CN111971273A - Novel compound and organic light emitting device comprising same - Google Patents
Novel compound and organic light emitting device comprising same Download PDFInfo
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- CN111971273A CN111971273A CN201980024892.XA CN201980024892A CN111971273A CN 111971273 A CN111971273 A CN 111971273A CN 201980024892 A CN201980024892 A CN 201980024892A CN 111971273 A CN111971273 A CN 111971273A
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- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/16—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom
- C07D251/18—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom with nitrogen atoms directly attached to the two other ring carbon atoms, e.g. guanamines
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
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- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D405/10—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
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- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
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- H10K85/649—Aromatic compounds comprising a hetero atom
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
Abstract
The invention provides a novel compound and an organic light emitting device using the same.
Description
Technical Field
Cross reference to related applications
The present application claims priority based on korean patent application No. 10-2018-0103626 at 31.8.2018 and korean patent application No. 10-2019-0105960 at 28.8.2019, the entire contents of which are incorporated herein by reference.
The present invention relates to a novel compound and an organic light emitting device comprising the same.
Background
In general, the organic light emitting phenomenon refers to a phenomenon of converting electric energy into light energy using an organic substance. An organic light emitting device 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 device generally has a structure including an anode and a cathode, and an organic layer between the anode and the cathode. In order to improve the efficiency and stability of the organic light emitting device, the 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. In the structure of such an organic light emitting device, 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, and when the injected holes and electrons meet, excitons (exiton) are formed, which emit light when they transition to the ground state again.
For organic materials used for the organic light emitting devices as described above, development of new materials is continuously demanded.
Documents of the prior art
Patent document
(patent document 0001) Korean patent laid-open publication No. 10-2000-0051826
Disclosure of Invention
Problems to be solved
The present invention relates to a novel compound and an organic light emitting device comprising the same.
Means for solving the problems
The present invention provides a compound represented by the following chemical formula 1:
[ chemical formula 1]
In the above-described chemical formula 1,
Q1and Q2Each independently is C6-30An aromatic ring, a cyclic aromatic ring,
n is an integer of 1 to 3,
a and b are each independently an integer of 0 to 3,
x is a single bond, CR3R4、SiR5R6、NR7、O、S、SO2Or a substituent represented by the following chemical formula 2,
[ chemical formula 2]
R1To R7Each independently is hydrogen; deuterium; substituted or unsubstituted C1-60An alkyl group; substituted or unsubstitutedC1-60An alkoxy group; substituted or unsubstituted C6-60An aryl group; substituted or unsubstituted C containing 1 or more heteroatoms selected from N, O and S5-60A heteroaryl group; or combine with an adjacent group to form a ring,
l is a single bond; substituted or unsubstituted C6-60An arylene group; or substituted or unsubstituted C containing 1 or more heteroatoms selected from N, O and S2-60A heteroarylene group, a heteroaryl group,
ar is substituted or unsubstituted C6-60An aryl group; or substituted or unsubstituted C containing 1 or more heteroatoms selected from N, O and S2-60A heteroaryl group; or two (C)6-60Aryl) phosphine oxide group.
In addition, the present invention provides an organic light emitting device, comprising: 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.
Effects of the invention
The compound represented by the above chemical formula 1 may be used as a material of an organic layer of an organic light emitting device in which improvement of efficiency, lower driving voltage, and/or improvement of life span characteristics can be achieved. In particular, the compound represented by the above chemical formula 1 may be used as a material for hole injection, hole transport, hole injection and transport, light emission, electron transport, or electron injection.
Drawings
Fig. 1 illustrates an example of an organic light-emitting device composed of a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4.
Fig. 2 illustrates an example of an organic light-emitting device composed of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light-emitting layer 7, an electron transport layer 8, and a cathode 4.
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 context of the present specification,
represents a bond to other substituents.
In the present specification, the term "substituted or unsubstituted" means substituted with a substituent 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; alkylthio radicals (A), (B), (C), (D), (
alkyl thio xy); arylthio radicals (A), (B), (C
aryl thio xy); alkylsulfonyl (
alkyl sulfoxy); arylsulfonyl (
aryl sulfoxy); a silyl group; a boron group; an alkyl group; a cycloalkyl group; an alkenyl group; an aryl group; aralkyl group; an aralkenyl group; an alkylaryl group; an alkylamino group; an aralkylamino group; a heteroaryl amino group; an arylamine group; an aryl phosphine group; or 1 or more substituents of 1 or more heterocyclic groups containing N, O and S atoms, or substituents formed by connecting 2 or more substituents of 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 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, 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 specifically includes 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, as examples of the halogen group, there are fluorine, chlorine, bromine or 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-, 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-butadienyl, 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 number of carbon atoms of the cycloalkyl group is 3 to 30. 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 aryl is absentThe aryl group 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 aromatic group may be a naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a perylene group,
And a fluorenyl group, 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. In the case where the above-mentioned fluorenyl group is substituted, it may be
And the like. But is not limited thereto.
