CN108424420B - Triazine compound containing silicon atom, application thereof and organic electroluminescent device - Google Patents
Triazine compound containing silicon atom, application thereof and organic electroluminescent device Download PDFInfo
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- CN108424420B CN108424420B CN201710940389.1A CN201710940389A CN108424420B CN 108424420 B CN108424420 B CN 108424420B CN 201710940389 A CN201710940389 A CN 201710940389A CN 108424420 B CN108424420 B CN 108424420B
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- -1 Triazine compound Chemical class 0.000 title claims abstract description 51
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 title claims abstract description 27
- 229910052710 silicon Inorganic materials 0.000 title claims abstract description 23
- 150000001875 compounds Chemical class 0.000 claims abstract description 39
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims abstract description 36
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 24
- 239000004305 biphenyl Substances 0.000 claims abstract description 18
- 235000010290 biphenyl Nutrition 0.000 claims abstract description 18
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 11
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 10
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 claims description 13
- 125000001424 substituent group Chemical group 0.000 claims description 13
- 238000002347 injection Methods 0.000 claims description 10
- 239000007924 injection Substances 0.000 claims description 10
- 230000000903 blocking effect Effects 0.000 claims description 9
- 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 claims description 8
- 150000003918 triazines Chemical class 0.000 claims description 8
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 7
- 239000000758 substrate Substances 0.000 claims description 7
- 230000005525 hole transport Effects 0.000 claims description 6
- 239000000463 material Substances 0.000 abstract description 22
- 230000002035 prolonged effect Effects 0.000 abstract description 2
- 239000000543 intermediate Substances 0.000 description 34
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 32
- 230000015572 biosynthetic process Effects 0.000 description 22
- 238000003786 synthesis reaction Methods 0.000 description 22
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 18
- 238000005160 1H NMR spectroscopy Methods 0.000 description 16
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
- 238000002360 preparation method Methods 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- 239000012295 chemical reaction liquid Substances 0.000 description 10
- 238000004440 column chromatography Methods 0.000 description 10
- 239000002994 raw material Substances 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- 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 description 8
- 229910000027 potassium carbonate Inorganic materials 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
- 125000003545 alkoxy group Chemical group 0.000 description 7
- 238000001035 drying Methods 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- 238000004128 high performance liquid chromatography Methods 0.000 description 7
- 238000001308 synthesis method Methods 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 238000005259 measurement Methods 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- ABRVLXLNVJHDRQ-UHFFFAOYSA-N [2-pyridin-3-yl-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound FC(C1=CC(=CC(=N1)C=1C=NC=CC=1)CN)(F)F ABRVLXLNVJHDRQ-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000002019 doping agent Substances 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 description 3
- 238000004770 highest occupied molecular orbital Methods 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- DDGPPAMADXTGTN-UHFFFAOYSA-N 2-chloro-4,6-diphenyl-1,3,5-triazine Chemical compound N=1C(Cl)=NC(C=2C=CC=CC=2)=NC=1C1=CC=CC=C1 DDGPPAMADXTGTN-UHFFFAOYSA-N 0.000 description 2
- GDSLUYKCPYECNN-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-[(4-fluorophenyl)methyl]benzamide Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C(=O)NCC2=CC=C(C=C2)F)C=CC=1 GDSLUYKCPYECNN-UHFFFAOYSA-N 0.000 description 2
- LZPWAYBEOJRFAX-UHFFFAOYSA-N 4,4,5,5-tetramethyl-1,3,2$l^{2}-dioxaborolane Chemical compound CC1(C)O[B]OC1(C)C LZPWAYBEOJRFAX-UHFFFAOYSA-N 0.000 description 2
- 239000007818 Grignard reagent Substances 0.000 description 2
- 239000010405 anode material Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 150000004795 grignard reagents Chemical class 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 2
- 238000001771 vacuum deposition Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 description 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 1
- FPNVMCMDWZNTEU-UHFFFAOYSA-N 1-bromo-4-chloro-2-fluorobenzene Chemical compound FC1=CC(Cl)=CC=C1Br FPNVMCMDWZNTEU-UHFFFAOYSA-N 0.000 description 1
- IYZMXHQDXZKNCY-UHFFFAOYSA-N 1-n,1-n-diphenyl-4-n,4-n-bis[4-(n-phenylanilino)phenyl]benzene-1,4-diamine Chemical compound C1=CC=CC=C1N(C=1C=CC(=CC=1)N(C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 IYZMXHQDXZKNCY-UHFFFAOYSA-N 0.000 description 1
- WNEXSUAHKVAPFK-UHFFFAOYSA-N 2,8-dibromodibenzothiophene Chemical compound C1=C(Br)C=C2C3=CC(Br)=CC=C3SC2=C1 WNEXSUAHKVAPFK-UHFFFAOYSA-N 0.000 description 1
- ZPZKLVBUXHZVAC-UHFFFAOYSA-N 3-bromo-7-chlorodibenzofuran Chemical compound BrC=1C=CC2=C(OC3=C2C=CC(=C3)Cl)C=1 ZPZKLVBUXHZVAC-UHFFFAOYSA-N 0.000 description 1
- XSJLDNSNUICSQC-UHFFFAOYSA-N 4,6-dibromodibenzofuran Chemical compound O1C2=C(Br)C=CC=C2C2=C1C(Br)=CC=C2 XSJLDNSNUICSQC-UHFFFAOYSA-N 0.000 description 1
- DHDHJYNTEFLIHY-UHFFFAOYSA-N 4,7-diphenyl-1,10-phenanthroline Chemical compound C1=CC=CC=C1C1=CC=NC2=C1C=CC1=C(C=3C=CC=CC=3)C=CN=C21 DHDHJYNTEFLIHY-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
