CN111051292B - Heterocyclic compound and organic light-emitting device using same - Google Patents
Heterocyclic compound and organic light-emitting device using same Download PDFInfo
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- CN111051292B CN111051292B CN201880058690.2A CN201880058690A CN111051292B CN 111051292 B CN111051292 B CN 111051292B CN 201880058690 A CN201880058690 A CN 201880058690A CN 111051292 B CN111051292 B CN 111051292B
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- 150000002391 heterocyclic compounds Chemical class 0.000 title abstract description 7
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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
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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 group [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
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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
- 238000001771 vacuum deposition Methods 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
- 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
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 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
- 239000011787 zinc oxide Substances 0.000 description 1
Images
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-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/96—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings spiro-condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—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
- 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
- C07D405/10—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
-
- 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
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- 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
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- 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
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
-
- 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
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/18—Carrier blocking layers
-
- 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
- H10K50/80—Constructional details
- H10K50/85—Arrangements for extracting light from the devices
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The present invention provides a novel heterocyclic 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. 10-2017-0166760, 12/6/2017, the entire contents of the disclosure of which are incorporated as part of the present specification.
The present invention relates to a heterocyclic compound and an organic light-emitting device including 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, fast response time, and excellent brightness, driving voltage, and response speed characteristics, and thus a great deal of research is being conducted.
The organic light emitting device generally has a structure including an anode and a cathode and an organic layer between the anode and the cathode. In order to improve 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 a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, or the like. With such a structure of an organic light emitting device, if a voltage is applied between both electrodes, holes are injected from an anode to an organic layer, electrons are injected from a cathode to the organic layer, excitons (exiton) are formed when the injected holes and electrons meet, and light is emitted when the excitons re-transition to a ground state.
As for the organic matter used for the organic light emitting device as described above, development of new materials is continuously demanded.
[ Prior Art literature ]
Patent document 1: korean patent laid-open No. 10-2000-0051826
Disclosure of Invention
Technical problem
The present invention relates to a heterocyclic compound and an organic light-emitting device including the same.
Solution to the problem
The present invention provides a compound represented by the following chemical formula 1.
[ chemical formula 1]
In the above-mentioned chemical formula 1,
L 1 is a bond, substituted or unsubstituted C 6-60 Arylene, or substituted or unsubstituted C comprising more than 1 of N, O and S 2-60 A heteroarylene group,
X 1 、X 2 and X 3 Each of which is independently N or CH,
Ar 1 and Ar is a group 2 Each independently is a substituted or unsubstituted C 6-60 Aryl, or substituted or unsubstituted C containing more than 1 of N, O and S 2-60 Heteroaryl groups.
In addition, the present invention provides an organic light emitting device, comprising: a first electrode, a second electrode provided opposite to the first electrode, and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers contains a compound represented by the chemical formula 1.
Effects of the invention
The compound represented by the above chemical formula 1 can 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 lifetime 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, an organic layer 3, and a cathode 4.
Fig. 2 illustrates an example of an organic light-emitting device constituted by a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light-emitting layer 7, a hole blocking layer 8, an electron transport layer 9, an electron injection layer 10, and a cathode 4.
Detailed Description
In the following, the invention will be described in more detail in order to aid understanding thereof.
In the present description of the invention,
refers to and is connected with otherA bond to which the substituent is attached.
In the present specification, the term "substituted or unsubstituted" means that it is 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 group [ ]
Alkylthio) is described; arylthio (/ ->
Aryl thio xy); alkylsulfonyl [ ]
Alkylsulfoxy); arylsulfonyl (+)>
Aryl sulfoxy); a silyl group; a boron base; an alkyl group; cycloalkyl; alkenyl groups; an aryl group; an aralkyl group; aralkenyl; alkylaryl groups; an alkylamino group; an aralkylamine group; heteroaryl amine groups; an arylamine group; aryl phosphino; or a substituent comprising N, O and 1 or more substituents in a heterocyclic group comprising 1 or more of S atoms, or a substituent which is bonded to 2 or more substituents in the above-exemplified substituents. For example, the "substituent in which 2 or more substituents are linked" may be a biphenyl group. That is, biphenyl may be aryl 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 the number of carbon atoms 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, 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 of the imide group is not particularly limited, but the number of carbon atoms is preferably 1 to 25. Specifically, the compound may have the following structure, but is not limited thereto.
