CN116444502A - Organic light-emitting compound containing dibenzosuberone, preparation method and application - Google Patents
Organic light-emitting compound containing dibenzosuberone, preparation method and application Download PDFInfo
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- CN116444502A CN116444502A CN202310396893.5A CN202310396893A CN116444502A CN 116444502 A CN116444502 A CN 116444502A CN 202310396893 A CN202310396893 A CN 202310396893A CN 116444502 A CN116444502 A CN 116444502A
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- Prior art keywords
- dibenzosuberone
- organic light
- compound
- emitting compound
- atom
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 96
- BMVWCPGVLSILMU-UHFFFAOYSA-N 5,6-dihydrodibenzo[2,1-b:2',1'-f][7]annulen-11-one Chemical compound C1CC2=CC=CC=C2C(=O)C2=CC=CC=C21 BMVWCPGVLSILMU-UHFFFAOYSA-N 0.000 title claims abstract description 72
- 238000002360 preparation method Methods 0.000 title claims abstract description 15
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 21
- 238000003786 synthesis reaction Methods 0.000 claims abstract description 21
- 239000000126 substance Substances 0.000 claims abstract description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 47
- 238000010438 heat treatment Methods 0.000 claims description 19
- 239000002904 solvent Substances 0.000 claims description 19
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 16
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 12
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 8
- -1 aromatic amino Chemical group 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 5
- BKPDQETYXNGMRE-UHFFFAOYSA-N 1-tert-butyl-9h-carbazole Chemical compound N1C2=CC=CC=C2C2=C1C(C(C)(C)C)=CC=C2 BKPDQETYXNGMRE-UHFFFAOYSA-N 0.000 claims description 4
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 claims description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 239000007858 starting material Substances 0.000 claims description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- 238000006443 Buchwald-Hartwig cross coupling reaction Methods 0.000 claims description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 2
- 238000006069 Suzuki reaction reaction Methods 0.000 claims description 2
- 238000005576 amination reaction Methods 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 2
- 150000002430 hydrocarbons Chemical group 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 229940078552 o-xylene Drugs 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 239000002994 raw material Substances 0.000 claims description 2
- 229910052710 silicon Inorganic materials 0.000 claims description 2
- 125000003003 spiro group Chemical group 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 230000002194 synthesizing effect Effects 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims 1
- 238000000746 purification Methods 0.000 abstract description 16
- 238000000859 sublimation Methods 0.000 abstract description 15
- 230000008022 sublimation Effects 0.000 abstract description 15
- 239000000463 material Substances 0.000 abstract description 14
- 230000021615 conjugation Effects 0.000 abstract description 3
- 230000001105 regulatory effect Effects 0.000 abstract description 3
- 238000011160 research Methods 0.000 abstract description 3
- 230000001276 controlling effect Effects 0.000 abstract description 2
- 238000000354 decomposition reaction Methods 0.000 abstract description 2
- 230000000704 physical effect Effects 0.000 abstract description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 49
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 26
- 238000000926 separation method Methods 0.000 description 26
- 238000001035 drying Methods 0.000 description 22
- 239000000203 mixture Substances 0.000 description 21
- 239000007787 solid Substances 0.000 description 19
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
- 239000000741 silica gel Substances 0.000 description 17
- 229910002027 silica gel Inorganic materials 0.000 description 17
- 238000001816 cooling Methods 0.000 description 13
- CSNNHWWHGAXBCP-UHFFFAOYSA-L magnesium sulphate Substances [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 13
- 239000012074 organic phase Substances 0.000 description 13
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 13
- 229910000027 potassium carbonate Inorganic materials 0.000 description 13
- 238000010992 reflux Methods 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 230000000052 comparative effect Effects 0.000 description 10
- 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 10
- GUVUOGQBMYCBQP-UHFFFAOYSA-N dmpu Chemical compound CN1CCCN(C)C1=O GUVUOGQBMYCBQP-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 3
- CQXYINNETWHZTR-UHFFFAOYSA-N tritert-butyl phosphate Chemical compound CC(C)(C)OP(=O)(OC(C)(C)C)OC(C)(C)C CQXYINNETWHZTR-UHFFFAOYSA-N 0.000 description 3
- ATTVYRDSOVWELU-UHFFFAOYSA-N 1-diphenylphosphoryl-2-(2-diphenylphosphorylphenoxy)benzene Chemical compound C=1C=CC=CC=1P(C=1C(=CC=CC=1)OC=1C(=CC=CC=1)P(=O)(C=1C=CC=CC=1)C=1C=CC=CC=1)(=O)C1=CC=CC=C1 ATTVYRDSOVWELU-UHFFFAOYSA-N 0.000 description 2
