CN111051292A - Novel heterocyclic compound and organic light emitting device using the same - Google Patents
Novel heterocyclic compound and organic light emitting device using the same Download PDFInfo
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- CN111051292A CN111051292A CN201880058690.2A CN201880058690A CN111051292A CN 111051292 A CN111051292 A CN 111051292A CN 201880058690 A CN201880058690 A CN 201880058690A CN 111051292 A CN111051292 A CN 111051292A
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- 150000002391 heterocyclic compounds Chemical class 0.000 title abstract description 6
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- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- IHZHBWRUTRZTGM-UHFFFAOYSA-N benzo[h]quinolin-10-ol zinc Chemical compound [Zn].Oc1cccc2ccc3cccnc3c12.Oc1cccc2ccc3cccnc3c12 IHZHBWRUTRZTGM-UHFFFAOYSA-N 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
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- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 1
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
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- 125000001309 chloro group Chemical group Cl* 0.000 description 1
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- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
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- 239000011737 fluorine Substances 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
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- 239000011521 glass Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
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- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
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- 238000007641 inkjet printing Methods 0.000 description 1
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- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
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- 125000004430 oxygen atom Chemical group O* 0.000 description 1
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- 229910052763 palladium Inorganic materials 0.000 description 1
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- FVDOBFPYBSDRKH-UHFFFAOYSA-N perylene-3,4,9,10-tetracarboxylic acid Chemical compound C=12C3=CC=C(C(O)=O)C2=C(C(O)=O)C=CC=1C1=CC=C(C(O)=O)C2=C1C3=CC=C2C(=O)O FVDOBFPYBSDRKH-UHFFFAOYSA-N 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
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- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
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- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 1
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- 239000011591 potassium Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
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- 239000002356 single layer Substances 0.000 description 1
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- 239000011734 sodium Substances 0.000 description 1
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- JLBRGNFGBDNNSF-UHFFFAOYSA-N tert-butyl(dimethyl)borane Chemical group CB(C)C(C)(C)C JLBRGNFGBDNNSF-UHFFFAOYSA-N 0.000 description 1
- 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
- AGGKEGLBGGJEBZ-UHFFFAOYSA-N tetramethylenedisulfotetramine Chemical compound C1N(S2(=O)=O)CN3S(=O)(=O)N1CN2C3 AGGKEGLBGGJEBZ-UHFFFAOYSA-N 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 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
- 238000012546 transfer Methods 0.000 description 1
- 230000007704 transition Effects 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
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 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
- 239000011787 zinc oxide Substances 0.000 description 1
Images
Classifications
-
- 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
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, which is incorporated herein in its entirety by reference.
The present invention relates to a novel 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, 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 located between the anode and the cathode. In order to improve the efficiency and stability of the organic light emitting device, the organic layer is often formed of a multilayer structure formed of different materials, and may be formed of, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, or the like. With the structure of such an organic light emitting device, if a voltage is applied between both electrodes, holes are injected from the anode into the organic layer, electrons are injected from the cathode into the organic layer, excitons (exitons) are formed when the injected holes and electrons meet, and light is emitted when the excitons transition to the ground state again.
For organic materials used for the organic light emitting devices as described above, development of new materials is continuously demanded.
[ Prior art documents ]
Patent document 1: korean patent laid-open No. 10-2000-0051826
Disclosure of Invention
Technical subject
The present invention relates to a novel heterocyclic compound and an organic light emitting device including the same.
Means for solving the problems
The present invention provides a compound represented by the following chemical formula 1.
[ chemical formula 1]
In the above-described chemical formula 1,
L1is a bond, substituted or unsubstituted C6-60Arylene, or substituted or unsubstituted C containing more than 1 of N, O and S2-60A heteroarylene group, a heteroaryl group,
X1、X2and X3Each independently of the other is N or CH,
Ar1and Ar2Each independently is substituted or unsubstituted C6-60Aryl, or substituted or unsubstituted C containing more than 1 of N, O and S2-60A heteroaryl group.
In addition, the present invention provides an organic light emitting device, comprising: the organic light emitting device includes a first electrode, a second electrode provided to face the first electrode, and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers include a compound represented by the chemical formula 1.