In the present specification, the silyl group specifically includes, but is not limited to, trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like.
In the present specification, the boron group specifically includes trimethylboron group, triethylboron group, t-butyldimethylboroyl group, triphenylboron group, phenylboron group, and the like, but is not limited thereto.
In the present specification, examples of the halogen group include fluorine, chlorine, bromine and iodine.
In the present specification, the alkyl group may be a straight chain or branched chain, 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 above alkyl group has 1 to 10 carbon atoms. According to another embodiment, the above alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group include, but are not limited to, methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, t-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, t-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, t-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2-dimethylheptyl, 1-ethyl-propyl, 1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl and the like.
In the present specification, the alkenyl group may be a straight chain or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples thereof include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-methyl-1-butenyl, 1, 3-butadienyl, allyl, 1-phenylene1-yl, 2-diphenylethylene1-yl, 2-phenyl-2- (naphthalen-1-yl) ethylene1-yl, 2-bis (diphenyl-1-yl) ethylene1-yl, stilbene, styryl and the like, but are not limited thereto.
In the present specification, cycloalkyl is not particularly limited, but cycloalkyl having 3 to 60 carbon atoms is preferable. According to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, there are 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, but the present invention is not limited thereto.
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. With respect to the above mentioned aromatic groupsThe aryl group may be a monocyclic aryl group, such as phenyl, biphenyl, and terphenyl, but is not limited thereto. The polycyclic aryl group may be naphthyl, anthryl, phenanthryl, pyrenyl, perylenyl, and the like,
A group, a fluorenyl group, etc., but is not limited thereto.
In this specification, a 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 fluorenyl group is substituted, it may be
Etc. However, the present invention 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 a hetero atom, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60. Examples of the heterocyclic group include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, and the like,
Azolyl, (-) -and (II) radicals>
Diazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzo->
Oxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothiophenyl, benzofuranyl, phenanthroline (phenanthrinyl), iso>
Oxazolyl, thiadiazolyl, phenothiazinyl, dibenzofuranyl, and the like, but are not limited thereto.
In the present specification, the aryl group in the aralkyl group, the aralkenyl group, the alkylaryl group, and the arylamine group is the same as the above-mentioned examples of the aryl group. In the present specification, the alkyl group in the aralkyl group, alkylaryl group, or alkylamino group is the same as the above-mentioned examples of the alkyl group. In this specification, the heteroaryl group in the heteroaryl amine may be as described above with respect to the heterocyclic group. In this specification, alkenyl groups in aralkenyl groups are the same as the examples of alkenyl groups described above. In this specification, arylene is a 2-valent group, and the above description of aryl can be applied thereto. In this specification, the heteroarylene group is a 2-valent group, and the above description of the heterocyclic group can be applied thereto. In the present specification, the hydrocarbon ring is not a 1-valent group, but a combination of 2 substituents, and the above description of the aryl group or cycloalkyl group can be applied. In this specification, the heterocyclic ring is not a 1-valent group, but a combination of 2 substituents, and the above description of the heterocyclic group can be applied thereto.
In the above chemical formula 1, according to L 1 The above chemical formula 1 may be represented by the following chemical formulas 2 to 4:
[ chemical formula 2]
[ chemical formula 3]
[ chemical formula 4]
Preferably, the above X 1 、X 2 And X 3 At least 2 of them are N.
In addition, preferably L 1 Is a bond, or is selected from any of the following structures.
