = 757.91

Example 9: Production of Compound 9

The compound 9 was produced by the same method as the production method of the compound 1 except that the compound B1 was used instead of the compound A1.

MS[M+H] ⁺ = 742.89

Example 10: Preparation of Compound 10

In the production of the above compound 1, compound B2 was used in place of compound A1, and N,9,9-triphenyl-9H-fluoren-4-amine was used in place of bis([1,1'-biphenyl]-4-yl) The amine was produced by the same method as the production method of the compound 1, except that the compound 10 was produced.

MS[M+H] ⁺ = 831.00

Example 11: Production of Compound 11

In the production of the above compound 1, compound B3 was used in place of compound A1, and N-([1,1'-biphenyl]-4-yl)-(1,1'-biphenyl)-2-amine was used in place of bis( [1,1'-biphenyl]-4-yl)amine was produced by the same method as the production method of Compound 1 except that the compound 11 was produced.

MS[M+H] ⁺ = 742.89

Example 12: Preparation of Compound 12

In the production of the above compound 1, compound B4 was used in place of compound A1, and N-phenyl-[1,1;4',1'-terphenyl]-4-amine was used in place of bis([1,1'-bi) The compound 12 was produced by the same method as the production method of the compound 1 except for the production of phenyl]-4-yl)amine.

MS[M+H] ⁺ = 742.89

Example 13: Production of Compound 13

Use compound B5 instead of A-2-1, use N,N-diphenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2 The compound 13 was produced by the same method as the production method of the above-mentioned compound A-3-1, except that 2-bromo-4-chloro-1-iodobenzene was replaced with 2-bromo-4-chloro-1-iodobenzene.

MS[M+H] ⁺ = 910.10

Example 14: Production of Compound 14

In the production of the above compound 1, compound B6 was used in place of compound A1, and N-phenyl-[1,1'-biphenyl]-2-amine was used in place of bis([1,1'-biphenyl]-4-yl) The amine was produced by the same method as the production method of the compound 1, except that the compound 14 was produced.

MS[M+H] ⁺ = 910.10

Example 15: Production of Compound 15

In the production of the above compound 1, compound C1 was used in place of compound A1, and N-phenyl-[1,1'-biphenyl]-2-amine was used in place of bis([1,1'-biphenyl]-4-yl) The amine was produced by the same method as the production method of the compound 1, except that the compound 15 was produced.

MS[M+H] ⁺ = 666.79

Experimental Example 1-1

的厚度薄膜涂布有ITO(氧化铟锡)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(Fischer Co.)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、甲醇的溶剂顺序进行超声波洗涤并干燥。will be

A glass substrate (Corning 7059 glass) coated with a thin film of ITO (indium tin oxide) was placed in distilled water in which a dispersant was dissolved and washed with ultrasonic waves. As the detergent, a product from Fischer Co. was used, and as distilled water, distilled water filtered twice by a filter manufactured by Millipore Co. was used. After washing ITO for 30 minutes, ultrasonic washing was performed twice with distilled water for 10 minutes. 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真空蒸镀作为传输空穴的物质的上述制造的化合物1

后，接着在上述空穴传输层上以

的膜厚度真空蒸镀下述HT2化合物而形成空穴调节层。在上述空穴调节层上将下述H1化合物(主体)和下述D1化合物(掺杂剂)以25:1的重量比进行真空蒸镀而形成

厚度的发光层。然后，将下述E1化合物

和LiQ以1:1的比率进行蒸镀而作为电子注入和传输层依次进行热真空蒸镀。在上述电子传输层上依次将氟化锂(LiF)以

的厚度、将铝以

厚度进行蒸镀而形成阴极，从而制造了有机发光元件。On the thus prepared ITO transparent electrode, the following HAT compound was prepared as

A hole injection layer was formed by thermal vacuum evaporation. Compound 1 produced above, which is a substance for transporting holes, was vacuum-deposited on the hole injection layer.

Then, on the above hole transport layer,

The following HT2 compound was vacuum-deposited to form a hole regulating layer with a film thickness of 100 Å. On the hole regulating layer, the following H1 compound (host) and the following D1 compound (dopant) were vacuum-deposited at a weight ratio of 25:1 to form

thickness of the light-emitting layer. Then, the following E1 compound was

It was vapor-deposited with LiQ at a ratio of 1:1 to sequentially perform thermal vacuum vapor deposition as an electron injection and transport layer. On the above-mentioned electron transport layer, lithium fluoride (LiF) was sequentially mixed with

thickness, aluminum to

The thickness was evaporated to form a cathode, and an organic light-emitting element was manufactured.

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1×10^-7～5×10^-8托。During the above process, the evaporation rate of organic substances is maintained

Lithium fluoride maintenance

The evaporation rate of aluminum maintains

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

Experimental Examples 1-2 to 1-15

An organic light-emitting element 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 Compound 1.

Comparative Experimental Examples 1-1 to 1-6

An organic light-emitting element 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 Compound 1. In Table 1 below, HT1, HT3, and HT4 are shown below, respectively.

Comparative Experimental Example 1-4

Production was carried out in the same manner as in the above-mentioned Experimental Example 1-1, except that the following HT3 compound was used instead of Compound 1 as the hole transport layer, and the following HT5 compound was used instead of Compound HT2 as the hole regulating layer, and the same method to fabricate organic light-emitting elements.

Comparative Experimental Examples 1-5 and 1-6

An organic light-emitting element 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 Compound 1. In Table 1 below, HT7 and HT8 are shown below, respectively.

A current was applied to the organic light-emitting elements produced in the above-described experimental examples and comparative experimental examples, and the driving voltage and efficiency were measured. The results are shown in Table 1 below. At this time, the lifetime is defined as the time required for the brightness to decrease to 95% when the initial brightness is set to 100%.