In the present specification, the heterocyclic group is a heterocyclic group containing 1 or more of O, N, P, Si and S as heteroatoms, and the number of carbon atoms is not particularly limited, but preferably 2 to 60 carbon atoms. Examples of the heterocyclic group include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, and the like,
Azolyl group,
Oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolyl, carbazolyl, benzobenzoxazinyl
Azolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, benzofuranyl, phenanthrolinyl,Different from each other
Oxazolyl, thiadiazolyl, phenothiazinyl, dibenzofuranyl, and the like, but is not limited thereto.
In the present specification, the aryl group in the aralkyl group, aralkenyl group, alkylaryl group, and 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 alkyl group. In the present specification, the heteroaryl group in the heteroarylamine can be applied to the above description about the heterocyclic group. In the present specification, the alkenyl group in the aralkenyl group is the same as exemplified above for 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, a heteroarylene group is a 2-valent group, and in addition to this, the above description about a 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 in addition to this, the above description on the heterocyclic group can be applied.
In the above chemical formula 1, preferably, Q1And Q2May each independently be a benzene or naphthalene ring, more preferably, Q1And Q2May all be benzene rings.
In the above chemical formula 1, preferably, X may be a single bond, C (CH)3)2C (phenyl)2N (phenyl), O, S, SO2Or a substituent represented by the following chemical formula 2:
[ chemical formula 2]
For example, the above chemical formula 1 may be the following chemical formulae 1-1 to 1-7:
[ chemical formula 1-1]
[ chemical formulas 1-2]
[ chemical formulas 1-3]
[ chemical formulas 1 to 4]
[ chemical formulas 1 to 5]
[ chemical formulas 1 to 6]
[ chemical formulas 1 to 7]
In the above chemical formulas 1-1 to 1-7,
R1、R2l, Ar, n, a and b are the same as defined in the above chemical formula 1.
In the above chemical formula 1, preferably, n may be 1.
Generally, the electron mobility of a compound differs depending on the orientation of the molecule in a three-dimensional structure (orientation), and is enhanced in a horizontal structure (horizontal structure). Therefore, when n is 1, the horizontal structure tendency of the molecule is strong, so that the electron mobility can be relatively high.
In the above chemical formula 1, preferably, a and b may both be 0.
Preferably, L may be a single bond, phenylene, biphenyldiyl, naphthalenediyl, furandiyl, thiophenediyl, or pyridinediyl, and more preferably, L may be a single bond, phenylene, biphenyldiyl, or naphthalenediyl.
Preferably, Ar may be phenyl substituted by cyano, -P (O) (phenyl)2Or selected from any of the following groups:
in the above-mentioned group, the group,
L1and L2Each independently is a single bond; substituted or unsubstituted C6-60An arylene group; or substituted or unsubstituted C containing any one or more heteroatoms selected from N, O and S2-60A heteroarylene group, a heteroaryl group,
each X is independently N or C (R)8) But at least one of X is N,
Ar1and Ar2Each independently is hydrogen; substituted or unsubstituted C6-60An aryl group; or substituted or unsubstituted C containing any one or more heteroatoms selected from N, O and S2-60(ii) a heteroaryl group, wherein,
R8each independently hydrogen, deuterium, substituted or unsubstituted C1-60An alkyl group; substituted or unsubstituted C1-60An alkoxy group; substituted or unsubstituted C6-60An aryl group; substituted or unsubstituted C containing 1 or more heteroatoms selected from N, O and S5-60A heteroaryl group.
Preferably, L1And L2May each independently be a single bond, phenylene, biphenyldiyl group, or naphthalenediyl group.
Preferably, Ar1And Ar2Can be each independently hydrogen, phenyl substituted by cyanoBiphenyl, terphenyl, naphthyl, phenanthryl, 9, 10-dimethylphenanthryl, triphenylene, pyridyl, dimethylfluorenyl, dibenzofuranyl, dibenzothienyl, carbazolyl, benzocarbazolyl, phenalenyl, quinolyl, fluoranthenyl, and phenoxenyl
An oxazinyl group, a phenothiazinyl group, a 10-phenylphenazinyl group, or a 9, 9-dimethylazinyl group.