More preferably, the L 1 Is a bond or phenylene.
In addition, preferably Ar 1 And Ar is a group 2 Each independently is selected from any one of the following structures.
Representative examples of the compounds represented by the above chemical formula 1 are shown below:
the compound represented by the above chemical formula 1 can be produced by the following production method represented by the following reaction formula 1 or reaction formula 2.
[ reaction type 1]
[ reaction type 2]
In the above reaction formulae 1 and 2, L 1 、X 1 、X 2 、X 3 、Ar 1 And Ar is a group 2 As defined above, X is halogen, preferably X is chlorine or bromine.
The above equations 1 and 2 are suzuki coupling reactions, preferably carried out in the presence of a palladium catalyst and a base, and the reactive groups for the suzuki coupling reactions may be varied according to techniques known in the art.
The above-described production method can be more specifically described in the production example described later.
In addition, the present invention provides an organic light emitting device including the compound represented by the above chemical formula 1. As one example, the present invention provides an organic light emitting device, comprising: a first electrode, a second electrode provided opposite to the first electrode, and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers contains 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, a hole blocking layer, an electron transport layer, an electron injection layer, and the like as the organic layer. However, the structure of the organic light emitting device is not limited thereto, and may include a smaller number of organic layers.
The organic layer may include a hole injection layer, a hole transport layer, or a layer that performs hole injection and transport simultaneously, and the hole injection layer, the hole transport layer, or the layer that performs hole injection and transport simultaneously may include a compound represented by chemical formula 1.
The organic layer may include a light-emitting layer including a compound represented by chemical formula 1.
The organic layer may include a hole blocking layer, and the hole blocking layer may include a compound represented by chemical formula 1.
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 a compound represented by chemical formula 1.
The electron transport layer, the electron injection layer, or the layer in which both electron transport and electron injection are performed contains the compound represented by the chemical formula 1.
The organic layer may include a light-emitting layer and an electron-transporting layer, and the electron-transporting layer may include a compound represented by 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, one 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 organic light emitting device of a reverse structure (inverted type) in which a cathode, one 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, an organic layer 3, and a cathode 4. In the structure as described above, the compound represented by the above chemical formula 1 may be contained in the above organic layer.
Fig. 2 illustrates an example of an organic light-emitting device constituted by a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light-emitting layer 7, a hole blocking layer 8, an electron transport layer 9, an electron injection layer 10, and a cathode 4. In the structure described above, the compound represented by the above chemical formula 1 may be contained in one or more of the above hole injection layer, hole transport layer, light emitting layer, hole blocking layer, electron transport layer, and electron injection layer, and preferably may be contained in one or more of the hole blocking 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 one or more of the organic layers contains the compound represented by chemical formula 1. In addition, in the case where the organic light emitting device includes a plurality of organic layers, the organic layers may be formed of the same material or different materials.
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 manufactured as follows: PVD (physicalVapor Deposition) such as sputtering (sputtering) or electron beam evaporation (physical vapor deposition) is used to deposit a metal or a metal oxide having conductivity or an alloy thereof on a substrate to form an anode, then an organic layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer is formed on the anode, and then a substance that can be used as a cathode is deposited on the organic layer. In addition to this method, an organic light-emitting device may be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate.
In addition, the compound represented by the above chemical formula 1 may be used not only in a vacuum deposition method but also in a solution coating method to form an organic layer 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, spray coating, roll coating, and the like, but is not limited thereto.
In addition to these methods, an organic light-emitting device can be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate (WO 2003/012890). However, the manufacturing method is not limited thereto.
As an example, the first electrode may be an anode, the second electrode may be a cathode, or the first electrode may be a cathode, and the second electrode may be an anode.
As the anode material, a material having a large work function is generally preferable in order to allow holes to be smoothly injected 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 SNO 2 A combination of metals such as Sb and the like and oxides; poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene](PEDOT), polypyrrole andconductive polymers such as polyaniline, etc., but are not limited thereto.
