CN111689889B - Aromatic amine compound and use thereof - Google Patents

Aromatic amine compound and use thereof Download PDF

Info

Publication number
CN111689889B
CN111689889B CN202010704032.5A CN202010704032A CN111689889B CN 111689889 B CN111689889 B CN 111689889B CN 202010704032 A CN202010704032 A CN 202010704032A CN 111689889 B CN111689889 B CN 111689889B
Authority
CN
China
Prior art keywords
substituted
aromatic amine
amine compound
carbon number
unsubstituted
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Active
Application number
CN202010704032.5A
Other languages
Chinese (zh)
Other versions
CN111689889A (en
Inventor
范洪涛
王湘成
向传义
何为
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Shanghai Yaoyi Electronic Technology Co ltd
Original Assignee
Shanghai Yaoyi Electronic Technology Co ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Shanghai Yaoyi Electronic Technology Co ltd filed Critical Shanghai Yaoyi Electronic Technology Co ltd
Priority to CN202010704032.5A priority Critical patent/CN111689889B/en
Publication of CN111689889A publication Critical patent/CN111689889A/en
Application granted granted Critical
Publication of CN111689889B publication Critical patent/CN111689889B/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Images

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
    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/76—Dibenzothiophenes
    • 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
    • C07D405/12—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 chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • 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
    • 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
    • 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
    • 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
    • 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
    • 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
    • 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
    • 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
    • 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
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1011—Condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/549—Organic PV cells

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Optics & Photonics (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

The invention discloses an aromatic amine compound and application thereof, belonging to the technical field of organic electroluminescence. The aromatic amine compound has a general structure shown by the following formula:
Figure DDA0002594015080000011
x is selected from O, S or-NR-, and R 1 、R 2 、R 3 、R 4 And R is independently selected from hydrogen, deuterium, a substituted or unsubstituted aryl group having a ring-forming carbon number of 6 to 30, a substituted or unsubstituted heteroaryl group having a ring-forming carbon number of 5 to 30, a substituted or unsubstituted alkyl group having a carbon number of 1 to 30, a substituted or unsubstituted fluoroalkyl group having a carbon number of 1 to 30, a substituted or unsubstituted cycloalkyl group having a ring-forming carbon number of 3 to 30, and a substituted or unsubstituted aralkyl group having a carbon number of 7 to 30, respectively, as a hole transporting material in the organic electroluminescent device. Due to the addition of the naphthalene heterocyclic ring structure, the aromatic amine compound can effectively improve the hole transport capability of the OLED device, thereby improving the light efficiency and prolonging the service life of the device.