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 2
- CINYXYWQPZSTOT-UHFFFAOYSA-N 3-[3-[3,5-bis(3-pyridin-3-ylphenyl)phenyl]phenyl]pyridine Chemical compound C1=CN=CC(C=2C=C(C=CC=2)C=2C=C(C=C(C=2)C=2C=C(C=CC=2)C=2C=NC=CC=2)C=2C=C(C=CC=2)C=2C=NC=CC=2)=C1 CINYXYWQPZSTOT-UHFFFAOYSA-N 0.000 description 2
- AWXGSYPUMWKTBR-UHFFFAOYSA-N 4-carbazol-9-yl-n,n-bis(4-carbazol-9-ylphenyl)aniline Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(N(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 AWXGSYPUMWKTBR-UHFFFAOYSA-N 0.000 description 2
- ZOKIJILZFXPFTO-UHFFFAOYSA-N 4-methyl-n-[4-[1-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]cyclohexyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C1(CCCCC1)C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 ZOKIJILZFXPFTO-UHFFFAOYSA-N 0.000 description 2
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 2
- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- 229950000688 phenothiazine Drugs 0.000 description 2
- 150000003384 small molecules Chemical class 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- ABEVIHIQUUXDMS-UHFFFAOYSA-N (2-bromophenyl)-phenylmethanone Chemical compound BrC1=CC=CC=C1C(=O)C1=CC=CC=C1 ABEVIHIQUUXDMS-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 150000001502 aryl halides Chemical class 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000012984 biological imaging Methods 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- YMHQVDAATAEZLO-UHFFFAOYSA-N cyclohexane-1,1-diamine Chemical group NC1(N)CCCCC1 YMHQVDAATAEZLO-UHFFFAOYSA-N 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000010365 information processing Effects 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000007725 thermal activation Methods 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
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- 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
- C07D405/04—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 directly linked by a ring-member-to-ring-member bond
-
- 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
- C07D401/04—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 directly linked by a ring-member-to-ring-member bond
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- 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
- C07D409/04—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 directly linked by a ring-member-to-ring-member bond
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/10—Spiro-condensed systems
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- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
- C07F7/0816—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring said ring comprising Si as a ring atom
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- 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
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
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- H10K85/649—Aromatic compounds comprising a hetero atom
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- 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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- 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
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- 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
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- 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
- C09K2211/1033—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with oxygen
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- 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
- C09K2211/1037—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with sulfur
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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- 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
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- 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
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- Engineering & Computer Science (AREA)
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- Spectroscopy & Molecular Physics (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The invention provides an organic light-emitting compound containing dibenzosuberone, a preparation method and application thereof. The organic luminescent compound containing the dibenzosuberone has the advantages of single material structure, definite molecular weight, convenient purification, good repeated synthesis reproducibility, convenient research on the relation of structure and performance, low sublimation temperature and decomposition temperature, stable film morphology, convenient preparation of devices, and capability of effectively regulating and controlling the conjugation length and the luminescent color of the material by changing the connected chemical structure, and further improving the physical properties of the organic luminescent compound containing the dibenzosuberone and the performance of photoelectric devices based on the organic luminescent compound.