As the cathode material, a material having a small work function is generally preferred in order to facilitate injection of 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 LiO 2 And/or Al, but is not limited thereto.
The hole injection layer is a layer that injects holes from an electrode, and the following compounds are preferable as the hole injection substance: the light-emitting device has a hole transporting capability, a hole injecting effect from an anode, an excellent hole injecting effect for a light-emitting layer or a light-emitting material, prevention of migration of excitons generated in the light-emitting layer to the electron injecting layer or the electron injecting material, and an excellent thin film forming capability. The HOMO (highest occupied molecular orbital ) of the hole-injecting substance is preferably between the work function of the anode substance and the HOMO of the surrounding organic layer. Specific examples of the hole injection substance include, but are not limited to, metalloporphyrin (porphyrin), oligothiophenes, arylamine-based organic substances, hexanitrile hexaazabenzophenanthrene-based organic substances, quinacridone-based organic substances, perylene-based organic substances, anthraquinones, polyaniline and polythiophene-based conductive polymers.
The hole-transporting layer is a layer that receives holes from the hole-injecting layer and transports the holes to the light-emitting layer, and a hole-transporting substance that can receive holes from the anode or the hole-injecting layer and transfer the holes to the light-emitting layer is preferable, and a substance having a large mobility to the holes is preferable. Specific examples include, but are not limited to, arylamine-based organic substances, conductive polymers, and block copolymers having both conjugated and unconjugated portions.
The light-emitting substance is a substance capable of receiving holes and electrons from the hole-transporting layer and the electron-transporting layer, respectively, and combining them to emit light in the visible light region, and preferably has high quantum efficiency for fluorescence or phosphorescence. As a specific example, there is 8-hydroxyquinoline aluminum complex (Alq 3 ) The method comprises the steps of carrying out a first treatment on the surface of the Carbazole-based compounds; dimeric styryl (dimerized styryl) compounds; BAlq; 10-hydroxybenzoquinoline metal compounds; benzo (E) benzo (E
Azole, benzothiazole, and benzimidazole compounds; poly (p-phenylene vinylene) (PPV) based polymers; spiro (spiro) compounds; polyfluorene, rubrene, and the like, but is not limited thereto.
The light emitting layer may include a host material and a dopant material. The host material includes aromatic condensed ring derivatives, heterocyclic compounds, and the like. Specifically, examples of the aromatic condensed ring derivative include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and examples of the heterocyclic compound include carbazole derivatives, dibenzofuran derivatives, and ladder-type furan compounds
Pyrimidine derivatives, etc., but are not limited thereto.
Examples of the dopant material include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, the aromatic amine derivative is an aromatic condensed ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene having an arylamino group,
Bisindenopyrene (perillanthene), and the like, the styrylamine compound is a compound in which at least one aryl vinyl group is substituted on a substituted or unsubstituted aryl amine, and is substituted or unsubstituted with 1 or 2 or more substituents selected from the group consisting of aryl, silyl, alkyl, cycloalkyl, and arylamino groups. Specifically, there are styrylamine, styrylenediamine, styrylenetriamine, styrylenetetramine, and the like, but the present invention is not limited thereto. The metal complex includes, but is not limited to, iridium complex, platinum complex, and the like.
The electron transport layer is used for receiving electrons from the electron injection layer and transmitting electronsThe electron transporting substance is a substance that can well receive electrons from the cathode and transfer them to the light-emitting layer, and is suitable for a substance having a large mobility of electrons. As a specific example, there are Al complexes of 8-hydroxyquinoline containing Alq 3 But not limited to, complexes of (c) and (d), organic radical compounds, hydroxyflavone-metal complexes, and the like. The electron transport layer may be used with any desired cathode material as used in the art. In particular, examples of suitable cathode materials are the usual materials having a low work function accompanied by an aluminum layer or a silver layer. In particular cesium, barium, calcium, ytterbium and samarium, in each case accompanied by an aluminum layer or a silver layer.