Description

Aromatic amine compound and use thereof
Technical Field
The invention belongs to the field of organic electroluminescence, and particularly relates to an aromatic amine compound and application thereof in an organic electroluminescent device and display.
Background
The OLED can emit light in a solid state, and is widely used in the fields of display, illumination, and the like, and the OLED device is composed of an anode, a cathode, and an organic material therebetween, holes are injected from the anode and transported to a light emitting layer, and electrons are injected from the cathode and transported to the light emitting layer, and in order to achieve the best light emitting performance, the amounts of the holes and the electrons entering the light emitting layer are often balanced. While suitable hole transport materials have a great influence on the light emitting performance of OLEDs, common amine-containing hole transport materials have poor hole injection capability and a small hole injection amount, resulting in high device voltage and low efficiency, and aromatic amine compounds are widely used as hole transport materials, but the hole transport capability still needs to be improved.
Disclosure of Invention
In order to overcome the above defects of the prior art, the present invention provides an aromatic amine compound having a naphtho-heterocycle, which is used as a hole transport material of an OLED device to effectively improve the hole transport ability of the OLED device, thereby improving the device performance, and the aromatic amine compound has a chemical structure shown in formula (i):
Figure BDA0002594015060000011
wherein X is selected from O, S or-NR-;
R 1 、R 2 、R 3 、R 4 and R is independently selected from hydrogen, deuterium, substituted or unsubstituted aryl group having 6 to 30 carbon atoms in a ring, substituted or unsubstituted heteroaryl group having 5 to 30 carbon atoms in a ring, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms in a ring, substituted or unsubstituted fluoroalkyl group having 1 to 30 carbon atoms in a ring, substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms in a ring, and substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms in a ring.
According to some embodiments of the invention, the aromatic amine compound is selected from the group consisting of the chemical structures shown as any one of C1 to C36:
Figure BDA0002594015060000021
/>
Figure BDA0002594015060000031
the invention provides application of any one of the aromatic amine compounds as a hole transport material in an organic electroluminescent device.
According to some embodiments of the present invention, the organic electroluminescent device is a top emission structure, and sequentially comprises a first electrode, a hole injection layer, a first hole transport layer, a second hole transport layer, a light emitting layer, a hole blocking layer, an electron transport layer, a second electrode, and a cap layer; wherein the content of the first and second substances,
any of the aromatic amine compounds having a chemical structure represented by the general formula (I) is used as the first hole transport layer and/or the second hole transport layer.
The invention also provides a display panel comprising any one of the organic electroluminescent devices.
The invention also provides a display device comprising any one of the display panels.
The display panel or the display device comprising the organic electroluminescent device has the following advantages: high luminous efficiency, low driving voltage and long service life.
Compared with the prior art, the aromatic amine compound used as the hole transport material can effectively improve the hole transport capability of the OLED device due to the addition of the naphthalene heterocyclic structure, so that the light efficiency and the service life of the device are improved.