Effects of the invention
The compound represented by the above chemical formula 1 may be used as a material of an organic layer of an organic light emitting device in which improvement of efficiency, lower driving voltage, and/or improvement of life span characteristics can be achieved. In particular, the compound represented by the above chemical formula 1 may be used as a material for hole injection, hole transport, hole injection and transport, light emission, electron transport, or electron injection.
Drawings
Fig. 1 illustrates an example of an organic light emitting device composed of a substrate 1, an anode 2, an organic layer 3, and a cathode 4.
Fig. 2 illustrates an example of an organic light-emitting device composed of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light-emitting layer 7, a hole blocking layer 8, an electron transport layer 9, an electron injection layer 10, 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,
refers to a bond to another substituent.
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), (
Alkylthioxy); 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; an alkylamino group; an aralkylamino group; a heteroaryl amino group; an arylamine group; an aryl phosphine group; or 1 or more substituents of the heterocyclic group containing 1 or more substituents of N, O and S atoms, or substituted or unsubstituted by substituents formed by connecting 2 or more substituents of the above-exemplified substituentsAnd (4) generation. For example, "a substituent in which 2 or more substituents are linked" may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent in which 2 phenyl groups are linked.
In the present specification, the number of carbon atoms of the carbonyl group is not particularly limited, but is preferably 1 to 40. Specifically, the compound may have the following structure, but is not limited thereto.
In the ester group, the oxygen of the ester group may be 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 includes specifically a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, a phenylboron group and the like, but is not limited thereto.
In the present specification, examples of the halogen group include fluorine, chlorine, bromine, and iodine.
In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the alkyl group has 1 to 20 carbon atoms. According to another embodiment, the alkyl group has 1 to 10 carbon atoms. According to another embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an n-propyl group, an isopropyl group, a butyl group, an n-butyl group, an isobutyl group, a tert-butyl group, a sec-butyl group, a 1-methylbutyl group, a 1-ethylbutyl group, a pentyl group, an n-pentyl group, an isopentyl group, a neopentyl group, a tert-pentyl group, a hexyl group, a n-hexyl group, a 1-methylpentyl group, a 2-methylpentyl group, a 4-methyl-2-pentyl group, 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. According to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the number of carbon atoms of the above cycloalkyl group is 3 to 6. Specifically, there may be mentioned, but not limited to, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2, 3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2, 3-dimethylcyclohexyl, 3,4, 5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl and the like.
In the present specification, the aryl group is not particularly limited, but is preferably an aryl group having 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a monocyclic aryl group such as a phenyl group, a biphenyl group, or a terphenyl group, but is not limited thereto. The polycyclic 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 at least 1 of O, N, Si and S as a heteroatom, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60. Examples of the heterocyclic group include 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, carbazoleRadical, benzo
Azolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, benzofuranyl, phenanthrolinyl (phenanthroline), isoquinoyl
Oxazolyl, thiadiazolyl, phenothiazinyl, dibenzofuranyl, and the like, but is not limited thereto.
In the present specification, the aryl group in the aralkyl group, aralkenyl group, alkylaryl group, arylamine group is the same as the above-mentioned aryl group. In the present specification, the alkyl group in the aralkyl group, the alkylaryl group, and the alkylamino group is the same as the above-mentioned examples of the alkyl group. In the present specification, the heteroaryl group in the heteroarylamine can be applied to the above 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 the above description of the heterocyclic group can be applied.
In the above chemical formula 1, according to L1The above chemical formula 1 may be represented by the following chemical formulae 2 to 4:
[ chemical formula 2]
[ chemical formula 3]
[ chemical formula 4]
Preferably, in the above X1、X2And X3At least 2 or more of them are N.
Further, preferably, L1Is a bond or is selected from any of the following structures.
More preferably, L is as defined above1Is a bond or phenylene.
In addition, preferably, Ar1And Ar2Each independently is any one selected from the following structures.
Representative examples of the compound represented by the above chemical formula 1 are as follows:
the compound represented by the above chemical formula 1 can be produced by a production method represented by the following reaction formula 1 or reaction formula 2.