Preferably, Ar may be any one selected from the following groups:
in the above groups, X 'is N or CH, but at least one of X' is N.
For example, the above compound may be selected from the following compounds:
in addition, the compound represented by the above chemical formula 1 can be produced by the method shown in the following reaction formula 1.
[ reaction formula 1]
In the above reaction formula 1, T is halogen, preferably bromine or chlorine, and the definition of other substituents is the same as that described above.
Specifically, the compound represented by the above chemical formula 1 is produced by binding a starting material through a suzuki coupling reaction. Such suzuki coupling reaction is preferably carried out in the presence of a palladium catalyst and a base, and the reactive groups used for the suzuki coupling reaction may be modified according to techniques known in the art. The above-described manufacturing method can be further embodied in the manufacturing examples described later.
In addition, the present invention provides an organic light emitting device comprising the compound represented by the above chemical formula 1. As an example, the present invention provides an organic light emitting device, comprising: 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.
In general, Adamantane (Adamantane) has excellent sublimability due to space size and robustness, has stability of chemical structure, and thus exhibits excellent thermal stability. Thus, the compound represented by the above chemical formula 1 has excellent sublimation property and chemical structure stability by introducing a bulky (bulk) and rigid (rigidy) structure of adamantane, and thus has very excellent thermal stability. Therefore, efficiency and lifespan may be improved when an organic light emitting device including the compound represented by the above chemical formula 1 is manufactured.
The organic layer of the organic light-emitting device of the present invention may have a single-layer structure, or may have a multilayer structure in which 2 or more organic layers are stacked. For example, the organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like as an organic layer. However, the structure of the organic light emitting device is not limited thereto, and a smaller number of organic layers may be included.
In addition, the organic layer may include a hole injection layer, a hole transport layer, or a layer simultaneously performing hole injection and transport, and the hole injection layer, the hole transport layer, or the layer simultaneously performing hole injection and transport may include the compound represented by the above chemical formula 1.
In addition, the organic layer may include a light emitting layer, and the light emitting layer may include the compound represented by the chemical formula 1.
In addition, the organic 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 the chemical formula 1.
In addition, the electron transport layer, the electron injection layer, or the layer simultaneously performing electron transport and electron injection may include the compound represented by the above chemical formula 1.
In addition, the organic layer may include a light emitting layer and an electron transport layer, and the electron transport layer may include a compound represented by the chemical formula 1.
In addition, the organic light emitting device according to the present invention may be an organic light emitting device having a structure (normal type) in which an anode, 1 or more organic layers, and a cathode are sequentially stacked on a substrate. Further, the organic light emitting device according to the present invention may be an inverted (inverted type) organic light emitting device in which a cathode, 1 or more organic layers, and an anode are sequentially stacked on a substrate. For example, a structure of an organic light emitting device according to an embodiment of the present invention is illustrated in fig. 1 and 2.
Fig. 1 illustrates an example of an organic light-emitting device composed of a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4. In the 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 device 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 structure as described above, the compound represented by the above chemical formula 1 may be contained in 1 or more layers among the above hole injection layer, hole transport layer, light emitting layer, and electron transport layer.
The organic light emitting device according to the present invention may be manufactured using materials and methods known in the art, except that 1 or more of the above organic layers include the compound represented by the above chemical formula 1. In addition, when the organic light emitting device 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 device according to the present invention may be manufactured by sequentially stacking 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 display 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 device.
In addition, the compound represented by the above chemical formula 1 may be used not only for forming an organic layer by a vacuum evaporation method but also for forming an organic layer by a solution coating method in the manufacture of an organic light emitting device. 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 device may 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 in order to smoothly inject holes into the organic layer. Specific examples of the anode material include vanadium, chromium and copperMetals such as zinc and gold, or alloys thereof; metal oxides such as zinc oxide, Indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); ZnO-Al or SnO2A combination of a metal such as Sb and an oxide; poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene]Conductive polymers such as (PEDOT), polypyrrole, and polyaniline, but the present invention is not limited thereto.