The electron injection layer is a layer that injects electrons from an electrode, and is preferably a compound as follows: has an electron transporting ability, an electron injecting effect from a cathode, an excellent electron injecting effect to a light emitting layer or a light emitting material, prevents excitons generated in the light emitting layer from migrating to a hole injecting layer, and has an excellent thin film forming ability. Specifically, fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, and the like,
Azole,/->
Examples of the organic compound include, but are not limited to, diazoles, triazoles, imidazoles, perylenetetracarboxylic acids, fluorenylenemethanes, anthrones, and derivatives thereof, metal complexes, and nitrogen-containing five-membered ring derivatives.
Examples of the metal complex include, but are not limited to, lithium 8-hydroxyquinoline, zinc bis (8-hydroxyquinoline), copper bis (8-hydroxyquinoline), manganese bis (8-hydroxyquinoline), aluminum tris (2-methyl-8-hydroxyquinoline), gallium tris (8-hydroxyquinoline), beryllium bis (10-hydroxybenzo [ h ] quinoline), zinc bis (10-hydroxybenzo [ h ] quinoline), gallium chloride bis (2-methyl-8-quinoline) (o-cresol) gallium, aluminum bis (2-methyl-8-quinoline) (1-naphthol), gallium bis (2-methyl-8-quinoline) (2-naphthol).
The organic light emitting device according to the present invention may be of a top emission type, a bottom emission type, or a bi-directional emission type, depending on the materials 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 an organic light emitting device.
The production 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 given by way of illustration of the present invention, and the scope of the present invention is not limited thereto.
Production example 1
After compound A (8.80 g,22.00 mmol) and compound a1 (9.32 g,24.20 mmol) were completely dissolved in 220ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate solution (110 ml) was added, and tetrakis (triphenylphosphine) palladium (0.76 g,0.66 mmol) was added, followed by stirring with heating for 2 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, concentration was performed under reduced pressure, and recrystallization was performed with 200ml of tetrahydrofuran, whereby production example 1 (12.27 g, 80%) was produced.
MS[M+H] + ＝639
Production example 2
After compound A (8.80 g,22.00 mmol) and compound a2 (9.32 g,24.20 mmol) were completely dissolved in 200ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate solution (110 ml) was added, tetrakis (triphenylphosphine) palladium (0.76 g,0.66 mmol) was added, and then heated and stirred for 3 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, concentration was performed under reduced pressure, and recrystallization was performed with 200ml of ethyl acetate, whereby production example 2 (10.89 g, 71%) was produced.
MS[M+H] + ＝639
Production example 3
A complete solution of compound A (7.34 g,20.00 mmol) and compound a3 (7.75 g,22.00 mmol) in 220ml of tetrahydrofuran was added to a 500ml round bottom flask under nitrogen atmosphere, and after adding 2M aqueous potassium carbonate (100 ml), tetrakis (triphenylphosphine) palladium (0.46 g,0.40 mmol) was heated and stirred for 2 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, concentration was performed under reduced pressure, and recrystallization was performed with 150ml of ethyl acetate, whereby production example 3 (9.58 g, 68%) was produced.
MS[M+H] + ＝638
Production example 4
After compound A (7.34 g,20.00 mmol) and compound a4 (9.44 g,22.00 mmol) were completely dissolved in 180ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate solution (100 ml) was added, and tetrakis (triphenylphosphine) palladium (0.59 g,0.50 mmol) was added, followed by stirring with heating for 2 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, concentration was performed under reduced pressure, and recrystallization was performed with 100ml of tetrahydrofuran, whereby production example 4 (8.45 g, 59%) was produced.