[ reaction formula 1]
[ reaction formula 2]
In the above reaction formulae 1 and 2, L1、X1、X2、X3、Ar1And Ar2As defined above, X is halogen, preferably X is chlorine or bromine.
The above reaction formulas 1 and 2 are suzuki coupling reactions, preferably carried out in the presence of a palladium catalyst and a base, and the reactive groups used for the suzuki coupling reactions may be modified according to techniques known in the art.
The above-described manufacturing method can be further embodied in the manufacturing examples described later.
In addition, the present invention provides an organic light emitting device comprising the compound represented by the above chemical formula 1. As an example, the present invention provides an organic light emitting device, comprising: the organic light emitting device includes a first electrode, a second electrode provided to face the first electrode, and one or more organic layers provided between the first electrode and the second electrode, wherein one 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, a hole blocking 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 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 may include a hole blocking layer including the compound represented by the chemical formula 1.
In addition, the organic layer may include an electron transport layer or an electron injection layer including the compound represented by the chemical formula 1.
In addition, the electron transport layer, the electron injection layer, or the layer simultaneously performing electron transport and electron injection includes the compound represented by the above chemical formula 1.
In addition, the organic layer may include a light emitting layer and an electron transport layer, and the electron transport layer may include a compound represented by the chemical formula 1.
In addition, the organic light emitting device according to the present invention may be an organic light emitting device of a structure (normal type) in which an anode, one 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, 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 included in the above organic layer.
Fig. 2 illustrates an example of an organic light-emitting device composed of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light-emitting layer 7, a hole blocking layer 8, an electron transport layer 9, an electron injection layer 10, and a cathode 4. In the structure as described above, the compound represented by the above chemical formula 1 may be included 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 included 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 above organic layers include the compound represented by the above 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 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 device is manufactured by depositing a metal, a metal oxide having conductivity, or an alloy thereof on a substrate by a Physical Vapor Deposition (PVD) method such as a sputtering method or an electron beam evaporation method, forming an anode, forming an organic layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer on the anode, and then depositing a substance that can be used as a cathode on the organic layer. In addition to this method, a cathode material, an organic layer, and an anode material may be sequentially deposited on a substrate to manufacture an organic light-emitting device.
In addition, the compound represented by the above chemical formula 1 may be formed into an organic layer not only by a vacuum evaporation method but also by a solution coating method in the manufacture of an organic light emitting device. Here, the solution coating method refers to spin coating, dip coating, blade coating, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited thereto.
In addition to these methods, an organic light-emitting device 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 above-mentioned anode materialMetals such as vanadium, chromium, copper, zinc, gold, etc., or alloys thereof; metal oxides such as zinc oxide, Indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); ZnO-Al or SNO2A combination of a metal such as Sb and an oxide; poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene]Conductive polymers such as (PEDOT), polypyrrole, and polyaniline, but the present invention is not limited thereto.
The cathode material is preferably a material having a small work function in order to easily inject electrons into the organic layer. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, and alloys thereof; LiF/Al or LiO2And a multilayer structure material such as Al, but not limited thereto.
The hole injection layer is a layer for injecting holes from the electrode, and the following compounds are preferable as the hole injection substance: the organic light-emitting device has an ability to transport holes, has a hole injection effect from an anode, has an excellent hole injection effect for a light-emitting layer or a light-emitting material, prevents excitons generated in the light-emitting layer from migrating to an electron injection layer or an electron injection material, and has excellent thin film formation 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 substance is a substance 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 substance having a high mobility to holes. Specific examples thereof include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers in which a conjugated portion and a non-conjugated portion are present simultaneously.
The light-emitting substance is a substance that can receive holes and electrons from the hole-transporting layer and the electron-transporting layer, respectively, and combine them to emit light in the visible light region, and is preferably a substance having high quantum efficiency with respect to fluorescence or phosphorescence. As a specific example, there is 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; polyfluorene, rubrene, and the like, but are not limited thereto.
The light emitting layer may include a host material and a dopant material. The host material includes aromatic fused ring derivatives, heterocyclic compounds, and the like. Specifically, the aromatic condensed ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and the heterocyclic ring-containing compounds include carbazole derivatives, dibenzofuran derivatives, and ladder-type furan compounds
Pyrimidine derivatives, etc., but are not limited thereto.
