CN110540527A - Novel triphenylene compound and organic light-emitting device using same - Google Patents

Novel triphenylene compound and organic light-emitting device using same Download PDF

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CN110540527A
CN110540527A CN201910438359.XA CN201910438359A CN110540527A CN 110540527 A CN110540527 A CN 110540527A CN 201910438359 A CN201910438359 A CN 201910438359A CN 110540527 A CN110540527 A CN 110540527A
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CN110540527B (en
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车龙范
洪玩杓
洪性佶
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LG Chem Ltd
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Abstract

The invention provides a novel triphenylene compound and an organic light-emitting device using the same. The novel triphenylene compound is represented by the following chemical formula: wherein L is a single bond, a substituted or unsubstituted C6-20 arylene; r is substituted or unsubstituted C6-20 aryl; each X is independently N or CH, wherein more than one of X is N; ar1 and Ar2 are each independently a substituted or unsubstituted C6-20 aryl group, or a substituted or unsubstituted C2-20 heteroaryl group comprising any one or more selected from N, O and S.

Description

Novel triphenylene compound and organic light-emitting device using same
Technical Field
The present invention relates to a novel triphenylene compound and an organic light-emitting element including the same.
Background
In general, the organic light emission phenomenon refers to a phenomenon in which electric energy is converted into light energy by using an organic substance. An organic light emitting element using an organic light emitting phenomenon has a wide viewing angle, excellent contrast, a fast response time, and excellent luminance, driving voltage, and response speed characteristics, and thus a great deal of research is being conducted.
an organic light emitting element generally has a structure including an anode and a cathode, and an organic layer located between the anode and the cathode. In order to improve the efficiency and stability of the organic light-emitting device, the organic layer is often formed of a multilayer structure formed of different materials, and may be formed of, for example, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, or the like. With the structure of such an organic electroluminescent element, if a voltage is applied between both electrodes, holes are injected from the anode into the organic layer, electrons are injected from the cathode into the organic layer, excitons (exiton) are formed when the injected holes and electrons meet, and light is emitted when the excitons are transitioned again to the ground state.
As for organic materials used for the organic light emitting element as described above, development of new materials is continuously demanded.
Documents of the prior art
Patent document
Patent document 1: korean patent laid-open No. 10-2000-0051826
Disclosure of Invention
the present invention relates to a novel triphenylene compound and an organic light-emitting element including the same.
The present invention provides a compound represented by the following chemical formula 1:
[ chemical formula 1]
In the chemical formula 1 described above,
L is a single bond, a substituted or unsubstituted C6-20 arylene group,
R is substituted or unsubstituted C6-20 aryl,
Each X is independently N or CH, wherein more than one of X is N,
ar1 and Ar2 are each independently substituted or unsubstituted C6-20 aryl; or a substituted or unsubstituted C2-20 heteroaryl group comprising any one or more selected from N, O and S.
In addition, the present invention provides an organic light emitting element including: the organic light emitting device includes a first electrode, a second electrode provided to face the first electrode, and 1 or more organic layers provided between the first electrode and the second electrode, wherein 1 or more of the organic layers include a compound represented by the chemical formula 1.
The compound represented by chemical formula 1 described above can be used as a material for an organic layer of an organic light emitting element in which improvement in efficiency, lower driving voltage, and/or improvement in lifetime characteristics can be achieved. In particular, the above-described compound represented by chemical formula 1 may be used as a hole injection, hole transport, hole injection and transport, light emission, electron transport, or electron injection material.
Drawings
Fig. 1 shows an example of an organic light-emitting element including 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, an electron suppression layer 7, a light-emitting layer 3, a hole suppression layer 8, an electron injection and transport layer 9, and a cathode 4.
description of the symbols
1: substrate 2: anode
3: light-emitting layer 4: cathode electrode
5: hole injection layer 6: hole transport layer
7: electron suppression layer 8: hole inhibiting layer
9: electron injection and transport layer
Detailed Description
Hereinafter, the present invention will be described in more detail to assist understanding thereof.
The present invention provides a compound represented by the above chemical formula 1.
In the present specification, a bond to another substituent is shown.