[Table 1]

Experimental example 2-1

的厚度薄膜涂布有ITO(氧化铟锡)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(Fischer Co.)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、甲醇的溶剂顺序进行超声波洗涤并干燥。will be

A glass substrate (Corning 7059 glass) coated with a thin film of ITO (indium tin oxide) was placed in distilled water in which a dispersant was dissolved and washed with ultrasonic waves. As the detergent, a product from Fischer Co. was used, and as distilled water, distilled water filtered twice by a filter manufactured by Millipore Co. was used. After washing ITO for 30 minutes, ultrasonic washing was performed twice with distilled water for 10 minutes. 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真空蒸镀作为传输空穴的物质的下述HT1化合物

后，接着在上述空穴传输层上以

的膜厚度真空蒸镀上述制造的化合物1而形成空穴调节层。在上述空穴调节层上将下述H1化合物(主体)和下述D1化合物(掺杂剂)以25:1的重量比进行真空蒸镀而形成

厚度的发光层。然后，将下述E1化合物

作为电子注入和传输层依次进行热真空蒸镀。在上述电子传输层上依次将氟化锂(LiF)以

的厚度、将铝以

的厚度进行蒸镀而形成阴极，从而制造了有机发光元件。On the thus prepared ITO transparent electrode, the following HAT compound was prepared as

A hole injection layer was formed by thermal vacuum evaporation. The following HT1 compound as a hole-transporting substance was vacuum-deposited on the above-mentioned hole injection layer

Then, on the above hole transport layer,

The film thickness of the compound 1 produced above was vacuum-deposited to form a hole regulating layer. On the hole regulating layer, the following H1 compound (host) and the following D1 compound (dopant) were vacuum-deposited at a weight ratio of 25:1 to form

thickness of the light-emitting layer. Then, the following E1 compound was

Thermal vacuum evaporation was sequentially performed as electron injection and transport layers. On the above-mentioned electron transport layer, lithium fluoride (LiF) was sequentially mixed with

thickness, aluminum to

An organic light-emitting element was produced by vapor deposition to form a cathode.

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1×10^-7至5×10^-8托。During the above process, the evaporation rate of organic substances is maintained

Lithium fluoride maintenance

The evaporation rate of aluminum maintains

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

Experimental Examples 2-2 to 2-17

An organic light-emitting element was produced by the same method as in the above-mentioned Experimental Example 2-1, except that the compound described in Table 2 below was used instead of Compound 1.

Comparative Experimental Examples 2-1 to 2-6

An organic light-emitting element was produced by the same method as in the above-mentioned Experimental Example 2-1, except that the compounds described in Table 2 below were used instead of Compound HT1 and Compound 1, respectively. In Table 2 below, HT3, HT4, HT5, and HT6 are respectively shown below.

A current was applied to the organic light-emitting elements produced in the above-described experimental examples and comparative experimental examples, and the driving voltage and efficiency were measured. The results are shown in Table 2 below. At this time, the lifetime is defined as the time required for the brightness to decrease to 95% when the initial brightness is set to 100%.

[Table 2]

The compound derivative of the chemical formula according to the present invention can play the role of hole transport and hole regulation in organic electronic elements represented by organic light-emitting elements, and the element according to the present invention exhibits efficiency, driving voltage, and stability. Excellent properties.

【Symbol Description】

1: Substrate 2: Anode

3: Light-emitting layer 4: Cathode

5: Hole injection layer 6: Hole transport layer

7: Light-emitting layer 8: Electron transport layer.

Claims (7)

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

chemical formula 1

In the chemical formula 1, the metal oxide is represented by,

X₁To X₄In, X₁And X₂、X₂And X₃Or X₃And X₄Respectively connected with the following chemical formula 2, and the rest is hydrogen,

chemical formula 2

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

x is 1 or 2, and the compound is,

R₁to R₅Is a hydrogen atom, and is,

r is each independently represented by the following chemical formula 3,

chemical formula 3

In the chemical formula 3, the first and second organic solvents,

L₁、L₂and L₃Each independently is a single bond; or C which is unsubstituted or substituted by methyl or phenyl_6-30An arylene group, a cyclic or cyclic alkylene group,

Ar₁and Ar₂Each independently being unsubstituted or substituted by methyl or phenyl_6-30Aryl, heteroaryl, and heteroaryl,Dibenzofuranyl, dibenzothienyl, carbazolyl, or 9-phenyl-9H-carbazolyl.

2. The compound according to claim 1, wherein the chemical formula 1 is represented by the following chemical formula 1-1, 1-2 or 1-3:

chemical formula 1-1

Chemical formula 1-2

Chemical formulas 1 to 3

3. The compound of claim 1, wherein L₁Is a single bond, phenylene, biphenyldiyl, terphenyldiyl, tetrabiphenyldiyl, naphthalenediyl, anthracenediyl, phenanthrenediyl, triphenylenediyl, pyrenediyl, dimethylfluorenediyl, methylphenylfluorenediyl, or diphenylfluorenediyl.

4. The compound of claim 1, wherein L₂And L₃Each independently is a single bond, phenylene, biphenyldiyl, terphenyldiyl, tetrabiphenyldiyl, naphthalenediyl, anthracenediyl, phenanthrenediyl, triphenylenediyl, pyrenediyl, dimethylfluorenediyl, methylphenylfluorenediyl, diphenylfluorenediyl, or spirofluorenediyl.

5. The compound of claim 1, wherein Ar₁And Ar₂Each independently of the others phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl,Phenanthryl, dimethylfluorenyl, dibenzofluorenyl, spirofluorenyl, dibenzofuranyl, dibenzothienyl, carbazolyl, or 9-phenyl-9H-carbazolyl.

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 element 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.

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