Description
Technical Field
The invention belongs to the technical field of electroluminescent materials, and particularly relates to an organic luminescent compound containing dibenzosuberone, a preparation method and application thereof.
Background
Organic Light Emitting Diodes (OLEDs) are highly valued in academia and industry because of their advantages of all-solid state, self-luminescence, wide viewing angle, fast response, thinness, flexibility, etc., have become the main stream direction of the current display industry development, and play an important role in new generation flat panel displays and solid state lighting. In the whole OLED industry chain, organic luminescent materials play a crucial role all the time, and are one of the fields with the highest technical barriers. The thermal activation delay fluorescent material (TADF) has the advantages of realizing 100% exciton utilization rate in theory, avoiding the use of high-cost noble metals, and the like, and becomes a hot spot for domestic and foreign research. In recent years, organic circularly polarized light emitting devices and detecting devices have received great attention from scientists due to their potential application in the fields of 3D display, information processing, quantum communication, biological imaging, and the like. In these devices, chiral organic optoelectronic materials are the core and the foundation.
However, most of the light-emitting molecules with circular polarization characteristics currently used for organic photoelectric devices have a skeleton with chiral cyclohexanediamine units and chiral biaryl compounds as cores, but few organic light-emitting small molecules with dibenzosuberone as cores are reported, and the organic small molecules have a single structure, definite molecular weight and simple purification steps and can be applied to organic photoelectric devices including organic light-emitting diodes and the like;
based on the above, the invention provides an organic light-emitting compound containing dibenzosuberone, a preparation method and application thereof, which can further improve the capability of balancing carriers of the material, thereby improving the efficiency and stability of a device.
Disclosure of Invention
In order to overcome the defects in the prior art, the invention provides an organic light-emitting compound containing dibenzosuberone, a preparation method and application thereof, which are used for solving the problem that the capability of improving the balance carrier of the organic light-emitting compound in the prior art is improved, thereby improving the efficiency and the stability of a device.
One embodiment of the present invention provides a dibenzosuberone-containing organic light emitting compound represented by the following structural formula:
wherein,,
x is independently selected from an oxygen atom, a sulfur atom, a nitrogen atom, and a silicon atom;
a1 is independently selected from phenyl, aromatic amino, or methyl;
r1 is independently selected from C1-C16 alkyl;
r2 is independently selected from C1-C16 alkyl;
a2 is selected from one or more of vinyl group with electron donating property, acetylene group, aromatic ring formed by hydrocarbon atom, aromatic heterocyclic ring formed by carbon nitrogen hydrogen atom, aromatic heterocyclic ring formed by carbon nitrogen oxygen hydrogen atom, aromatic heterocyclic ring formed by carbon nitrogen sulfur hydrogen atom, aromatic heterocyclic ring formed by carbon nitrogen silicon hydrogen atom, alkyl substituted conjugated unit, alkoxy substituted conjugated unit or alkyl and alkoxy substituted conjugated unit.
Specifically, the novel dibenzosuberone-containing organic light-emitting compound takes the dibenzosuberone as a framework unit, and the molecular weight, pi conjugation and intramolecular charge transfer property of the material can be regulated by changing the heterocyclic atoms, the two-side connecting units and the number of the novel dibenzosuberone-containing organic light-emitting compound, so that the preparation problem of the high-efficiency circularly polarized light-emitting material can be effectively solved.
Further, the starting materials for the synthesis of the dibenzosuberone-containing organic light emitting compounds are selected from the following structures:
wherein,,
y is independently selected from chlorine atom, bromine atom, iodine atom.
Further, Y is a chlorine atom.
Further, the dibenzosuberone-containing organic light emitting compound is selected from the following structures:
the invention also provides a preparation method of the organic luminescent compound containing dibenzosuberone, which is characterized by comprising the following steps of:
dissolving a raw material for synthesizing the organic luminescent compound containing the dibenzosuberone and a substance containing an active hydrogen aromatic group in a solvent, heating, and reacting to obtain the organic luminescent compound containing the dibenzosuberone.
