CN110452227A - A kind of organic blue-light fluorescent material and blue-light device based on indole derivatives - Google Patents
A kind of organic blue-light fluorescent material and blue-light device based on indole derivatives Download PDFInfo
- Publication number
- CN110452227A CN110452227A CN201910717049.1A CN201910717049A CN110452227A CN 110452227 A CN110452227 A CN 110452227A CN 201910717049 A CN201910717049 A CN 201910717049A CN 110452227 A CN110452227 A CN 110452227A
- Authority
- CN
- China
- Prior art keywords
- blue
- light
- indole derivatives
- organic
- fluorescent material
- 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.)
- Pending
Links
- 239000000463 material Substances 0.000 title claims abstract description 64
- 150000002475 indoles Chemical class 0.000 title claims abstract description 30
- 229940054051 antipsychotic indole derivative Drugs 0.000 title claims abstract description 26
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims abstract description 10
- 150000001875 compounds Chemical class 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- 150000003457 sulfones Chemical class 0.000 claims description 2
- 230000000694 effects Effects 0.000 abstract description 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- 238000006243 chemical reaction Methods 0.000 description 14
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 10
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 230000003111 delayed effect Effects 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 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 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 230000008878 coupling Effects 0.000 description 5
- 238000010168 coupling process Methods 0.000 description 5
- 238000005859 coupling reaction Methods 0.000 description 5
- 229910001873 dinitrogen Inorganic materials 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 239000012467 final product Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- JHUUPUMBZGWODW-UHFFFAOYSA-N 3,6-dihydro-1,2-dioxine Chemical compound C1OOCC=C1 JHUUPUMBZGWODW-UHFFFAOYSA-N 0.000 description 4
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 238000005893 bromination reaction Methods 0.000 description 4
- 230000005284 excitation Effects 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 239000011574 phosphorus Substances 0.000 description 3
- WMMGRPSGJRRNLN-UHFFFAOYSA-N 1-$l^{1}-phosphanylbutane Chemical compound CCCC[P] WMMGRPSGJRRNLN-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 241001062009 Indigofera Species 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 230000031709 bromination Effects 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 230000005684 electric field Effects 0.000 description 2
- 125000004494 ethyl ester group Chemical group 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 238000002390 rotary evaporation Methods 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- GYGKJNGSQQORRG-UHFFFAOYSA-N 2,3-diphenyl-1h-indole Chemical compound C1=CC=CC=C1C1=C(C=2C=CC=CC=2)C2=CC=CC=C2N1 GYGKJNGSQQORRG-UHFFFAOYSA-N 0.000 description 1
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical group C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 239000009289 huang-lien-chieh-tu-tang Substances 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000003809 water extraction 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/027—Organoboranes and organoborohydrides
-
- 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]
- H10K50/11—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
- 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
- H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
-
- 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
- H10K85/631—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
- H10K85/654—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
-
- 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
- C09K2211/1007—Non-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
- C09K2211/1011—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
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
-
- 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
- C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
-
- 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
- C09K2211/1096—Heterocyclic compounds characterised by ligands containing other heteroatoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The present invention discloses a kind of organic blue-light fluorescent material and blue-light device based on indole derivatives, and organic blue-light fluorescent material includes D-A structure, and the D is electron donor, and the A is electron acceptor, and the D is indole derivatives.The present invention provides a kind of organic blue-light fluorescent material based on indole derivatives as electron donor, and the photochromic purity of the blue-light device based on the material has good blue phosphor effect.Meanwhile the blue-light device based on the material has high luminance purity, luminous efficiency and device stability；Additionally due to the characteristics of material itself, can simplify device architecture, reduces device and prepare complexity.
Description
Technical field
The present invention relates to organic photoelectrical material field more particularly to a kind of organic blue phosphor materials based on indole derivatives
Material and blue-light device.