The cathode material is preferably a material having a small work function in order to easily inject electrons 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, and alloys thereof; LiF/Al or LiO2And a multilayer structure material such as 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: a compound having an ability to transport holes, having an effect of injecting holes from an anode, having an excellent hole injection effect for a light-emitting layer or a light-emitting material, preventing excitons generated in the light-emitting layer from migrating to an electron injection layer or an electron injection material, and having an 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, and is preferably a material having a high mobility to holes. 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 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 a high quantum efficiency with respect to fluorescence or phosphorescence. As a specific example, there is an 8-hydroxyquinoline aluminum complex (Alq)3) (ii) a A carbazole-based compound; dimeric styryl (dimerized styryl) compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo (b) is
Azole, benzothiazole and benzimidazole-based compounds; poly (p-phenylene vinylene) (PPV) polymers; spiro (spiroo) compounds; a polyfluorene; rubrene, etc., but not limited thereto.
The light emitting layer may include a host material and a dopant material. The host material includes aromatic fused ring derivatives, heterocyclic compounds, and the like. Specifically, the aromatic condensed ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and the heterocyclic ring-containing compounds include carbazole derivatives, dibenzofuran derivatives, and ladder-type furan compounds
Pyrimidine derivatives, etc., but are not limited thereto.
As the dopant material, there are an aromatic amine derivative, a styryl 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 arylamino group, and includes pyrene, anthracene, or the like having an arylamino group,
Diindenopyrene, and the like, and styrylamine compounds are compounds in which at least one arylvinyl group is substituted on a substituted or unsubstituted arylamine, and are substituted or unsubstituted with 1 or 2 or more substituents selected from aryl, silyl, alkyl, cycloalkyl, and arylamino groups. Concretely, there are styrylamine and benzeneVinyl diamine, styrene triamine, styrene tetramine, etc., but are not limited thereto. The metal complex includes, but is not limited to, iridium complexes and platinum complexes.
The electron transport layer is a layer that receives electrons from the electron injection layer and transports the electrons to the light-emitting layer, and the electron transport layer is a substance that can favorably receive electrons from the cathode and transfer the electrons to the light-emitting layer, and is preferably a substance having a high mobility to electrons. Specific examples thereof include Al complexes of 8-hydroxyquinoline and Al complexes containing Alq3The complex of (a), an organic radical compound, a hydroxyflavone-metal complex, etc., but are not limited thereto. 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, in each case accompanied by an aluminum or silver layer.
The electron injection layer is a layer for injecting electrons from the electrode, and is preferably a compound of: a compound having an ability to transport electrons, having an effect of injecting electrons from a cathode, having an excellent electron injection effect with respect to a light-emitting layer or a light-emitting material, preventing excitons generated in the light-emitting layer from migrating to a hole-injecting layer, and having an excellent thin-film-forming ability. Specifically, there are fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, and the like,
Azole,
Oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidene methane, anthrone, and the like, and derivatives thereof, metal complex compounds, nitrogen-containing five-membered ring derivatives, and the like, but are not limited thereto.
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 device 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 device.
The production of the compound represented by the above chemical formula 1 and the organic light emitting device comprising the same is specifically described in the following examples. However, the following examples are provided to illustrate the present invention, and the scope of the present invention is not limited thereto.
[ production example ]
Production example 1: production of Compound 1
10g (1 equivalent) of the above-mentioned compound A-1 and 8.3g (1 equivalent) of the above-mentioned compound B-1 were added to tetrahydrofuran (150 mL). After addition of 2M aqueous potassium carbonate (100mL), tetrakis (triphenylphosphine) palladium (0.56g, 0.02 eq), it was stirred and refluxed for 5 hours. The temperature was reduced to normal temperature, and after the reaction was completed, the potassium carbonate solution was removed and the above white solid was filtered. The solid obtained by filtration was washed 2 times with tetrahydrofuran and ethyl acetate, respectively, to produce the above compound 1(11.1g, yield 77%).
MS:[M+H]+＝594
Production example 2: production of Compound 2
10g (1 equivalent) of the above-mentioned compound A-1 and 11.3g (1 equivalent) of the above-mentioned compound B-2 were added to tetrahydrofuran (150 mL). After addition of 2M aqueous potassium carbonate (100mL), tetrakis (triphenylphosphine) palladium (0.56g, 0.02 eq), it was stirred and refluxed for 5 hours. The temperature was reduced to normal temperature, and after the reaction was completed, the potassium carbonate solution was removed and the above white solid was filtered. The solid obtained by filtration was washed 2 times with tetrahydrofuran and ethyl acetate, respectively, to produce the above-mentioned compound 2(13.8g, yield 85%).
