CN113912531A - Novel arylamine compound and application thereof - Google Patents
Novel arylamine compound and application thereof Download PDFInfo
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- CN113912531A CN113912531A CN202110970984.6A CN202110970984A CN113912531A CN 113912531 A CN113912531 A CN 113912531A CN 202110970984 A CN202110970984 A CN 202110970984A CN 113912531 A CN113912531 A CN 113912531A
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- -1 arylamine compound Chemical class 0.000 title claims abstract description 21
- 239000000463 material Substances 0.000 claims abstract description 32
- 230000005525 hole transport Effects 0.000 claims abstract description 21
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 5
- 125000003118 aryl group Chemical group 0.000 claims abstract description 3
- 125000000732 arylene group Chemical group 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 22
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- 125000002971 oxazolyl group Chemical group 0.000 claims description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 2
- 125000000335 thiazolyl group Chemical group 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- 238000002347 injection Methods 0.000 abstract description 9
- 239000007924 injection Substances 0.000 abstract description 9
- 239000010410 layer Substances 0.000 description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 238000001914 filtration Methods 0.000 description 7
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 6
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 6
- 238000007738 vacuum evaporation Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 229940126062 Compound A Drugs 0.000 description 4
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 230000000903 blocking effect Effects 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 3
- 150000004982 aromatic amines Chemical class 0.000 description 3
- 229940125904 compound 1 Drugs 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- 239000002346 layers by function Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- IUBQJLUDMLPAGT-UHFFFAOYSA-N potassium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([K])[Si](C)(C)C IUBQJLUDMLPAGT-UHFFFAOYSA-N 0.000 description 2
- 230000006798 recombination Effects 0.000 description 2
- 238000005215 recombination Methods 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 238000010025 steaming Methods 0.000 description 2
- GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 description 1
- SFFSGPCYJCMDJM-UHFFFAOYSA-N 2-[2-(3-oxo-1,2-benzoselenazol-2-yl)ethyl]-1,2-benzoselenazol-3-one Chemical compound [se]1C2=CC=CC=C2C(=O)N1CCN1C(=O)C(C=CC=C2)=C2[se]1 SFFSGPCYJCMDJM-UHFFFAOYSA-N 0.000 description 1
- DMEVMYSQZPJFOK-UHFFFAOYSA-N 3,4,5,6,9,10-hexazatetracyclo[12.4.0.02,7.08,13]octadeca-1(18),2(7),3,5,8(13),9,11,14,16-nonaene Chemical group N1=NN=C2C3=CC=CC=C3C3=CC=NN=C3C2=N1 DMEVMYSQZPJFOK-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- NUGPIZCTELGDOS-QHCPKHFHSA-N N-[(1S)-3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-pyridin-3-ylpropyl]cyclopentanecarboxamide Chemical compound C(C)(C)C1=NN=C(N1C1CCN(CC1)CC[C@@H](C=1C=NC=CC=1)NC(=O)C1CCCC1)C NUGPIZCTELGDOS-QHCPKHFHSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229940125758 compound 15 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 238000001194 electroluminescence spectrum Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000004770 highest occupied molecular orbital Methods 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
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- 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]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting 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
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/624—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing six or more rings
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- 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
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
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- 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
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
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- 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
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
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- 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
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
- C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
- C07C2603/18—Fluorenes; Hydrogenated fluorenes
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/93—Spiro compounds
- C07C2603/94—Spiro compounds containing "free" spiro atoms
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- Electroluminescent Light Sources (AREA)
Abstract
The invention relates to a novel arylamine compound, which has a structure shown in a formula (I) or a formula (II); wherein L is1And L2Each independently selected from a direct bond, a substituted or unsubstituted arylene group; r1And R2Each independently selected from substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl. The novel arylamine compound has excellent OLED device performance, such as lower driving voltage and higher efficiency; compared with HTL materials which are representative in the field, the material has higher current efficiency under the condition of basically equivalent voltage(LE) and Power Efficiency (PE); therefore, the novel arylamine compound has good application prospect in hole transport materials and hole injection materials.