- OSQXTXTYKAEHQV-WXUKJITCSA-N 4-methyl-n-[4-[(e)-2-[4-[4-[(e)-2-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]ethenyl]phenyl]phenyl]ethenyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(\C=C\C=2C=CC(=CC=2)C=2C=CC(\C=C\C=3C=CC(=CC=3)N(C=3C=CC(C)=CC=3)C=3C=CC(C)=CC=3)=CC=2)=CC=1)C1=CC=C(C)C=C1 OSQXTXTYKAEHQV-WXUKJITCSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 229910014265 BrCl Inorganic materials 0.000 description 1
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-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
- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- UNXISIRQWPTTSN-UHFFFAOYSA-N boron;2,3-dimethylbutane-2,3-diol Chemical compound [B].[B].CC(C)(O)C(C)(C)O UNXISIRQWPTTSN-UHFFFAOYSA-N 0.000 description 1
- CODNYICXDISAEA-UHFFFAOYSA-N bromine monochloride Chemical compound BrCl CODNYICXDISAEA-UHFFFAOYSA-N 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 229910052593 corundum Inorganic materials 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229910001845 yogo sapphire Inorganic materials 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- 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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- 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
- H10K85/40—Organosilicon compounds, e.g. TIPS pentacene
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- 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
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
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- 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
- C09K2211/1074—Heterocyclic compounds characterised by ligands containing more than three nitrogen atoms as heteroatoms
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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
- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only 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
- C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only 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
- C09K2211/1096—Heterocyclic compounds characterised by ligands containing other 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)
- Electroluminescent Light Sources (AREA)
Abstract
The invention relates to the field of organic electroluminescent devices, and discloses a triazine compound containing silicon atoms, application thereof and an organic electroluminescent device, wherein the compound has a structure shown in a formula (I) or a formula (II), and L in the formula (I) and the formula (II)1And L2Each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, or L1And L2Each independently is absent; a is a structure shown as A1, A2, A3 or A4; x is O or S. When the triazine compound containing the silicon atom is used as an electron transport material, the driving voltage can be effectively reduced, the current efficiency and the brightness are improved, and the service life is prolonged.
Description
Technical Field
The invention relates to the field of organic electroluminescent devices, in particular to a triazine compound containing a silicon atom, application of the triazine compound containing the silicon atom in an organic electroluminescent device, and an organic electroluminescent device containing the triazine compound containing the silicon atom.
Background
Compared with the traditional liquid crystal technology, the organic electroluminescence (OLED) technology does not need backlight source irradiation and a color filter, pixels can emit light to be displayed on a color display panel, and the OLED technology has the characteristics of ultrahigh contrast, ultra-wide visual angle, curved surface, thinness and the like.
The properties of OLEDs are not only influenced by the emitter, but in particular the materials forming the individual layers of the OLED have a very important influence on the properties of the OLED, for example substrate materials, hole-blocking materials, electron-transporting materials, hole-transporting materials and electron-or exciton-blocking materials. The materials used for forming the layers of the OLED at present still have the defects of high driving voltage, short service life, low current efficiency and low brightness, so that an organic electroluminescent device with good performance cannot be obtained.
Disclosure of Invention
The triazine compound provided by the invention can regulate and control the HOMO energy level and LUMO energy level of an organic electroluminescent material, and can enable the organic electroluminescent material containing the triazine compound to have high electron mobility, so that the luminous efficiency is improved.
The inventor of the invention finds that the new compound simultaneously containing any one group selected from dibenzofuranyl and dibenzothienyl, any one group selected from triphenylsilyl and diphenyl-substituted silafluorenyl and diphenyl triazinyl can regulate and control the HOMO energy level of the organic electroluminescent material, so that the organic electroluminescent material containing the new compound has higher electron mobility, and the luminous efficiency of an organic electroluminescent device formed by the new compound is improved. Accordingly, the inventors have completed the technical solution of the present invention.
In order to achieve the above object, a first aspect of the present invention provides a silicon atom-containing triazine compound having a structure represented by formula (I) or formula (II):
wherein, in the formula (I) and the formula (II),
L1and L2Each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, or L1And L2Each independently is absent;
R1and R2Each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted dibenzofuranyl;
a is a structure shown as A1, A2, A3 or A4;
x is O or S;
wherein the substituents are each independently selected from C1-20Alkyl of (C)1-20Alkoxy group of (2).