MS:[M+H]+＝670
Production example 3: production of Compound 3
10g (1 equivalent) of the above-mentioned compound A-2 and 10.5g (1 equivalent) of the above-mentioned compound B-3 were added to tetrahydrofuran (150 mL). After addition of 2M aqueous potassium carbonate (100mL), tetrakis (triphenylphosphine) palladium (0.56g, 0.02 eq), it was stirred and refluxed for 5 hours. The temperature was reduced to normal temperature, and after the reaction was completed, the potassium carbonate solution was removed and the above white solid was filtered. The solid obtained by filtration was washed 2 times with tetrahydrofuran and ethyl acetate, respectively, to produce the above-mentioned compound 3(11.4g, yield 69%).
MS:[M+H]+＝684
Production example 4: production of Compound 4
10g (1 equivalent) of the above-mentioned compound A-3 and 11.3g (1 equivalent) of the above-mentioned compound B-2 were added to tetrahydrofuran (150 mL). After addition of 2M aqueous potassium carbonate (100mL), tetrakis (triphenylphosphine) palladium (0.56g, 0.02 eq), it was stirred and refluxed for 5 hours. The temperature was reduced to normal temperature, and after the reaction was completed, the potassium carbonate solution was removed and the above white solid was filtered. The solid obtained by filtration was washed 2 times with tetrahydrofuran and ethyl acetate, respectively, to produce the above-mentioned compound 4(10.1g, yield 62%).
MS:[M+H]+＝670
Production example 5: production of Compound 5
10g (1 equivalent) of the above-mentioned compound A-4 and 9.2g (1 equivalent) of the above-mentioned compound B-4 were added to tetrahydrofuran (150 mL). After addition of 2M aqueous potassium carbonate (100mL), tetrakis (triphenylphosphine) palladium (0.54g, 0.02 eq), it was stirred and refluxed for 5 hours. The temperature was reduced to normal temperature, and after the reaction was completed, the potassium carbonate solution was removed and the above white solid was filtered. The solid obtained by filtration was washed 2 times with tetrahydrofuran and ethyl acetate, respectively, to produce the above compound 5(11.1g, yield 72%).
MS:[M+H]+＝661
Production example 6: production of Compound 6
10g (1 equivalent) of the above-mentioned compound A-5 and 8.8g (1 equivalent) of the above-mentioned compound B-5 were added to tetrahydrofuran (150 mL). After addition of 2M aqueous potassium carbonate (100mL), tetrakis (triphenylphosphine) palladium (0.54g, 0.02 eq), it was stirred and refluxed for 5 hours. The temperature was reduced to normal temperature, and after the reaction was completed, the potassium carbonate solution was removed and the above white solid was filtered. The solid obtained by filtration was washed 2 times with tetrahydrofuran and ethyl acetate, respectively, to produce the above-mentioned compound 6(11.3g, yield 81%).
MS:[M+H]+＝599
Production example 7: production of Compound 7
10g (1 equivalent) of the above-mentioned compound A-6 and 7.3g (1 equivalent) of the above-mentioned compound B-6 were added to tetrahydrofuran (150 mL). After addition of 2M aqueous potassium carbonate (100mL), tetrakis (triphenylphosphine) palladium (0.46g, 0.02 eq), it was stirred and refluxed for 5 hours. The temperature was reduced to normal temperature, and after the reaction was completed, the potassium carbonate solution was removed and the above white solid was filtered. The solid obtained by filtration was washed 2 times with tetrahydrofuran and ethyl acetate, respectively, to produce the above-mentioned compound 7(12.0g, yield 85%).
MS:[M+H]+＝710
Production example 8: production of Compound 8
10g (1 equivalent) of the above-mentioned compound A-7 and 8.2g (1 equivalent) of the above-mentioned compound B-7 were added to tetrahydrofuran (150 mL). After addition of 2M aqueous potassium carbonate (100mL), tetrakis (triphenylphosphine) palladium (0.46g, 0.02 eq), it was stirred and refluxed for 5 hours. The temperature was reduced to normal temperature, and after the reaction was completed, the potassium carbonate solution was removed and the above white solid was filtered. The solid obtained by filtration was washed 2 times with tetrahydrofuran and ethyl acetate, respectively, to produce the above-mentioned compound 8(11.4g, yield 73%).