The term "substituted or unsubstituted" as used herein means that the substituent is substituted or unsubstituted with 1 or more substituents selected from deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, an amino group, a phosphine oxide group, an alkoxy group, an aryloxy group, an alkylthio group (alkylthioxy), an arylthio group (Aryl thio), an alkylsulfonyl group (alkylsulfonyxy), an arylsulfonyl group (Aryl suonyxy), a silyl group, a boryl group, an Alkyl group, a cycloalkyl group, an alkenyl group, an Aryl group, an aralkyl group, an aralkenyl group, an alkylaryl group, an alkylamino group, an aralkylamino group, a heteroarylamino group, an arylamino group, or an arylphosphino group, or a heterocyclic group containing 1 or more substituents selected from N, O and S atoms, or a substituent linked with 2 or more substituents selected from the above-exemplified substituents. For example, "a substituent in which 2 or more substituents are linked" may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent in which 2 phenyl groups are linked.
In the present specification, the number of carbon atoms of the carbonyl group is not particularly limited, but is preferably 1 to 40. Specifically, the compound may have the following structure, but is not limited thereto.
In the ester group, the oxygen of the ester group may be bonded to a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms. Specifically, the compound may be a compound of the following structural formula, but is not limited thereto.
In the present specification, the number of carbon atoms in the imide group is not particularly limited, but is preferably 1 to 25. Specifically, the compound may have the following structure, but is not limited thereto.
In the present specification, specific examples of the silyl group include, but are not limited to, a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, and a phenylsilyl group.
In the present specification, the boron group includes specifically a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, a phenylboron group and the like, but is not limited thereto.
in the present specification, examples of the halogen group include fluorine, chlorine, bromine, and iodine.
In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the alkyl group has 1 to 20 carbon atoms. According to another embodiment, the alkyl group has 1 to 10 carbon atoms. According to another embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an n-propyl group, an isopropyl group, a butyl group, an n-butyl group, an isobutyl group, a tert-butyl group, a sec-butyl group, a 1-methylbutyl group, a 1-ethylbutyl group, a pentyl group, an n-pentyl group, an isopentyl group, a neopentyl group, a tert-pentyl group, a hexyl group, a n-hexyl group, a 1-methylpentyl group, a 2-methylpentyl group, a 4-methyl-2-pentyl group, a 3, 3-dimethylbutyl group, a 2-ethylbutyl group, a heptyl group, a n-heptyl group, a 1-methylhexyl group, a cyclopentylmethyl group, a cyclohexylmethyl group, an octyl group, a n-octyl group, a tert-octyl group, a 1-methylheptyl group, a 2-ethylhexyl group, a 2-propyl, Isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like, but are not limited thereto.
In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the number of carbon atoms of the alkenyl group is 2 to 20. According to another embodiment, the number of carbon atoms of the alkenyl group is 2 to 10. According to another embodiment, the number of carbon atoms of the above alkenyl group is 2 to 6. Specific examples thereof include, but are not limited to, vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-methyl-1-butenyl, 1, 3-butadiene, allyl, 1-phenylethen-1-yl, 2-diphenylethen-1-yl, 2-phenyl-2- (naphthalen-1-yl) ethen-1-yl, 2-bis (biphenyl-1-yl) ethen-1-yl, stilbenyl, and styryl.
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 cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the number of carbon atoms of the above cycloalkyl group is 3 to 6. Specifically, there may be mentioned, but not limited to, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2, 3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2, 3-dimethylcyclohexyl, 3,4, 5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl and the like.
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 aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a monocyclic aryl group such as a phenyl group, a biphenyl group, or a terphenyl group, but is not limited thereto. The polycyclic aryl group may be a naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a perylene group, a fluorenyl group, or the like, but is not limited thereto.
In the present specification, the fluorenyl group may be substituted, and 2 substituents may be combined with each other to form a spiro structure. When the fluorenyl group is substituted, the substituents may be, for example, substituted. But is not limited thereto.
In the present specification, the heterocyclic group is a heterocyclic group containing at least one of O, N, Si and S as a heteroatom, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60. Examples of the heterocyclic group include, but are not limited to, thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinyl, isoquinolyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, benzofuryl, phenanthrolinyl (phenanthroline), isoxazolyl, thiadiazolyl, phenothiazinyl, and dibenzofuryl.