A second aspect of the present invention provides a use of the triazine compound containing a silicon atom described in the first aspect described above in an organic electroluminescent device.
In a third aspect, the present invention provides an organic electroluminescent element comprising one or more compounds selected from the group consisting of the triazine compounds containing silicon atoms.
When the triazine compound containing the silicon atom is used as an electron transport material, the driving voltage can be effectively reduced, the current efficiency and the brightness are improved, and the service life is prolonged.
Detailed Description
The endpoints of the ranges and any values disclosed herein are not limited to the precise range or value, and such ranges or values should be understood to encompass values close to those ranges or values. For ranges of values, between the endpoints of each of the ranges and the individual points, and between the individual points may be combined with each other to give one or more new ranges of values, and these ranges of values should be considered as specifically disclosed herein.
As described above, the first aspect of the present invention provides a triazine compound containing a silicon atom, which has a structure represented by formula (I) or formula (II):
wherein, in the formula (I) and the formula (II),
L1and L2Each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, or L1And L2Each independently is absent;
R1and R2Each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted dibenzofuranyl;
a is a structure shown as A1, A2, A3 or A4;
x is O or S;
wherein the substituents are each independently selected from C1-20Alkyl of (C)1-20Alkoxy group of (2).
"terphenyl group" means a group in which three phenyl groups are connected in sequence, and the terminal phenyl group of the group in which three phenyl groups are connected in sequence is linked to the parent structure, and the manner of linking the three phenyl groups to each other is not particularly limited.
"wherein the substituents are each independently selected from C1-20Alkyl of (C)1-20The "substituent(s)" in the "alkoxy group(s) of (1) represents, in L1And L2In, if L1Or L2In the case of substituted phenyl, substituted biphenyl, the substituents therein are selected from those defined herein. In particular, the substitution position and the number of substitutions of "substituent(s)" are not particularly limited, and substitution may be made at any position that can be substituted.
In the formulae (I) and (II) of the present invention, the pairs A and L1Is connected, and L1A linkage to a dibenzofuranyl or dibenzothienyl group, and L2A linkage to a dibenzofuranyl or dibenzothienyl group, and L2The linkage relationship with the diphenyltriazinyl group is not particularly limited, and the linkage may be at any position capable of linkage to form a novel compound.
“C1-20The "alkyl group" of (A) is an alkyl group having 1 to 20 carbon atoms in total, and may be a straight-chain, branched or cyclic alkyl groupA radical group.
“C1-20The "alkoxy group of (a) is an alkoxy group having 1 to 20 carbon atoms in total, and may be a linear, branched or cyclic alkoxy group.
To "C1-12Alkyl of (2), "" C1-12Alkoxy group of (1), "" C1-6Alkyl of (2), "" C1-6Alkoxy group of (1), "" C1-3Alkyl of (2), "" C1-3The "alkoxy group" of (A) also has the aforementioned "C1-20Alkyl of and C1-20The "alkoxy group" of (1) "is similarly defined, only in terms of the number of carbon atoms.
Several preferred embodiments of the triazine compounds of the invention are provided below:
embodiment mode 1:
L1and L2Each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, or L1And L2Each independently is absent;
R1and R2Each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, dibenzothienyl and dibenzofuranyl;
a is a structure shown as A1, A2, A3 or A4;
x is O or S;
wherein the substituents are each independently selected from C1-12Alkyl of (C)1-12Alkoxy group of (2).
Embodiment mode 2:
in the formula (I) and the formula (II),
L1and L2Each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, or L1And L2Each independently is absent;
R1and R2Each independently selected from phenyl, biphenyl, terphenyl, fluorenyl, dibenzothienyl and dibenzofuranyl;
a is a structure shown as A1, A2, A3 or A4;
x is O or S;
wherein the substituents are each independently selected from C1-6Alkyl of (C)1-6Alkoxy group of (2).
Embodiment mode 3:
in the formula (I) and the formula (II),
L1and L2Each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, or L1And L2Each independently is absent;
R1and R2Are all phenyl;
a is a structure shown as A1, A2, A3 or A4;
x is O or S;
wherein the substituents are each independently selected from C1-3Alkyl of (C)1-3Alkoxy group of (2).
Said C is1-6The alkyl group of (b) may be, for example, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a cyclopropyl group, a n-butyl group, an isobutyl group, a tert-butyl group, a n-pentyl group, a cyclopentyl group, a n-hexyl group, a cyclohexyl group.
Said C is1-6The alkoxy group of (A) may be, for example, methoxy, ethoxy, n-propoxy, isopropoxy, cyclopropoxy, n-butoxy, isobutoxy, tert-butoxy, n-pentoxy, cyclopentoxy, n-hexoxy, cyclohexoxy.
Embodiment 4:
the triazine compound is at least one of the specific compounds listed in claim 4.