Further, the solvent is selected from one or more of toluene, chloroform and o-xylene.
Preferably, the solvent is toluene.
Further, the substance containing an active hydrogen aromatic group is selected from one of acridine, spiro acridine-thioxanthene, phenoxazine, carbazole and tert-butylcarbazole.
Further, the reaction is selected from one of a Suzuki coupling or a Buchwald-Hartwig coupling or a copper catalyzed haloarene amination reaction.
The invention also provides an organic electroluminescent device comprising the organic luminescent compound containing dibenzosuberone.
The invention provides an organic light-emitting compound containing dibenzosuberone, a preparation method and application thereof
The beneficial effects are that:
1. the organic luminescent compound containing the dibenzosuberone has the advantages of single material structure, definite molecular weight, convenient purification, good repeated synthesis reproducibility, convenient research on the relation between structure and performance, lower sublimation temperature and decomposition temperature, better solubility and film forming property in common solvents, stable film morphology, convenient preparation of devices, and capability of effectively regulating and controlling the conjugation length and the luminescent color of the material by changing the connected chemical structure, and further improving the physical property of the organic luminescent compound containing the dibenzosuberone and the performance of photoelectric devices based on the organic luminescent compound.
Drawings
FIG. 1 is a spectrum diagram of an organic electroluminescent blue light device of application example 1;
FIG. 2 is a graph showing the relationship between current density and voltage and luminance of the organic electroluminescent device according to application example 1;
FIG. 3 is a graph showing the relationship between the external quantum efficiency and the current density of the organic electroluminescent blue light device according to application example 1;
FIG. 4 is a graph showing the relationship between external quantum efficiency and current density in comparative application example 1.
Detailed Description
In order to more clearly illustrate the technical solution of the present invention, the following examples are set forth. The starting materials, reactions and workup procedures used in the examples are those commonly practiced in the market and known to those skilled in the art unless otherwise indicated.
In the examples of the present invention, the compounds M1 to M17 containing dibenzosuberone as the final products were prepared independently and without interference.
Example 1
Synthesis of dibenzosuberone-containing Compound M1
3mmol of P1 and 3.5mmol of acridine are added into 100mL of toluene, 60mg of palladium acetate, 0.5mmol of tri-tert-butyl phosphorus and 0.11g of potassium carbonate are added, the mixture is stirred under heating and refluxing for reaction for 24 hours, after cooling, the mixture is poured into 200mL of water, the product is extracted by dichloromethane, anhydrous magnesium sulfate is used for drying the organic phase, the solvent is removed after separation, a white solid is obtained after separation and purification by a silica gel chromatographic column, and the compound M1 containing dibenzosuberone is obtained after drying and sublimation under vacuum.
The yield of compound M1 was 70%.
Example 2
Synthesis of dibenzosuberone-containing Compound M2
3mmol of P1 and 3.5mmol of phenoxazine 100mL of toluene are added with 60mg of palladium acetate, 0.5mmol of tri-tert-butyl phosphorus, 0.11g of potassium carbonate, stirred under heating and refluxing for reaction for 24 hours, after cooling, the mixture is poured into 200mL of water, the product is extracted by dichloromethane, the organic phase is dried by anhydrous magnesium sulfate, the solvent is removed after separation, a white solid is obtained after separation and purification by a silica gel chromatographic column, and the compound M2 containing dibenzosuberone is obtained after drying and sublimation under vacuum.
The yield of compound M2 was 75%.
Example 3
Synthesis of dibenzosuberone-containing Compound M3
3mmol of P1, 3.3mmol of carbazole, 0.23g of CuI, 0.55g of K 2 CO 3 0.1g of C 18 O 6 Dissolving in DMPU, heating to 180deg.C, reacting for 24 hr, extracting with dichloromethane, drying, extracting with chloroform, separating and purifying with silica gel chromatographic column to obtain white solid, drying, and sublimating under vacuum to obtain compound M3 containing dibenzosuberone.