As the dopant material, there are an aromatic amine derivative, a styryl amine compound, a boron complex, a fluoranthene compound, a metal complex, and the like. Specifically, the aromatic amine derivative is an aromatic fused ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene, or the like having an arylamino group,
Diindenoperene (Periflanthene), etc., and the styrylamine compound is a compound substituted with at least one arylvinyl group on a substituted or unsubstituted arylamine, and is substituted or unsubstituted with 1 or 2 or more substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamine group. Concretely, there are styrylamine and benzeneVinyl diamine, styrene triamine, styrene tetramine, etc., but are not limited thereto. The metal complex includes, but is not limited to, iridium complexes and platinum complexes.
The electron transporting layer is a layer that receives electrons from the electron injecting layer and transports the electrons to the light emitting layer, and the electron transporting substance is a substance that can 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. As specific examples, there are Al complexes of 8-hydroxyquinoline, Al complexes containing Alq3Organic radical compounds, hydroxyl brass-metal complexes, etc., but are not limited thereto. The electron transport layer may be used with any desired cathode material as used in the art. Examples of suitable cathode substances are, in particular, the customary substances having a low work function and accompanied by an aluminum or silver layer. In particular cesium, barium, calcium, ytterbium and samarium, in each case accompanied by an aluminum or silver layer.
The electron injection layer is a layer for injecting electrons from the electrode, and is preferably a compound of: has an ability to transport electrons, an electron injection effect from a cathode, an excellent electron injection effect with respect 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 is excellent in thin-film formability. Specifically, there are fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, and the like,
Azole,
Oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidene methane, anthrone, and derivatives thereof, metal complex compounds, and nitrogen-containing five-membered ring derivatives, but the present invention is not limited thereto.
Examples of the metal complex include lithium 8-quinolinolato, zinc bis (8-quinolinolato), copper bis (8-quinolinolato), manganese bis (8-quinolinolato), aluminum tris (2-methyl-8-quinolinolato), and gallium tris (8-quinolinolato), bis (10-hydroxybenzo [ h ] quinoline) beryllium, bis (10-hydroxybenzo [ h ] quinoline) zinc, bis (2-methyl-8-quinoline) gallium chloride, bis (2-methyl-8-quinoline) (o-cresol) gallium, bis (2-methyl-8-quinoline) (1-naphthol) aluminum, bis (2-methyl-8-quinoline) (2-naphthol) gallium, and the like, but are not limited thereto.
The organic light emitting device according to the present invention may be a top emission type, a bottom emission type, or a bi-directional emission type, depending on the material used.
In addition, the compound represented by the above chemical formula 1 may be included in an organic solar cell or an organic transistor, in addition to the organic light emitting device.
The production of the compound represented by the above chemical formula 1 and the organic light emitting device comprising the same is specifically described in the following examples. However, the following examples are provided to illustrate the present invention, and the scope of the present invention is not limited thereto.
Production example 1
After completely dissolving compound A (8.80g, 22.00mmol) and compound a1(9.32g, 24.20mmol) in 220ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate (110ml) was added, and after adding tetrakis (triphenylphosphine) palladium (0.76g, 0.66mmol), stirring was performed under heating for 2 hours. Production example 1(12.27g, 80%) was prepared by reducing the temperature to normal temperature, removing the water layer, drying over anhydrous magnesium sulfate, concentrating under reduced pressure, and recrystallizing from 200ml of tetrahydrofuran.
MS[M+H]+＝639
Production example 2
In a 500ml round-bottomed flask under nitrogen atmosphere, after completely dissolving Compound A (8.80g, 22.00mmol) and Compound a2(9.32g, 24.20mmol) in 200ml of tetrahydrofuran, 2M aqueous potassium carbonate (110ml) was added, and after adding tetrakis (triphenylphosphine) palladium (0.76g, 0.66mmol), the mixture was stirred under heating for 3 hours. Production example 2(10.89g, 71%) was prepared by reducing the temperature to normal temperature, removing the water layer, drying over anhydrous magnesium sulfate, concentrating under reduced pressure, and recrystallizing from 200ml of ethyl acetate.
