CN112771029A - 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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- CN112771029A CN112771029A CN201980063033.1A CN201980063033A CN112771029A CN 112771029 A CN112771029 A CN 112771029A CN 201980063033 A CN201980063033 A CN 201980063033A CN 112771029 A CN112771029 A CN 112771029A
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- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
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- 238000011161 development Methods 0.000 description 1
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- 238000003618 dip coating Methods 0.000 description 1
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- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
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- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
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- 125000001425 triazolyl group Chemical group 0.000 description 1
- LALRXNPLTWZJIJ-UHFFFAOYSA-N triethylborane Chemical group CCB(CC)CC LALRXNPLTWZJIJ-UHFFFAOYSA-N 0.000 description 1
- WXRGABKACDFXMG-UHFFFAOYSA-N trimethylborane Chemical group CB(C)C WXRGABKACDFXMG-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- MXSVLWZRHLXFKH-UHFFFAOYSA-N triphenylborane Chemical group C1=CC=CC=C1B(C=1C=CC=CC=1)C1=CC=CC=C1 MXSVLWZRHLXFKH-UHFFFAOYSA-N 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/76—Dibenzothiophenes
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D409/12—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 chain containing hetero atoms as chain links
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- H—ELECTRICITY
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- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
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- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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Abstract
The invention provides a novel compound and an organic light emitting device using the same.
Description
Technical Field
The present invention relates to a novel compound and an organic light emitting device using the same.
Background
Cross reference to related applications
The present application claims priority based on korean patent application No. 10-2018-0166732, 12/20/2018, the entire contents of which are incorporated herein by reference.
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. With the structure of such an organic electroluminescent device, if a voltage is applied between two electrodes, holes are injected from an anode into an organic layer, electrons are injected from a cathode into the organic layer, an exciton (exiton) is formed when the injected holes and electrons meet, and light is emitted when the exciton falls back to a ground state.
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 1) Korean patent laid-open publication No. 10-2013-073537
Disclosure of Invention
Technical subject
The present invention relates to organic light emitting devices comprising novel compounds.
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,
x is S or O, and X is S or O,
L1and L2Each independently being a direct bond, or a substituted or unsubstituted C6-60An arylene group, a cyclic or cyclic alkylene group,
Ar1and Ar2Each independently is substituted or unsubstituted C6-60An aryl group; or substituted or unsubstituted C containing one or more heteroatoms selected from N, O and S5-60(ii) a heteroaryl group, wherein,
R1to R3Each independently hydrogen, or substituted or unsubstituted C1-60An alkyl group, a carboxyl group,
m and n are each independently an integer of 0 to 4,
o is an integer of 0 to 7.
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 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 of the present invention.
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, low 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, or electron suppression.
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, an electron suppression layer 7, a light-emitting layer 3, an electron transport layer 8, an electron injection layer 9, and a cathode 4.
Detailed Description
Hereinafter, the present invention will be described in more detail to assist understanding thereof.
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 sulfo xy); 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; alkylamineA 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, a3, 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-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, 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 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, 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, thiazolyl, isoquinoyl
Azolyl group,
Oxadiazolyl, thiadiazolyl, benzothiazolyl, 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, arylamine group is the same as the above-mentioned examples of the aryl group. In the present specification, the alkyl group in the aralkyl group, the alkylaryl group, and the 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 description about the 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, 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.
The present invention provides a compound represented by the following chemical formula 1:
[ chemical formula 1]
In the above-described chemical formula 1,
x is S or O, and X is S or O,
L1and L2Each independently being a direct bond, or a substituted or unsubstituted C6-60An arylene group, a cyclic or cyclic alkylene group,
Ar1and Ar2Each independently is substituted or unsubstituted C6-60An aryl group; or substituted or unsubstituted C containing one or more heteroatoms selected from N, O and S5-60(ii) a heteroaryl group, wherein,
R1to R3Each independently hydrogen, or substituted or unsubstituted C1-60An alkyl group, a carboxyl group,
m and n are each independently an integer of 0 to 4,
o is an integer of 0 to 7.
Preferably, L1And L2May each independently be a direct bond, phenylene, biphenylene, or naphthylene.
Preferably, Ar1And Ar2May each independently be phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylenyl, dimethylfluorenyl, dibenzylfluorenyl, dibenzofuranyl, dibenzothienyl, carbazolyl, 9-phenyl-9H-carbazolyl.
More preferably, Ar1And Ar2May each independently be any one selected from the following groups:
preferably, R1To R3May each independently be hydrogen or methyl.
