CN118239962A - Di (benzopyrrole) phenothiazine luminescent material, and preparation method and application thereof - Google Patents
Di (benzopyrrole) phenothiazine luminescent material, and preparation method and application thereof Download PDFInfo
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- CN118239962A CN118239962A CN202410274355.3A CN202410274355A CN118239962A CN 118239962 A CN118239962 A CN 118239962A CN 202410274355 A CN202410274355 A CN 202410274355A CN 118239962 A CN118239962 A CN 118239962A
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- phenothiazine
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- 239000000463 material Substances 0.000 title claims abstract description 53
- -1 Di (benzopyrrole) phenothiazine Chemical compound 0.000 title claims abstract description 38
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- 238000006243 chemical reaction Methods 0.000 claims description 16
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
- 229940125782 compound 2 Drugs 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 10
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 8
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 8
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 claims description 7
- 229940125904 compound 1 Drugs 0.000 claims description 7
- 229940126214 compound 3 Drugs 0.000 claims description 7
- 238000006959 Williamson synthesis reaction Methods 0.000 claims description 6
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims description 6
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 6
- 238000005859 coupling reaction Methods 0.000 claims description 6
- 239000011261 inert gas Substances 0.000 claims description 6
- ORPVVAKYSXQCJI-UHFFFAOYSA-N 1-bromo-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Br ORPVVAKYSXQCJI-UHFFFAOYSA-N 0.000 claims description 5
- BMIBJCFFZPYJHF-UHFFFAOYSA-N 2-methoxy-5-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine Chemical compound COC1=NC=C(C)C=C1B1OC(C)(C)C(C)(C)O1 BMIBJCFFZPYJHF-UHFFFAOYSA-N 0.000 claims description 5
- 238000007363 ring formation reaction Methods 0.000 claims description 5
- 150000001351 alkyl iodides Chemical class 0.000 claims description 4
- 238000006555 catalytic reaction Methods 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 claims description 4
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 claims description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 2
- 238000005885 boration reaction Methods 0.000 claims description 2
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 230000008569 process Effects 0.000 claims description 2
- 238000004528 spin coating Methods 0.000 abstract description 3
- 238000007725 thermal activation Methods 0.000 abstract description 3
- 238000007738 vacuum evaporation Methods 0.000 abstract description 2
- 239000010409 thin film Substances 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- 150000001875 compounds Chemical class 0.000 description 28
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 6
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 6
- 238000000295 emission spectrum Methods 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 5
- 238000000862 absorption spectrum Methods 0.000 description 5
- 239000003208 petroleum Substances 0.000 description 5
- 229950000688 phenothiazine Drugs 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 238000001194 electroluminescence spectrum Methods 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 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 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 230000003111 delayed effect Effects 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000005401 electroluminescence Methods 0.000 description 2
- 125000006575 electron-withdrawing group Chemical group 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000002189 fluorescence spectrum Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000031700 light absorption Effects 0.000 description 2
- 238000004020 luminiscence type Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000012265 solid product Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 125000004434 sulfur atom Chemical group 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- AGIJRRREJXSQJR-UHFFFAOYSA-N 2h-thiazine Chemical group N1SC=CC=C1 AGIJRRREJXSQJR-UHFFFAOYSA-N 0.000 description 1
- BWGRDBSNKQABCB-UHFFFAOYSA-N 4,4-difluoro-N-[3-[3-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octan-8-yl]-1-thiophen-2-ylpropyl]cyclohexane-1-carboxamide Chemical compound CC(C)C1=NN=C(C)N1C1CC2CCC(C1)N2CCC(NC(=O)C1CCC(F)(F)CC1)C1=CC=CS1 BWGRDBSNKQABCB-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- LFZAGIJXANFPFN-UHFFFAOYSA-N N-[3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-thiophen-2-ylpropyl]acetamide Chemical compound C(C)(C)C1=NN=C(N1C1CCN(CC1)CCC(C=1SC=CC=1)NC(C)=O)C LFZAGIJXANFPFN-UHFFFAOYSA-N 0.000 description 1
- 229920000144 PEDOT:PSS Polymers 0.000 description 1
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
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- 230000021615 conjugation Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
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- 239000003599 detergent Substances 0.000 description 1
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- 230000007613 environmental effect Effects 0.000 description 1
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- 238000001914 filtration Methods 0.000 description 1
- 210000004317 gizzard Anatomy 0.000 description 1
- 230000005525 hole transport Effects 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 239000002648 laminated material Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 150000002990 phenothiazines Chemical class 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 238000000746 purification 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
- 238000010992 reflux Methods 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000007761 roller coating Methods 0.000 description 1
- 238000010020 roller printing Methods 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000005556 structure-activity relationship Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 238000002207 thermal evaporation Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains three hetero rings
- C07D513/14—Ortho-condensed systems
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- 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
- 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
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- 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
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- 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
- C09K2211/1066—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms with sulfur
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2101/00—Properties of the organic materials covered by group H10K85/00
- H10K2101/20—Delayed fluorescence emission
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- 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 invention discloses a bis (benzopyrrole) phenothiazine luminescent material, and a preparation method and application thereof. The structural general formula of the di (benzopyrrole) phenothiazine luminescent material is shown as a formula (I) or a formula (II). The di (benzopyrrole) phenothiazine luminescent material has the property of thermal activation delay fluorescence, and can be used as a single-molecule white light material; the organic thin film is formed by vacuum evaporation or spin coating and is applied to organic photoelectric devices including organic light emitting diodes and the like.