Description
Technical Field
The invention relates to the field of organic electroluminescence, in particular to a novel arylamine compound and application thereof.
Background
In an OLED electronic device, a hole transport layer has the function of improving the transport efficiency of holes in the device and realizing the maximum recombination of carriers. The hole transport layer can reduce the energy barrier of holes in the injection process, increase the hole injection efficiency, and improve the brightness and the service life of the device. Generally, a good hole transport material should have a high hole mobility; can form a uniform amorphous film; the thermal stability is better; and the appropriate HOMO energy level is provided, so that the effective injection and transmission of holes at each interface are ensured, and the like. At present, because the application performance of small molecule hole transport materials and polymer hole transport materials is good and bad, finding a novel hole transport material with excellent performance is always a hotspot in the field.
In the research of a novel material for an OLED, it was found that a compound having a combination of a structural component of a fluorene-based derivative and a structural component of arylamine is an excellent functional material for an electronic device. These compounds are particularly suitable for materials having a hole transporting function, for example, in a hole transporting layer and a light-emitting layer.
Disclosure of Invention
The invention aims to provide a novel arylamine compound and application thereof aiming at the defects in the prior art.
In order to achieve the purpose, the invention adopts the technical scheme that:
the first aspect of the invention provides a novel arylamine compound, the structure of which is shown in formula (I) or formula (II):
wherein L is1And L2Each independently selected from a direct bond, a substituted or unsubstituted arylene group; r1And R2Each independently selected from substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl.
Preferably, L1And L2Each independently selected from a direct bond or a phenylene group.
Preferably, R1And R2Each independently selected from substituted or unsubstituted C6-C20Aryl, substituted or unsubstituted C6-C20A heteroaryl group.
Preferably, R1And R2Each independently selected from the group consisting of fluorenyl, spirofluorenyl, furyl, thienyl, pyrrolyl, imidazolyl, oxazolyl, thiazolyl, and mixtures thereof,Benzofuranyl, benzimidazolyl.
Preferably, the compound is selected from:
a second aspect of the present invention provides a hole transport material comprising a compound as described above.
A third aspect of the invention provides a hole transport layer comprising a hole transport material as described above.
A fourth aspect of the invention provides an organic electroluminescent device comprising a hole transport layer as described above.
By adopting the technical scheme, compared with the prior art, the invention has the following technical effects:
the novel arylamine compound is used as a hole transport material, so that the efficiency of an organic electroluminescent device can be improved to a certain extent, and the service life of the device is prolonged. In the OLED material, the hole transport layer has the functions of improving the transport efficiency of holes in the device and blocking electrons in the light emitting layer to realize the recombination of carriers. The novel arylamine compound has excellent OLED device performance, and has higher current efficiency (LE) and Power Efficiency (PE) under the condition of basically equivalent voltage compared with the HTL material which is representative in the field; therefore, the compound has good application prospect in hole transport materials and hole injection materials.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
It should be noted that the embodiments and features of the embodiments may be combined with each other without conflict.
The present invention is further illustrated by the following examples, which are not to be construed as limiting the invention.
Example 1
This example provides a novel arylamine compound selected from:
example 2
This example provides a method for synthesizing a novel arylamine compound as described in example 1, comprising the steps of:
under the protection of nitrogen, adding a compound A and a compound B into a dry two-neck flask according to the molar ratio of 1:1.2, dissolving the compound A and the compound B by dioxane, slowly dripping a toluene solution of KHMDS (0.5M), heating to 80 ℃, reacting for 20 hours, cooling to room temperature, filtering the reaction solution, and extracting the mixture by DCM/water; drying with magnesium sulfate, filtering and rotary steaming; purifying the residue by silica gel column chromatography to obtain an intermediate C;
under the protection of nitrogen, adding a compound A and a compound E into a dry two-neck flask according to the molar ratio of 1:1.2, dissolving the compound A and the compound E by dioxane, slowly dripping a toluene solution of KHMDS (0.5M), heating to 80 ℃, reacting for 20 hours, cooling to room temperature, filtering the reaction solution, and extracting the mixture by DCM/water; drying with magnesium sulfate, filtering and rotary steaming; purifying the residue by silica gel column chromatography to obtain intermediate F;
under the protection of nitrogen, adding the intermediate C or the intermediate F, the formula (III) or the formula (IV), sodium tert-butoxide, tris (dibenzylideneacetone) dipalladium and tri-tert-butylphosphine in a molar ratio of 1:1:1.2:0.05:0.05 into a dry two-neck flask, and taking toluene as a solvent. Heating and refluxing for 5h, cooling to room temperature after the reaction is finished, adding 12mL of water, stirring, filtering, separating to obtain an organic phase, and purifying by a chromatographic column to obtain the compound of the formula (I) or the formula (II).