Preferably, m, n and o may each independently be 0 or 1.
Preferably, the compound represented by the above chemical formula 1 may be any one selected from the following compounds:
the compound represented by chemical formula 1 according to the present invention may have high efficiency, low driving voltage, high brightness, long life, and the like, as compared to an organic light emitting device using a compound other than the compound having such a structure, by virtue of the structural characteristics that dibenzofuran (dibenzothiophene) and an amine group are bonded at specific positions on a biphenylene bond.
The compound represented by the above chemical formula 1 can be produced by the following reaction formula 1.
[ reaction formula 1]
In the above reaction formula 1, all variables are the same as defined above. The above reaction formula 1 is a reaction of performing a reaction in the presence of a palladium catalyst and a base to produce a compound represented by chemical formula 1 as a suzuki coupling reaction and an amine substitution reaction. 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.
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 device 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, 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 includes the compound represented by the above chemical formula 1.
In addition, the organic layer may include an electron inhibiting layer including the compound represented by the chemical formula 1.
In addition, the organic layer may include a light emitting layer including the compound represented by the chemical formula 1.
In addition, the organic layer includes a hole injection layer, a hole transport layer, an electron suppression layer, and a light emitting layer, and any one or more selected from the hole injection layer, the hole transport layer, and the electron suppression layer may include a compound represented by the above chemical formula 1.
In addition, the electron transport layer, the electron injection layer, or the layer simultaneously performing electron injection and electron transport includes the compound represented by the above chemical formula 1. In particular, the compound represented by chemical formula 1 according to the present invention is excellent in thermal stability, and has a high HOMO level of 6.0eV or more, a high triplet Energy (ET), and hole stability. In addition, when the compound represented by the above chemical formula 1 is used for an organic layer that can simultaneously perform electron injection and electron transport, an n-type dopant used in this field may be mixed and used.
119 additionally, the organic layer may include an emission 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. In addition, 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, an electron suppression layer 7, a light-emitting layer 3, an electron transport layer 8, an electron injection 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 hole injection layer, hole transport layer, electron suppression layer, light emitting layer, electron transport layer, and electron injection 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. This can be produced as follows: 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.
131. the compound represented by the above chemical formula 1 may be used not only for forming an organic layer by a vacuum deposition method but also for forming an organic layer by a solution coating method in the production 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 can be manufactured by depositing a cathode material, an organic 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 metals such as vanadium, chromium, copper, zinc, and gold, and 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 electron inhibiting layer is a layer provided between the hole transporting layer and the light emitting layer in order to prevent electrons injected from the cathode from being transferred to the hole transporting layer without being recombined in the light emitting layer, and is also referred to as an electron blocking layer. In the electron-suppressing layer, a substance having a smaller electron affinity than that of the electron-transporting layer is preferably used.
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 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 onlyAnd is 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: (
) And pyrimidine derivatives, 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. 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 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 Alq3Organic radical compounds, hydroxyl brass-metal complexes, etc., but are not limited thereto. The electron transport layer may be as used in the prior art with any desiredThe cathode material is used together. Examples of suitable cathode substances are, in particular, the usual 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, an effect of injecting electrons from a cathode, an excellent electron injection effect with respect to a light-emitting layer or a light-emitting material, prevention of transfer of excitons generated in the light-emitting layer to a hole-injecting layer, and 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 manufacture of the compound represented by the above chemical formula 1 and the organic light emitting device including 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 of intermediate ]
Production of intermediate A
[ reaction formula A ]
In a 3000mL round-bottomed flask under nitrogen, 2-bromo-4'-chloro-1,1' -biphenyl (2-bromo-4'-chloro-1,1' -biphenyl) (100.0g, 376.01mmol) and dibenzo [ b, d ] furan-4-ylboronic acid (83.72g, 394.81mmol) were completely dissolved in 1400mL of tetrahydrofuran, and then 2M aqueous potassium carbonate (700mL) was added, followed by addition of tetrakis- (triphenylphosphine) palladium (13.04g, 11.28mmol), followed by stirring with heating for 13 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 2400ml of ethyl acetate, thereby producing compound a (87.64g, 66%).