Description
Technical Field
The invention relates to the technical field of luminescent materials, in particular to a di (benzopyrrole) phenothiazine luminescent material, and a preparation method and application thereof.
Background
With the advent of the informatization age, display technology has gained popularity and application in life production; compared with the electroluminescence (LED) technology of inorganic materials, the organic electroluminescence (OLEDs) new generation display luminescence technology has the advantages of low production cost, light weight, flexibility and controllable photophysical characteristics, can produce and prepare flexible curved folding screens with pure chromaticity and larger size, and has larger application scenes and space. The organic light-emitting micromolecules have the advantages of simple synthesis and easy regulation and control, so that the organic light-emitting micromolecules become the first choice of materials of the OLEDs light-emitting layer. White Organic Light Emitting Devices (WOLEDs) have received wide attention in the fields of display, sensing, solid state lighting, and the like, due to their advantages of energy saving, environmental protection, high efficiency, mass production, high color rendering index, and the like. Most current ways to produce white organic light emitting devices are mixtures of different colored organic substances, such as a combination of blue/yellow and blue/green/red emitters. Thus, although WOLED is easy to control and manufacture, the device has complex multilayer structure characteristics, and the defects of complex manufacturing process, high cost, phase separation, color aging, serious efficiency roll-off and the like exist, so that the further development of the device is prevented. The single organic molecule white light diode is a focus of attention because of the advantages of simple manufacturing process, good repeatability, stable luminescence color and the like.
Phenothiazine is an excellent electron donor, has stronger power supply property than carbazole and arylamine electron donor groups, and is easy to modify and synthesize. There are multiple functional sites on the phenothiazine core, such as the C-2, C-3, C-7, C-8, N-10 sites and the sulfur atom of the thiazine ring. Wherein the C-3 and C-7 positions are typically functionalized with various electron donating or electron withdrawing groups. The N-10 site may then be functionalized by the introduction of a suitable solubilizing group, such as an alkyl or aryl substituent. In addition, the sulfur atom in the phenothiazine unit is readily reactive with an oxidizing agent and can be oxidized to sulfoxide (4+ oxidation) or sulfone (6+ oxidation). Previous studies have been directed to these aspects, while few have been directed to the effect of the degree of conjugation of phenothiazines on conformation and the relationship between subsequent photophysical properties. Therefore, the development of the luminescent material based on phenothiazine has important significance and application prospect.
Disclosure of Invention
Aiming at the defects existing in the prior art, the invention aims to provide a di (benzopyrrole) phenothiazine luminescent material (D-A luminescent material) and a preparation method and application thereof.
It is an object of the present invention to provide a class of bis (benzopyrrole) phenothiazine luminescent materials.
The second purpose of the invention is to provide a preparation method of the di (benzopyrrole) phenothiazine luminescent material.
The invention further aims at providing an application of the di (benzopyrrole) phenothiazine luminescent material as a single-molecule white light material.
The fourth object of the invention is to provide an organic electroluminescent device.
In order to achieve the above purpose, the technical scheme adopted by the invention is as follows:
The first aspect of the invention provides a di (benzopyrrole) phenothiazine luminescent material, and the structural general formula of the di (benzopyrrole) phenothiazine luminescent material is shown as formula (I) or formula (II):
In the formulas (I) and (II), R 1 and R 2 are any one of a hydrogen atom or a C 1～C6 alkyl chain.
