CN110734432A - nitrogenous heterocyclic ring substituted triazine derivatives, preparation method and application thereof - Google Patents
nitrogenous heterocyclic ring substituted triazine derivatives, preparation method and application thereof Download PDFInfo
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- CN110734432A CN110734432A CN201810801606.3A CN201810801606A CN110734432A CN 110734432 A CN110734432 A CN 110734432A CN 201810801606 A CN201810801606 A CN 201810801606A CN 110734432 A CN110734432 A CN 110734432A
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- 150000003918 triazines Chemical class 0.000 title claims abstract description 22
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 title claims description 22
- 125000000623 heterocyclic group Chemical group 0.000 title claims description 15
- 238000002360 preparation method Methods 0.000 title description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 7
- -1 6-pyrimidyl Chemical group 0.000 claims description 24
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 22
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 12
- 239000000243 solution Substances 0.000 claims description 12
- 229910052763 palladium Inorganic materials 0.000 claims description 10
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 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
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 6
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 230000002950 deficient Effects 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000004944 pyrazin-3-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 4
- 239000012670 alkaline solution Substances 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
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical group 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- 229910003002 lithium salt Inorganic materials 0.000 claims description 4
- 159000000002 lithium salts Chemical class 0.000 claims description 4
- 238000000034 method Methods 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 2
- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].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 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 claims description 2
- 238000005859 coupling reaction Methods 0.000 claims description 2
- YDGSUPBDGKOGQT-UHFFFAOYSA-N lithium;dimethylazanide Chemical group [Li+].C[N-]C YDGSUPBDGKOGQT-UHFFFAOYSA-N 0.000 claims description 2
- SZAVVKVUMPLRRS-UHFFFAOYSA-N lithium;propane Chemical compound [Li+].C[CH-]C SZAVVKVUMPLRRS-UHFFFAOYSA-N 0.000 claims description 2
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 claims description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 2
- PBDBXAQKXCXZCJ-UHFFFAOYSA-L palladium(2+);2,2,2-trifluoroacetate Chemical compound [Pd+2].[O-]C(=O)C(F)(F)F.[O-]C(=O)C(F)(F)F PBDBXAQKXCXZCJ-UHFFFAOYSA-L 0.000 claims description 2
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical group Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 claims description 2
- LUMVCLJFHCTMCV-UHFFFAOYSA-M potassium;hydroxide;hydrate Chemical compound O.[OH-].[K+] LUMVCLJFHCTMCV-UHFFFAOYSA-M 0.000 claims description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
- 150000003222 pyridines Chemical class 0.000 claims 3
- 150000002940 palladium Chemical class 0.000 claims 1
- 239000000975 dye Substances 0.000 abstract description 3
- 238000006862 quantum yield reaction Methods 0.000 abstract description 3
- 238000007725 thermal activation Methods 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- 239000000047 product Substances 0.000 description 8
- 239000000758 substrate Substances 0.000 description 7
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000001035 drying Methods 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 230000005525 hole transport Effects 0.000 description 4
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- 230000000903 blocking effect Effects 0.000 description 3
- 238000012512 characterization method Methods 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- HQSCPPCMBMFJJN-UHFFFAOYSA-N 4-bromobenzonitrile Chemical compound BrC1=CC=C(C#N)C=C1 HQSCPPCMBMFJJN-UHFFFAOYSA-N 0.000 description 2
- HWBOSRMGKRNJAO-UHFFFAOYSA-N [N]C1=CC=C(Br)C=C1 Chemical compound [N]C1=CC=C(Br)C=C1 HWBOSRMGKRNJAO-UHFFFAOYSA-N 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- YQHVEGTZGGQQMV-UHFFFAOYSA-N dicyclohexyl hydrogen phosphate Chemical compound C1CCCCC1OP(=O)(O)OC1CCCCC1 YQHVEGTZGGQQMV-UHFFFAOYSA-N 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000004770 highest occupied molecular orbital Methods 0.000 description 2
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 2
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000007789 sealing Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 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 2
- 238000001771 vacuum deposition Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 description 1
- RKVIAZWOECXCCM-UHFFFAOYSA-N 2-carbazol-9-yl-n,n-diphenylaniline Chemical compound C1=CC=CC=C1N(C=1C(=CC=CC=1)N1C2=CC=CC=C2C2=CC=CC=C21)C1=CC=CC=C1 RKVIAZWOECXCCM-UHFFFAOYSA-N 0.000 description 1
- STXAVEHFKAXGOX-UHFFFAOYSA-N 3-bromobenzonitrile Chemical compound BrC1=CC=CC(C#N)=C1 STXAVEHFKAXGOX-UHFFFAOYSA-N 0.000 description 1
- 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 1
- YWKKLBATUCJUHI-UHFFFAOYSA-N 4-methyl-n-(4-methylphenyl)-n-phenylaniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(C)=CC=1)C1=CC=CC=C1 YWKKLBATUCJUHI-UHFFFAOYSA-N 0.000 description 1
- 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 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- CYZDJFFHZNDUNI-UHFFFAOYSA-N C1=CC(=CC=C1C2=NN=NC=C2)Br Chemical class C1=CC(=CC=C1C2=NN=NC=C2)Br CYZDJFFHZNDUNI-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 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
- 230000008859 change Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000005352 clarification Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- 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
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- 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
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
The invention relates to novel nitrogen heterocyclic ring substituted triazine derivatives with high fluorescence quantum yield and thermal activation fluorescence delay property, so that organic electroluminescent devices using the derivatives as fluorescence doped dyes have the advantages of low working voltage, high efficiency and high fluorescence quantum yield.