The yield of compound M3 was 70%.
Example 4
Synthesis of dibenzosuberone-containing Compound M4
3mmol of P1, 3.3mmol of tert-butylcarbazole, 0.23g of Cu and 0.55g of K 2 CO 3 0.1g of C 18 O 6 Dissolving in DMPU, heating to 180deg.C, reacting for 24 hr, extracting with dichloromethane, drying, extracting with chloroform, separating and purifying with silica gel chromatographic column to obtain white solid, drying, and sublimating under vacuum to obtain compound M4 containing dibenzosuberone.
The yield of compound M4 was 71%.
Example 5
Synthesis of dibenzosuberone-containing Compound M5
3mmol of P1 and 3.5mmol of phenothiazine are added into 100mL of toluene, 60mg of palladium acetate, 0.5mmol of tri-tert-butyl phosphate, 0.11g of potassium carbonate and the mixture are added, stirred under heating and refluxing for reaction for 24 hours, after cooling, the mixture is poured into 200mL of water, the product is extracted by dichloromethane, the organic phase is dried by anhydrous magnesium sulfate, the solvent is removed after separation, a white solid is obtained after separation and purification by a silica gel chromatographic column, and the compound M5 containing dibenzosuberone is obtained after drying and sublimation under vacuum.
The yield of compound M5 was 71%.
Example 6
Synthesis of dibenzosuberone-containing Compound M6
3mmol of P1 and 3.5mmol of helical acridine-thioxanthene are added into 100mL of toluene, 60mg of palladium acetate, 0.5mmol of tri-tertiary butyl phosphorus, 0.11g of potassium carbonate are added, stirring reaction is carried out for 24h under heating and refluxing, after cooling, the mixed solution is poured into 200mL of water, the product is extracted by dichloromethane, an organic phase is dried by anhydrous magnesium sulfate, the solvent is removed after separation, a white solid is obtained after separation and purification by a silica gel chromatographic column, and the compound M6 containing dibenzosuberone is obtained after drying and sublimation under vacuum.
The yield of compound M6 was 81%.
Example 7
Synthesis of dibenzosuberone-containing Compound M7
3mmol of P2 and 3.5mmol of acridine are added into 100mL of toluene, 60mg of palladium acetate, 0.5mmol of tri-tert-butyl phosphorus, 0.11g of potassium carbonate and the mixture are added, stirred under heating and refluxing for reaction for 24 hours, after cooling, the mixture is poured into 200mL of water, the product is extracted by dichloromethane, an organic phase is dried by anhydrous magnesium sulfate, the solvent is removed after separation, a white solid is obtained after separation and purification by a silica gel chromatographic column, and the compound M7 containing dibenzosuberone is obtained after drying and sublimation under vacuum.
The yield of compound M7 was 68%.
Example 8
Synthesis of dibenzosuberone-containing Compound M8
3mmol of P2 and 3.5mmol of phenoxazine are added into 100mL of toluene, 60mg of palladium acetate, 0.5mmol of tri-tert-butyl phosphate, 0.11g of potassium carbonate and the mixture are added, stirred under heating and refluxing for reaction for 24 hours, after cooling, the mixture is poured into 200mL of water, the product is extracted by dichloromethane, an organic phase is dried by anhydrous magnesium sulfate, the solvent is removed after separation, a white solid is obtained after separation and purification by a silica gel chromatographic column, and the compound M8 containing dibenzosuberone is obtained after drying and sublimation under vacuum.
The yield of compound M8 was 74%.
Example 9
Synthesis of dibenzosuberone-containing Compound M9
3mmol of P2, 3.3mmol of carbazole, 0.23g of CuI, 0.55g of K 2 CO 3 0.1g of C 18 O 6 Dissolving in DMPU, heating to 180deg.C, reacting for 24 hr, extracting with dichloromethane, drying, extracting with chloroform, separating and purifying with silica gel chromatographic column to obtain white solid, drying, and sublimating under vacuum to obtain compound M9 containing dibenzosuberone.