Preferably, R 1 and R 2 are methyl. Namely, the structure of the di (benzopyrrole) phenothiazine luminescent material is shown as the formula (I-a) and the formula (II-a):
The second aspect of the invention provides a preparation method of the di (benzopyrrole) phenothiazine luminescent material, which comprises the following steps:
(a) Under the protection of inert gas, the compound 1 and the pinacol ester of the bisdiphenylphosphino ferrocene are subjected to Miyaura boration reaction under the catalysis of 1,1' -bis-diphenylphosphino ferrocene palladium dichloride to generate a compound 2;
(b) Under the protection of inert gas, the compound 2 and o-bromonitrobenzene undergo a Suzuki carbon-carbon coupling reaction under the alkaline condition and under the catalysis of tetra (triphenylphosphine) palladium to obtain a compound 3;
(c) Under the protection of inert gas, i) cyclizing reaction of the compound 3 and triphenylphosphine serving as a reducing agent (the product is shown as a formula (I) or a formula (II) with a substituent of hydrogen); ii) Williamson reaction of the product obtained in step i) with an alkyl iodide under alkaline conditions (the product is a formula (I) or a formula (II) with a substituent of C 1-C6 alkyl chain);
The iodinated alkane is I-R, and R is C 1-C6 alkyl chain;
the synthetic route is as follows:
Preferably, in step (a), the molar ratio of compound 1 to pinacol ester of bisdiboronic acid is 1 (2-4); the mol ratio of the compound 1 to the 1,1' -bis-diphenylphosphino ferrocene palladium dichloride is 1 (0.01-0.5); the temperature of Miyaura boronation reaction is 90-110 ℃, and the time of Miyaura boronation reaction is 12-24h.
Preferably, in step (b), the molar ratio of compound 2 to o-bromonitrobenzene is 1 (2-4); the molar ratio of the compound 2 to the tetra (triphenylphosphine) palladium is 1 (0.01-0.5); the temperature of the Suzuki carbon-carbon coupling reaction is 80-85 ℃, and the time of the Suzuki carbon-carbon coupling reaction is 24-36h.
Preferably, in step (b), the alkaline condition is that sodium carbonate or potassium carbonate is added, and the molar ratio of the compound 2 to sodium carbonate or potassium carbonate is 1 (2-4).
Preferably, in step (c), the molar ratio of compound 3 to triphenylphosphine is 1 (4-10); the temperature of the cyclization reaction is 170-210 ℃, and the time of the cyclization reaction is 12-24 hours; the molar ratio of the product obtained in the step i) to the alkyl iodide is 1 (4-10); the temperature of the Williamson reaction is 70-85 ℃, and the time of the Williamson reaction is 12-24h.
Preferably, in step (c), the alkaline condition is that sodium hydroxide or potassium hydroxide is added, and the molar ratio of the intermediate to sodium hydroxide or potassium hydroxide is 1 (4-10).
A third aspect of the invention provides the use of a bis (benzopyrrole) phenothiazine light-emitting material as described above as a single-molecule white-light material.
A fourth aspect of the invention provides an organic electroluminescent device comprising a bis (benzopyrrole) phenothiazine light-emitting material according to claim 1 or 2.
Preferably, the bis (benzopyrrole) phenothiazine luminescent material is used as a luminescent layer of an organic electroluminescent device;
Preferably, the organic electroluminescent device is a white organic electroluminescent device. Further preferably, the structural general formula of the di (benzopyrrole) phenothiazine luminescent material is a compound shown in formula (II).
Preferably, the organic light emitting layer unit in the organic electroluminescent device includes a hole injection layer, a hole transport layer, one or more light emitting layers and an electron transport layer.
Preferably, the preparation method of the organic electroluminescent device comprises at least one of thermal evaporation, spin coating, brush coating, spray coating, dip coating, roller coating, printing or ink-jet printing.