Drawings
Fig. 1 is a schematic structural diagram of an OLED device.
Detailed Description
The present invention is further illustrated by the following examples and comparative examples, which are intended to be illustrative only and are not to be construed as limiting the invention. The technical scheme of the invention is to be modified or replaced equivalently without departing from the scope of the technical scheme of the invention, and the technical scheme of the invention is covered by the protection scope of the invention.
The aromatic amine compound provided by the invention has a chemical structure shown as a general formula (I):
Figure BDA0002594015060000041
wherein X is selected from O, S or-NR-;
R 1 、R 2 、R 3 、R 4 and R are each independently selected from hydrogen, deuterium, a substituted or unsubstituted aryl group having a carbon number of 6 to 30 in the ring, a substituted or unsubstituted heteroaryl group having a carbon number of 5 to 30 in the ring, a substituted or unsubstituted alkyl group having a carbon number of 1 to 30 in the ring, a substituted or unsubstituted fluoroalkyl group having a carbon number of 1 to 30 in the ring, a substituted or unsubstituted cycloalkyl group having a carbon number of 3 to 30 in the ring, or a substituted or unsubstituted aralkyl group having a carbon number of 7 to 30, the above aromatic amine compound may in some embodiments be selected from the chemical structures as shown in any one of C1 to C36:
Figure BDA0002594015060000051
/>
Figure BDA0002594015060000061
/>
Figure BDA0002594015060000071
the invention also provides the application of the aromatic amine compound as a hole transport material in the organic electroluminescent device; in some embodiments, the organic electroluminescent device may be a top emission structure and sequentially include a first electrode, a hole injection layer, a first hole transport layer, a second hole transport layer, a light emitting layer, a hole blocking layer, an electron transport layer, a second electrode, and a cap layer; wherein the aromatic amine compound having a chemical structure represented by the above general formula (I) is used as the first hole transporting layer and/or the second hole transporting layer.
The invention also provides a display panel comprising the organic electroluminescent device.
The invention also provides a display device comprising the display panel.
The following synthetic examples 1 to 5 exemplarily describe the synthesis of the above-described compounds C1, C2, C7, C19 and C28, wherein the starting materials for the preparation methods are not indicated to be commercially available.
Synthesis example 1
This example synthesizes compound C1 (1-1), the synthetic route is shown below:
Figure BDA0002594015060000072
the preparation method comprises the following specific steps:
m-1 was synthesized by charging M-1A (100g, 553.6 mmol), M-1B (102g, 553.6 mmol) and 1, 4-dioxane (1.00L) in this order into a three-necked flask, displacing nitrogen gas three times, adding concentrated sulfuric acid (33.8mL, 609mmol) dropwise while stirring, after completion, heating, setting the external temperature at 100 ℃ and refluxing for 10hrs, cooling the reaction liquid, pouring it into water (2.00L), extracting with toluene (1.00 Lx 2), washing the organic phase with a saturated aqueous NaCl solution (1.00 Lx 3), purifying by column chromatography to obtain M-1 (155.2g, 85%), MS (70eV, EI) + ):m/z:329.10。
Synthesis of M-2: adding M-1 (100g, 303.2mmol), toluene (1.00L) and DDQ (77.1g, 333.5mmol) into a three-neck flask in sequence, replacing nitrogen for three times, starting stirring and heating, setting the external temperature at 120 ℃, carrying out reflux reaction for 5hrs, adding saturated NaOH aqueous solution (200 mL), continuing reaction for 1hr, cooling, filtering, washing the filtrate with saturated NaCl aqueous solution (300 mL multiplied by 3), purifying by a column to obtain M-2 (79.5g, 80%), MS (70eV, EI + ):m/z:327.08。