MS[M+H]+＝355
Production of intermediate B
[ reaction formula B ]
In a 3000mL round-bottomed flask under nitrogen, 2-bromo-4'-chloro-1,1' -biphenyl (100.0g, 376.01mmol) and dibenzo [ b, d ] thiophen-4-ylboronic acid (90.02g, 394.81mmol) were completely dissolved in 1400mL of tetrahydrofuran, and then 2M aqueous potassium carbonate (700mL) was added, followed by addition of tetrakis- (triphenylphosphine) palladium (13.04g, 11.28mmol), followed by stirring with heating for 18 hours. After the temperature was lowered to normal temperature, the aqueous layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 2200ml of ethyl acetate, thereby producing compound B (75.49g, 54%).
MS[M+H]+＝371
[ production example ]
Production example 1
[ reaction formula 1-1]
After completely dissolving compound A (8.27g, 23.36mmol) and compound a1(7.65g, 23.83mmol) in 220mL of Xylene (XYLENE) in a 500mL round-bottomed flask under a nitrogen atmosphere, NaOtBu (3.37g, 35.04mmol) was added, Bis (tri-tert-butylphosphine) palladium (0) (Bis (tri-tert-butylphosphine) palladium (0)) (0.12g, 0.23mmol) was added, and the mixture was stirred under heating for 4 hours. After the temperature was lowered to room temperature and the base (base) was removed by filtration (filter), xylene was concentrated under reduced pressure and recrystallized from 250mL of ethyl acetate, thereby producing production example 1(10.57g, yield: 71%).
MS[M+H]+＝640
Production example 2
[ reaction formulae 1-2]
In a 500mL round-bottomed flask under nitrogen atmosphere, after completely dissolving Compound A (8.56g, 24.18mmol) and Compound a2(8.90g, 24.66mmol) in 250mL of xylene, NaOtBu (3.49g, 36.27mmol) was added, bis (tri-tert-butylphosphine) palladium (0) (0.12g, 0.24mmol) was added, and the mixture was stirred under heating for 5 hours. After the temperature was lowered to room temperature and the alkali was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 250mL of ethyl acetate, thereby producing production example 2(7.49g, yield: 46%).
MS[M+H]+＝680
Production example 3
[ reaction formulae 1 to 3]
In a 500mL round-bottomed flask, after completely dissolving compound A (7.46g, 21.07mmol) and compound a3(8.49g, 21.49mmol) in 240mL of xylene under a nitrogen atmosphere, NaOtBu (3.04g, 31.61mmol) was added, bis (tri-tert-butylphosphine) palladium (0) (0.11g, 0.21mmol) was added, and the mixture was stirred under heating for 2 hours. After the temperature was lowered to room temperature and the alkali was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 230mL of tetrahydrofuran, thereby producing production example 3(6.97g, yield: 46%).
MS[M+H]+＝714
Production example 4
[ reaction formulae 1 to 4]
In a 500mL round-bottomed flask, after completely dissolving compound A (6.76g, 19.10mmol) and compound a4(9.45g, 19.48mmol) in 240mL of xylene under a nitrogen atmosphere, NaOtBu (2.75g, 28.64mmol) was added, bis (tri-tert-butylphosphine) palladium (0) (0.10g, 0.19mmol) was added, and the mixture was stirred under heating for 3 hours. After the temperature was lowered to room temperature and the alkali was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 250mL of ethyl acetate, thereby producing production example 4(8.93g, yield: 58%).
MS[M+H]+＝714
Production example 5
[ reaction formulae 1 to 5]
In a 500mL round-bottomed flask under nitrogen atmosphere, after completely dissolving compound A (9.23g, 26.07mmol) and compound a5(6.89g, 26.59mmol) in 260mL of xylene, NaOtBu (3.76g, 39.11mmol) was added, bis (tri-tert-butylphosphine) palladium (0) (0.13g, 0.26mmol) was added, and the mixture was stirred under heating for 2 hours. After the temperature was lowered to room temperature and the alkali was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 240mL of ethyl acetate, thereby producing production example 5(9.23g, yield: 61%).
MS[M+H]+＝740
Production example 6
[ reaction formulae 1 to 6]
In a 500mL round-bottomed flask under nitrogen atmosphere, after completely dissolving compound A (8.59g, 24.27mmol) and compound a6(8.69g, 24.75mmol) in 230mL of xylene, NaOtBu (3.50g, 36.40mmol) was added, bis (tri-tert-butylphosphine) palladium (0) (0.12g, 0.24mmol) was added, and the mixture was stirred under heating for 4 hours. After the temperature was lowered to room temperature and the alkali was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 240mL of ethyl acetate, thereby producing production example 6(8.69g, yield: 53%).