The beneficial effects of the invention are as follows:
The invention discloses a bis (benzopyrrole) phenothiazine luminescent material, which is a D-A bis (benzopyrrole) phenothiazine luminescent material, wherein a donor D is bis (benzopyrrole) phenothiazine, and an acceptor A is benzophenone. Benzophenone is a structurally simple and efficient electron withdrawing group that can increase SOC values by n-pi transitions. Phenothiazine is an excellent electron donor, has stronger power supply than carbazole and arylamine electron donor groups, and is easy to modify and synthesize; carbazole has better carrier transmission capability, diindole groups are introduced into two sides of phenothiazine, and similar carbazole groups on two sides of a donor can improve the carrier transmission capability of molecules; the organic micromolecular derivative has the thermal activation delayed fluorescence property, can form an organic film through vacuum evaporation or spin coating, and is applied to organic photoelectric devices including organic light-emitting diodes for the first time; the invention has important significance for developing novel single-molecule white light materials with low cost and good performance.
Compared with the prior art, the invention has the following advantages:
1. The organic small molecular material prepared by the invention and taking the di (benzopyrrole) phenothiazine as a donor core unit has the advantages of simple structure, definite molecular weight, good electrochemical stability and easiness in researching the structure-activity relationship.
2. The preparation method of the di (benzopyrrole) phenothiazine derivative disclosed by the invention comprises the steps of taking phenothiazine as a main body, expanding rings to two sides, and obtaining a target compound through a series of reactions. The preparation method disclosed by the invention has the advantages of easiness in purification, stable yield, mild reaction conditions and simplicity in operation.
3. The organic small molecular material using the di (benzopyrrole) phenothiazine as a donor core unit has the characteristic of photoinduced white light in a film, and has the characteristic of thermal activation delayed fluorescence. Meanwhile, the bipolar photoelectric material connected with the electron donor and the electron acceptor can form a large torsion angle between the donor and the electron acceptor, so that the non-planarity of the structure is improved, the stacking degree of the material is reduced, the aggregation quenching of the material is effectively inhibited, and the problem of unbalanced carrier of the unipolar organic photoelectric material is avoided. The material disclosed by the invention has the advantages of single-molecule white light emission, high efficiency, high stability and the like when being used as a light-emitting layer of an organic electroluminescent device, and has important significance for developing novel organic photoelectric materials with low cost and good performance.
Drawings
FIG. 1 is an absorption spectrum-emission spectrum of the compound I-a in toluene solution.
FIG. 2 is a graph showing absorption spectrum and emission spectrum of the compound II-a in toluene solution.
FIG. 3 is an electroluminescence spectrum of the compound I-a.
FIG. 4 is an electroluminescence spectrum of the compound II-a.
Detailed Description
Specific implementations of the invention are further described below with reference to the drawings and examples, but the implementation and protection of the invention are not limited thereto. It should be noted that the following processes, if not specifically described in detail, can be realized or understood by those skilled in the art with reference to the prior art. The reagents or instruments used did not identify the manufacturer and were considered conventional products available commercially.
Example 1
The bis (benzopyrrole) phenothiazine luminescent material synthesized in the embodiment has the following specific structure:
The specific synthesis steps are as follows:
(a) Synthesis of Compound 2
In a 100mL two-port flask, compound 1 (2.11 mmol,1.13 g), pinacol ester of bisdiboronic acid (6.37 mmol,1.61 g), potassium acetate (7.96 mmol,0.78 g), pd (dppf) Cl 2 (0.2 mmol,150 mg) and 30mL of 1,4 dioxane were added, nitrogen was introduced and purged with vacuum pump for 10 minutes, stirred and heated to 92℃for a continuous reaction of 24 hours; the TCL point plate monitors that the raw materials are completely reacted, the reaction is stopped, the temperature is reduced to room temperature, the reaction liquid is poured into a 500ml separating funnel, 100ml of water is added, and 1000ml of dichloromethane is used for extraction for 3 to 4 times, then anhydrous magnesium sulfate is used for drying, filtering and collecting filtrate, the solvent is removed, the crude product is stirred with 200 to 300 meshes of silica gel, column chromatographic separation is carried out, petroleum ether is adopted as the mobile phase, dichloromethane (volume ratio is 5:1), ethanol and dichloromethane are used for recrystallization, and finally 1.105g of yellowish green solid product is obtained, and the yield is 83%; melting point 216.7～217.9℃.1H NMR(400MHz,CDCl3)δ8.00–7.98(m,2H),7.87–7.84(m,2H),7.63–7.59(m,1H),7.53–7.49(m,4H),7.43–7.40(m,2H),7.37(dd,J＝8.24,1.4Hz,2H),6.38(d,J＝8.16Hz,2H),1.31(s,24H).