Background technique
Organic electroluminescent LED (OLED) refers to excitation of the organic material under electric field action, by electric current or electric field
And generate the display technology of new generation of light.OLED display technology based on electroluminescent organic material, smart phone, TV,
Illumination, large-size screen monitors such as show at the application that fields have been succeeded, and Flexible Displays, quality be frivolous, response quickly, high-purity colour developing, master
The dynamic luminous and advantages such as low energy consumption have received the extensive attention and research of academia and industry.It is organic according to the three primary colors of light
Luminescent material can be divided into blue, red and green three kinds of luminescent materials, current white light show in maximum bottleneck be exactly indigo plant
Luminescent material and device, it is especially light blue to arrive navy blue high-performance blue light material.It is analyzed from material itself, the energy gap of blue light
Space requirement brings challenges in 2.9eV or more to the design of the comprehensive performance of material；Molecule on device, wide band gap is to function
Level-density parameter between layer also proposed high requirement.So designing and developing a series of high-fluorescence quantum yields and high stable
The blue light material of property is very necessary.
Since Organic Light Emitting Diode (OLED) is found, small organic molecule blue light material and blue-light device are persistently taken
Progress was obtained, was all greatly improved on luminous efficiency and stability.Your gold Phosphorescent blue light material due to needing
Belong to (Ir, Pt etc.), and the stability of device and luminance purity have very big difficulty, organic fluorescence blue light material more has excellent
Gesture.Fluorescent material can be divided into common fluorescent and delayed fluorescence according to luminous process.Common fluorescent is exactly on singlet
The fluorescence that ground state is emitted, the theoretical maximum internal quantum of this kind of fluorescent material are returned in the direct transition of 25% singlet exciton
It is 25%, if exterior light quantum coupling efficiency is 0.2, its maximum external light emission efficiency is 5%, this is far from satisfying quotient
The demand of industry, although its stability and photochromic purity are very outstanding；Another kind of is exactly delayed fluorescence material, at present according to delay
Luminescence mechanism difference is divided into three kinds: thermal excitation delayed fluorescence (TADF), triplet state-triplet state exciton annihilation delayed fluorescence (TTA)
With high line state inverse conversion delayed fluorescence (HLCT).At present most study be also effect it is best be exactly TADF blue light material, due to
Triplet excitons can be with inverse conversion singlet, so that internal quantum may be implemented 100% under thermal excitation, this kind of delayed fluorescence
Material is compared with conventional fluorescent in luminous efficiency and achieves huge breakthrough.But the light of the blue-light device based on TADF material
Excitation purity is extremely difficult to ethereal blue or dark blue, this is because TADF luminescent material due to D-A structure exist stronger charge transfer state,
It is very wide spectrally then to show as half-peak breadth, generally all in 90nm or so.
Therefore, the existing technology needs to be improved and developed.
Summary of the invention
In view of above-mentioned deficiencies of the prior art, organic indigo plant based on indole derivatives that the purpose of the present invention is to provide a kind of
Fluorescence material and blue-light device, it is intended to which the photochromic purity for solving the existing blue-light device based on TADF material is extremely difficult to ethereal blue
Or dark blue problem.
Technical scheme is as follows:
The present invention provides a kind of organic blue-light fluorescent material based on indole derivatives, wherein including D-A structure, the D
For electron donor, the A is electron acceptor, and the D is indole derivatives.
The present invention provides a kind of blue-light device, including luminescent layer, wherein the material of the luminescent layer includes of the present invention
Organic blue-light fluorescent material.
The utility model has the advantages that the present invention provides a kind of organic blue-light fluorescent material based on indole derivatives as electron donor,
The photochromic purity of blue-light device based on the material has good blue phosphor effect.Meanwhile the blue light device based on the material
Part has high luminance purity, luminous efficiency and device stability；Additionally due to the characteristics of material itself, can simplify device junction
Structure reduces device and prepares complexity.
Specific embodiment
The present invention provides a kind of organic blue-light fluorescent material and blue-light device based on indole derivatives, of the invention to make
Purpose, technical solution and effect are clearer, clear, and the present invention is described in more detail below.It should be appreciated that this place is retouched
The specific embodiment stated is only used to explain the present invention, is not intended to limit the present invention.