In the present specification, the aryl group in the aralkyl group, aralkenyl group, alkylaryl group, arylamine group is the same as the above-mentioned aryl group. In the present specification, the alkyl group in the aralkyl group, the alkylaryl group, and the alkylamino group is the same as the above-mentioned examples of the alkyl group. In the present specification, the heteroaryl group in the heteroarylamine can be applied to the above-mentioned heterocyclic group. In the present specification, the alkenyl group in the aralkenyl group is the same as the above-mentioned examples of the alkenyl group. In the present specification, the arylene group is a 2-valent group, and the above description of the aryl group can be applied thereto. In the present specification, the heteroarylene group is a 2-valent group, and in addition to this, the above description about the heterocyclic group can be applied. In the present specification, the hydrocarbon ring is not a 1-valent group but is formed by combining 2 substituents, and in addition to this, the above description about the aryl group or the cycloalkyl group can be applied. In the present specification, the heterocyclic group is not a 1-valent group but a combination of 2 substituents, and the above description of the heterocyclic group can be applied.
Preferably, L is a single bond, or an unsubstituted C6-20 arylene group,
More preferably, L is a single bond, phenylene, biphenylene, naphthylene, phenanthrylene, dimethylfluorenylene, or diphenylfluorenylene,
Most preferably, L is a single bond, phenylene, biphenylene, or naphthylene.
Preferably, R is phenyl, biphenyl, naphthyl, phenyl substituted with 1 cyano, or 9, 9-dimethyl-9H-fluorenyl.
Preferably, at least one of Ar1 and Ar2 is a substituted or unsubstituted C6-20 aryl or pyridyl group.
Preferably, Ar1 and Ar2 are each independently phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, pyridyl, pyridylphenyl, quinolylphenyl, dibenzofuranyl, dibenzothiophenyl, 9-dimethyl-9H-fluorenyl, 9-phenyl-9H-carbazolyl, 9-diphenyl-9H-fluorenyl, 9' -spirobi [ fluorenyl ], phenyl substituted with 1 or 2 cyano groups, biphenyl substituted with 1 or 2 cyano groups, dibenzofuranyl substituted with 1 or 2 phenyl groups, or dibenzothiophenyl substituted with 1 or 2 phenyl groups.
Representative examples of the compound represented by the above chemical formula 1 are as follows:
The present invention can be produced by a production method represented by the following reaction formula 1.
[ reaction formula 1]
In the above reaction formula 1, L, R, X, Ar1 and Ar2 are as defined in the above chemical formula 1, Z is a halogen group, and Z is preferably chlorine or bromine.
in the above reaction formula 1, step 1 and step 2 are each a suzuki coupling reaction, and are preferably carried out in the presence of a palladium catalyst and a base, and the reactive group used in the suzuki coupling reaction may be changed according to a reactive group known in the art.
In addition, the present invention provides an organic light emitting element comprising the compound represented by the above chemical formula 1. As an example, the present invention provides an organic light emitting element including: the organic light emitting device includes a first electrode, a second electrode provided to face the first electrode, and 1 or more organic layers provided between the first electrode and the second electrode, wherein 1 or more of the organic layers include a compound represented by the chemical formula 1.
The organic 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 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, an electron suppression layer, a light-emitting layer, a hole suppression layer, an electron transport layer, an electron injection layer, and the like as organic layers. However, the structure of the organic light emitting element is not limited thereto, and a smaller number of organic layers may be included.
In addition, the organic layer may include a light emitting layer, and the light emitting layer may include the compound represented by chemical formula 1.
In addition, the organic layer may include an electron transport layer, an electron injection layer, or a hole inhibition layer, and the electron transport layer, the electron injection layer, or the hole inhibition layer may include the compound represented by the chemical formula 1.
in addition, the organic layer may include a light emitting layer, a hole inhibiting layer, an electron transporting layer, or an electron injecting layer, and the light emitting layer, the hole inhibiting layer, the electron transporting layer, or the electron injecting layer may include the compound represented by the chemical formula 1.
The organic light-emitting element according to the present invention may be an organic light-emitting element having a structure in which an anode, 1 or more organic layers, and a cathode are sequentially stacked on a substrate (normal type). The organic light-emitting element according to the present invention may be an inverted (inverted) type organic light-emitting element in which a cathode, 1 or more organic layers, and an anode are sequentially stacked on a substrate. For example, a structure example of an organic light emitting element according to an embodiment of the present invention is shown in fig. 1 and 2.