(B) Synthesis of Compound 3
In a two-port flask of 100ml, compound 2 (1.8 mmol,1.14 g), o-bromonitrobenzene (5.41 mmol,1.09 g), potassium phosphate (6.6 mmol,1.40 g), pd (PPh 3)4 (0.18 mmol,207 mg), and 50ml toluene, 10ml ethanol and 5ml water were added, nitrogen was introduced and ventilation was performed by vacuum pumping for 10 minutes, stirring and heating to 85℃for 24 hours, the reaction was stopped when the TCL spot plate was monitored that the starting material had completely reacted, the temperature was lowered to room temperature, the reaction solution was poured into a 500ml separating funnel, 100ml water was added and extracted 3 to 4 times with 1000ml dichloromethane, then the filtrate was collected by drying using anhydrous magnesium sulfate, the solvent was removed, the crude product was stirred with 200 to 300 mesh silica gel, column chromatography was performed, the mobile phase was petroleum ether: dichloromethane (volume ratio 5:2), and recrystallization was performed with ethanol and dichloromethane, finally 895mg of red solid product was obtained, the yield was 80%; melting point was obtained 232.4～235.0℃.1H NMR(500MHz,CDCl3)δ8.04–8.02(m,2H),7.88–7.82(m,4H),7.65–7.58(m,3H),7.55–7.45(m,6H),7.40(dd,J＝7.65,1.00Hz,2H),7.10(d,J＝2.00Hz,2H),6.91(dd,J＝8.45,2.05Hz,2H),6.50(d,J＝8.45Hz,2H).
(C) Synthesis of Compound I-a
I) Compound 3 (0.97 mmol,603 mg), PPh 3 (9.7 mmol,2.54 g) and ultra-dry o-dichlorobenzene (ODCB) were added in a 100ml single-port flask, 20ml of nitrogen was introduced and purged with a vacuum pump for 30 minutes, stirred and heated to reflux, the reaction was continued for 24 hours, the reaction was stopped, o-dichlorobenzene was removed by distillation under reduced pressure, and the crude product obtained was subjected to column chromatography separation using a developing solvent petroleum ether of dichloromethane to ethyl acetate (volume ratio=12:2:1) to obtain a earthy yellow solid which was directly fed to the next reaction. ii) the yellowish brown solid (0.19 mmol,106 mg) obtained in the previous step was added to a 100ml two-port bottle, 1-iodomethane (1.90 mmol,270 mg), potassium hydroxide (1.90 mmol,106 mg) was weighed, dimethyl sulfoxide (40 ml) was added, nitrogen was introduced and vacuum was applied to the bottle for 15 minutes, stirring and heating to 85 ℃ for 24 hours, the reaction was stopped and cooled to room temperature, the reaction solution was extracted, 200ml of water and 1500ml of methylene chloride were repeatedly extracted 3 to 4 times, the obtained organic extract was dried with anhydrous magnesium sulfate, separated by 300-400 mesh silica gel column chromatography, and the developing agent was petroleum ether: methylene chloride: ethyl acetate (volume ratio: 200:1:1) and recrystallized with ethanol and methylene chloride to finally obtain 113mg of pale yellow flocculent solid, final yield 20%, melting point was repeatedly extracted 3 to 4 times, and the developing solvent was petroleum ether: ethyl acetate was used as a solvent 279.9-282.9℃.1H NMR(400MHz,CDCl3)δ8.28(s,1H),8.09-8.06(m,3H),7.78-7.74(m,4H),7.69(s,1H),7.54-7.50(m,4H),7.47-7.41(m,4H),7.31-7.28(m,2H),7.15-7.12(d,J＝8.80Hz,2H),4.32(s,3H),3.86(s,3H).
Example 2
The bis (benzopyrrole) phenothiazine luminescent material synthesized in the embodiment has the following specific structure:
the specific synthetic procedure for compounds 2, 3 was consistent with example 1.
(D) Synthesis of Compound II-a
Synthesis method of Compound II-a referring to the synthesis method of (c), pale yellow flocculent solid was finally obtained in 5% yield, melting point 291.5–293.9℃.1H NMR(500MHz,CDCl3)δ8.06–8.03(m,4H),7.71–7.67(m,4H),7.49–7.46(m,5H),7.41–7.38(m,4H),7.24(d,J＝6.45Hz,2H),7.04(d,J＝8.90Hz,2H),4.3(s,6H).