MS:[M+H]+＝708
Production example 9: production of Compound 9
10g (1 equivalent) of the above-mentioned compound A-8 and 9.2g (1 equivalent) of the above-mentioned compound B-8 were added to tetrahydrofuran (150 mL). After addition of 2M aqueous potassium carbonate (100mL) and tetrakis (triphenylphosphine) palladium (0.51g, 0.02 eq), the mixture was stirred and refluxed for 5 hours. The temperature was reduced to normal temperature, and after the reaction was completed, the potassium carbonate solution was removed and the above white solid was filtered. The solid obtained by filtration was washed 2 times with tetrahydrofuran and ethyl acetate, respectively, to produce the above-mentioned compound 9(10.5g, yield 67%).
MS:[M+H]+＝712
Production example 10: production of Compound 10
10g (1 equivalent) of the above-mentioned compound A-9 and 11.3g (1 equivalent) of the above-mentioned compound B-9 were added to tetrahydrofuran (150 mL). After addition of 2M aqueous potassium carbonate (100mL) and tetrakis (triphenylphosphine) palladium (0.51g, 0.02 eq), the mixture was stirred and refluxed for 5 hours. The temperature was reduced to normal temperature, and after the reaction was completed, the potassium carbonate solution was removed and the above white solid was filtered. The solid obtained by filtration was washed 2 times with tetrahydrofuran and ethyl acetate, respectively, to produce the above-mentioned compound 10(12.4g, yield 74%).
MS:[M+H]+＝762
Production example 11: production of Compound 11
10g (1 equivalent) of the above-mentioned compound A-10 and 9.1g (1 equivalent) of the above-mentioned compound B-10 were added to tetrahydrofuran (150 mL). After addition of 2M aqueous potassium carbonate (100mL), tetrakis (triphenylphosphine) palladium (0.40g, 0.02 eq), it was stirred and refluxed for 5 hours. The temperature was reduced to normal temperature, and after the reaction was completed, the potassium carbonate solution was removed and the above white solid was filtered. The solid obtained by filtration was washed 2 times with tetrahydrofuran and ethyl acetate, respectively, to produce the above-mentioned compound 11(10.9g, yield 70%).
MS:[M+H]+＝901
Production example 12: production of Compound 12
10g (1 equivalent) of the above-mentioned compound A-11 and 9.4g (1 equivalent) of the above-mentioned compound B-10 were added to tetrahydrofuran (150 mL). After addition of 2M aqueous potassium carbonate (100mL), tetrakis (triphenylphosphine) palladium (0.40g, 0.02 eq), it was stirred and refluxed for 5 hours. The temperature was reduced to normal temperature, and after the reaction was completed, the potassium carbonate solution was removed and the above white solid was filtered. The solid obtained by filtration was washed 2 times with tetrahydrofuran and ethyl acetate, respectively, to produce the above-mentioned compound 12(13.1g, yield 79%).
MS:[M+H]+＝961
Production example 13: production of Compound 13
10g (1 equivalent) of the above-mentioned compound A-12 and 7.8g (1 equivalent) of the above-mentioned compound B-12 were added to tetrahydrofuran (150 mL). After addition of 2M aqueous potassium carbonate (100mL), tetrakis (triphenylphosphine) palladium (0.40g, 0.02 eq), it was stirred and refluxed for 5 hours. The temperature was reduced to normal temperature, and after the reaction was completed, the potassium carbonate solution was removed and the above white solid was filtered. The solid obtained by filtration was washed 2 times with tetrahydrofuran and ethyl acetate, respectively, to produce the above-mentioned compound 13(10.6g, yield 71%).
MS:[M+H]+＝865
Production example 14: production of Compound 14
10g (1 equivalent) of the above-mentioned compound A-13 and 3.7g (1 equivalent) of the above-mentioned compound B-13 were added to tetrahydrofuran (150 mL). After addition of 2M aqueous potassium carbonate (100mL), tetrakis (triphenylphosphine) palladium (0.40g, 0.02 eq), it was stirred and refluxed for 5 hours. The temperature was reduced to normal temperature, and after the reaction was completed, the potassium carbonate solution was removed and the above white solid was filtered. The solid obtained by filtration was washed 2 times with tetrahydrofuran and ethyl acetate, respectively, to produce the above-mentioned compound 14(9.2g, yield 84%).