The yield of compound M9 was 69%.
Example 10
Synthesis of dibenzosuberone-containing Compound M10
3mmol of P2, 3.3mmol of tert-butylcarbazole, 0.23g of CuI, 0.55g of K 2 CO 3 0.1g of C 18 O 6 Dissolving in DMPU, heating to 180deg.C, reacting for 24 hr, extracting with dichloromethane, drying, extracting with chloroform, separating and purifying with silica gel chromatographic column to obtain white solid, drying, and sublimating under vacuum to obtain compound M10 containing dibenzosuberone.
The yield of compound M10 was 71%.
Example 11
Synthesis of dibenzosuberone-containing Compound M11
3mmol of P2 and 3.5mmol of phenothiazine are added into 100mL of toluene, 60mg of palladium acetate, 0.5mmol of tri-tert-butyl phosphate, 0.11g of potassium carbonate and the mixture are added, stirred under heating and refluxing for reaction for 24 hours, after cooling, the mixture is poured into 200mL of water, the product is extracted by dichloromethane, an organic phase is dried by anhydrous magnesium sulfate, the solvent is removed after separation, a white solid is obtained after separation and purification by a silica gel chromatographic column, and the compound M11 containing dibenzosuberone is obtained after drying and sublimation under vacuum.
The yield of compound M11 was 71%.
Example 12
Synthesis of dibenzosuberone-containing Compound M12
3mmol of P2 and 3.5mmol of helical acridine-thioxanthene are added into 100mL of toluene, 60mg of palladium acetate, 0.5mmol of tri-tertiary butyl phosphorus, 0.11g of potassium carbonate are added, stirring reaction is carried out for 24h under heating and refluxing, after cooling, the mixed solution is poured into 200mL of water, the product is extracted by dichloromethane, an organic phase is dried by anhydrous magnesium sulfate, the solvent is removed after separation, a white solid is obtained after separation and purification by a silica gel chromatographic column, and the compound M12 containing dibenzosuberone is obtained after drying and sublimation under vacuum.
The yield of compound M12 was 81%.
Example 13
Synthesis of dibenzosuberone-containing Compound M13
3mmol of P3 and 3.5mmol of acridine are added into 100mL of toluene, 60mg of palladium acetate, 0.5mmol of tri-tert-butyl phosphorus, 0.11g of potassium carbonate and the mixture are added, stirred under heating and refluxing for reaction for 24 hours, after cooling, the mixture is poured into 200mL of water, the product is extracted by dichloromethane, an organic phase is dried by anhydrous magnesium sulfate, the solvent is removed after separation, a white solid is obtained after separation and purification by a silica gel chromatographic column, and the compound M13 containing dibenzosuberone is obtained after drying and sublimation under vacuum.
The yield of compound M13 was 70%.
Example 14
Synthesis of dibenzosuberone-containing Compound M14
3mmol of P4 and 3.5mmol of acridine are added into 100mL of toluene, 60mg of palladium acetate, 0.5mmol of tri-tert-butyl phosphorus, 0.11g of potassium carbonate and the mixture are added, stirred under heating and refluxing for reaction for 24 hours, after cooling, the mixture is poured into 200mL of water, the product is extracted by dichloromethane, an organic phase is dried by anhydrous magnesium sulfate, the solvent is removed after separation, a white solid is obtained after separation and purification by a silica gel chromatographic column, and the compound M14 containing dibenzosuberone is obtained after drying and sublimation under vacuum.
The yield of compound M14 was 69%.
Example 15
Synthesis of dibenzosuberone-containing Compound M15
3mmol of P5 and 3.5mmol of acridine are added into 100mL of toluene, 60mg of palladium acetate, 0.5mmol of tri-tert-butyl phosphorus, 0.11g of potassium carbonate and the mixture are added, stirred under heating and refluxing for reaction for 24 hours, after cooling, the mixture is poured into 200mL of water, the product is extracted by dichloromethane, the organic phase is dried by anhydrous magnesium sulfate, the solvent is removed after separation, a white solid is obtained after separation and purification by a silica gel chromatographic column, and the compound M15 containing dibenzosuberone is obtained after drying and sublimation under vacuum.