MS[M+H]+＝639
Production example 3
A complete solution of Compound A (7.34g, 20.00mmol) and Compound a3(7.75g, 22.00mmol) in 220ml of tetrahydrofuran was placed in a 500ml round bottom flask under a nitrogen atmosphere, and after addition of a 2M aqueous solution of potassium carbonate (100ml), tetrakis (triphenylphosphine) palladium (0.46g, 0.40mmol) was added and the mixture was stirred for 2 hours under heating. Production example 3(9.58g, 68%) was prepared by reducing the temperature to normal temperature, removing the water layer, drying over anhydrous magnesium sulfate, concentrating under reduced pressure, and recrystallizing from 150ml of ethyl acetate.
MS[M+H]+＝638
Production example 4
After completely dissolving compound A (7.34g, 20.00mmol) and compound a4(9.44g, 22.00mmol) in 180ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate (100ml) was added, and after adding tetrakis (triphenylphosphine) palladium (0.59g, 0.50mmol), the mixture was stirred under heating for 2 hours. Production example 4(8.45g, 59%) was prepared by reducing the temperature to normal temperature, removing the water layer, drying over anhydrous magnesium sulfate, concentrating under reduced pressure, and recrystallizing from 100ml of tetrahydrofuran.
MS[M+H]+＝715
Production example 5
After completely dissolving compound B (9.17g, 20.00mmol) and compound a5(5.26g, 22.00mmol) in 200ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate (100ml) was added, and bis (tri-tert-butylphosphine) palladium (0.23g, 0.20mmol) was added, followed by stirring under heating for 4 hours. Production example 5(10.36g, 81%) was prepared by reducing the temperature to normal temperature, removing the water layer, drying over anhydrous magnesium sulfate, concentrating under reduced pressure, and recrystallizing from 150ml of ethyl acetate.
MS[M+H]+＝563
Production example 6
After completely dissolving compound C (7.34g, 20.00mmol) and compound a6(7.77g, 22.00mmol) in 200ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate (100ml) was added, bis (tri-tert-butylphosphine) palladium (0.23g, 0.20mmol) was added, and the mixture was stirred under heating for 2 hours. Production example 6(10.24g, 80%) was prepared by reducing the temperature to normal temperature, removing the water layer, drying over anhydrous magnesium sulfate, concentrating under reduced pressure, and recrystallizing from 150ml of ethyl acetate.
MS[M+H]+＝639
Production example 7
After completely dissolving compound C (7.34g, 20.00mmol) and compound a7(8.87g, 22.00mmol) in 250ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate (125ml) was added, bis (tri-tert-butylphosphine) palladium (0.60g, 0.50mmol) was added, and the mixture was stirred under heating for 3 hours. Production example 7(12.42g, 90%) was prepared by reducing the temperature to normal temperature, removing the water layer, drying over anhydrous magnesium sulfate, concentrating under reduced pressure, and recrystallizing from 50ml of ethyl acetate.
MS[M+H]+＝689
Production example 8
In a 500ml round-bottomed flask under nitrogen atmosphere, after completely dissolving compound D (9.17g, 20.00mmol) and compound a8(7.56g, 22.00mmol) in 200ml of tetrahydrofuran, 2M aqueous potassium carbonate (100ml) was added, bis (tri-tert-butylphosphine) palladium (0.60g, 0.50mmol) was added, and the mixture was stirred under heating for 3 hours. Production example 8(9.21g, 72%) was prepared by reducing the temperature to normal temperature, removing the water layer, drying over anhydrous magnesium sulfate, concentrating under reduced pressure, and recrystallizing from 200ml of ethyl acetate.
MS[M+H]+＝639
Production example 9
After completely dissolving compound D (9.17g, 20.00mmol) and compound a9(4.79g, 8.37mmol) fmf in 200ml of tetrahydrofuran in a 500ml round bottom flask under nitrogen atmosphere, 2M aqueous potassium carbonate (100ml) was added, bis (tri-tert-butylphosphine) palladium (0.60g, 0.50mmol) was added, and the mixture was stirred under heating for 3 hours. Production example 9(8.02g, 56%) was prepared by reducing the temperature to normal temperature, removing the water layer, drying over anhydrous magnesium sulfate, concentrating under reduced pressure, and recrystallizing from 200ml of ethyl acetate.