MS[M+H] + ＝715
Production example 5
After compound B (9.17 g,20.00 mmol) and compound a5 (5.26 g,22.00 mmol) were completely dissolved in 200ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate (100 ml) was added, and bis (tri-t-butylphosphine) palladium (0.23 g,0.20 mmol) was added, followed by stirring with heating for 4 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, concentration was performed under reduced pressure, and recrystallization was performed with 150ml of ethyl acetate, whereby production example 5 (10.36 g, 81%) was produced.
MS[M+H] + ＝563
Production example 6
After compound C (7.34 g,20.00 mmol) and compound a6 (7.77 g,22.00 mmol) were completely dissolved in 200ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate (100 ml) was added, and bis (tri-t-butylphosphine) palladium (0.23 g,0.20 mmol) was added, followed by stirring with heating for 2 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, concentration was performed under reduced pressure, and recrystallization was performed with 150ml of ethyl acetate, whereby production example 6 (10.24 g, 80%) was produced.
MS[M+H] + ＝639
PREPARATION EXAMPLE 7
After compound C (7.34 g,20.00 mmol) and compound a7 (8.87 g,22.00 mmol) were completely dissolved in 250ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate (125 ml) was added, and bis (tri-t-butylphosphine) palladium (0.60 g,0.50 mmol) was added, followed by stirring with heating for 3 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, concentration was performed under reduced pressure, and recrystallization was performed with 50ml of ethyl acetate, whereby production example 7 (12.42 g, 90%) was produced.
MS[M+H] + ＝689
Production example 8
After compound D (9.17 g,20.00 mmol) and compound a8 (7.56 g,22.00 mmol) were completely dissolved in 200ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate (100 ml) was added, and bis (tri-t-butylphosphine) palladium (0.60 g,0.50 mmol) was added, followed by stirring with heating for 3 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, concentration was performed under reduced pressure, and recrystallization was performed with 200ml of ethyl acetate, whereby production example 8 (9.21 g, 72%) was produced.
MS[M+H] + ＝639
Production example 9
After compound D (9.17 g,20.00 mmol) and compound a9 (4.79 g,8.37 mmol) fmf were completely dissolved in 200ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate (100 ml) was added, and after bis (tri-t-butylphosphine) palladium (0.60 g,0.50 mmol) was added, the mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, concentration was performed under reduced pressure, and recrystallization was performed with 200ml of ethyl acetate, whereby production example 9 (8.02 g, 56%) was produced.
MS[M+H] + ＝715
Production example 10
After compound D (9.17 g,20.00 mmol) and compound a10 (8.09 g,22.00 mmol) were completely dissolved in 200ml of tetrahydrofuran in a 500ml round-bottomed flask under a nitrogen atmosphere, 2M aqueous potassium carbonate solution (10 ml) was added, and bis (tri-t-butylphosphine) palladium (0.60 g,0.50 mmol) was added, followed by stirring with heating for 12 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, concentration was performed under reduced pressure, and recrystallization was performed with 200ml of ethyl acetate, whereby production example 10 (8.89 g, 687%) was produced.
MS[M+H] + ＝663
Production example 11
After compound E (7.34 g,20.00 mmol) and compound a11 (9.97 g,22.00 mmol) were completely dissolved in 200ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate (100 ml) was added, and bis (tri-t-butylphosphine) palladium (0.30 g,0.25 mmol) was added, followed by stirring with heating for 9 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, concentration was performed under reduced pressure, and recrystallization was performed with 100ml of ethyl acetate, whereby production example 11 (10.21 g, 69%) was produced.
MS[M+H] + ＝739
Production example 12
After compound E (7.34 g,20.00 mmol) and compound a12 (5.23 g,14.25 mmol) were completely dissolved in 500ml of tetrahydrofuran in a 1000ml round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate (150 ml) was added, and bis (tri-t-butylphosphine) palladium (0.30 g,0.25 mmol) was added, followed by stirring with heating for 1 hour. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, concentration was performed under reduced pressure, and recrystallization was performed with 600ml of ethyl acetate, whereby production example 12 (9.66 g, 61%) was produced.