In order to realize ethereal blue or dark blue, it is necessary to new electron donor and new electron acceptor are designed, it is the most frequently used at present
The electron donor of blue light material be carbazole and its derivative, in order to reduce charge transfer state, the present embodiment design has weaker
The group of electron supplying capacity.The study found that structure-based modification, the supplied for electronic energy of the group based on indoles and indole derivatives
Power is weaker than carbazole, while having very strong fluorescence, is a kind of very potential applied to blue light and dark blue smooth OLED material research
System.Therefore, the present invention is based on indole derivatives to make electron donor, devises a series of novel blue light fluorescent material.
Specifically, the embodiment of the present invention provides a kind of organic blue-light fluorescent material based on indole derivatives, wherein including
D-A structure, the D are electron donor, and the A is electron acceptor, and the D is indole derivatives.
That is, invention embodiment material structural model are as follows: D-A (Donor-Acceptor).Wherein D (Donor,
Donor) what is selected is indole derivatives, this is that one kind is easily modified, and has good cavity transmission ability and weak electron supplying capacity
Group.
In one embodiment, the A (Acceptor, receptor) is nitrogen-containing heterocycle；Or
The A is the aromatic group with electrophilic characteristic such as boracic, ketone or sulfone.
By calculating and testing, the band gap of organic blue-light fluorescent material described in the present embodiment based on indole derivatives exists
2.80eV or more, and all have good blue phosphor.When as luminescent material, since the bipolarity of itself is special
Property and indole derivatives structure spatial warping, can effectively slow down the quenching of intermolecular exciton, therefore can be used for mixing
Miscellaneous and undoped blue-light device.
In one embodiment, the chemical structural formula of organic blue phosphor is Wherein, R1, R2, R3, R4It is independently selected from: H, CH3,t-(Bu)3, In any one,
R5, R6It is independently selected from H, CH3,t-(Bu)3,In any one；A is selected from One of group or a variety of groups independent assortment.
In one embodiment, any one of organic blue-light fluorescent material in following compound 1-112:
The embodiment of the present invention provides a kind of blue-light device, including luminescent layer, wherein the material of the luminescent layer includes this hair
Organic blue-light fluorescent material described in bright embodiment.
The embodiment of the present invention provides a kind of preparation method of organic blue-light fluorescent material, can be coupled by Buchward anti-
It should be prepared, using popular response condition well-known to those skilled in the art.Below by specific embodiment pair
The present invention further illustrates:
Embodiment 1
By taking compound 3 as an example, preparation method is introduced, simple indole derivatives raw material and electron accepting groups are equal
Easily purchase, reaction equation are as follows:
Specific preparation process: 2,3- diphenyl indole is added under condition of nitrogen gas into 100ml1,4- dioxane solvent
(1.70g, 10.0mmol) and 4- bromine triphenyl triazine (4.27g, 11.0mmol), tris(dibenzylideneacetone) dipalladium (0.58g,
0.5mmol), tri-tert phosphorus (15%, 0.15mmol) is stirred 12 hours at 110 DEG C.Reaction is cooled to room temperature rear silica gel funnel
Filtering, methylene chloride and n-hexane progress column chromatograph to obtain final product (4.90g, 8.5mmol), yield after the concentration of solution low pressure
85%.