Embodiment 5:
the triazine compound is at least one of the specific compounds listed in claim 5.
In particular, the specific compound provided in the foregoing embodiment mode 4 of the invention can regulate the HOMO level and LUMO level of the organic electroluminescent material when used in at least one of an electron transport layer, a light-emitting layer, and a hole blocking layer of an organic electroluminescent device. More preferably, the specific compound provided in the foregoing embodiment 5 of the present invention, when used in an electron transport layer of an organic electroluminescent device, enables an organic electroluminescent material containing the triazine compound to have significantly higher electron mobility, thereby providing significantly higher luminous efficiency.
The present invention is not particularly limited to the method for synthesizing the silicon atom-containing triazine compound provided by the present invention, and those skilled in the art can determine an appropriate synthesis method based on the structural formula of the silicon atom-containing triazine compound provided by the present invention in combination with the preparation method of the preparation example.
Further, some preparation methods of the triazine compounds containing silicon atoms are exemplarily given in the preparation examples of the present invention, and those skilled in the art can obtain all the triazine compounds containing silicon atoms provided by the present invention according to the preparation methods of these exemplary preparation examples. The present invention will not be described in detail herein with respect to specific methods of preparing the various compounds of the present invention, which should not be construed as limiting the invention to those skilled in the art.
As described above, the second aspect of the present invention provides the use of the triazine compound containing a silicon atom described in the first aspect described above in an organic electroluminescent device.
As described above, the third aspect of the present invention provides an organic electroluminescent device comprising one or two or more compounds of the silicon atom-containing triazine compounds described in the first aspect.
Preferably, the triazine compound containing a silicon atom is present in at least one of an electron transport layer, a light emitting layer and a hole blocking layer of the organic electroluminescent device.
More preferably, the triazine compound containing a silicon atom is present in an electron transport layer of the organic electroluminescent device.
Preferably, the organic electroluminescent device includes a substrate, an anode, a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), an optional electron blocking layer, an emission layer (EML), an optional hole blocking layer, an Electron Transport Layer (ETL), an Electron Injection Layer (EIL), and a cathode, which are sequentially stacked.
Preferably, the anode material forming the anode is selected from one or more of indium tin oxide, indium zinc oxide and tin dioxide. The thickness of the anode active layer formed by the anode material can be, for example, 1000-1700 angstroms.
Preferably, the hole injection layer contains a hole injection material selected from one or more of the following formulas TDATA, 2-TNATA, and TCTA:
preferably, the thickness of the hole injection layer is, for example, 100-800 angstroms, and more preferably 200-600 angstroms.
Preferably, the hole transport material in the hole transport layer is selected from at least one of the following formulae NPB, TPD, and HT-1:
preferably, the thickness of the hole transport layer is 100-600 angstroms, and more preferably 200-400 angstroms.
Preferably, the light-emitting layer contains a light-emitting host material and a dopant, the dopant preferably being selected from the group consisting of DPAVBi, BD1, Ir (ppy)3And TBPe. The light-emitting host material is at least one of compounds shown in formulas CBP, ADN and 1, 2-ADN.
Preferably, the thickness of the light-emitting layer is 100-600 angstroms, and more preferably 200-400 angstroms.
The electron transport layer of the present invention preferably contains at least one of the aforementioned novel compounds of the present invention. According to a preferred embodiment, the electron transport layer further comprises a material selected from the group consisting of BPhen, Alq3One or more light emitting hosts of the formulae TPBi and ET-1Materials:
preferably, the thickness of the electron transport layer is 100-600 angstroms.
Preferably, the material of the hole blocking layer contains a compound represented by the formula BCP.
Preferably, the hole blocking layer has a thickness of 10 to 100 angstroms.
Preferably, the electron injection layer contains LiF and Al2O3MnO or a combination of more of them.
Preferably, the electron injection layer has a thickness of 1 to 50 angstroms, more preferably 1 to 10 angstroms.
Preferably, the material forming the cathode is one or more of Al, Mg and Ag.
Preferably, the cathode layer has a thickness of 800-.
Preferably, the organic electroluminescent device further comprises a first cover layer and/or a second cover layer, wherein the first cover layer is disposed on the outer surface of the anode, and the second cover layer is disposed on the outer surface of the cathode.
More preferably, the first cover layer and the second cover layer each independently contain one or two or more compounds of the silicon atom-containing triazine compounds of the present invention.
The method of the present invention is not particularly limited to the method of preparing the organic electroluminescent device, and may be prepared by various methods that are conventional in the art as long as the organic electroluminescent device having the aforementioned structure of the present invention can be obtained, and those skilled in the art should not be construed as limiting the present invention.
The present invention will be described in detail below by way of examples.
Evaluation: evaluation of characteristics of organic light-emitting device
The driving voltage, emission efficiency and lifetime of the organic light emitting devices in examples and comparative examples were measured using a current-voltage source meter (Keithley 2400) and a Minolta CS-1000A spectroradiometer. The results are shown in table 1 below.