MS[M+H] + ＝791
PREPARATION EXAMPLE 13
After compound E (7.34 g,20.00 mmol) and compound a13 (7.77 g,22.00 mmol) were completely dissolved in 200ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, 2M potassium carbonate solution (100 ml) was added, and bis (tri-t-butylphosphine) palladium (0.30 g,0.25 mmol) was added, followed by stirring with heating for 12 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, concentration was performed under reduced pressure, and recrystallization was performed with 300ml of ethyl acetate, whereby production example 13 (12.80 g, 61%) was produced.
MS[M+H] + ＝639
PREPARATION EXAMPLE 14
A complete solution of compound F (9.17 g,20.00 mmol) and compound a14 (5.89 g,22.00 mmol) in 250ml of tetrahydrofuran was added to a 500ml round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate (125 ml) was added, and bis (tri-t-butylphosphine) palladium (0.30 g,0.25 mmol) was added and the mixture was heated and stirred for 12 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, concentration was performed under reduced pressure, and recrystallization was performed with 160ml of ethanol, whereby production example 14 (7.89 g, 70%) was produced.
MS[M+H] + ＝563
Production example 15
After compound F (9.17 g,20.00 mmol) and compound a15 (8.09 g,22.00 mmol) were completely dissolved in 200ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate (100 ml) was added, and bis (tri-t-butylphosphine) palladium (0.30 g,0.25 mmol) was added, followed by stirring with heating for 12 hours. The temperature was lowered to room temperature, the aqueous layer was removed, and after drying over anhydrous magnesium sulfate, concentration was performed under reduced pressure, and recrystallization was performed with 150ml of ethanol, whereby production example 15 (9.43 g, 71%) was produced.
MS[M+H] + ＝663
Example 1-1
To ITO (indium tin oxide)
The glass substrate coated to have a thin film thickness is put into distilled water in which a detergent is dissolved, and washed with ultrasonic waves. In this case, a product of fei he er (Fischer co.) was used as the detergent, and distilled water was filtered twice using a Filter (Filter) manufactured by millbore co. After washing the ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After the distilled water washing is completed, ultrasonic washing is performed by using solvents of isopropanol, acetone and methanol, and the obtained product is dried and then conveyed to a plasma cleaning machine. After the substrate was cleaned with oxygen plasma for 5 minutes, the substrate was transferred to a vacuum vapor deposition machine. />
On the ITO transparent electrode thus prepared, a compound represented by the following formula HAT was prepared
And performing thermal vacuum evaporation to form a hole injection layer. On the hole injection layer, a compound represented by the following chemical formula HT1 is added as a hole transporting substance>
Vacuum evaporation is performed to form a hole transport layer. Next, on the hole transport layer, a compound represented by the following chemical formula EB1 is represented by film thickness +.>
Vacuum evaporation is performed to form an electron blocking layer. Next, on the above electron blocking layer, a compound represented by the following chemical formula BH and a compound represented by the following chemical formula BD were added at a weight ratio of 25:1 and at a film thickness +.>
Vacuum vapor deposition is performed to form a light-emitting layer. On the above light-emitting layer, the compound of production example 1 produced in the above was produced as a film thickness +.>
Vacuum evaporation is performed 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 ∈ ->
An electron transport layer is formed by the thickness of (a). On the electron transport layer, lithium fluoride (LiF) is added in sequence +.>
Is made of aluminum +.>
And vapor deposition is performed to the thickness of the substrate, thereby forming a cathode.
In the above process, the vapor deposition rate of the organic matter is maintained
Lithium fluoride maintenance of cathode
Is kept at>
Is to maintain a vacuum degree of 2X 10 during vapor deposition -7 ～5×10 -6 The support is thus fabricated into an organic light emitting device.