Fig. 1 shows an example of an organic light-emitting element including a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4. In the structure as described above, the compound represented by the above chemical formula 1 may be included in the above 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, an electron suppression layer 7, a light-emitting layer 3, a hole suppression layer 8, an electron injection and transport layer 9, and a cathode 4. In the structure as described above, the compound represented by the above chemical formula 1 may be contained in 1 or more layers among the above light emitting layer, hole inhibiting layer, and electron injecting and transporting layer.
In the organic light emitting element according to the present invention, 1 or more of the organic layers include the compound represented by the above chemical formula 1, and in addition, may be manufactured by materials and methods well known in the art. In addition, when the organic light emitting element includes a plurality of organic layers, the organic 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 laminating a first electrode, an organic layer, and a second electrode on a substrate. In this case, the following production can be performed: the organic el device is manufactured by depositing a metal, a metal oxide having conductivity, or an alloy thereof on a substrate by a PVD (physical Vapor Deposition) method such as a sputtering method or an electron beam evaporation method (e-beam evaporation) method to form an anode, forming an organic layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer on the anode, and then depositing a substance that can be used as a cathode on the organic layer. In addition to this method, a cathode material, an organic layer, and an anode material may be sequentially deposited on a substrate to manufacture an organic light-emitting element.
In addition, with respect to the compound represented by the above chemical formula 1, in the manufacture of the organic light emitting element, the organic layer may be formed not only by a vacuum evaporation method but also by a solution coating method. Here, the solution coating method refers to spin coating, dip coating, blade coating, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited thereto.
In addition to these methods, an organic light-emitting element can be manufactured by depositing a cathode material, an organic material layer, and an anode material on a substrate in this order (WO 2003/012890). However, the production method is not limited thereto.
In one example, the first electrode is an anode and the second electrode is a cathode, or the first electrode is a cathode and the second electrode is an anode.
The anode material is preferably a material having a large work function so that holes can be smoothly injected into the organic layer. Specific examples of the above-mentioned anode material include metals such as vanadium, chromium, copper, zinc, gold, etc., or alloys thereof; metal oxides such as zinc oxide, Indium Tin Oxide (ITO), Indium Zinc Oxide (IZO), and the like; combinations of metals and oxides such as ZnO: Al or SnO2: Sb; for example, a conductive polymer such as poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene ] (PEDOT), polypyrrole, polyaniline, or the like, but is not limited thereto.
the cathode material is preferably a material having a small work function so that electrons can be easily injected into the organic layer. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; for example, a multilayer structure such as LiF/Al or LiO2/Al, but not limited thereto.
The hole injection layer is a layer for injecting holes from the electrode, and the following compounds are preferable as the hole injection substance: has an ability to transport holes, has a hole injection effect from the anode, has an excellent hole injection effect with respect to the light-emitting layer or the light-emitting material, prevents excitons generated in the light-emitting layer from migrating to the electron injection layer or the electron injection material, and has excellent thin film-forming ability. Preferably, the HOMO (highest occupied molecular orbital) of the hole injecting substance is between the work function of the anode substance and the HOMO of the surrounding organic layer. Specific examples of the hole injecting substance include, but are not limited to, metalloporphyrin (porphyrin), oligothiophene, arylamine-based organic substances, hexanitrile-hexaazatriphenylene-based organic substances, quinacridone-based organic substances, perylene-based organic substances, anthraquinone, polyaniline, and polythiophene-based conductive polymers.
The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light-emitting layer, and the hole transport material is a material that can receive holes from the anode or the hole injection layer and transport the holes to the light-emitting layer. Specific examples thereof include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers in which a conjugated portion and a non-conjugated portion are present simultaneously.
The electron inhibiting layer is a layer provided between the hole transporting layer and the light emitting layer to prevent electrons injected from the cathode from moving to the hole transporting layer without being recombined in the light emitting layer, and is also called an electron blocking layer. The electron inhibiting layer is preferably a material having a lower electron affinity than the electron transporting layer.
