CN113444097A - 三并咔唑衍生物、有机光电器件及显示或照明装置 - Google Patents
三并咔唑衍生物、有机光电器件及显示或照明装置 Download PDFInfo
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- MIJXYTWQSWKMJX-UHFFFAOYSA-N 9-[3-(1,8-naphthyridin-4-yl)phenyl]-2,7-bis(2-nitrophenyl)carbazole Chemical compound [O-][N+](C(C=CC=C1)=C1C(C=C1)=CC(N(C2=C3)C4=CC(C5=CC=NC6=NC=CC=C56)=CC=C4)=C1C2=CC=C3C(C=CC=C1)=C1[N+]([O-])=O)=O MIJXYTWQSWKMJX-UHFFFAOYSA-N 0.000 description 1
- JDYPFPOAOFRIHH-UHFFFAOYSA-N 9-naphthalen-2-yl-2,7-bis(2-nitrophenyl)carbazole Chemical compound [O-][N+](C(C=CC=C1)=C1C(C=C1)=CC(N(C2=C3)C4=CC5=CC=CC=C5C=C4)=C1C2=CC=C3C(C=CC=C1)=C1[N+]([O-])=O)=O JDYPFPOAOFRIHH-UHFFFAOYSA-N 0.000 description 1
- 238000007125 Buchwald synthesis reaction Methods 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 229910000976 Electrical steel Inorganic materials 0.000 description 1
- 229910052693 Europium Inorganic materials 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000004111 Potassium silicate Substances 0.000 description 1
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical class N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 238000006069 Suzuki reaction reaction Methods 0.000 description 1
- 229910052771 Terbium Inorganic materials 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- VWLUNVLTTXQKGM-UHFFFAOYSA-N [N+](=O)([O-])C1=C(C=C(C=C1)C1=CC=CC=C1)B(O)O Chemical group [N+](=O)([O-])C1=C(C=C(C=C1)C1=CC=CC=C1)B(O)O VWLUNVLTTXQKGM-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001339 alkali metal compounds Chemical class 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 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
- 150000001412 amines Chemical class 0.000 description 1
- HAQFCILFQVZOJC-UHFFFAOYSA-N anthracene-9,10-dione;methane Chemical compound C.C.C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 HAQFCILFQVZOJC-UHFFFAOYSA-N 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000008425 anthrones Chemical class 0.000 description 1
- 229940054051 antipsychotic indole derivative Drugs 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000001556 benzimidazoles Chemical class 0.000 description 1
- BMWYMEQOMFGKSN-UHFFFAOYSA-N benzo[g]cinnoline Chemical class N1=NC=CC2=CC3=CC=CC=C3C=C21 BMWYMEQOMFGKSN-UHFFFAOYSA-N 0.000 description 1
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 1
- 150000001649 bromium compounds Chemical group 0.000 description 1
- QARVLSVVCXYDNA-IDEBNGHGSA-N bromobenzene Chemical group Br[13C]1=[13CH][13CH]=[13CH][13CH]=[13CH]1 QARVLSVVCXYDNA-IDEBNGHGSA-N 0.000 description 1
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- WUKWITHWXAAZEY-UHFFFAOYSA-L calcium difluoride Chemical compound [F-].[F-].[Ca+2] WUKWITHWXAAZEY-UHFFFAOYSA-L 0.000 description 1
- 229910001634 calcium fluoride Inorganic materials 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 239000010406 cathode material Substances 0.000 description 1
- RWWUBXBYBPQIJI-UHFFFAOYSA-N cesium;quinolin-8-ol Chemical compound [Cs].C1=CN=C2C(O)=CC=CC2=C1 RWWUBXBYBPQIJI-UHFFFAOYSA-N 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000006880 cross-coupling reaction Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 1
- 125000003983 fluorenyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004404 heteroalkyl group Chemical group 0.000 description 1
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 1
- 238000004770 highest occupied molecular orbital Methods 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 150000002475 indoles Chemical class 0.000 description 1
- 238000007733 ion plating Methods 0.000 description 1
- 150000002503 iridium Chemical class 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- FUJCRWPEOMXPAD-UHFFFAOYSA-N lithium oxide Chemical compound [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 1
- 229910001947 lithium oxide Inorganic materials 0.000 description 1
- MORCTKJOZRLKHC-UHFFFAOYSA-N lithium;oxoboron Chemical compound [Li].O=[B] MORCTKJOZRLKHC-UHFFFAOYSA-N 0.000 description 1
- SKEDXQSRJSUMRP-UHFFFAOYSA-N lithium;quinolin-8-ol Chemical compound [Li].C1=CN=C2C(O)=CC=CC2=C1 SKEDXQSRJSUMRP-UHFFFAOYSA-N 0.000 description 1
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 1