MS[M+H]+＝715
Production example 10
In a 500ml round-bottomed flask under nitrogen atmosphere, after completely dissolving compound D (9.17g, 20.00mmol) and compound a10(8.09g, 22.00mmol) in 200ml of tetrahydrofuran, 2M aqueous potassium carbonate (10ml) was added, bis (tri-tert-butylphosphine) palladium (0.60g, 0.50mmol) was added, and the mixture was stirred under heating for 12 hours. Production example 10(8.89g, 687%) was prepared by reducing the temperature to normal temperature, removing the water layer, drying over anhydrous magnesium sulfate, concentrating under reduced pressure, and recrystallizing from 200ml of ethyl acetate.
MS[M+H]+＝663
Production example 11
In a 500ml round-bottomed flask under nitrogen atmosphere, after completely dissolving compound E (7.34g, 20.00mmol) and compound a11(9.97g, 22.00mmol) in 200ml of tetrahydrofuran, 2M aqueous potassium carbonate (100ml) was added, bis (tri-tert-butylphosphine) palladium (0.30g, 0.25mmol) was added, and the mixture was stirred under heating for 9 hours. Production example 11(10.21g, 69%) was prepared by reducing the temperature to normal temperature, removing the water layer, drying over anhydrous magnesium sulfate, concentrating under reduced pressure, and recrystallizing from 100ml of ethyl acetate.
MS[M+H]+＝739
Production example 12
In a 1000ml round bottom flask under nitrogen atmosphere, after completely dissolving compound E (7.34g, 20.00mmol) and compound a12(5.23g, 14.25mmol) in 500ml tetrahydrofuran, 2M aqueous potassium carbonate (150ml) was added, bis (tri-tert-butylphosphine) palladium (0.30g, 0.25mmol) was added, and the mixture was stirred under heating for 1 hour. Production example 12(9.66g, 61%) was prepared by reducing the temperature to normal temperature, removing the water layer, drying over anhydrous magnesium sulfate, concentrating under reduced pressure, and recrystallizing from 600ml of ethyl acetate.
MS[M+H]+＝791
Production example 13
In a 500ml round-bottomed flask under nitrogen atmosphere, after completely dissolving compound E (7.34g, 20.00mmol) and compound a13(7.77g, 22.00mmol) in 200ml of tetrahydrofuran, a 2M potassium carbonate solution (100ml) was added, and after adding bis (tri-tert-butylphosphine) palladium (0.30g, 0.25mmol), the mixture was stirred under heating for 12 hours. Production example 13(12.80g, 61%) was prepared by reducing the temperature to normal temperature, removing the water layer, drying over anhydrous magnesium sulfate, concentrating under reduced pressure, and recrystallizing from 300ml of ethyl acetate.
MS[M+H]+＝639
Production example 14
In a 500ml round bottom flask under nitrogen atmosphere, after a complete solution of compound F (9.17g, 20.00mmol) and compound a14(5.89g, 22.00mmol) in 250ml tetrahydrofuran was added 2M aqueous potassium carbonate (125ml), bis (tri-tert-butylphosphine) palladium (0.30g, 0.25mmol) was added, and the mixture was stirred under heating for 12 hours. Production example 14(7.89g, 70%) was prepared by reducing the temperature to normal temperature, removing the water layer, drying over anhydrous magnesium sulfate, concentrating under reduced pressure, and recrystallizing from 160ml of ethanol.
MS[M+H]+＝563
Production example 15
In a 500ml round-bottomed flask under nitrogen atmosphere, after completely dissolving compound F (9.17g, 20.00mmol) and compound a15(8.09g, 22.00mmol) in 200ml of tetrahydrofuran, a 2M aqueous potassium carbonate solution (100ml) was added, bis (tri-tert-butylphosphine) palladium (0.30g, 0.25mmol) was added, and the mixture was stirred under heating for 12 hours. Production example 15(9.43g, 71%) was prepared by reducing the temperature to normal temperature, removing the water layer, drying over anhydrous magnesium sulfate, concentrating under reduced pressure, and recrystallizing from 150ml of ethanol.