The light-emitting substance is a substance that can receive holes and electrons from the hole-transporting layer and the electron-transporting layer, respectively, and combine them to emit light in the visible light region, and is preferably a substance having high quantum efficiency with respect to fluorescence or phosphorescence. As specific examples, there are 8-hydroxyquinoline aluminum complex (Alq 3); a carbazole-based compound; dimeric styryl (dimerized styryl) compounds; BAlq; 10-hydroxybenzoquinoline metal compounds; benzoxazole, benzothiazole and benzimidazole compounds; poly (p-phenylenevinylene) (PPV) based polymers; spiro (spiroo) compounds; polyfluorene, rubrene, and the like, but are not limited thereto.
The light emitting layer may include a host material and a dopant material. As the host material, there are aromatic fused ring derivatives, heterocyclic ring-containing compounds, and the like. Specifically, the aromatic fused ring derivative includes an anthracene derivative, a pyrene derivative, a naphthalene derivative, a pentacene derivative, a phenanthrene compound, a fluoranthene compound, and the like, and the heterocyclic ring-containing compound includes a carbazole derivative, a dibenzofuran derivative, a ladder furan compound, a pyrimidine derivative, and the like, but is not limited thereto.
As the dopant material, there are an aromatic amine derivative, a styrene amine compound, a boron complex, a fluoranthene compound, a metal complex, and the like. Specifically, the aromatic amine derivative is an aromatic fused ring derivative having a substituted or unsubstituted arylamine group, and examples thereof include pyrene, anthracene, diindenopyrene (Periflanthene) having an arylamine group, and the styrylamine compound is a compound in which at least one arylvinyl group is substituted on a substituted or unsubstituted arylamine group, and is substituted or unsubstituted with one or two or more substituents selected from an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamine group. Specific examples thereof include, but are not limited to, styrylamine, styryldiamine, styryltrimethylamine, and styryltretramine. The metal complex includes, but is not limited to, iridium complexes and platinum complexes.
The hole-inhibiting layer is a layer provided between the electron-transporting layer and the light-emitting layer to prevent holes injected from the anode from moving to the electron-transporting layer without being recombined in the light-emitting layer, and is also called a hole-blocking layer. The hole-inhibiting layer is preferably a substance having a large ionization energy. Preferably, a compound represented by the above chemical formula 1 may be included as a substance of the hole inhibiting layer.
The electron transporting layer is a layer that receives electrons from the electron injecting layer and transports the electrons to the light emitting layer, and the electron transporting substance is a substance that can inject electrons from the cathode well and transfer the electrons to the light emitting layer, and a substance having a high electron mobility is preferable. Specific examples thereof include, but are not limited to, Al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic radical compounds, and hydroxyflavone-metal complexes. The electron transport layer may be used with any desired cathode material as used in the art. Examples of suitable cathode substances are, in particular, the customary substances having a low work function and accompanied by an aluminum or silver layer. In particular cesium, barium, calcium, ytterbium and samarium, which are accompanied by an aluminum or silver layer. Preferably, the compound represented by the above chemical formula 1 may be included as a substance of the electron transport layer.
The electron injection layer is a layer for injecting electrons from the electrode, and is preferably a compound of: has an ability to transport electrons, has an electron injection effect from a cathode, has an excellent electron injection effect for a light-emitting layer or a light-emitting material, prevents excitons generated in the light-emitting layer from migrating to a hole-injecting layer, and is excellent in film-forming properties. Specific examples thereof include, but are not limited to, fluorenone, anthraquinone dimethane (Anthraquinodimethane), diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidene methane, anthrone, and derivatives thereof, metal complexes, and nitrogen-containing five-membered ring derivatives. Preferably, the compound represented by the above chemical formula 1 may be included as a substance of the electron injection layer.
Examples of the metal complex include lithium 8-quinolinolato, zinc bis (8-quinolinolato), copper bis (8-quinolinolato), manganese bis (8-quinolinolato), aluminum tris (2-methyl-8-quinolinolato), and gallium tris (8-quinolinolato), bis (10-hydroxybenzo [ h ] quinoline) beryllium, bis (10-hydroxybenzo [ h ] quinoline) zinc, bis (2-methyl-8-quinoline) gallium chloride, bis (2-methyl-8-quinoline) (o-cresol) gallium, bis (2-methyl-8-quinoline) (1-naphthol) aluminum, bis (2-methyl-8-quinoline) (2-naphthol) gallium, and the like, but are not limited thereto.
The organic light emitting element according to the present invention may be a top emission type, a bottom emission type, or a bi-directional emission type depending on the material used.
in addition, the compound represented by the above chemical formula 1 may be included in an organic solar cell or an organic transistor, in addition to the organic light emitting element.