(1) Measurement of current density change with respect to voltage change
A current value flowing through each of the organic light emitting devices was measured while increasing a voltage from 0 volt (V) to about 10V by using a current-voltage source meter (Keithley 2400), and then divided by an area of the corresponding light emitting device to obtain a current density.
(2) Measurement of brightness variation with respect to voltage variation
The brightness of the organic light emitting device was measured while increasing the voltage from about 0V to about 10V by using a Minolta CS-1000A spectroradiometer.
(3) Measurement of emission efficiency
The organic light emitting device was calculated at 10 milliamperes per square centimeter (mA/cm) based on the current density, voltage, and luminance obtained from the measurements (1) and (2) described above2) Or 50 milliamps per square centimeter (mA/cm)2) Current efficiency at a certain current density.
(4) Measurement of lifetime
Hold 5000cd/m2Luminance (cd/m)2) And the time for the current efficiency (cd/A) to decrease to 50% was measured.
Preparation example 1: synthesis of Compounds 1-9
Synthesis of intermediate 1-9-1: dissolving 0.1mol of 4, 6-dibromo-dibenzofuran in 320ml of 1, 4-dioxane solvent, introducing nitrogen, stirring, sequentially adding 0.09mol of 4- (triphenylsilane) phenylboronic acid, 0.25mol of potassium carbonate and 0.0001mol of tetrakis (triphenylphosphine) palladium, heating to reflux reaction, after 5 hours, detecting by HPLC that the raw materials are basically reacted, decompressing and spin-drying reaction liquid, and performing column chromatography on residues to obtain an intermediate 1-9-1. (yield: 63%)
Calcd for C36H25 BrOSi: 581.57 + -1. 1H-NMR (400MHz, CDCl3) (ppm) delta 7.21-7.22 (1H, m), 7.36-7.55 (19H, m), 7.83-7.89 (5H, m).
Synthesis of intermediates 1-9-2: 0.0567mol of intermediate 1-9-1 is dissolved in 330ml of 1, 4-dioxane solvent, nitrogen is introduced for stirring, 0.0567mol of boronic acid pinacol ester, 0.142mol of potassium carbonate and 0.00057mol of ferrocene palladium dichloride are sequentially added, the temperature is raised to reflux reaction, after 4 hours, HPLC detection shows that the raw materials basically react, the reaction liquid is decompressed and dried in a rotary manner, and the residue is subjected to column chromatography to obtain the intermediate 1-9-2 (yield: 76%).
Calcd for C42H37BO3 Si: 628.64 + -1. 1H-NMR (400MHz, CDCl3) (ppm) delta is 1.24-1.24 (12H, s), 7.32-7.55 (20H, m), 7.81-7.89 (5H, m).
Synthesis of Compounds 1-9: the synthesis method was the same as that of intermediate 1-9-1, to obtain compound 1-9 (yield 69%).
Calcd for C51H35N3 OSi: 733.93 + -1. 1H-NMR (400MHz, CDCl3) (ppm) delta 7.37-7.55 (25H, m), 7.81-7.89 (6H, m), 8.28-8.30 (4H, m).
Preparation example 2: synthesis of Compounds 1-26
Synthesis of intermediate 1-26-1: dissolving 0.1mol of 2, 8-dibromo dibenzothiophene in 340ml of 1, 4-dioxane solvent, introducing nitrogen, stirring, sequentially adding 0.09mol of 4- (triphenylsilane) phenylboronic acid, 0.25mol of potassium carbonate and 0.0001mol of tetrakis (triphenylphosphine) palladium, heating to reflux reaction, detecting basic reaction of raw materials by HPLC after 6 hours, decompressing and spin-drying reaction liquid, and performing column chromatography on residues to obtain an intermediate 1-26-1. (yield: 54%)
Calcd for C36H25 BrSSi: 597.64 + -1. 1H-NMR (400MHz, CDCl3) (ppm) delta 7.37-7.55 (18H, m), 7.86-7.92 (5H, m), 8.00-8.01 (2H, m).
Synthesis of intermediates 1-26-2: 0.0486mol of intermediate 1-26-1 is dissolved in 290ml of 1, 4-dioxane solvent, nitrogen is introduced for stirring, 0.0486mol of boronic acid pinacol ester, 0.1215mol of potassium carbonate and 0.00049mol of ferrocene palladium dichloride are sequentially added, the temperature is raised to reflux reaction, after 4 hours, HPLC detection shows that the raw materials basically react, reaction liquid is decompressed and dried in a rotary manner, and the residue is subjected to column chromatography to obtain the intermediate 1-26-2 (yield: 76%).
Calcd for C42H37BO2 SSi: 644.70 + -1. 1H-NMR (400MHz, CDCl3) (ppm) delta is 1.24-1.24 (12H, s), 7.37-7.39 (6H, m), 7.46-7.55 (12H, m), 7.89-8.00 (7H, m).
Synthesis of Compounds 1-26: the synthesis method was the same as that of intermediate 1-9-1, to obtain compound 1-9 (yield 59%).