Synthesis of M-3: to a three-necked flask, toluene (800 mL), M-2 (79.0 g, 241mmol), bromobenzene (37.9 g, 241mmol), sodium tert-butoxide (57.9 g, 602mmol), pd were added successively with stirring 2 dba 3 (2.20g, 2.41mmol) and tri-tert-butylphosphine (15.0mL, 10% toluene solution, 6.02 mmol), replacing nitrogen for three times, heating, setting the external temperature at 120 ℃, refluxing for 3hrs, cooling, filtering, purifying the filtrate by column chromatography to obtain M-3 (87.6g, 90%), MS (70eV, EI) + ):m/z:403.11。
1-1 Synthesis: to a three-necked flask, toluene (100 mL), absolute ethanol (50 mL), water (50 mL), M-3 (20.0 g, 49.5) were added with stirringmmol)，M-3A(14.3g，49.5mmol)，K 2 CO 3 (13.7g，99.0mmol)，Pd(PPh 3 ) 4 (575mg, 0.49mmol), replacing nitrogen for three times, starting heating, setting the external temperature at 100 ℃, refluxing for 3hrs, cooling, separating liquid, washing the organic phase with saturated NaCl aqueous solution (100 mL. Times.3), purifying by column chromatography to obtain 1-1 (25.8g, 85%), MS (70eV, EI) + ):m/z:612.26； 1 H NMR(CDCl 3 ,400Hz):δ8.12-8.23(m,4H),7.89(s,1H),7.37-7.62(m,15H),7.01-7.24(m,12H)。
Synthesis example 2
Compound C2 (1-2) of this example was synthesized using M-3 as obtained in example 1, the synthetic route being as follows:
Figure BDA0002594015060000081
the preparation method comprises the following specific steps:
1-2 Synthesis: to a three-necked flask, toluene (100 mL), absolute ethanol (50 mL), water (50 mL), M-3 (20.0 g,49.5 mmol), M-3B (21.9g, 49.5 mmol), and K were added under stirring 2 CO 3 (13.7g，99.0mmol)，Pd(PPh 3 ) 4 (575mg, 0.49mmol), replacing nitrogen for three times, heating, setting the external temperature at 100 deg.C, refluxing for 3hrs, cooling, separating, washing the organic phase with saturated NaCl aqueous solution (100 mL. Times.3), purifying by column chromatography to obtain 1-2 (31.1g, 82%), MS (70eV, EI) + ):m/z:764.32； 1 H NMR(CDCl 3 ,400Hz):δ8.12-8.30(m,4H),7.60-7.75(m,6H),7.31-7.58(m,30H)。
Synthesis example 3
Compound C7 (1-3) of this example was synthesized using M-3 obtained in example 1, the synthetic route being as follows:
Figure BDA0002594015060000091
the preparation method comprises the following specific steps:
synthesis of M-4: toluene (100 mL) was added to a three-necked flask with stirringEtOH (50 mL), water (50 mL), M-3 (20.0 g,49.5 mmol), M-3C (7.74g, 49.5 mmol), K 2 CO 3 (13.7g，99.0mmol)，Pd(PPh 3 ) 4 (575mg, 0.49mmol), replacing nitrogen for three times, heating, reflux-reacting at 100 deg.C for 3hrs, cooling, separating, washing the organic phase with saturated NaCl aqueous solution (100 mL. Times.3), and purifying by column chromatography to obtain M-4 (19.7g, 83%), MS (70eV, EI) + ):m/z:479.14。
1-3 Synthesis: to a three-necked flask, toluene (190 mL), M-4 (19.0g, 39.58mmol), M-4A (12.7g, 39.58mmol), sodium tert-butoxide (7.61g, 79.17mmol) and Pd were added in this order while stirring 2 dba 3 (365mg, 0.40mmol) and tricyclohexylphosphine (280mg, 0.99mmol), replacing nitrogen for three times, heating, setting the external temperature at 120 deg.C, refluxing for 3hrs, cooling, filtering, purifying the filtrate by column chromatography to obtain 1-3 (30.0 g, 90%), MS (70eV, EI) + ):m/z:840.35； 1 H NMR(CDCl 3 ,400Hz):δ8.12-8.30(m,4H),7.89(s,1H)7.34-7.75(m,35H),7.25(s,4H)。
Synthesis example 4
Compound C19 (2-1) was synthesized in this example, following the following synthetic route:
Figure BDA0002594015060000101
the preparation method comprises the following specific steps:
m-5 Synthesis by adding acetonitrile (500 mL), M-5A (50.0 g,281.5 mmol), M-5B (70.7 g,281.5 mmol), cesium carbonate (183.5 g, 5631 mmol) to a three-necked flask while stirring, replacing nitrogen three times, heating, refluxing at 100 deg.C for 10hrs, cooling, quenching the reaction mixture in water (500 mL), extracting with ethyl acetate (200 mL. Times.2), concentrating the organic phase, and purifying by column chromatography to obtain M-5 (99.2g, 86%), MS (70eV, EI, E, C, and E + ):m/z:407.99。
Synthesis of M-6: to a three-necked flask, toluene (200 mL), M-5 (20.0 g, 48.82mmol), sodium t-butoxide (9.38g, 97.63mmol) and Pa were added in this order under stirring 2 (dba) 3 (447mg，0.488mmol)，P(t-Bu) 3 (2.0 g,10% toluene solution, 0.989 mmol), nitrogen was replaced three times, heating was started, the external temperature was set at 120 deg.C, reflux reaction was carried out for 2hrs, cooling was carried out, filtration was carried out, and the filtrate was purified by column chromatography to obtain M-6 (13.24g, 82.5%), MS (70eV, EI) + ):m/z:328.07。
2-1 Synthesis: to a three-necked flask, toluene (40 mL), absolute ethanol (20 mL), water (20 mL), M-6 (10.0 g, 30.41mmol), M-6A (8.79g, 30.41mmol), and K were added under stirring 2 CO 3 (6.31g，45.62mmol)，Pd(PPh 3 ) 4 (351mg, 0.3mmol), replacing nitrogen for three times, starting heating, setting the external temperature at 100 ℃, refluxing for 3hrs, cooling, separating liquid, washing the organic phase with saturated NaCl aqueous solution (50 mL. Times.3), purifying by column chromatography to obtain 2-1 (15.53g, 95%), MS (70eV, EI) + ):m/z:537.21； 1 H NMR(CDCl 3 ,400Hz):δ8.23(d,1H),7.75-7.88(m,6H),7.37-7.55(m,10H),7.00-7.24(m,10H)。
Synthesis example 5
This example synthesizes compound C28 (2-2), the synthetic route is shown below:
Figure BDA0002594015060000111
the preparation method comprises the following specific steps:
synthesis of M-7: to a three-necked flask, toluene (200 mL), absolute ethanol (100 mL), water (100 mL), M-7A (50.0 g, 194.62mmol), M-7B (60.43g, 194.62mmol), and K were added under stirring 2 CO 3 (40.35g，292mmol)，Pd(PPh 3 ) 4 (2.25g, 1.95mmol), replacing nitrogen for three times, starting heating, setting the external temperature at 100 ℃, refluxing for 3hrs, cooling, separating liquid, washing the organic phase with saturated aqueous NaCl solution (100 mL. Times.3), purifying by column chromatography to obtain M-7 (70.1g, 91%), MS (70eV, EI) + ):m/z:393.94。
Synthesis of M-8: adding methanesulfonic acid (350 mL) and M-7 (70.0 g,176.9 mmol) into a three-necked flask, replacing nitrogen for three times, starting heating, setting the external temperature at 150 ℃, reacting for 12hrs, cooling, pouring the reaction solution into the final mixed solution of water (1L) and toluene (1L), and stirring uniformlyHomogenizing, separating, washing organic phase with saturated NaCl aqueous solution (300 mL. Times.3), and purifying by column chromatography to obtain M-8 (59.8 g), MS (70eV, EI) + ):m/z:361.92。
Synthesis of M-9: adding M-8 (50.0 g, 137.49mmol), toluene (500 mL) and DDQ (34.33g, 151.24mmol) into a three-necked flask in sequence, replacing nitrogen for three times, stirring and heating, setting the external temperature at 120 ℃, refluxing for 5hrs, adding saturated NaOH aqueous solution (200 mL), continuing to react for 1hr, cooling, filtering, washing the filtrate with saturated NaCl aqueous solution (300 mL. Times.3), purifying with a column to obtain M-9 (43.26g, 90.5%), MS (70eV, EI) + ):m/z:345.92。
Synthesis of M-10: to a three-necked flask were added toluene (160 mL), absolute ethanol (80 mL), water (80 mL), M-9 (40.0 g, 115.06mmol), phenylboronic acid (14.03g, 115.06mmol), and K with stirring 2 CO 3 (23.85g，172.6mmol)，Pd(PPh 3 ) 4 (1.33g, 1.15mmol), replacing nitrogen for three times, starting heating, setting the external temperature at 100 ℃, refluxing for 3hrs, cooling, separating liquid, washing the organic phase with saturated NaCl aqueous solution (100 mL. Times.3), purifying by column chromatography to obtain M-10 (37.7g, 95%), MS (70eV, EI) + ):m/z:344.04。