In the following, preferred embodiments are suggested to aid in understanding the present invention. However, the following examples are provided only for easier understanding of the present invention, and the present invention is not limited thereto.
Production example 1: production of Compound 1
After completely dissolving intermediate A-1(9.37g,16.46mmol) and intermediate a-1(2.31g,18.93mmol) in tetrahydrofuran (240ml) in a 500ml round-bottom flask under a nitrogen atmosphere, a 2M aqueous potassium carbonate solution (120ml) was added, tetrakis (triphenylphosphine) palladium (0.57g,0.49mmol) was added, and the mixture was stirred under heating for 3 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 tetrahydrofuran (150ml), whereby compound 1(6.27g, yield 62%) was produced.
MS[M+H]＝612
Production example 2: production of Compound 2
After completely dissolving intermediate A-2(8.26g,14.51mmol) and intermediate a-2(2.87g,16.69mmol) in tetrahydrofuran (240ml) in a 500ml round-bottomed flask under a nitrogen atmosphere, a 2M aqueous potassium carbonate solution (120ml) was added, and after adding tetrakis (triphenylphosphine) palladium (0.50g,0.44mmol), the mixture was stirred under heating for 3 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 ethyl acetate (170ml), whereby compound 2(5.69g, yield 59%) was produced.
MS[M+H]＝662
Production example 3: production of Compound 3
After completely dissolving intermediate A-3(7.49g,12.85mmol) and intermediate a-3(2.54g,14.77mmol) in tetrahydrofuran (240ml) in a 500ml round-bottom flask under a nitrogen atmosphere, a 2M aqueous potassium carbonate solution (120ml) was added, tetrakis (triphenylphosphine) palladium (0.45g,0.39mmol) was added, and the mixture was stirred under heating for 5 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 ethyl acetate (210ml), whereby compound 3(5.33g, yield 63%) was produced.
MS[M+H]＝676
Production example 4: production of Compound 4
After completely dissolving intermediate A-4(6.92g,11.55mmol) and intermediate a-4(2.63g,13.29mmol) in tetrahydrofuran (240ml) in a 500ml round-bottom flask under a nitrogen atmosphere, a 2M aqueous potassium carbonate solution (120ml) was added, tetrakis (triphenylphosphine) palladium (0.40g,0.35mmol) was added, and the mixture was stirred under heating for 2 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 ethyl acetate (250ml), whereby compound 4(6.11g, yield 74%) was produced.
MS[M+H]＝718
Production example 5: production of Compound 5
After completely dissolving intermediate B-1(6.57g,11.55mmol) and intermediate a-5(2.63g,13.28mmol) in tetrahydrofuran (240ml) in a 500ml round-bottom flask under a nitrogen atmosphere, a 2M aqueous potassium carbonate solution (120ml) was added, tetrakis (triphenylphosphine) palladium (0.40g,0.35mmol) was added, and the mixture was stirred under heating 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 ethyl acetate (230ml), whereby compound 5(4.67g, yield 59%) was produced.
MS[M+H]＝688
Production example 6: production of Compound 6
After completely dissolving intermediate B-2(7.11g,12.50mmol) and intermediate a-4(2.85g,14.37mmol) in tetrahydrofuran (240ml) in a 500ml round-bottomed flask under a nitrogen atmosphere, a 2M aqueous potassium carbonate solution (120ml) was added, and after adding tetrakis (triphenylphosphine) palladium (0.43g,0.37mmol), the mixture was stirred under heating for 4 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 ethyl acetate (210ml), whereby compound 6(6.78g, yield 79%) was produced.
MS[M+H]＝688
Production example 7: production of Compound 7
After completely dissolving intermediate B-3(6.77g,10.94mmol) and intermediate a-1(1.53g,12.58mmol) in tetrahydrofuran (240ml) in a 500ml round-bottom flask under a nitrogen atmosphere, a 2M aqueous potassium carbonate solution (120ml) was added, tetrakis (triphenylphosphine) palladium (0.38g,0.33mmol) was added, and the mixture was stirred under heating for 3 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 tetrahydrofuran (210ml), whereby compound 7(5.26g, yield 65%) was produced.