Example 3
The compound I-a and the compound II-a are respectively subjected to test analysis of absorption spectrum and emission spectrum, and the test experimental steps are as follows:
chlorobenzene solutions of 10mg/mol were prepared for Compound I-a and Compound II-a, respectively, and 50. Mu.L of the solution was dropped on the center of the cleaned quartz glass piece, immediately rotated at 3000rpm, and annealed at 80℃for 15 minutes. Then ultraviolet-visible light absorption spectrum and light-induced fluorescence emission spectrum are respectively tested. Wherein the ultraviolet-visible light absorption spectrum and the photo-induced fluorescence emission spectrum are measured by an Edinburgh FL980 fluorescence spectrophotometer.
FIG. 1 is an absorption spectrum-emission spectrum of the compound I-a in a pure film, and FIG. 2 is an absorption spectrum-emission spectrum of the compound II-a in a pure film. As can be seen from FIGS. 1 and 2, the compound I-a and the compound II-a have similar absorption spectra, and the emission spectrum peak of the compound II-a is larger than the wavelength of the compound I-a.
Application example
The compounds I-a and II-a prepared above are applied to an Organic Light Emitting Diode (OLED) device, and specific application embodiments are as follows:
the specific laminated material and thickness of the organic electroluminescent device are as follows:
Glass substrate/ITO/PEDOT PSS (35 nm)/10 wt% of compound X (compounds I-a, II-a) +90wt% of CBP (30 nm)/TmPyPB (40 nm)/CsF (1 nm)/Al. ITO is anode, PEDOT: PSS is hole injection layer, CBP is luminescent material doped body, tmPyPB is electron transport layer, csF is electron injection layer, al is cathode.
Wherein, the molecular structural formulas of CBP and TmPyPB in the application examples are respectively shown as follows:
The manufacturing steps of the light emitting device are as follows:
The ITO transparent conductive glass is cleaned by acetone, a micron-sized semiconductor special detergent, deionized water and isopropanol for 15 minutes in sequence, so as to remove dirt on the surface of the substrate. And then placing the mixture into an incubator to be dried at 80 ℃ for standby. The dried ITO substrate was treated with an oxygen plasma cleaning apparatus for 3 minutes to further remove organic attachments on the surface. PEDOT PSS was spin coated on the treated ITO at 3000rpm for 30s to form a 35nm hole injection layer, which was then annealed at 80℃for 15min. At the same time, the preheated (@ 50 ℃ C., 12 h) luminescent layer solution dissolved in chlorobenzene (bulk CBP,10 mg/mL) was cooled to room temperature. Then, 50. Mu.L of the liquid was dropped at the center of the ITO substrate, and immediately a light emitting layer of 30nm was spin-coated at 3000rpm to reduce mixing of adjacent two layers. Finally, the luminescent layer was annealed at 80 ℃ for 15min and then immediately transferred to the evaporation chamber to avoid solvent attack. Then, the electron transport layer TmPyPB and the cathode (i.e., csF and Al) were sequentially deposited under vacuum conditions of less than 1X 10 -4 pa (active area: 10mm 2), to obtain the organic light-emitting diode device of the present embodiment.
The light emitting devices of compound I-a and compound II-a were subjected to an electroluminescent spectrum test, which was performed as follows:
The devices prepared were tested directly at room temperature without encapsulation, and the electroluminescence spectrum was measured by optical analyzer Photo RESEARCH PR745, and the current density and luminance versus drive voltage characteristics were measured by Keithley 2420 from gizzard and konikamada colorimeter CS-200. The area of the prepared light-emitting region is 3mm by 3mm, and the External Quantum Efficiency (EQE) is calculated from the brightness, the current density and the EL spectrum, provided that the light distribution is assumed to be lambertian distribution.
The test results are shown in Table 1, FIG. 3 and FIG. 4.
Table 1: performance test results of OLED devices made of Compounds I-a, II-a
As can be seen from table 1, fig. 3 and fig. 4, the CIE color coordinate value of the organic electroluminescent device manufactured by the compound I-a is (0.38,0.44); the CIE color coordinate value of the organic electroluminescent device manufactured by the compound II-a is (0.33,0.36). The CIE color coordinates of the application example are close to the white light color coordinates (0.33 ), and the organic small molecular material taking the di (benzopyrrole) phenothiazine as the donor has great application potential in single-molecule white light luminescent materials and high-efficiency single-molecule white light devices.