Description
Technical Field
The present invention relates to a process for the preparation of novel nitrogen-containing heterocyclic substituted triazine derivatives and to electronic components which contain these compounds.
Background
An organic electroluminescent device is a device in which a light emitting layer (EML) containing a light emitting material is sandwiched between an Electron Transport Layer (ETL) and a Hole Transport Layer (HTL), and a cathode (Al) and an anode (ITO) are further installed at the outer side thereof, electrons and holes are injected into the device by an applied voltage and excitons are formed by recombination in the light emitting layer to emit photons outward through a fluorescence or phosphorescence process and deactivate.
In recent years, thermally activated delayed-mechanism fluorescent materials (TADF) have been used -generalized as luminescent dyes for OLED devices, which can simultaneously utilize singlet excitons having a generation probability of 25% and triplet excitons having a generation probability of 75% to obtain an Internal Quantum Efficiency (IQE) of theoretically 100%, energy system difference (△ E) between singlet state (S1) and triplet state (T1) of fluorescent materials for realizing high-efficiency TADFST) Below 0.1eV, this can be accomplished by reducing the overlap between the highest occupied orbital (HOMO) and the lowest unoccupied orbital (LUMO) of the fluorescent material, however, the fluorescence radiation transition rate (kr) of the fluorescent material is indeed proportional to the orbital overlap of HOMO and LUMOSTThe coordination with kr is very important issues for designing a fluorescent material with efficient TADF mechanism.
Disclosure of Invention
In order to solve the defects and shortcomings in the prior art, the invention provides nitrogenous heterocyclic ring substituted triazine derivatives which can be used as a doped light-emitting layer of an organic electroluminescent device and endow the organic electroluminescent device with high efficiency and low efficiency roll-off and a preparation method thereof.
In order to solve the technical problems, the invention provides nitrogen-containing heterocyclic ring substituted triazine derivatives, wherein the nitrogen-containing heterocyclic ring substituted triazine derivatives are shown as the following general formula (1).
[ chemical formula 1 ]
In the formula (1), Ar1Is an electron-deficient substituent of at least nitrogens, and n is the number of bridged benzene rings.
Step , Ar1Pyridine derivatives such as 2-pyridyl, 3-pyridyl, 4-pyridyl, 2, 6-pyrimidyl, 3, 5-pyrimidyl, 2, 3-pyrazinyl, 4, 5-pyrazinyl and the like; n may be 1, 2, 3.
The present invention also provides a method for producing a triazine derivative having a nitrogen-containing heterocycle substituted represented by the formula (1), wherein a compound represented by the following formula (2) and a phenoxazine boronic acid pinacol ester represented by the formula (3) are subjected to a coupling reaction in the presence of a palladium catalyst in the presence of an alkaline solution. The alkaline solution is potassium carbonate, sodium carbonate or potassium hydroxide water or alcohol solution; the palladium catalyst is palladium salt or palladium complex is palladium chloride, tetrakis (triphenylphosphine) palladium, palladium trifluoroacetate or dichlorobis (triphenylphosphine) palladium; the molar ratio of the palladium catalyst to the compound represented by the formula (2) is 1 to 10: 100, respectively; the molar ratio of the compound shown in the formula (3) to the compound shown in the formula (2) is 1-5: 1; the solvent used in the reaction is toluene, tetrahydrofuran, 1, 4-dioxane or dimethyl sulfoxide.