Example 3
This example provides a method for the synthesis of compound 1 (numbered sequentially from left to right, top to bottom, with the compounds shown in example 1), comprising the steps of:
under the protection of nitrogen, the intermediate C, the compound D, sodium tert-butoxide, tris (dibenzylideneacetone) dipalladium and tri-tert-butylphosphine are added into a dry two-neck flask according to the molar ratio of 1:1:1.2:0.05:0.05, and toluene is used as a solvent. Heating and refluxing for 5h, cooling to room temperature after the reaction is finished, adding 12mL of water, stirring, filtering, separating liquid to obtain an organic phase, and purifying by a chromatographic column to obtain a compound 1; yield 69.3%, ms (ei): 739.
example 4
This example provides a method for the synthesis of compound 9, comprising the steps of:
under the protection of nitrogen, the intermediate F, the compound G, sodium tert-butoxide, tris (dibenzylideneacetone) dipalladium and tri-tert-butylphosphine are added into a dry two-neck flask according to the molar ratio of 1:1:1.2:0.05:0.05, and toluene is used as a solvent. Heating and refluxing for 5h, cooling to room temperature after the reaction is finished, adding 12mL of water, stirring, filtering, separating liquid to obtain an organic phase, and purifying by a chromatographic column to obtain a compound 9; yield 72.3%, ms (ei): 726.
example 5
The novel arylamine compound of example 1 was synthesized by the synthesis method of example 2, mass spectrometry and elemental analysis were performed, and the results are shown below:
compound 1: MS (EI) m/z: 738.93, respectively; [ M ] A]+calcd for C56H38N2 738.30；C 91.03，N 3.79，H 5.18。
Compound 2: MS (EI) m/z: 765.34, respectively; [ M ] A]+calcd for C59H43N 765.30；C 92.51，N 1.83，H 5.66。
Compound 5: MS (EI) m/z: 623.26, respectively; [ M ] A]+calcd for C48H33N 623.30；C 92.42，N 2.25，H 5.33。
Compound 9: MS (EI) m/z: 726.92, respectively; [ M ] A]+calcd for C55H38N2 726.3；C 90.88，N 3.85，H 5.27。
Compound 15: MS (EI) m/z: 649.28; [ M ] A]+calcd for C50H35N 649.3；C 92.42，N 2.16，H 5.43。
Application examples
The application embodiment provides an OLED device, and the preparation method comprises the following steps:
step S1, forming an anode on the substrate by adopting an ITO material, and ultrasonically cleaning for 15 minutes by sequentially using deionized water, acetone and ethanol;
step S2, forming a hole injection layer with the thickness of 10nm on the anode in a vacuum evaporation mode, wherein the hole injection layer is formed by evaporation of a compound PD with the material of 2% doping of hexanitrile Hexaazatriphenylene (HI);
step S3, forming a hole transport layer with the thickness of 40nm on the hole injection layer in a vacuum evaporation mode, wherein the hole transport layer is evaporated by adopting a material of the compound;
step S4, forming an electron blocking layer with the thickness of 5nm on the hole transmission layer in a vacuum evaporation mode, wherein the electron blocking layer is evaporated by adopting a compound EB as a main body material;
step S5, forming a light-emitting functional layer with the thickness of 40nm on the electron blocking layer in a vacuum evaporation mode, wherein the light-emitting functional layer adopts a compound RH as a main body material and a compound RD as a doping material, and the mass ratio of the main body material to the doping material is 97: 3;
step S6, forming an electron transport layer with the thickness of 30nm on the light-emitting function layer in a vacuum evaporation mode, wherein the electron transport layer is evaporated by adopting an ET (ETM 2) (Liq) 50% and 50%;
and step S7, evaporating a 15nm cathode on the electron transport layer in a vacuum evaporation mode according to the ratio of magnesium to silver (1: 9).