Calcd for C51H35N3 SSi: 749.99 + -1. 1H-NMR (400MHz, CDCl3) (ppm) delta is 7.37-7.55 (23H, m), 7.86-7.89 (5H, m), 8.00-8.01 (3H, m), 8.28-8.30 (4H, m).
Preparation example 3: synthesis of Compound 2-2
Synthesis of intermediate 2-2-1: dissolving 0.2000mol of 1-bromo-4-chloro-2-fluorobenzene in 500ml of mixed solvent of 1, 4-dioxane and 40ml of water, introducing nitrogen, stirring, sequentially adding 0.2400mol of 4-bromo-2-methoxyphenyl boric acid, 0.4000mol of potassium carbonate and 0.0020mol of tetrakis (triphenylphosphine) palladium, heating to reflux reaction, detecting basic reaction of raw materials by HPLC after 5h, performing reduced pressure spin drying on reaction liquid, and performing column chromatography on residues to obtain an intermediate 2-2-1(0.108 mol).
Calcd for C19H9 BrCl: 315.57 + -1. 1H-NMR (400MHz, CDCl3) (ppm) delta is 3.83-3.83 (3H, s), 7.22-7.25 (1H, m), 7.30-7.32 (2H, m), 7.57-7.59 (1H, m), 7.71-7.73 (1H, m), 7.90-7.92 (1H, m).
Synthesis of intermediate 2-2-2: dissolving the intermediate 2-2-1(0.108mol) in 500ml of dichloromethane solvent, cooling to about minus 5 ℃ under stirring, dropwise adding 0.162mol of boron tribromide, keeping the system temperature not more than 5 ℃, keeping the temperature and stirring for 1h after dropwise adding, raising the temperature to 25 ℃ for reaction for 10h, detecting the completion of the reaction of raw materials, pouring the reaction liquid into 2L of ice water, adding 2mol/L of sodium hydroxide aqueous solution to adjust the pH value to about 9-10, taking an organic phase for spin drying, and carrying out column chromatography on the residue to obtain the intermediate 2-2-2, thus obtaining the intermediate 2-2-2 (yield 70%).
Calcd for C12H7 BrClFO: 301.54 + -1. 1H-NMR (400MHz, CDCl3) (ppm) delta is 5.35-5.35 (1H, s), 7.22-7.32 (3H, m), 7.51-7.53 (1H, d), 7.71-7.73 (1H, m), 7.90-7.92 (1H, m).
Synthesis of intermediate 2-2-3: dissolving 0.140mol of intermediate 2-2-3 in 500ml of N-methylpyrrolidone solvent, adding 0.280mol of potassium carbonate, heating to 180 ℃ for reaction, detecting that the reaction of the raw materials is finished within about 6 hours, cooling the reaction liquid to 25 ℃, pouring the reaction liquid into 2L of ice water, standing for 2 hours, filtering, and performing column chromatography on the obtained solid to obtain the intermediate 2-2-3 (the yield is 62%).
Calcd for C12H6 BrClO: 281.53 + -1. 1H-NMR (400MHz, CDCl3) (ppm) delta is 7.14-7.16 (1H, m), 7.30-7.32 (1H, m), 7.43-7.43 (1H, s), 7.78-7.83 (2H, m), 8.26-8.28 (1H, m).
Synthesis of Compounds 2-2-4: preparing a Grignard reagent, adding 0.01mol of 3-bromo-7-chlorodibenzofuran and magnesium (0.12mol) into 30ml of tetrahydrofuran, heating until a reflux reaction is initiated, slowly dropping the residual 0.09mol of 3-bromo-7-chlorodibenzofuran tetrahydrofuran saturated solution, preserving heat and refluxing for about 1h, and keeping under nitrogen protection for later use. Adding 0.1mol of 2-chloro-4, 6-diphenyl-1, 3, 5-triazine and tetrahydrofuran into another three-necked flask, uniformly stirring, protecting with nitrogen, cooling to-5 ℃, transferring the prepared Grignard reagent into a dropping funnel, slowly dropping, keeping the temperature of the system not more than 10 ℃, stirring for 30min after dropping, slowly increasing to 25 ℃, detecting that the reaction of the raw materials is finished after 5h, dropping saturated ammonium chloride aqueous solution into the reaction solution, stirring for 5min, adding dichloromethane for extraction, taking organic phase, performing pressure spin drying on the organic phase, and performing column chromatography on the residue to obtain an intermediate 2-2-4 (yield is 52%).
Calcd for C27H16ClN 3O: 433.89 + -1. 1H-NMR (400MHz, CDCl3) (ppm) delta is 7.14-7.16 (1H, m), 7.41-7.51 (7H, m), 7.64-7.64 (1H, s), 7.75-7.78 (1H, m), 7.95-7.97 (1H, m), 8.28-8.30 (4H, m).
Synthesis of Compound 2: the synthesis method was the same as that of intermediate 2-2-4 to obtain compound 2 (yield 76%).