[ chemical formula 2 ]
In the above formula (2), X is a halogen leaving group; n-1 represents the number of bridged benzene rings; ar (Ar)1Denotes an electron-deficient substituent comprising at least nitrogens.
step, X is chlorine atom, bromine atom or iodine atom, Ar1Pyridine derivatives such as 2-pyridyl, 3-pyridyl, 4-pyridyl, 2, 6-pyrimidyl, 3, 5-pyrimidyl, 2, 3-pyrazinyl, and 4, 5-pyrazinyl; n-1 may be 1, 2.
[ chemical formula 3 ]
The invention also provides a preparation method of the nitrogen-containing heterocyclic ring substituted triazine derivative shown in the formula (2), wherein the following formula (4) and the compound shown in the formula (5) are subjected to a cycloreaction in the presence of lithium salt and an ultra-dry solvent according to the situation; the lithium salt is dimethylamino lithium, butyl lithium, methyl lithium or isopropyl lithium; the molar ratio of the compound shown in the formula (4) to the compound shown in the formula (5) is 1-5: 1; the ultra-dry solvent used in the reaction is tetrahydrofuran, diethyl ether, cyclohexane or normal hexane.
[ chemical formula 4 ]
In the above formula (4), Ar1Denotes an electron-deficient substituent comprising at least nitrogens.
Step , Ar1Pyridine derivatives such as 2-pyridyl, 3-pyridyl, 4-pyridyl, 2, 6-pyrimidyl, 3, 5-pyrimidyl, 2, 3-pyrazinyl, 4, 5-pyrazinyl and the like can be used.
[ chemical formula 5 ]
In the above formula (5), n-1 represents the number of bridged benzene rings; x is a halogen leaving group. Preferably, n-1 may be 1, 2; x is a chlorine atom, a bromine atom or an iodine atom.
The invention also provides application of the nitrogen-containing heterocyclic ring substituted triazine derivative in an organic electroluminescent device.
The invention achieves the following beneficial technical effects: the novel nitrogen-containing heterocyclic ring substituted triazine derivative provided by the invention has high fluorescence quantum yield and thermally activated delayed fluorescence, and therefore, can be used for yellow materials of organic electroluminescent devices. The organic electroluminescent device formed by the doped fluorescent agent has the characteristics of low efficiency roll-off, high efficiency and the like. Therefore, the novel nitrogen-containing heterocyclic ring substituted triazine derivative can be used as a component of an organic electroluminescent device with high efficiency and low efficiency roll-off.
Drawings
FIG. 1 is a schematic cross-sectional view showing the application of the novel nitrogen-containing heterocycle-substituted triazine derivative of the present invention to an organic electroluminescent device.
Wherein, 1 a glass substrate; 2 a hole transport layer; 3 an electron blocking layer; 4 a light emitting layer; 5 an electron transport layer; 6 cathode layer.
Detailed Description
The present invention will be further described with reference to the following specific examples, which are provided for more clearly illustrating the technical solutions of the present invention and should not be construed as limiting the scope of the present invention.
Example 1: synthesis of 4-biphenyl- (2, 6-bis (3-pyridyl) -1,3, 5-triazinyl) -phenoxazine
Adding a magnetic stirrer into a 250ml three-neck flask, adding 1.65ml (2.0mol/L) of dimethylamine and 50ml of anhydrous ether into the three-neck flask, slowly dropwise adding 2.06ml (1.6mol/L) of butyl lithium at room temperature, changing the reaction solution from clear to white turbid solution, stirring the mixture at room temperature for 20 minutes, quickly adding 0.55g of solid p-bromobenzonitrile, continuously reacting for 1 hour, quickly adding 0.66g of m-bromobenzonitrile into the mixture under the protection of nitrogen, continuously reacting for 4 hours, removing the protection of nitrogen, continuously reacting for 1 hour under the atmosphere, filtering under reduced pressure, washing a filter cake with ether, recrystallizing the filter plate with ethanol and water (1: 2), filtering, drying in vacuum, and directly purifying the product in the next step without steps.