Embodiment 2
By taking compound 4 as an example, chemical equation is as follows:
The specific preparation process of compound 4 includes:
It is protected on BOC: indoles (3.51g, 30mmol) and 4-dimethylaminopyridine (1.22g, 10mmol) is dissolved in 80ml
Then di-tert-butyl dicarbonate (9.81g, 45mmol) is added in tetrahydrofuran solvent, concentration ether and water after reaction reflux 6h
Extraction was spin-dried for column, yield 96% after organic phase anhydrous sodium sulfate drying；
Bromination reaction: product obtained in the previous step (6.08g, 28mmol) is dissolved in DMF solvent, liquid is added dropwise under low temperature
Bromine (9.6g, 60mmol) is stirred overnight at room temperature after low temperature stirs 30 minutes.After the reaction was completed, it is washed with hypo solution
It washs, is extracted with dichloromethane, drying is spin-dried for upper prop, yield 76%；
Buchward coupling: previous step bromination product is added under condition of nitrogen gas into 150ml1,4- dioxane solvent
(7.98g, 21.0mmol) and carbazole (8.35g, 50mmol), tris(dibenzylideneacetone) dipalladium (1.16g, 1.0mmol), three uncles
Butyl phosphorus (30%, 0.3mmol) stirs 12 hours at 110 DEG C.Reaction is cooled to room temperature rear silica gel funnel filtering, solution low pressure
Methylene chloride and n-hexane progress column chromatograph to obtain final product (5.49g, 10mmol), yield 50% after concentration；
De- BOC reaction: the product (5.49g, 10mmol) of previous step is added to trifluoroacetic acid (9ml) and methylene chloride
1h or so is stirred at room temperature in the mixed solution of (10ml), and method rather stops, rotary evaporation.Appropriate acetic acid is added in surplus materials
Dissolved in ethyl ester, using 5% sodium carbonate liquor wash to pH be 8~9, drying be spin-dried for upper prop, obtain white solid (3.58g,
8mmol) product 80%；
Buchward coupling: bis- carbazyl indoles of 2,3- is added under condition of nitrogen gas into 100ml1,4- dioxane solvent
(2.24g, 5.0mmol) and 4- bromine triphenyl triazine (2.14g, 5.5mmol), tris(dibenzylideneacetone) dipalladium (0.28g,
0.25mmol), tri-tert phosphorus (15%, 0.8mmol) is stirred 12 hours at 110 DEG C.Reaction is cooled to room temperature rear silica gel funnel
Filtering, methylene chloride and n-hexane progress column chromatograph to obtain final product (2.42g, 3.2mmol), yield after the concentration of solution low pressure
65%.
Embodiment 3
By taking compound 98 as an example, chemical equation is as follows:
The preparation process of the compound 98 comprising steps of
It is protected on BOC: 2-phenylindone (5.79g, 30mmol) and 4-dimethylaminopyridine (1.22g, 10mmol) is molten
In 80ml tetrahydrofuran solvent, di-tert-butyl dicarbonate (9.81g, 45mmol) then is added, second is used in concentration after reaction reflux 6h
Ether and water extraction were spin-dried for column, yield 95% after organic phase anhydrous sodium sulfate drying；
Bromination reaction: product obtained in the previous step (8.20g, 28mmol) is dissolved in DMF solvent, liquid is added dropwise under low temperature
Bromine (9.6g, 60mmol), after low temperature stirs 30 minutes, 60 DEG C are stirred overnight.After the reaction was completed, it is washed with hypo solution
It washs, is extracted with dichloromethane, drying is spin-dried for upper prop, yield 70%；
Buchward coupling: previous step bromination product is added under condition of nitrogen gas into 150ml1,4- dioxane solvent
(9.00g, 20.0mmol) and carbazole (8.35g, 50mmol), tris(dibenzylideneacetone) dipalladium (1.16g, 1.0mmol), three uncles
Butyl phosphorus (30%, 0.3mmol) stirs 12 hours at 110 DEG C.Reaction is cooled to room temperature rear silica gel funnel filtering, solution low pressure
Methylene chloride and n-hexane progress column chromatograph to obtain final product (5.61g, 9mmol), yield 45% after concentration；
De- BOC reaction: the product (5.61g, 9mmol) of previous step is added to trifluoroacetic acid (9ml) and methylene chloride
1h or so is stirred at room temperature in the mixed solution of (10ml), and method rather stops, rotary evaporation.Appropriate acetic acid is added in surplus materials
Dissolved in ethyl ester, using 5% sodium carbonate liquor wash to pH be 8~9, drying be spin-dried for upper prop, obtain white solid (3.76g,
7.2mmol) product 80%；
Buchward coupling: bis- carbazyl indoles of 2,3- is added under condition of nitrogen gas into 100mL 1,4- dioxane solvent
(2.62g, 5.0mmol) and 4- bromine triphenyl triazine (2.14g, 5.5mmol), tris(dibenzylideneacetone) dipalladium (0.28g,
0.25mmol), tri-tert phosphorus (15%, 0.8mmol) is stirred 12 hours at 110 DEG C.Reaction is cooled to room temperature rear silica gel funnel
Filtering, methylene chloride and n-hexane progress column chromatograph to obtain final product (1.78g, 3.2mmol), yield after the concentration of solution low pressure
45%.