Calcd for C51H33N3 OSi: 731.91 + -1. 1H-NMR (400MHz, CDCl3) (ppm) delta 7.35-7.64 (22H, s), 7.75-7.77 (2H, m), 7.82-7.84 (1H, d), 7.89-7.95 (4H, m), 8.28-8.30 (4H, m).
Preparation example 4: synthesis of Compounds 2-7
Synthesis of intermediate 2-7-1: the synthesis method is the same as the synthesis of the intermediate 2-2-4, and the intermediate 2-7-1 is obtained (yield 76%).
Calcd for C27H16BrN 3O: 478.34 + -1. 1H-NMR (400MHz, CDCl3) (ppm) delta is 7.36-7.55 (8H, s), 7.71-7.72 (2H, m), 7.81-7.82 (1H, m), 8.17-8.20 (1H, s), 8.28-8.30 (4H, m).
Synthesis of Compounds 2-7: the synthesis method is the same as the synthesis of the intermediate 2-2-4, and the compound 2-7 is obtained (yield 70%).
Calcd for C51H33N3 OSi: 731.91 + -1. 1H-NMR (400MHz, CDCl3) (ppm) delta 7.37-7.61 (20H, s), 7.71-7.72 (4H, m), 7.75-7.81 (5H, m), 8.28-8.30 (4H, m).
Preparation example 5: compounds 3 to 9
Synthesis of intermediate 3-9-1: the synthesis method is the same as the synthesis of the intermediate 2-2-4, and the intermediate 3-9-1 is obtained from 0.1mol of 2-chloro-4, 6-diphenyl-1, 3, 5-triazine (yield 50%).
Calcd for C27H16BrN 3S: 494.41 + -1. 1H-NMR (400MHz, CDCl3) (ppm) delta 7.41-7.51 (7H, m), 7.80-7.92 (4H, m), 8.00-8.01 (1H, d), 8.28-8029 (4H, m)
Synthesis of intermediate 3-9-2: dissolving 0.05mol of intermediate 3-9-1 in 250ml of 1, 4-dioxane solvent, introducing nitrogen, stirring, sequentially adding 0.05mol of pinacol diboron, 0.125mol of potassium carbonate and 0.0005mol of ferrocene palladium dichloride, heating to reflux reaction, after 4 hours, detecting basic reaction of raw materials by HPLC, decompressing and spin-drying reaction liquid, and performing column chromatography on residues to obtain intermediate 3-9-2 (yield: 81%).
Calcd for C27H18BN3O 2S: 459.33 + -1. 1H-NMR (400MHz, CDCl3) (ppm) delta is 2.0-2.0 (2H, s), 7.41-7.51 (7H, s), 7.80-7.86 (2H, m), 7.94-8.00 (3H, m), 8.28-8.29 (4H, m).
Synthesis of Compounds 3-9: dissolving 0.04mol of intermediate 3-9-2 in 180ml of 1, 4-dioxane solvent, stirring under nitrogen, sequentially adding 0.04mol of 3-bromo-5, 5-dimethyl-5H-dibenzothiapyrrole, 0.12mol of potassium carbonate and 0.46g (0.0004mol) of tetrakis (triphenylphosphine) palladium, heating to reflux reaction, detecting basic reaction of raw materials by HPLC after 4H, carrying out reduced pressure spin drying on reaction liquid, and carrying out column chromatography on residues to obtain the compound 3-9 (yield: 58%).
Calcd for C41H29N3 SSi: 623.84 + -1. 1H-NMR (400MHz, CDCl3) (ppm) delta is 0.66-0.66 (6H, s), 7.33-7.61 (10H, m), 7.80-8.00 (9H, m), 8.28-8.28 (4H, m).
Example 1: preparation of organic light emitting device
After ultrasonically washing a glass substrate having an Indium Tin Oxide (ITO) electrode (first electrode, anode) with a thickness of about 1500 angstroms with distilled water and methanol in sequence, the washed glass substrate was dried, moved to a plasma cleaning system, and then cleaned using an oxygen plasma for about 5 minutes. The glass substrate is then loaded into a vacuum deposition apparatus.
Vacuum depositing 2-HNATA onto the ITO electrode of the glass substrate to form a HIL having a thickness of about 500 angstroms; vacuum deposition of NPB onto the hole injection layer formed an HTL having a thickness of about 200 angstroms.
1,2-ADN and BD1 (dopants) were mixed at 98: a weight ratio of 2 was co-deposited on the hole transport region to form an EML having a thickness of about 300 angstroms.
Subsequently, compound 1-1 was vacuum deposited on the EML to form an ETL having a thickness of about 250 angstroms. Then, LiF was deposited on the ETL to form an EIL having a thickness of about 5 angstroms, and Al was deposited on the EIL to a thickness of about 1000 angstroms to form a second electrode (cathode), thereby completing the fabrication of the organic light emitting device.
Other embodiments
Organic light-emitting devices of the remaining examples were prepared in a similar manner to example 1, except that the compounds shown in table 1 were used instead of compound 1-1 in example 1.