The yield of compound M15 was 71%.
Example 16
Synthesis of dibenzosuberone-containing Compound M16
3mmol of P6 and 3.5mmol of acridine are added into 100mL of toluene, 60mg of palladium acetate, 0.5mmol of tri-tert-butyl phosphorus, 0.11g of potassium carbonate and the mixture are added, stirred under heating and refluxing for reaction for 24 hours, after cooling, the mixture is poured into 200mL of water, the product is extracted by dichloromethane, an organic phase is dried by anhydrous magnesium sulfate, the solvent is removed after separation, a white solid is obtained after separation and purification by a silica gel chromatographic column, and the compound M16 containing dibenzosuberone is obtained after drying and sublimation under vacuum.
The yield of compound M16 was 71%.
Example 17
Synthesis of dibenzosuberone-containing Compound M17
3mmol of P7 and 3.5mmol of acridine are added into 100mL of toluene, 60mg of palladium acetate, 0.5mmol of tri-tert-butyl phosphorus, 0.11g of potassium carbonate and the mixture are added, stirred under heating and refluxing for reaction for 24 hours, after cooling, the mixture is poured into 200mL of water, the product is extracted by dichloromethane, an organic phase is dried by anhydrous magnesium sulfate, the solvent is removed after separation, a white solid is obtained after separation and purification by a silica gel chromatographic column, and the compound M17 containing dibenzosuberone is obtained after drying and sublimation under vacuum.
The yield of compound M17 was 72%.
Comparative example 1
A method for producing an organic light-emitting compound, the comparative example differs from example 7 in that: the organic light-emitting compound N1 prepared by substituting P7 with achiral bromobenzophenone was shown in the following figure, and the other steps and materials were the same as in example 7.
Application example 1
The compound M7 of example 7 of the present invention and the compound N1 prepared in comparative example 1 were applied to a light emitting layer in an OLED device to further illustrate the practical technical effects of the present invention.
In example 7 of the present invention, M7 was used as a guest material for a light emitting layer, and an OLED structure of the device was prepared as follows: ITO/HATCN (5 nm)/TAPC (30 nm)/TCTA (10 nm)/mCBP (10 nm)/M7 doped PPF (M7 accounts for 15wt% of the layer) (20 nm)/DPEPO (10 nm)/TmPyPB (40 nm)/LiF (1 nm)/Al (150 nm).
FIG. 1 is a spectrum diagram of an organic electroluminescent blue light device of application example 1; FIG. 2 is a graph showing the relationship between current density and voltage and luminance of the organic electroluminescent device according to application example 1; fig. 3 is a graph showing the relationship between external quantum efficiency and current density of the organic electroluminescent blue device according to application example 1.
Comparative application example 1
The compound prepared in comparative example 1 is used as a guest material of a light emitting layer, and the OLED structure of the prepared device is as follows: ITO/HATCN (5 nm)/TAPC (30 nm)/TCTA (10 nm)/mCBP (10 nm)/N1 doped PPF (N1 accounting for 15wt% of the layer) (20 nm)/DPEPO (10 nm)/TmPyPB (40 nm)/LiF (1 nm)/Al (150 nm).
FIG. 4 is a graph showing the relationship between external quantum efficiency and current density in comparative application example 1.
Test case
The device OLED was prepared in application example 1 and comparative application example 1, respectively, and the characteristics of the device were tested at different currents with a positive bias applied between the ITO and the metal electrode.