Example 1: under the protection of argon, 0.39g of 4-bromophenyl nitrogen-containing heterocyclic ring substituted triazine derivative (intermediate 1), 0.42g of phenoxazine pinacol ester, 115mg of palladium tetratriphenylphosphine, 35mg of 2- (dicyclohexyl phosphate) biphenyl, 0.42g of potassium carbonate and 60mL of toluene are added into a 100mL two-port reactor provided with a reflux pipe. The resulting solution was heated to 100 ℃ and stirred for 12 hours. After cooling to room temperature, the organic solvent was distilled off. The organic phase was extracted by adding a large amount of water and dichloromethane and dried over anhydrous sodium sulfate, and after distilling off the organic phase, the product was purified by column chromatography using ethyl acetate and methanol. After drying, an orange powder was obtained (yield 0.44g, yield 78%).
And (3) product characterization:1H NMR(600MHz,Chloroform-d)δ10.08(s,2H),9.01(d,J＝7.8Hz,2H),8.88–8.84(m,4H),7.92(d,J＝8.0Hz,2H),7.88(d,J＝8.1Hz,2H),7.54(dd,J＝7.9,4.8Hz,2H),7.48(d,J＝8.0Hz,2H),6.71(dd,J＝7.8,1.5Hz,2H),6.66(td,J＝7.5,1.5Hz,2H),6.62(td,J＝7.6,1.5Hz,2H),6.02(dd,J＝8.0,1.5Hz,2H).13C NMR(151MHz,Chloroform-d)δ171.64,170.53,153.30,150.67,144.62,143.96,140.21,138.99,136.21,134.74,134.23,131.43,131.38,129.84,129.74,127.52,123.55,123.24,121.43,115.50,113.26.MS(EI).Calcd for C37H24N6O([M]+):m/z 568.20.Found:m/z 568.32.
example 2: synthesis of 4-phenyl- (2, 6-bis (3-pyridyl) -1,3, 5-triazinyl) -phenoxazine
Example 2: under the protection of argon, 0.78g of 4-bromophenyl triazine derivative (intermediate 1), 0.40g of phenoxazine, 15mg of palladium acetate, 0.5mL of 10% toluene solution of tri-tert-butylphosphine, and 60mL of toluene were added to a 100mL two-port reactor equipped with a reflux tube. The resulting solution was heated to 90 ℃ and stirred for 12 hours. After cooling to room temperature, the organic solvent was distilled off. The organic phase was extracted by adding a large amount of water and methylene chloride and dried over anhydrous sodium sulfate, and after distilling off the organic phase, the product was purified by column chromatography using methylene chloride and methanol. After drying, 800mg of red powder was obtained, yield 81.2%.
And (3) product characterization:1H NMR(600MHz,Chloroform-d)δ9.95(s,2H),9.00(dd,J＝8.0,1.9Hz,2H),8.97(d,J＝8.1Hz,2H),8.87(d,J＝4.8Hz,2H),7.60(d,J＝8.1Hz,2H),7.54(dd,J＝8.0,4.8Hz,2H),6.73(dd,J＝8.0,1.4Hz,2H),6.68(td,J＝7.9,1.4Hz,2H),6.61(td,J＝7.7,1.5Hz,2H),6.04(dd,J＝8.1,1.4Hz,2H)；13C NMR(151MHz,Chloroform-d)δ171.24,170.71,153.43,150.66,143.99,143.65,136.23,135.38,133.79,131.81,131.24,123.59,123.28,121.75,115.67,113.31.MS(EI).Calcd for C31H20N6O([M]+):m/z 492.20.Found:m/z 492.32.
example 3: synthesis of 4-biphenyl- (2, 6-bis (3, 5-pyrimidinyl) -1,3, 5-triazinyl) -phenoxazine
And (2) adding a magnetic stirrer into a 250ml three-neck flask, adding 1.65ml (2.0mol/L) of dimethylamine and 50ml of anhydrous ether under the protection of nitrogen, slowly dropwise adding 2.06ml (1.6mol/L) of butyl lithium at room temperature, changing the reaction solution from clarification to a white turbid solution, stirring for 20 minutes at room temperature, quickly adding 0.55g of solid p-bromobenzonitrile, continuously reacting for 1 hour, quickly adding 0.66g of m-bromopyrimidine under the protection of nitrogen, continuously reacting for 4 hours, removing the protection of nitrogen, continuously reacting for 1 hour under the atmosphere, filtering under reduced pressure, washing a filter cake with ether, recrystallizing the filter plate with ethanol and water (1: 2), filtering, drying in vacuum, and directly purifying a product in the next step without steps.