Comparative example 1
An organic light-emitting device was produced in a similar manner to that in example 1, except that compound D1 was used instead of compound 1-1 in example 1.
The structural formula of compound D1 in comparative example 1 is:
Comparative example 2
An organic light-emitting device was produced in a similar manner to that in example 1, except that ET-1 was used instead of compound 1-1 in example 1.
TABLE 1
As can be seen from the data in table 1, the organic electroluminescent device formed from the novel compound of the present invention has a low driving voltage and significantly higher lifetime, current efficiency and brightness than the prior art.
The preferred embodiments of the present invention have been described above in detail, but the present invention is not limited thereto. Within the scope of the technical idea of the invention, many simple modifications can be made to the technical solution of the invention, including combinations of various technical features in any other suitable way, and these simple modifications and combinations should also be regarded as the disclosure of the invention, and all fall within the scope of the invention.
Claims (13)
1. A triazine compound containing a silicon atom, which has a structure represented by formula (I) or formula (II),
wherein, in the formula (I) and the formula (II),
L1and L2Each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, or L1And L2Each independently is absent;
R1and R2Each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted dibenzofuranyl;
a is a structure shown as A1, A2 or A3;
x is O or S;
wherein the substituents are each independently selected from C1-20Alkyl of (C)1-20Alkoxy group of (a);
and in the formulae (I) and (II), L2The connecting positions with dibenzofuranyl or dibenzothienyl are 1,2 and 3 positions.
2. Triazine compound according to claim 1, wherein, in formula (I) and formula (II),
L1and L2Each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, or L1And L2Each independently is absent;
R1and R2Each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, dibenzothienyl and dibenzofuranyl;
a is a structure shown as A1, A2 or A3;
x is O or S;
wherein the substituents are each independently selected from C1-12Alkyl of (C)1-12Alkoxy group of (a);
and in the formulae (I) and (II), L2The connecting positions with dibenzofuranyl or dibenzothienyl are 1,2 and 3 positions.
3. Triazine compound according to claim 2, wherein, in formula (I) and formula (II),
L1and L2Each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, or L1And L2Each independently is absent;
R1and R2Each independently selected from phenyl, biphenyl, terphenyl, fluorenyl, dibenzothienyl and dibenzofuranyl;
a is a structure shown as A1, A2 or A3;
x is O or S;
wherein the substituents are each independently selected from C1-6Alkyl of (C)1-6Alkoxy group of (a);
and in the formulae (I) and (II), L2The connecting positions with dibenzofuranyl or dibenzothienyl are 1,2 and 3 positions.
4. Triazine compound according to claim 2, wherein, in formula (I) and formula (II),
L1and L2Each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, or L1And L2Each independently is absent;
R1and R2Are all phenyl;
a is a structure shown as A1, A2 or A3;
x is O or S;
wherein the substituents are each independently selected from C1-3Alkyl of (C)1-3Alkoxy group of (a);
and in the formulae (I) and (II), L2To dibenzofuranyl or dibenzothienylSetting the positions as 1,2 and 3.
5. The compound according to any one of claims 2-4, wherein the triazine compound is at least one of the following specific compounds:
6. the compound according to any one of claims 2-4, wherein the triazine compound is at least one of the following specific compounds:
7. use of a triazine compound containing a silicon atom according to any of claims 1 to 6 in an organic electroluminescent device.
8. An organic electroluminescent device comprising one or more compounds of the triazine compounds containing a silicon atom described in any one of claims 1 to 6.
9. The organic electroluminescent device according to claim 8, wherein the triazine compound containing a silicon atom is present in at least one of an electron transport layer, a light emitting layer, and a hole blocking layer of the organic electroluminescent device.
10. The organic electroluminescent device according to claim 9, wherein the triazine compound containing a silicon atom is present in an electron transport layer of the organic electroluminescent device.
11. The organic electroluminescent device according to any one of claims 8 to 10, wherein the organic electroluminescent device comprises a substrate, an anode, a hole injection layer, a hole transport layer, an optional electron blocking layer, a light emitting layer, an optional hole blocking layer, an electron transport layer, an electron injection layer, and a cathode, which are sequentially stacked.
12. The organic electroluminescent device according to any one of claims 8 to 10, wherein the organic electroluminescent device further comprises a first cover layer and/or a second cover layer, the first cover layer is disposed on an outer surface of the anode, and the second cover layer is disposed on an outer surface of the cathode.
13. The organic electroluminescent device according to claim 12, wherein the first cover layer and the second cover layer each independently contain one or more compounds of the silicon atom-containing triazine compounds according to any one of claims 1 to 6.
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| KR102234372B1 (en) * | 2019-11-05 | 2021-04-01 | 엘티소재주식회사 | Heterocyclic compound and organic light emitting device comprising same |
| CN114560858B (en) * | 2020-10-30 | 2023-04-07 | 武汉天马微电子有限公司 | Compound, electron transport material, display panel, and display device |
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