The test data of the organic electroluminescent device prepared above are shown in table 1 below:
table 1 device application 1 and comparative application 1 data
As can be seen from table 1 and fig. 1 to 4, the addition of the dibenzosuberone-containing compound as the light emitting layer in the OLED device can achieve the effects of high luminance and small roll-off of efficiency in the device, and improve the ability of the device to balance carriers, thereby improving the efficiency and stability of the device, and thus achieve high efficiency performance in the organic electroluminescent device, whereas the stability of the device prepared from N1 in comparative application example 1 is significantly reduced, and the same technical effects as those of application example 1 cannot be achieved.
It will be evident to those skilled in the art that the invention is not limited to the details of the foregoing illustrative embodiments, and that the present invention may be embodied in other specific forms without departing from the spirit or essential characteristics thereof. The present embodiments are, therefore, to be considered in all respects as illustrative and not restrictive, the scope of the invention being indicated by the appended claims rather than by the foregoing description, and all changes which come within the meaning and range of equivalency of the claims are therefore intended to be embraced therein.
Furthermore, it should be understood that although the present disclosure describes embodiments, not every embodiment is provided with a separate embodiment, and that this description is provided for clarity only, and that the disclosure is not limited to the embodiments described in detail below, and that the embodiments described in the examples may be combined as appropriate to form other embodiments that will be apparent to those skilled in the art.
Claims (9)
1. A dibenzosuberone-containing organic light-emitting compound, wherein the dibenzosuberone-containing organic light-emitting compound is represented by the following structural formula:
wherein,,
x is independently selected from an oxygen atom, a sulfur atom, a nitrogen atom, and a silicon atom;
a1 is independently selected from phenyl, aromatic amino, or methyl;
r1 is independently selected from C1-C16 alkyl;
r2 is independently selected from C1-C16 alkyl;
a2 is selected from one or more of vinyl group with electron donating property, acetylene group, aromatic ring formed by hydrocarbon atom, aromatic heterocyclic ring formed by carbon nitrogen hydrogen atom, aromatic heterocyclic ring formed by carbon nitrogen oxygen hydrogen atom, aromatic heterocyclic ring formed by carbon nitrogen sulfur hydrogen atom, aromatic heterocyclic ring formed by carbon nitrogen silicon hydrogen atom, alkyl substituted conjugated unit, alkoxy substituted conjugated unit or alkyl and alkoxy substituted conjugated unit.
2. The dibenzosuberone-containing organic light-emitting compound of claim 1, wherein the starting material for the synthesis of the dibenzosuberone-containing organic light-emitting compound is selected from the following structures:
wherein,,
y is independently selected from chlorine atom, bromine atom, iodine atom.
3. The organic light-emitting compound comprising dibenzosuberone according to claim 2,
and Y is a chlorine atom.
4. The organic light-emitting compound comprising dibenzosuberone according to claim 1,
the dibenzosuberone-containing organic light emitting compound is selected from the following structures:
5. a process for the preparation of a dibenzosuberone-containing organic light emitting compound according to any one of claims 1 to 4, comprising the steps of:
dissolving a raw material for synthesizing the organic luminescent compound containing the dibenzosuberone and a substance containing an active hydrogen aromatic group in a solvent, heating, and reacting to obtain the organic luminescent compound containing the dibenzosuberone.
6. A process for the preparation of an organic light-emitting compound comprising dibenzosuberone according to claim 5,
the solvent is selected from one or more of toluene, chloroform and o-xylene.
7. A process for the preparation of an organic light-emitting compound comprising dibenzosuberone according to claim 5,
the substance containing active hydrogen aromatic groups is selected from one of acridine, spiro acridine-thioxanthene, phenoxazine, carbazole and tert-butylcarbazole.
8. A process for the preparation of an organic light-emitting compound comprising dibenzosuberone according to claim 5,
the reaction is selected from one of Suzuki coupling or Buchwald-Hartwig coupling or copper-catalyzed halogenated aromatic hydrocarbon amination reaction.
9. An organic electroluminescent device, characterized in that: an organic light-emitting compound comprising a dibenzosuberone-containing compound of any one of claims 1 to 4.
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