MS:[M+H]+＝629
Production example 15: production of Compound 15
10g (1 equivalent) of the above-mentioned compound A-14 and 11.0g (1 equivalent) of the above-mentioned compound B-14 were added to tetrahydrofuran (150 mL). After addition of 2M aqueous potassium carbonate (100mL), tetrakis (triphenylphosphine) palladium (0.49g, 0.02 eq), it was stirred and refluxed for 5 hours. The temperature was reduced to normal temperature, and after the reaction was completed, the potassium carbonate solution was removed and the above white solid was filtered. The solid obtained by filtration was washed 2 times with tetrahydrofuran and ethyl acetate, respectively, to produce the above-mentioned compound 15(14.3g, yield 81%).
MS:[M+H]+＝840
Production example 16: production of Compound 16
10g (1 equivalent) of the above-mentioned compound A-15 and 9.9g (1 equivalent) of the above-mentioned compound B-15(1 equivalent) were added to tetrahydrofuran (150 mL). After addition of 2M aqueous potassium carbonate (100mL), tetrakis (triphenylphosphine) palladium (0.49g, 0.02 eq), it was stirred and refluxed for 5 hours. The temperature was reduced to normal temperature, and after the reaction was completed, the potassium carbonate solution was removed and the above white solid was filtered. The solid obtained by filtration was washed 2 times with tetrahydrofuran and ethyl acetate, respectively, to produce the above-mentioned compound 16(13.0g, yield 79%).
MS:[M+H]+＝785
[ Experimental example ]
< Experimental example 1>
Indium Tin Oxide (ITO) and a process for producing the same
The glass substrate coated with a thin film of (3) is put in distilled water in which a detergent is dissolved, and washed by ultrasonic waves. In this case, the detergent was prepared by Fisher Co, and the distilled water was filtered twice using a Filter (Filter) manufactured by Millipore CoAnd (4) distilled water. After washing ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After the completion of the distilled water washing, the resultant was ultrasonically washed with a solvent of isopropyl alcohol, acetone, or 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 thus prepared, the following compound [ HI-A ] was added]To be provided with
The hole injection layer is formed by thermal vacuum deposition. Sequentially vacuum-depositing hexanitrile Hexaazatriphenylene (HAT) of the following chemical formula on the hole injection layer
And the following compound [ HT-A]
Thereby forming a hole transport layer.
Next, on the hole transport layer, the following compound [ BH]And [ BD ]]At a weight ratio of 25:1, in film thickness
Vacuum evaporation is performed to form a light emitting layer.
On the above light-emitting layer, compound 1 produced in the above example 1 and the following compound [ LiQ ]](8-hydroxyquinoline lithium, lithium) was vacuum-evaporated at a weight ratio of 1:1 to obtain a film
The thickness of (a) forms an electron injection and transport layer. On the above electron injection and transport layer, lithium fluoride (LiF) is sequentially added to
Thickness of aluminum and
the cathode is formed by vapor deposition to a certain thickness.
In the above process, the evaporation rate of the organic material is maintained at 0.4-0.4
Lithium fluoride maintenance of cathode
Deposition rate of (3), aluminum maintenance
The vapor deposition rate of (2), the degree of vacuum of which is maintained at 1X 10 during vapor deposition-7To 5X 10-8And supporting to thereby fabricate an organic light emitting device.
< Experimental examples 2 to 16>
An organic light-emitting device was produced in the same manner as in experimental example 1, except that in experimental example 1, compounds described in table 1 below were used instead of compound 1.
< comparative examples 1 to 6>
An organic light-emitting device was produced in the same manner as in experimental example 1, except that in experimental example 1, compounds described in table 1 below were used instead of compound 1. ET-01 to ET-06 in Table 1 below are shown below.
The organic light-emitting devices manufactured in the above experimental examples and comparative examples using the respective compounds as electron transport layers were controlled at 10mA/cm2The driving voltage and the luminous efficiency were measured at a current density of 20mA/cm2The time required for the initial luminance to reach 98% was measured at the current density of (LT 98). The results are shown in table 1 below.
[ Table 1]
As shown in table 1, it was confirmed that the compound of the present invention exhibits excellent characteristics in efficiency and life as compared with the comparative examples when used as an electron transport layer material. This is because the chemical structure stability of the compound represented by the above chemical formula 1 is increased due to the inclusion of the adamantane structure in the core.
[ description of symbols ]
1: substrate 2: anode
3: light-emitting layer 4: cathode electrode
5: hole injection layer 6: hole transport layer
7: light-emitting layer 8: an electron transport layer.