In conclusion the present invention provides a kind of organic blue-light fluorescent material based on indole derivatives as electron donor,
The photochromic purity of blue-light device based on the material has good blue phosphor effect.Meanwhile the blue light device based on the material
Part has high luminance purity, luminous efficiency and device stability；Additionally due to the characteristics of material itself, can simplify device junction
Structure reduces device and prepares complexity.
It should be understood that the application of the present invention is not limited to the above for those of ordinary skills can
With improvement or transformation based on the above description, all these modifications and variations all should belong to the guarantor of appended claims of the present invention
Protect range.
Claims (6)
1. a kind of organic blue-light fluorescent material based on indole derivatives, which is characterized in that including D-A structure, the D is electronics
Donor, the A are electron acceptor, and the D is indole derivatives.
2. organic blue-light fluorescent material according to claim 1 based on indole derivatives, which is characterized in that the A is
Nitrogen-containing heterocycle；Alternatively, the A is the aromatic group of boracic, ketone or sulfone.
3. organic blue-light fluorescent material according to claim 1 based on indole derivatives, which is characterized in that the material
Band gap in 2.80eV or more.
4. organic blue-light fluorescent material according to claim 1 based on indole derivatives, which is characterized in that described organic
The chemical structural formula of blue phosphor isWherein, R1, R2, R3, R4Independent choosing
From: H, CH3,t-(Bu)3, In any one, R5, R6H is independently selected from,
CH3,t-(Bu)3,In any one；A is selected from One of group or a variety of groups independent assortment.
5. organic blue-light fluorescent material according to claim 1 based on indole derivatives, which is characterized in that described organic
Any one of blue-light fluorescent material in following compound 1-112:
6. a kind of blue-light device, including luminescent layer, which is characterized in that the material of the luminescent layer includes claim 1-5 any
Organic blue-light fluorescent material based on indole derivatives described in.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910717049.1A CN110452227A (en) | 2019-08-05 | 2019-08-05 | A kind of organic blue-light fluorescent material and blue-light device based on indole derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910717049.1A CN110452227A (en) | 2019-08-05 | 2019-08-05 | A kind of organic blue-light fluorescent material and blue-light device based on indole derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN110452227A true CN110452227A (en) | 2019-11-15 |
Family
ID=68484876
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201910717049.1A Pending CN110452227A (en) | 2019-08-05 | 2019-08-05 | A kind of organic blue-light fluorescent material and blue-light device based on indole derivatives |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN110452227A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111443068A (en) * | 2020-03-06 | 2020-07-24 | 天津大学 | Pure organic room temperature phosphorescent material with multiple stimulus response characteristics, screening method and application |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20130115161A (en) * | 2012-04-10 | 2013-10-21 | 에스에프씨 주식회사 | Heterocyclic com pounds and organic light-emitting diode including the same |
| CN107108570A (en) * | 2014-12-18 | 2017-08-29 | 东进世美肯株式会社 | Compounds and the organic luminescent device comprising it |
| CN108997318A (en) * | 2018-07-19 | 2018-12-14 | 赵东敏 | Biindolyl class electroluminescent organic material |
| CN109053687A (en) * | 2018-06-29 | 2018-12-21 | 赵东敏 | A kind of biindolyl class display material |
| CN109897029A (en) * | 2017-12-08 | 2019-06-18 | 武汉尚赛光电科技有限公司 | Terpyridyl analog derivative and preparation method thereof, application and device |
-
2019
- 2019-08-05 CN CN201910717049.1A patent/CN110452227A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20130115161A (en) * | 2012-04-10 | 2013-10-21 | 에스에프씨 주식회사 | Heterocyclic com pounds and organic light-emitting diode including the same |