MS[M+H]＝688
Production example 8: production of Compound 8
After completely dissolving intermediate B-4(6.34g,10.24mmol) and intermediate a-2(2.03g,11.78mmol) in tetrahydrofuran (240ml) in a 500ml round-bottom flask under a nitrogen atmosphere, a 2M aqueous potassium carbonate solution (120ml) was added, tetrakis (triphenylphosphine) palladium (0.36g,0.31mmol) was added, and the mixture was stirred under heating for 5 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 tetrahydrofuran (210ml), whereby compound 8(6.13g, yield 76%) was produced.
MS[M+H]＝712
Production example 9: production of Compound 9
After completely dissolving intermediate C-1(8.44g,17.15mmol) and intermediate a-4(3.91g,19.73mmol) in tetrahydrofuran (240ml) in a 500ml round-bottom flask under a nitrogen atmosphere, a 2M aqueous potassium carbonate solution (120ml) was added, tetrakis (triphenylphosphine) palladium (0.59g,0.51mmol) was added, and the mixture was stirred under heating for 4 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 ethyl acetate (220ml), whereby compound 9(7.11g, yield 68%) was produced.
MS[M+H]＝611
Production example 10: production of Compound 10
After completely dissolving intermediate C-2(7.86g,16.01mmol) and intermediate a-3(3.17g,18.41mmol) in tetrahydrofuran (240ml) in a 500ml round-bottomed flask under a nitrogen atmosphere, a 2M aqueous potassium carbonate solution (120ml) was added, and after adding tetrakis (triphenylphosphine) palladium (0.55g,0.48mmol), the mixture was stirred under heating for 3 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 ethyl acetate (230ml), whereby compound 10(7.11g, yield 68%) was produced.
MS[M+H]＝584
Production example 11: production of Compound 11
After completely dissolving intermediate C-3(6.78g,11.94mmol) and intermediate a-2(2.36g,13.73mmol) in tetrahydrofuran (240ml) in a 500ml round-bottom flask under a nitrogen atmosphere, a 2M aqueous potassium carbonate solution (120ml) was added, tetrakis (triphenylphosphine) palladium (0.41g,0.36mmol) was added, and the mixture was stirred under heating for 4 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 ethyl acetate (220ml), whereby compound 11(5.23g, yield 66%) was produced.
MS[M+H]＝661
Production example 12: production of Compound 12
After completely dissolving intermediate C-4(8.29g,14.60mmol) and intermediate a-2(2.89g,16.78mmol) in tetrahydrofuran (240ml) in a 500ml round-bottom flask under a nitrogen atmosphere, a 2M aqueous potassium carbonate solution (120ml) was added, tetrakis (triphenylphosphine) palladium (0.51g,0.44mmol) was added, and the mixture was stirred under heating for 4 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 ethyl acetate (240ml), whereby compound 12(5.34g, yield 55%) was produced.
MS[M+H]＝661
Example 1
The glass substrate coated with an ITO (indium tin oxide) thin film in the above thickness was put in distilled water in which a detergent was dissolved, and washed by ultrasonic waves. At this time, the detergent was prepared by Fischer Co, and the distilled water was filtered twice by a Filter (Filter) manufactured by Millipore Co. The ITO was washed for 30 minutes and then twice with distilled water to perform ultrasonic washing for 10 minutes. After the completion of the distilled water washing, the resultant was ultrasonically washed with solvents of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaning machine. After the substrate was cleaned with oxygen plasma for 5 minutes, the substrate was transported to a vacuum evaporator.
On the ITO transparent electrode as the anode thus prepared, a compound of the following compound HI1 and the compound of the following compound HI2 were thermally vacuum-evaporated at a molar ratio of 98:2 to form a hole injection layer. A compound represented by the following chemical formula HT1 was vacuum-evaporated on the hole injection layer to form a hole transport layer. Next, a compound of EB1 was vacuum-evaporated on the hole transport layer to a film thickness, thereby forming an electron inhibiting layer. Next, a compound represented by the following chemical formula BH and a compound represented by the following chemical formula BD were vacuum-evaporated on the electron-inhibiting layer at a weight ratio of 50:1 to form a light-emitting layer. The compound 1 produced previously was vacuum-deposited on the light-emitting layer to a film thickness to form a hole-inhibiting layer. Next, a compound represented by the following chemical formula ET1 and a compound represented by the following chemical formula LiQ were vacuum-evaporated on the hole-inhibiting layer at a weight ratio of 1:1 to form an electron injecting and transporting layer at a thickness of 1. A cathode is formed by sequentially depositing lithium fluoride (LiF) and aluminum on the electron injection and transport layer in this order.
in the above process, the deposition rate of the organic material was maintained at a rate at which lithium fluoride of the cathode was maintained, and the deposition rate of aluminum was maintained at a rate at which vacuum was maintained at 2X 10-7 to 5X 10-6 Torr during deposition, thereby producing an organic light-emitting device.