Claims (12)
1. A compound represented by the following chemical formula 1:
chemical formula 1
Wherein, in the chemical formula 1,
Q1and Q2Each independently is C6-30An aromatic ring, a cyclic aromatic ring,
n is an integer of 1 to 3,
a and b are each independently an integer of 0 to 3,
x is a single bond, CR3R4、SiR5R6、NR7、O、S、SO2Or a substituent represented by the following chemical formula 2,
chemical formula 2
R1To R7Each independently is hydrogen; deuterium; substituted or unsubstituted C1-60An alkyl group; substituted or unsubstituted C1-60An alkoxy group; substituted or unsubstituted C6-60An aryl group; substituted or unsubstituted C containing 1 or more heteroatoms selected from N, O and S5-60A heteroaryl group; or combine with an adjacent group to form a ring,
l is a single bond; substituted or unsubstituted C6-60An arylene group; or substituted or unsubstituted C containing 1 or more heteroatoms selected from N, O and S2-60A heteroarylene group, a heteroaryl group,
ar is substituted or unsubstituted C6-60An aryl group; or substituted or unsubstituted C containing 1 or more heteroatoms selected from N, O and S2-60A heteroaryl group; or two (C)6-60Aryl) phosphine oxide group.
2. The compound of claim 1, wherein Q1And Q2Each independently is a benzene or naphthalene ring.
3. The compound of claim 1, wherein X is a single bond, C (CH)3)2C (phenyl)2N (phenyl), O, S, SO2Or a substituent represented by the following chemical formula 2:
chemical formula 2
4. The compound of claim 1, wherein n is 1.
5. The compound of claim 1, wherein a and b are both 0.
6. The compound of claim 1, wherein L is a single bond, phenylene, biphenyldiyl, naphthalenediyl, furandiyl, thiophenediyl, or pyridinediyl.
7. The compound of claim 1, wherein Ar is phenyl substituted with cyano, -P (O) (phenyl)2Or selected from any of the following groups:
in the context of the group in question,
L1and L2Each independently is a single bond; substituted or unsubstituted C6-60An arylene group; or substituted or unsubstituted C containing any one or more heteroatoms selected from N, O and S2-60A heteroarylene group, a heteroaryl group,
each X is independently N or C (R)8) But at least one of X is N,
Ar1and Ar2Each independently is hydrogen; substituted or unsubstituted C6-60An aryl group; or substituted or unsubstituted C containing any one or more heteroatoms selected from N, O and S2-60(ii) a heteroaryl group, wherein,
R8each independently is hydrogen; deuterium; substituted or unsubstituted C1-60An alkyl group; substituted or unsubstituted C1-60An alkoxy group; substituted or unsubstituted C6-60An aryl group; substituted or unsubstituted C containing 1 or more heteroatoms selected from N, O and S5-60A heteroaryl group.
8. The compound of claim 7, wherein L1And L2Each independently a single bond, phenylene, biphenyldiyl, or naphthalenediyl.
9. The compound of claim 7, wherein Ar1And Ar2Each independently hydrogen, phenyl substituted by cyano, biphenyl, terphenyl, naphthyl, phenanthryl, 9, 10-dimethylphenanthryl, triphenylene, pyridyl, dimethylfluorenyl, dibenzofuranyl, dibenzfuranylBenzothienyl, carbazolyl, benzocarbazolyl, phenalene, quinolyl, fluoranthenyl, and thiophene
An oxazinyl group, a phenothiazinyl group, a 10-phenylphenazinyl group, or a 9, 9-dimethylazinyl group.
10. The compound of claim 1, wherein Ar is any one selected from the group consisting of:
in the context of the group in question,
x 'is N or CH, but at least one of X' is N.
11. The compound according to claim 1, wherein the compound represented by the chemical formula 1 is any one selected from the group consisting of:
12. an organic light emitting device, 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 11.
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| CN113717122A (en) * | 2021-09-17 | 2021-11-30 | 长春海谱润斯科技股份有限公司 | Adamantane spirofluorene derivative and organic electroluminescent device thereof |
| CN113717122B (en) * | 2021-09-17 | 2024-02-02 | 长春海谱润斯科技股份有限公司 | Adamantane spirofluorene derivative and organic electroluminescent device thereof |
| CN115109001A (en) * | 2022-07-26 | 2022-09-27 | 京东方科技集团股份有限公司 | Nitrogen-containing compound and organic electroluminescent device thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| KR20200026124A (en) | 2020-03-10 |
| CN111971273B (en) | 2023-08-18 |
| KR102163070B1 (en) | 2020-10-07 |
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