| CN107108570A (en) * | 2014-12-18 | 2017-08-29 | 东进世美肯株式会社 | Compounds and the organic luminescent device comprising it |
| CN109897029A (en) * | 2017-12-08 | 2019-06-18 | 武汉尚赛光电科技有限公司 | Terpyridyl analog derivative and preparation method thereof, application and device |
| CN109053687A (en) * | 2018-06-29 | 2018-12-21 | 赵东敏 | A kind of biindolyl class display material |
| CN108997318A (en) * | 2018-07-19 | 2018-12-14 | 赵东敏 | Biindolyl class electroluminescent organic material |
Non-Patent Citations (1)
| Title |
|---|
| MELISSA B. RODRIGUES等: "Ullmann-type copper-catalyzed coupling amination, photophysical and DNA/HSA-binding properties of new 4-(trifluoromethyl)quinoline", 《JOURNAL OF FLUORINE CHEMISTRY》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111443068A (en) * | 2020-03-06 | 2020-07-24 | 天津大学 | Pure organic room temperature phosphorescent material with multiple stimulus response characteristics, screening method and application |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN110452226A (en) | A kind of organic blue-light fluorescent material and blue-light device based on azole derivatives | |
| CN107573323A (en) | A kind of thermic delayed fluorescence material and its preparation and application | |
| CN105111230A (en) | Di-aza-carbazole derivatives and application thereof | |
| CN109678867B (en) | Phosphorescent compound and organic light emitting diode device using the same | |
| CN104592194A (en) | Thianthrene oxide-aromatic amine organic luminescent small molecule as well as preparation and application thereof | |
| CN102731406A (en) | Phenanthroimidazole derivatives and application of phenanthroimidazole derivatives in preparation of electroluminescent device | |
| CN110386923A (en) | Carbazole compound and its application and organic electroluminescence device | |
| WO2020215439A1 (en) | Red thermally activated delayed fluorescent material and preparation method therefor, and electroluminescent device | |
| CN103183710A (en) | Phosphorus oxy-group hydrogen anthracene di-triarylated amine compound and application thereof | |
| CN110551157A (en) | bivalent platinum complex and preparation method and application thereof | |
| CN109678868A (en) | A kind of red phosphorescent compound and its organic luminescent device using the compound | |
| CN111057112A (en) | Phosphorescent compound and preparation method and application thereof | |
| CN109678875A (en) | A kind of phosphorescent compound and the organic light emitting diode device using the compound | |
| CN106057863A (en) | Multi-primary-color OLED display device | |
| CN110229108A (en) | A kind of bis- phenanthro- imdazole derivatives of styrene-and the preparation method and application thereof | |
| CN110452227A (en) | A kind of organic blue-light fluorescent material and blue-light device based on indole derivatives | |
| CN104762079B (en) | Indole based luminescent compound | |
| CN106243086A (en) | One class connects the preparation method and applications of the pyrimidine derivatives of four identical electron donating groups | |
| CN109438468A (en) | A kind of phosphorescence host compound and its organic electroluminescence device using the compound | |
| CN105777809B (en) | Electroluminescent organic material and organic electroluminescence device | |
| CN112812123A (en) | Hole compound, preparation method thereof and organic electroluminescent device | |
| CN109988155A (en) | A kind of phosphorescence host compound and its organic electroluminescence device using the compound | |
| CN109988154A (en) | A kind of phosphorescence host compound and its organic electroluminescence device using the compound | |
| CN103666459B (en) | Blue-fluorescence organic material and organic light emitting diode panel employing same | |
| CN104140441A (en) | Red organic electrophosphorescent material iridium metal complex, preparation method thereof, and organic electroluminescent device |
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 | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20191115 |
|
| RJ01 | Rejection of invention patent application after publication |