MS[M+H]+＝740
Production example 7
[ reaction formulae 1 to 7]
In a 500mL round-bottomed flask under nitrogen atmosphere, after completely dissolving compound A (7.29g, 20.59mmol) and compound a7(6.70g, 21.01mmol) in 220mL xylene, NaOtBu (2.97g, 30.89mmol) was added, bis (tri-tert-butylphosphine) palladium (0) (0.11g, 0.21mmol) was added, and the mixture was stirred under heating for 3 hours. After the temperature was lowered to room temperature and the alkali was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 250mL of ethyl acetate, thereby producing production example 7(9.13g, yield: 69%).
MS[M+H]+＝674
Production example 8
[ reaction formulae 1 to 8]
In a 500mL round-bottomed flask under nitrogen atmosphere, after completely dissolving Compound A (6.87g, 19.41mmol) and Compound a8(7.86g, 19.79mmol) in 250mL xylene, NaOtBu (2.80g, 29.11mmol) was added, bis (tri-tert-butylphosphine) palladium (0) (0.10g, 0.19mmol) was added, and the mixture was stirred under heating for 3 hours. After the temperature was lowered to room temperature and the alkali was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 210mL of ethyl acetate, thereby producing production example 8(10.09g, yield: 73%).
MS[M+H]+＝716
Production example 9
[ reaction formulae 1 to 9]
In a 500mL round-bottomed flask under nitrogen atmosphere, after completely dissolving compound B (4.97g, 13.43mmol) and compound a9(5.44g, 13.70mmol) in 240mL xylene, NaOtBu (1.94g, 20.15mmol) was added, bis (tri-tert-butylphosphine) palladium (0) (0.07g, 0.13mmol) was added, and the mixture was stirred under heating for 5 hours. After the temperature was lowered to room temperature and the alkali was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 270mL of ethyl acetate, thereby producing production example 9(7.13g, yield: 73%).
MS[M+H]+＝732
Production example 10
[ reaction formulae 1 to 10]
After completely dissolving compound B (6.71g, 18.14mmol) and compound a10(5.94g, 18.50mmol) in 250mL of xylene in a 500mL round-bottomed flask under a nitrogen atmosphere, NaOtBu (2.61g, 27.20mmol) was added, bis (tri-tert-butylphosphine) palladium (0) (0.09g, 0.18mmol) was added, and the mixture was stirred under heating for 4 hours. After the temperature was lowered to room temperature and the alkali was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 230mL of ethyl acetate, thereby producing production example 10(6.34g, yield: 53%).
MS[M+H]+＝766
Production example 11
[ reaction formulae 1 to 11]
In a 500mL round-bottomed flask under nitrogen atmosphere, after completely dissolving compound B (7.11g, 19.22mmol) and compound a11(6.76g, 19.60mmol) in 260mL of xylene, NaOtBu (2.77g, 28.82mmol) was added, bis (tri-tert-butylphosphine) palladium (0) (0.10g, 0.19mmol) was added, and the mixture was stirred under heating for 3 hours. After the temperature was lowered to room temperature and the alkali was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 230mL of acetone, thereby producing production example 11(8.23g, yield: 63%).
MS[M+H]+＝766
Production example 12
[ reaction formulae 1 to 12]
After completely dissolving compound B (6.55g, 17.70mmol) and compound a12(7.39g, 18.06mmol) in 280mL of xylene in a 500mL round-bottomed flask under a nitrogen atmosphere, NaOtBu (2.55g, 26.55mmol) was added, bis (tri-tert-butylphosphine) palladium (0) (0.09g, 0.18mmol) was added, and the mixture was stirred under heating for 5 hours. After the temperature was lowered to room temperature and the alkali was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 240mL of acetone, thereby producing production example 12(9.11g, yield: 69%).
MS[M+H]+＝744
Production example 13
[ reaction formulae 1 to 13]
In a 500mL round-bottomed flask under nitrogen atmosphere, after completely dissolving compound B (7.26g, 19.62mmol) and compound a13(5.38g, 20.01mmol) in 260mL of xylene, NaOtBu (2.83g, 29.43mmol) was added, bis (tri-tert-butylphosphine) palladium (0) (0.10g, 0.20mmol) was added, and the mixture was stirred under heating for 5 hours. After the temperature was lowered to room temperature and the alkali was removed by filtration, xylene was concentrated under reduced pressure and recrystallized from 230mL of acetone, thereby producing production example 13(7.36g, yield: 62%).