2-2 Synthesis: to a three-necked flask were added toluene (120 mL), absolute ethanol (60 mL), water (60 mL), M-10 (30.0 g,87.0 mmol), M-10A (25.10 g,87.0 mmol), and K with stirring 2 CO 3 (18.0g，130.4mmol)，Pd(PPh 3 ) 4 (1.00g, 0.87mmol), replacing nitrogen for three times, heating, refluxing at 100 deg.C for 3hrs, cooling, separating, washing the organic phase with saturated aqueous NaCl solution (100 mL. Times.3), and purifying by column chromatography to obtain M-10 (43.35g, 90%), MS (70eV, EI) + ):m/z:553.19； 1 H NMR(CDCl 3 ,400Hz):δ7.99-8.23(m,5H),7.75-7.83(m,3H),7.38-7.55(m,6H),7.00-7.24(m,13H)。
The technical effects of the compounds of the invention are explained in detail below by means of device examples.
Comparative example 1
Comparative example 1 Using the Compound
Figure BDA0002594015060000121
As a first hole transport layer, an OLED display panel with a top emission structure was prepared according to the structure shown in fig. 1, and the specific preparation process was:
forming a reflecting anode Ag 100nm on a glass substrate, forming an ITO film layer on the Ag with a thickness of 15nm to obtain a first electrode as an anode, and then evaporating 30nm HATCN (
Figure BDA0002594015060000122
) As a hole-injecting layer, followed by evaporation of an HTL1 +in a thickness of 100nm>
Figure BDA0002594015060000123
A first hole transport layer is obtained, and then the layer with the thickness of 20nm is evaporated
Figure BDA0002594015060000124
Obtaining a second hole transport layer, and evaporating and coating on the substrate at an evaporation rate of 95% to 5%>
Figure BDA0002594015060000125
And/or>
Figure BDA0002594015060000126
30nm, a blue light emitting unit is manufactured, and then 10nm is evaporated>
Figure BDA0002594015060000131
Forming a hole blocking layer, and evaporating 30 nm/4 at a deposition rate of 50% to 50%>
Figure BDA0002594015060000132
And &>
Figure BDA0002594015060000133
The mixture is used as electron transport layer, and then formed into magnesium silver with thickness of 15nm at evaporation rate of 90% to 10%, used as second electrode, and formed into a layer in the range of 700nm +>
Figure BDA0002594015060000134
As a coverA cap layer.
Device examples 1 to 5
And comparative example 1 with HTL1 (
Figure BDA0002594015060000135
) Examples 1 to 5 used compounds C1, C2, C7, C19 and C28 prepared in the above-described synthesis examples 1 to 5, respectively, as the first hole transport layer, differently from the first hole transport layer, and the other structures were the same.
Comparative example 2
And comparative example 1 with HTL1 (
Figure BDA0002594015060000136
) In contrast to the first hole-transport layer, HTL2 (` vs. `) was used in comparative example 2>
Figure BDA0002594015060000137
) The first hole transport layer is different from the second hole transport layer, and the other structures are the same.
TABLE 1
Figure BDA0002594015060000141
The previous description of the disclosed embodiments is provided to enable any person skilled in the art to make or use the present invention. It will be apparent to those skilled in the art that various modifications to these embodiments can be readily made, and the generic principles described herein may be applied to other embodiments without the use of the inventive faculty. Therefore, the present invention is not limited to the above-described embodiments. Those skilled in the art, having the benefit of the teachings of this invention, will appreciate numerous modifications and variations there from without departing from the scope of the invention as defined by the appended claims.