Detection examples
The OLED devices as described in the application examples were characterized in a standard manner. For this purpose, the electroluminescence spectrum, the power efficiency (measured in cd/A) and the voltage (at 1000 cd/m) are determined from the current-voltage-luminance characteristic (JUL characteristic)2Lower measure, in V). For selected tests, the lifetime was determined. The lifetime is defined as the time after which the brightness has decreased from a certain starting brightness to a certain proportion. The numeral LT95 indicates that the specified lifetime is that the luminance has dropped to 95% of the starting luminance, i.e. for example from 1000cd/m2Down to 950cd/m2The time of day. Different initial brightness is selected according to the light emission color. May be assisted by transformations known to those skilled in the artAnd converting the life value into other values of initial brightness by a formula. In this context, the starting luminance is 1000cd/m2The life of (b) is a standard value.
As can be seen from the above table, application example 1 and application example 2, which use the novel arylamine-based compound of the present invention as an HTL material, have substantially equivalent properties to comparative example 1, which uses a HTL material representative in the art, indicating that the novel arylamine-based compound of the present invention can provide excellent OLED device properties, such as lower driving voltage and higher efficiency; even at substantially comparable voltages, current efficiency (LE) and Power Efficiency (PE) are improved; the results show that the novel arylamine compound has good prospect in the aspects of being used as a hole transport material and a hole injection material.
While the invention has been described with reference to a preferred embodiment, it will be understood by those skilled in the art that various changes in form and detail may be made therein without departing from the spirit and scope of the invention.
Claims (8)
1. A novel arylamine compound is characterized in that the structure of the compound is shown as a formula (I) or a formula (II):
wherein L is1And L2Each independently selected from a direct bond, a substituted or unsubstituted arylene group; r1And R2Each independently selected from substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl.
2. Novel aromatic amine compounds according to claim 1, characterized in that L1And L2Each independently selected from a direct bond or a phenylene group.
3. Novel aromatic amine compounds according to claim 1, characterized in that R1And R2Each independently selected from substituted or unsubstituted C6-C20Aryl, substituted or unsubstituted C6-C20A heteroaryl group.
4. Novel aromatic amine compounds according to claim 1, characterized in that R1And R2Independently selected from fluorenyl, spirofluorenyl, furyl, thienyl, pyrrolyl, imidazolyl, oxazolyl, thiazolyl, benzofuryl, benzimidazolyl.
5. A novel aromatic amine compound according to claim 1, characterized in that said compound is selected from:
6. a hole transport material comprising a compound according to any one of claims 1 to 5.
7. A hole transport layer comprising the hole transport material according to claim 6.
8. An organic electroluminescent device comprising the hole transport layer according to claim 7.
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| CN109467511A (en) * | 2018-11-13 | 2019-03-15 | 长春海谱润斯科技有限公司 | A kind of aromatic amine compounds and its organic luminescent device |
| CN112745229A (en) * | 2019-10-31 | 2021-05-04 | 南京高光半导体材料有限公司 | Hole transport material with excellent performance and organic electroluminescent device containing same |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN109467511A (en) * | 2018-11-13 | 2019-03-15 | 长春海谱润斯科技有限公司 | A kind of aromatic amine compounds and its organic luminescent device |
| CN112745229A (en) * | 2019-10-31 | 2021-05-04 | 南京高光半导体材料有限公司 | Hole transport material with excellent performance and organic electroluminescent device containing same |
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Application publication date: 20220111 |