Example 3: under the protection of argon, 0.39g of 4-bromophenyl nitrogen-containing heterocyclic ring substituted triazine derivative (intermediate 2), 0.42g of phenoxazine pinacol ester, 115mg of palladium tetratriphenylphosphine, 35mg of 2- (dicyclohexyl phosphate) biphenyl, 0.42g of potassium carbonate and 60mL of toluene are added into a 100mL two-port reactor provided with a reflux pipe. The resulting solution was heated to 100 ℃ and stirred for 12 hours. After cooling to room temperature, the organic solvent was distilled off. The organic phase was extracted by adding a large amount of water and dichloromethane and dried over anhydrous sodium sulfate, and after distilling off the organic phase, the product was purified by column chromatography using ethyl acetate and methanol. After drying, an orange powder was obtained (yield 0.40g, yield 70%).
And (3) product characterization:1H NMR(600MHz,Chloroform-d)δ10.20(s,2H),9.42(s,4H),8.10(d,J＝8.1Hz,2H),7.95(d,J＝8.0Hz,2H),7.68(dd,J＝8.0,4.9Hz,2H),7.52(d,J＝8.1Hz,2H),6.75(dd,J＝7.7,1.6Hz,2H),6.67(td,J＝7.4,1.5Hz,2H),6.65(td,J＝7.5,1.5Hz,2H),6.00(dd,J＝7.8,1.5Hz,2H).13C NMR(151MHz,Chloroform-d)δ173.20,171.33,155.21,150.17,143.62,142.96,140.21,138.59,136.21,135.74,135.23,130.43,130.38,129.84,129.74,121.24,120.43,115.20,113.01.MS(EI).Calcd for C35H22N8O([M]+):m/z570.19.Found:m/z 570.25.
the invention also provides application of the novel nitrogen-containing heterocyclic ring substituted triazine derivative in an organic doped electroluminescent device.
Test example-1
Preparation and performance evaluation of organic electroluminescent device with example 1 as fluorescent doped dye
A striped glass plate with transparent electrodes of Indium Tin Oxide (ITO) patterned with a 3mm wide film was used as the substrate. After the glass substrate was washed with isopropyl alcohol, surface treatment was performed by ozone ultraviolet rays. Vacuum deposition of each layer was performed on the cleaned substrate by vacuum deposition to produce a light-emitting area 9mm as shown in FIG. 1 in a cross-sectional view2The organic electroluminescent device of (1).
First, the glass substrate is introduced into a vacuum evaporation tank and reduced in pressure to 1X 10-4Pa. Then, on the glass substrate shown in fig. 1, a hole transport layer 2, an electron blocking layer 3, a light emitting layer 4, and an electron transport layer 5 are formed in this order as organic compound layers, and then a cathode layer 6 is formed. 4,4' -Cyclohexylbis [ N, N-bis (4-methylphenyl) aniline vacuum-evaporated in a film thickness of 35nm](TAPC) As the hole transport layer 2, 4' -tris (carbazol-9-yl) triphenylamine (TCTA) vacuum-evaporated at a thickness of 10nm as the electron blocking layer 3, 4-bis (9-Carbazol) Biphenyl (CBP) vacuum-evaporated at a ratio of 90:10 (mass%) at a thickness of 20nm as the light emitting layer 4, 3' - [5' - [3- (3-pyridyl) phenyl ] biphenyl (CBP) vacuum-evaporated at a thickness of 45nm as the light emitting layer 4 in example 1 synthesized in example 2 of the present invention][1,1':3', 1' -terphenyl]-3,3 "-diyl]Bipyridine (TmPyPb) was used as the electron transport layer 5. Wherein each organic material is formed into a film by means of resistance heating. Heating the compound to vacuum-evaporate at a film forming rate of 0.3-0.5 nm. Finally, a metal mask is disposed so as to be orthogonal to the ITO stripes, thereby forming a film cathode 6. The cathode layer 6 has a two-layer structure formed by vacuum-depositing lithium fluoride and aluminum in film thicknesses of 1nm and 100nm, respectively. Each film thickness was measured by a stylus type film thickness measuring instrument (DEKTAK). Further, the device was sealed in a nitrogen atmosphere glove box containing water and oxygen at a concentration of 1ppm or less. The sealing is carried out by using a vitreous sealing cap and the film-forming substrate made of an epoxy ultraviolet-curable resin (manufactured by Nagase ChemteXCorption).