MS[M+H]+＝663
Examples 1 to 1
Indium Tin Oxide (ITO) and a process for producing the same
Is covered withThe glass substrate coated in a thin film was put in distilled water in which a detergent was 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 obtained by twice filtration using a Filter (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, a compound represented by the following chemical formula HAT was added
The hole injection layer is formed by thermal vacuum deposition. On the hole injection layer, a compound represented by the following chemical formula HT1 as a substance transporting holes is added
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 was formed in a 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 mixed at a weight ratio of 25:1 and in a film thickness
Vacuum evaporation is performed to form a light emitting layer. On the light-emitting layer, the compound of production example 1 produced above was formed to have a film thickness
The hole blocking layer is formed by vacuum evaporation. Then, in the aboveOn 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 (2) forms an electron transport layer. On the electron transport layer, lithium fluoride (LiF) is sequentially added
Thickness of aluminum and
the thickness of (a) is evaporated 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 supporting to thereby fabricate an organic light emitting device.
Examples 1-3 to 1-15
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 1-3
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 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 are shown in table 1 below. T95 represents the time required for the luminance to decrease from the initial luminance (1600nit) to 95%.
[ TABLE 1]
As shown in table 1 above, in the case of the organic light emitting device manufactured using the compound of the present invention as a hole blocking layer, excellent characteristics are 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 shows characteristics of low voltage, high efficiency, and long life 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 high electron content as compared with the phenanthrene and spirobifluorene core, does not cause a decrease in lifetime when used as a hole blocking layer, and shows advantageous results 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 is excellent in hole blocking ability and thus can be suitably used for an organic light emitting device.
[ notation ] to show
1: substrate 2: anode
3: organic material 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 (7)
1. A compound represented by the following chemical formula 1:
chemical formula 1
In the chemical formula 1, the first and second organic solvents,
L1is a bond, substituted or unsubstituted C6-60Arylene, or substituted or unsubstituted C containing more than 1 of N, O and S2-60A heteroarylene group, a heteroaryl group,
X1、X2and X3Each independently of the other is N or CH,
Ar1and Ar2Each independently is substituted or unsubstituted C6-60Aryl, or substituted or unsubstituted C containing more than 1 of N, O and S2-60A heteroaryl group.
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 formulae 2 to 4:
chemical formula 2
Chemical formula 3
Chemical formula 4
In the chemical formulas 2 to 4,
L1、X1、X2、X3、Ar1and Ar2As defined in claim 1.
3. The compound of claim 1, wherein, at X1、X2And X3At least 2 or more of them are N.
4. The compound of claim 1, wherein L1Is a bond, or is selected from any of the following structures:
5. the compound of claim 1, wherein Ar1And Ar2Each independently is any one selected from the following structures:
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 one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers contain the compound according to any one of claims 1 to 6.
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| 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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| CN112480057A (en) * | 2020-11-26 | 2021-03-12 | 武汉华星光电半导体显示技术有限公司 | Oxacyclo compound, use thereof, and electronic device using the same |
| CN113754641A (en) * | 2020-06-05 | 2021-12-07 | 陕西莱特光电材料股份有限公司 | Organic compound, and electronic element and electronic device using same |
| CN114621205A (en) * | 2022-03-11 | 2022-06-14 | 京东方科技集团股份有限公司 | Derivative of oxygen-containing heterocyclic compound, light-emitting device, and display device |
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| KR20230105839A (en) | 2022-01-05 | 2023-07-12 | 롬엔드하스전자재료코리아유한회사 | A plurality of host materials, organic electroluminescent compound, and organic electroluminescent device comprising the same |
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| JP2004168999A (en) * | 2002-10-30 | 2004-06-17 | Sumitomo Chem Co Ltd | Polymer compound and polymer light-emitting element using the same |
| KR20130142971A (en) * | 2012-06-20 | 2013-12-30 | 에스에프씨 주식회사 | Heterocyclic compounds and organic light-emitting diode including the same |
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| CN113754641A (en) * | 2020-06-05 | 2021-12-07 | 陕西莱特光电材料股份有限公司 | Organic compound, and electronic element and electronic device using same |
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| KR20190066895A (en) | 2019-06-14 |
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