Examples 1-3 to 1-15
An organic light-emitting device was manufactured 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 manufacturing example 1.
Comparative examples 1-1 to 1-3
An organic light-emitting device was manufactured 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 manufacturing example 1. The compounds of HB1, HB2 and HB3 used in Table 1 below are shown below.
Experimental example 1
When a current was applied to the organic light emitting devices of the examples and comparative examples manufactured as described above, the voltage, efficiency, color coordinates, and lifetime were measured, and the results thereof are shown in table 1 below. T95 represents the time required for the luminance to decrease from the initial luminance (1600 nit) to 95%.
[ Table 1]
As shown in table 1 above, in the case of an organic light-emitting device manufactured using the compound of the present invention as a hole blocking layer, excellent characteristics were exhibited in terms of efficiency, driving voltage, and/or stability of the organic light-emitting device.
In particular, the organic light emitting device manufactured using the compound of the present invention as a hole blocking layer exhibited characteristics of low voltage, high efficiency, and long lifetime as compared to the organic light emitting device manufactured using the compounds of comparative example 1 of phenanthrene (Phnanthrene) core and comparative examples 2 to 3 of Spirobifluorene (Spirobifluorene) core as a hole blocking layer.
Specifically, it was confirmed that the core of the compound of the present invention has a relatively higher electron content than phenanthrene and spirobifluorene cores, does not decrease the lifetime when used as a hole blocking layer, and shows an advantage in terms of voltage and efficiency.
As shown in the results of table 1 above, it was confirmed that the compound according to the present invention was excellent in hole blocking ability, and thus applicable to an organic light emitting device.
[ symbolic description ]
1: substrate 2: anode
3: organic layer 4: cathode electrode
5: hole injection layer 6: hole transport layer
7: light emitting layer 8: hole blocking layer
9: electron transport layer 10: an electron injection layer.
Claims (5)
1. A compound represented by the following chemical formula 1:
chemical formula 1
In the chemical formula 1 described above, a compound having the formula,
L 1 is a bond, or is selected from any of the following structures:
X 1 、X 2 and X 3 Each independently is N or CH, wherein, in X 1 、X 2 And X 3 At least 2 of which are N,
Ar 1 and Ar is a group 2 Each independently is unsubstituted or deuterium substituted C 6-60 Aryl groups.
2. The compound according to claim 1, wherein the compound represented by the chemical formula 1 is represented by any one of the following chemical formulas 2 to 4:
chemical formula 2
Chemical formula 3
Chemical formula 4
In the chemical formulas 2 to 4,
L 1 、X 1 、X 2 、X 3 、Ar 1 and Ar is a group 2 As defined in claim 1.
3. The compound of claim 1, wherein Ar 1 And Ar is a group 2 Each independently is any one selected from the following structures:
4. the compound according to claim 1, wherein the compound represented by chemical formula 1 is any one selected from the group consisting of:
5. an organic light emitting device, comprising: a first electrode, a second electrode provided opposite to the first electrode, and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers contains the compound according to any one of claims 1 to 4.
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| KR1020170166760A KR102175712B1 (en) | 2017-12-06 | 2017-12-06 | Novel hetero-cyclic compound and organic light emitting device comprising the same |
| PCT/KR2018/008982 WO2019112143A1 (en) | 2017-12-06 | 2018-08-07 | Novel heterocyclic compound and organic light emitting device using same |
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| JP4048810B2 (en) * | 2001-03-27 | 2008-02-20 | 住友化学株式会社 | Polymer light emitter and polymer light emitting device using the same |
| GB2424895B (en) * | 2003-10-01 | 2008-07-09 | Sumitomo Chemical Co | Polymer light-emitting material and polymer light-emitting device |
| CN100432067C (en) * | 2006-06-05 | 2008-11-12 | 南开大学 | Dibenzanthracene, dinaphthopyran and dibenzanthracene, dinaphtho spiropyran analog compound and its preparation |
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