MS[M+H]+＝604
[ examples and comparative examples ]
Examples 1 to 1
Indium Tin Oxide (ITO) and a process for producing the same
The glass substrate coated to a thin film thickness of (2) is put in distilled water in which a detergent is dissolved, and washed by ultrasonic waves. In this case, the detergent used was a product of fisher (Fischer Co.) and the distilled water used was distilled water filtered twice with a filter manufactured by Millipore Co. 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 as an anode, the compound HI1 and the compound HI2 were added so that the ratio was 98:2 (molar ratio)
The hole injection layer is formed by thermal vacuum deposition. A compound represented by the following chemical formula HT1 (II)
) Vacuum evaporation is performed to form a hole transport layer. Then, on the hole transport layer, the film thickness
The compound of production example 1 was vacuum-evaporated to form an electron-inhibiting layer. Next, the electron inhibiting layer is formed on the substrate to a film thickness
A compound represented by the following chemical formula BH and a compound represented by the following chemical formula BD are subjected to vacuum evaporation at a weight ratio of 25:1 to form a light-emitting layer. On the light-emitting layer, the thickness of the film
The compound represented by the following chemical formula HB1 was vacuum-evaporated to form a hole blocking layer. Next, on the hole blocking layer, a compound represented by the following chemical formula ET1 and a compound represented by the following chemical formula LiQ were vacuum-evaporated at a weight ratio of 1:1 to form a hole blocking layer
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
is deposited to form a cathode.
In the above process, the evaporation speed of the organic material is maintained
Lithium fluoride maintenance of cathode
Deposition rate of (3), aluminum maintenance
The vapor deposition rate of (2) is maintained at a vacuum degree of 2X 10 during vapor deposition-7～5×？10-6And (4) supporting.
Examples 1-2 to examples 1-13
An organic light-emitting device was produced in the same manner as in example 1-1 above, except that the compound described in table 1 below was used instead of the compound of production example 1.
Comparative examples 1-1 to 1-4
An organic light-emitting device was produced in the same manner as in example 1-1 above, except that the compound described in table 1 below was used instead of the compound of production example 1. The compounds of EB1, EB2, EB3 and EB4 used in table 1 below are shown below.
Experimental example 1
When a current was applied to the organic light emitting devices manufactured in the above examples and comparative examples, the voltage, efficiency, color coordinates, and lifetime were measured, and the results are shown in table 1 below. T95 refers to the time required for the luminance to decrease from the initial luminance (1600 nits) to 95%.
[ TABLE 1]
As shown in table 1 above, it was confirmed that the organic light emitting device using the compound of the present invention as an electron inhibiting layer exhibited excellent characteristics in terms of efficiency, driving voltage and stability of the organic light emitting device.
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: electron transport layer
9: an electron injection layer.
Claims (7)
1. A compound represented by the following chemical formula 1:
chemical formula 1
Wherein, in the chemical formula 1,
x is S or O, and X is S or O,
L1and L2Each independently being a direct bond, or a substituted or unsubstituted C6-60An arylene group, a cyclic or cyclic alkylene group,
Ar1and Ar2Each independently is substituted or unsubstituted C6-60An aryl group; or substituted or unsubstituted C containing one or more heteroatoms selected from N, O and S5-60(ii) a heteroaryl group, wherein,
R1to R3Each independently hydrogen, or substituted or unsubstituted C1-60An alkyl group, a carboxyl group,
m and n are each independently an integer of 0 to 4, and
o is an integer of 0 to 7.
2. The compound of claim 1, wherein L1And L2Each independently a direct bond, phenylene, biphenylene, or naphthylene.
3. The compound of claim 1, wherein Ar1And Ar2Each independently is phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, triphenylenyl, dimethylfluorenyl, dibenzylfluorenyl, dibenzofuranyl, dibenzothienyl, carbazolyl, or 9-phenyl-9H-carbazolyl.
4. The compound of claim 1, wherein R1To R3Each independently hydrogen or methyl.
5. The compound of claim 1, wherein m, n, and o are each independently 0 or 1.
6. The compound according to claim 1, wherein the compound represented by the chemical formula 1 is any one selected from the group consisting of:
7. an organic light emitting device, comprising: a first electrode, a second electrode provided so as to face the first electrode, and 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.
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| PCT/KR2019/014617 WO2020130327A1 (en) | 2018-12-20 | 2019-10-31 | Novel compound and organic light-emitting device using same |
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| KR20200009971A (en) * | 2018-07-18 | 2020-01-30 | 주식회사 동진쎄미켐 | Novel compound and organic electroluminescent divice including the same |
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