The prepared organic electroluminescent device was subjected to direct current application, evaluated for light emission performance using a Spectrascan PR650 luminance meter, and measured for current-voltage characteristics using a computer-controlled Keithley 2400 digital source meter. The light emission characteristics were measured by measuring the CIE color coordinate value under the change of applied DC voltage,Maximum luminance (cd/m)2) External quantum efficiency (%), power efficiency (lm/W). The measured values of the fabricated devices were (0.41,0.55), 54990cd/m222.6% and 67.2 lm/W.
In conclusion, the novel nitrogen-containing heterocyclic ring substituted triazine derivative provided by the invention can be applied to organic electroluminescent devices, and has the advantages of low power consumption and high luminous efficiency. The novel nitrogen-containing heterocyclic ring substituted triazine derivative of the present invention can be applied to various organic electroluminescent devices such as fluorescent light-emitting materials and phosphorescent light-emitting materials, and can be applied to illumination applications such as flat panel displays and the like, which have both low power consumption and high efficiency.
The present invention has been disclosed in terms of the preferred embodiment, but is not intended to be limited to the embodiment, and all technical solutions obtained by substituting or converting equivalents thereof fall within the scope of the present invention.
Claims (7)
- A nitrogen-containing heterocyclic ring substituted triazine derivative, characterized by having a structural formula shown in formula (1):
in the formula (1), Ar1Is an electron-deficient substituent of at least nitrogens, and n is the number of bridged benzene rings. - 2. The nitrogen-containing heterocycle-substituted triazine derivative according to claim 1, wherein:Ar1is prepared from pyridine derivatives such as 2-pyridyl, 3-pyridyl, 4-pyridyl, 2, 6-pyrimidyl, 3, 5-pyrimidyl, 2, 3-pyrazinyl or 4, 5-pyrazinyl; n is 1, 2 or 3.
- 3. A process for producing the nitrogen-containing heterocycle-substituted triazine derivative according to claim 1, wherein: carrying out coupling reaction on a compound shown in a formula (2) and phenoxazine boronic acid pinacol ester shown in a formula (3) in the presence of an alkaline solution and a palladium catalyst;
in the above formula (2), X is a halogen leaving group and is a chlorine atom, a bromine atom or an iodine atom, n represents the number of bridged benzene rings, n-1 is 1 or 2, Ar1 represents an electron-deficient substituent containing at least nitrogen, and a pyridine derivative such as 2-pyridyl, 3-pyridyl, 4-pyridyl, 2, 6-pyrimidyl, 3, 5-pyrimidyl, 2, 3-pyrazinyl or 4, 5-pyrazinyl is used. - 4. The production method according to claim 3, characterized in that: the alkaline solution is potassium carbonate, sodium carbonate, potassium hydroxide water or alcohol solution; the palladium catalyst is palladium salt or palladium complex, the palladium salt is palladium chloride, tetrakis (triphenylphosphine) palladium, palladium trifluoroacetate or dichlorobis (triphenylphosphine) palladium, and the molar ratio of the palladium catalyst to the compound shown in the formula (2) is 1-10: 100, respectively; the molar ratio of the compound shown in the formula (3) to the compound shown in the formula (2) is 1-5: 1; the solvent used in the reaction is toluene, tetrahydrofuran, 1, 4-dioxane or dimethyl sulfoxide.
- 5. The production method according to claim 3, characterized in that: carrying out a cycloreaction on a compound shown as a formula (4) and a compound shown as a formula (5) in the presence of a lithium salt and an ultra-dry solvent to obtain a compound shown as a formula (2);in the above formula (4), Ar1Represents an electron-deficient substituent containing at least nitrogens, and is a pyridine derivative such as 2-pyridyl, 3-pyridyl, 4-pyridyl, 2, 6-pyrimidyl, 3, 5-pyrimidyl, 2, 3-pyrazinyl or 4, 5-pyrazinyl;in the above formula (5), n represents the number of bridged benzene rings, and n-1 is 1 or 2; x is a halogen leaving group and is a chlorine atom, a bromine atom or an iodine atom.
- 6. The method of claim 5, wherein: the lithium salt is dimethylamino lithium, butyl lithium, methyl lithium or isopropyl lithium; the molar ratio of the compound shown in the formula (4) to the compound shown in the formula (5) is 1-5: 1; the ultra-dry solvent used in the reaction is tetrahydrofuran, diethyl ether, cyclohexane or normal hexane.
- 7. The use of nitrogen-containing heterocycle-substituted triazine derivatives as claimed in claim 1 for doping organic electroluminescent devices.
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