The foregoing examples are illustrative of the present invention and are not intended to be limiting, and other changes, modifications, substitutions, combinations, and simplifications that do not depart from the spirit and principles of the invention are intended to be equivalent in scope.
Claims (10)
1. The di (benzopyrrole) phenothiazine luminescent material is characterized in that the structural general formula of the di (benzopyrrole) phenothiazine luminescent material is shown as formula (I) or formula (II):
In the formulas (I) and (II), R 1 and R 2 are any one of a hydrogen atom or a C 1～C6 alkyl chain.
2. A class of bis (benzopyrrolopyrrole) phenothiazine light emitting materials according to claim 1, wherein R 1 and R 2 are methyl groups.
3. A method for preparing a bis (benzopyrrolopyrrole) phenothiazine luminescent material according to claim 1 or 2, comprising the steps of:
(a) Under the protection of inert gas, the compound 1 and the pinacol ester of the bisdiphenylphosphino ferrocene are subjected to Miyaura boration reaction under the catalysis of 1,1' -bis-diphenylphosphino ferrocene palladium dichloride to generate a compound 2;
(b) Under the protection of inert gas, the compound 2 and o-bromonitrobenzene undergo a Suzuki carbon-carbon coupling reaction under the alkaline condition and under the catalysis of tetra (triphenylphosphine) palladium to obtain a compound 3;
(c) Under the protection of inert gas, i) carrying out cyclization reaction on the compound 3 and triphenylphosphine serving as a reducing agent; ii) carrying out Williamson reaction on the product obtained in the step i) and alkyl iodide under alkaline conditions;
The iodinated alkane is I-R, and R is C 1-C6 alkyl chain;
the synthetic route is as follows:
4. The method for producing a bis (benzopyrrole) phenothiazine light-emitting material according to claim 3, wherein in step (a), the molar ratio of compound 1 to pinacol ester of bisdiboronic acid is 1 (2-4); the mol ratio of the compound 1 to the 1,1' -bis-diphenylphosphino ferrocene palladium dichloride is 1 (0.01-0.5); the temperature of Miyaura boronation reaction is 90-110 ℃, and the time of Miyaura boronation reaction is 12-24h.
5. The method for producing a bis (benzopyrrole) phenothiazine light-emitting material according to claim 3, wherein in step (b), the molar ratio of compound 2 to o-bromonitrobenzene is 1 (2-4); the molar ratio of the compound 2 to the tetra (triphenylphosphine) palladium is 1 (0.01-0.5); the temperature of the Suzuki carbon-carbon coupling reaction is 80-85 ℃, and the time of the Suzuki carbon-carbon coupling reaction is 24-36h.
6. The method for producing a bis (benzopyrrole) phenothiazine light-emitting material according to claim 3, wherein in step (b), sodium carbonate or potassium carbonate is added under alkaline conditions, and the molar ratio of compound 2 to sodium carbonate or potassium carbonate is 1 (2-4).
7. A process for the preparation of a bis (benzopyrrolopyrrole) phenothiazine light-emitting material according to claim 3, wherein in step (c), the molar ratio of compound 3 to triphenylphosphine is 1 (4-10); the temperature of the cyclization reaction is 170-210 ℃, and the time of the cyclization reaction is 12-24 hours; the molar ratio of the product obtained in the step i) to the alkyl iodide is 1 (4-10); the temperature of the Williamson reaction is 70-85 ℃, and the time of the Williamson reaction is 12-24 hours;
In the step (c), the alkaline condition is that sodium hydroxide or potassium hydroxide is added, and the molar ratio of the intermediate to the sodium hydroxide or the potassium hydroxide is 1 (4-10).
8. Use of the bis (benzopyrrole) phenothiazine light-emitting material according to claim 1 or 2 as single molecule white light material.
9. An organic electroluminescent device comprising the bis (benzopyrrole) phenothiazine light-emitting material according to claim 1 or 2.
10. The organic electroluminescent device of claim 9, wherein the bis (benzopyrrole) phenothiazine light-emitting material is used as a light-emitting layer of the organic electroluminescent device;
The organic electroluminescent device is a white light organic electroluminescent device.
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