Claims (5)

1. An aromatic amine compound, characterized in that the aromatic amine compound is selected from the group consisting of the following chemical structures:
Figure FDA0004118174530000011
2. use of the aromatic amine compound according to claim 1 as a hole transport material in an organic electroluminescent device.
3. The use according to claim 2, wherein the organic electroluminescent device is a top-emitting structure comprising, in order, a first electrode, a hole injection layer, a first hole transport layer, a second hole transport layer, a light-emitting layer, a hole blocking layer, an electron transport layer, a second electrode, and a capping layer; wherein the aromatic amine compound according to claim 1 is used as the first hole transport layer and/or the second hole transport layer.
4. A display panel comprising the organic electroluminescent device as claimed in claim 3.
5. A display device characterized by comprising the display panel according to claim 4.
CN202010704032.5A 2020-07-21 2020-07-21 Aromatic amine compound and use thereof Active CN111689889B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN202010704032.5A CN111689889B (en) 2020-07-21 2020-07-21 Aromatic amine compound and use thereof

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN202010704032.5A CN111689889B (en) 2020-07-21 2020-07-21 Aromatic amine compound and use thereof

Publications (2)

Publication Number Publication Date
CN111689889A CN111689889A (en) 2020-09-22
CN111689889B true CN111689889B (en) 2023-04-14

Family

ID=72486566

Family Applications (1)

Application Number Title Priority Date Filing Date
CN202010704032.5A Active CN111689889B (en) 2020-07-21 2020-07-21 Aromatic amine compound and use thereof

Country Status (1)

Country Link
CN (1) CN111689889B (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115611884B (en) * 2021-07-13 2023-12-29 江苏三月科技股份有限公司 Monoamine organic compound containing naphthoheterocyclyl and benzoheterocyclyl and organic electroluminescent device containing same
CN113851599A (en) * 2021-09-13 2021-12-28 烟台显华光电材料研究院有限公司 Organic electroluminescent device and display device comprising same
CN116120265A (en) * 2021-11-12 2023-05-16 奥来德(上海)光电材料科技有限公司 Aromatic amine group-containing light-emitting auxiliary material and preparation method and application thereof

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2017188655A1 (en) * 2016-04-26 2017-11-02 덕산네오룩스 주식회사 Compound for organic electric element, organic electric element using same, and electronic device comprising same organic electronic element
KR102126442B1 (en) * 2016-05-04 2020-06-24 덕산네오룩스 주식회사 Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof
KR102211337B1 (en) * 2016-05-19 2021-02-03 덕산네오룩스 주식회사 Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof
CN110386894A (en) * 2018-04-20 2019-10-29 北京鼎材科技有限公司 A kind of hole mobile material and its application

Also Published As

Publication number Publication date
CN111689889A (en) 2020-09-22

Similar Documents

Publication Publication Date Title
CN111689889B (en) Aromatic amine compound and use thereof
JP5183142B2 (en) Binaphthyl compound and organic light-emitting device using the same
CN112979709B (en) Metal complex and application thereof
CN111004201B (en) Organic electroluminescent compound, preparation method thereof and organic electroluminescent device
CN111875608B (en) Seven-membered nitrogen-containing heterocyclic derivative and organic electroluminescent device thereof
CN111233867A (en) Organic compound with carbazole derivative as core and application thereof in organic electroluminescent device
CN106892903B (en) Organic electroluminescent compound based on phenazine and carbazole and luminescent device thereof
CN112110942B (en) High-efficiency deep blue fluorescent doped material and OLED organic electroluminescent device
CN115894491A (en) Electron transport material, preparation method thereof, light-emitting device and light-emitting device
CN111689968B (en) Organic luminescent material and preparation method and application thereof
CN113620860B (en) Organic electroluminescent compound and preparation method and application thereof
CN113307770A (en) Luminescent auxiliary material and preparation method and application thereof
CN111748338B (en) Organic electroluminescent compound, organic electroluminescent device and application thereof
CN116063293A (en) Light-emitting auxiliary material, preparation method thereof and organic electroluminescent device
CN114874192A (en) Organic electroluminescent material and application thereof in organic electroluminescent device
CN112940013B (en) Aromatic amine compound of imidazopyridine and application thereof
CN113248519A (en) Organic compound and organic light-emitting device using same
CN112079833A (en) Organic electroluminescent compound and preparation method and application thereof
EP3915982A1 (en) Compound and organic light-emitting device including same
CN113620861B (en) Organic electroluminescent compound and preparation method and application thereof
CN116217605B (en) Polycyclic compound and light-emitting device thereof
CN111187265B (en) Organic main body material, preparation method thereof and organic electroluminescent device
CN112300174B (en) Novel electron transport material and application thereof in OLED device
CN111747964B (en) Organic electroluminescent compound, organic electroluminescent device and application thereof
KR102026861B1 (en) Compound for organic electronic element, organic electronic element using the same, and a electronic device thereof

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination
GR01 Patent grant
GR01 Patent grant