Examples 2 to 12
An organic light-emitting device was produced in the same manner as in example 1, except that the compound described in table 1 below was used instead of compound 1.
Comparative examples 1 to 4
An organic light-emitting device was produced in the same manner as in example 1, except that the compound described in table 1 below was used instead of compound 1. The compounds of HB1, HB2, HB3 and HB4 used in table 1 below are as follows.
Examples of the experiments
The results of measuring the voltage, efficiency, color coordinates, and lifetime when a current was applied to the organic light-emitting elements fabricated in examples 1 to 12 and comparative examples 1 to 4 are shown in the following [ table 1 ]. T95 represents the time required for the luminance to decrease from the initial luminance (1600nit) to 95%.
[ TABLE 1]
As shown in table 1 above, in the case of the organic light-emitting devices of examples 1 to 12 produced using the compound of the present invention as a hole-inhibiting layer, the organic light-emitting devices exhibited superior characteristics in terms of efficiency, driving voltage, and/or stability, as compared to the organic light-emitting devices using triazine-based HB1 substituted at the 2-position of the triphenylene nucleus, which has been widely used conventionally, as a hole-inhibiting layer.
The organic light emitting elements of comparative examples 2 to 4, which were manufactured using compounds of HB2, HB3, and HB4 substituted with a triazine group at the 1-position of the triphenylene nucleus and having no substituent at the 3-position as the hole inhibiting layer like the compound of the present invention, were excellent in voltage and efficiency characteristics, but had lifetimes reduced by about 10% to 30% as compared to the lifetimes of examples 1 to 12. It was confirmed that the triazine-based compound substituted at the 1-position of the triphenylene nucleus exhibited low voltage and high efficiency, and the compound had long life characteristics because of increased stability when the aryl substituent was attached to the 3-position as in the present invention.

Claims (8)

1. A compound represented by the following chemical formula 1:
Chemical formula 1
In the chemical formula 1, the metal oxide is represented by,
L is a single bond, a substituted or unsubstituted C6-20 arylene group,
R is substituted or unsubstituted C6-20 aryl,
Each X is independently N or CH, wherein more than one of X is N,
Ar1 and Ar2 are each independently substituted or unsubstituted C6-20 aryl; or a substituted or unsubstituted C2-20 heteroaryl group comprising any one or more selected from N, O and S.
2. The compound of claim 1, wherein L is a single bond, phenylene, biphenylene, naphthylene, phenanthrylene, dimethylfluorenylene, or diphenylfluorenylene.
3. The compound of claim 1, wherein R is phenyl, biphenyl, naphthyl, phenyl substituted with 1 cyano, or 9, 9-dimethyl-9H-fluorenyl.
4. the compound of claim 1, wherein at least one of Ar1 and Ar2 is a substituted or unsubstituted C6-20 aryl or pyridyl.
5. The compound of claim 1, wherein Ar1 and Ar2 are each independently phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, pyridyl, pyridylphenyl, quinolylphenyl, dibenzofuranyl, dibenzothiophenyl, 9-dimethyl-9H-fluorenyl, 9-phenyl-9H-carbazolyl, 9-diphenyl-9H-fluorenyl, 9' -spirobi [ fluorenyl ], phenyl substituted with 1 or 2 cyano groups, biphenyl substituted with 1 or 2 cyano groups, dibenzofuranyl substituted with 1 or 2 phenyl groups, or dibenzothiophenyl substituted with 1 or 2 phenyl groups.
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 1 or more organic layers provided between the first electrode and the second electrode, wherein 1 or more of the organic layers contain the compound according to any one of claims 1 to 6.
8. The organic light-emitting element according to claim 7, wherein the organic layer is an electron injection layer, an electron transport layer, a hole-inhibiting layer, or a light-emitting layer.
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