- ORUIBWPALBXDOA-UHFFFAOYSA-L magnesium fluoride Chemical compound [F-].[F-].[Mg+2] ORUIBWPALBXDOA-UHFFFAOYSA-L 0.000 description 1
- 229910001635 magnesium fluoride Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 150000002907 osmium Chemical class 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 150000003057 platinum Chemical class 0.000 description 1
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920005596 polymer binder Polymers 0.000 description 1
- 239000002491 polymer binding agent Substances 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- NNHHDJVEYQHLHG-UHFFFAOYSA-N potassium silicate Chemical compound [K+].[K+].[O-][Si]([O-])=O NNHHDJVEYQHLHG-UHFFFAOYSA-N 0.000 description 1
- 229910052913 potassium silicate Inorganic materials 0.000 description 1
- 235000019353 potassium silicate Nutrition 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000002250 progressing effect Effects 0.000 description 1
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- 125000004159 quinolin-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C([H])C(*)=NC2=C1[H] 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- GZCRRIHWUXGPOV-UHFFFAOYSA-N terbium atom Chemical compound [Tb] GZCRRIHWUXGPOV-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 238000004506 ultrasonic cleaning Methods 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
- C07D487/14—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/22—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains four or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
-
- 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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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
- H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
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- H10K50/17—Carrier injection layers
- H10K50/171—Electron injection layers
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- 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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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
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- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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Abstract
本发明公开了一种三并咔唑衍生物、有机光电器件及显示或照明装置,其中该三并咔唑衍生物其具有下列式(1)所示的结构:
Description
技术领域
本发明涉及一种三并咔唑衍生物,尤其涉及一种三并咔唑衍生物、有机光电器件及显示或照明装置,属于有机电致发光领域。
背景技术
有机光电器件(例如有机电激发光二极管,简称为OLED)具有薄型且能在低驱动电压下高亮度发光以及能通过选择发光材料而进行多色发光的特点,因此倍受关注。自从由柯达公司的C.W.Tang等揭示有机薄膜元件能以高亮度发光以来,大量OLED 行业研究人员对于其应用,做了很多研究和推进。有机光电器件被广泛应用在各种主显示屏等中,其实用化取得长足的进展。尽管有机电致发光的研究进展非常迅速,但仍有很多亟待解决的问题,例如外量子效率(EQE)仍然需要提高,如何设计与合成出色纯度更高、高效电子传输、空穴阻挡新材料等等。对于有机电致发光器件来说,器件的发光量子效率是各种因素的综合反映,也是衡量器件品质的一重要指标。
电致发光一般可以分为荧光发光和磷光发光。在荧光发光中,单线态激发状态的有机分子跃迁至基态,由此发出光。另一方面,在磷光发光中,三线态激发状态的有机分子跃迁至基态,由此发出光。目前来看,部分有机电致发光材料性能优秀,具有一定的应用价值,但作为有机电致发光器件中的主体材料,除了三线态能级要高于客体材料,防止激子跃迁释放的能量逆传递以外,更重要的是具有良好的空穴迁移性能。然而,目前主体材料中同时具有高三线态能级和良好空穴迁移率的材料仍然缺乏。因此,如何设计具有更好性能的主体材料,一直是本领域技术人员亟待解决的问题。
发明内容
为了克服现有技术中存在的缺陷,本发明的目的是提供一种三并咔唑衍生物及包含该三并咔唑衍生物的有机光电器件,该有机光电器件具有较高的发光效率,同时其寿命也有所提升。
为了实现本发明的目的,本发明的技术方案如下:
本发明提供了一种三并咔唑衍生物,其具有下列式(1)所示的结构:
其中X1-X8各自独立地选自CR或N原子,其中,R选自氢、氘、卤素、氰基、取代或未取代的烷基、环烷基、杂烷基、杂环烷基、芳基或杂芳基。
X1-X8彼此相同或不同,其中,当X1-X8均不为N原子时,R1、R2和R3不全相同或全部不相同。
L1、L2和L3为单键或取代或未取代的芳基。
R1、R2和R3各自独立地选自取代或未取代的C6~C30芳基、取代或未取代的C4~C30杂芳基、或者与邻近的原子键合成环。
R4-R5各自独立地选自氢、取代或未取代的 C1-C15烷基、取代或未取代的C6~C30芳基或取代或未取代的C4~C30杂芳基。
其中,R1、R2和R3中至少一者选自如下取代或未取代的基团:
其中,R6-R10各自独立地选自氢、取代或未取代的 C1-C15烷基、取代或未取代的C6~C30芳基或取代或未取代的C4~C30杂芳基。
并且当R1为上述S-44,且R2和R3不为上述S-44时,L1为单键。
当R2为上述S-44,且R1和R3不为上述S-44时,L2为单键。
当R3为上述S-44,且R1和R2不为上述S-44时,L3为单键。
更优选地,该三并咔唑衍生物为以下结构中任一者:
本发明提供了一种有机光电器件,其包括:第一电极;
第二电极,其与该第一电极相面对;有机层,其夹设于该第一电极和该第二电极之间;其中,该有机层包含本发明的三并咔唑衍生物。
本发明提供了一种有机光电器件,其包括阴极层、阳极层和有机层,其中,该有机层为空穴注入层、空穴传输层、发光层、电子注入层或电子传输层中至少一层;
其中,该有机层包含本发明的三并咔唑衍生物。
优选地,该有机层为发光层,该发光层中还包含掺杂剂,其中该三并咔唑衍生物与该掺杂剂(客体材料)的质量比为1:99~99:1,且该掺杂剂没有任何限制。
优选地,该有机层为电子传输层。
优选地,有机光电器件为有机光伏器件、有机发光器件(OLED)、有机太阳电池(OSC)、电子纸(e-paper)、有机感光体(OPC)、有机薄膜晶体管(OTFT)或有机内存器件(Organic Memory Element)。
本发明还提供了一种显示或照明装置,其包括本发明的有机光电器件。
主体材料同时具有空穴传输性质和电子传输性质,对器件的性能有增益的效果。咔唑基团具有一定的三线态能级,并且有良好的空穴传输能力。本发明的三并咔唑衍生物具有双极性及较平衡的空穴和电子传输性质,因此,其能较好地作为主体材料应用在有机光电元件中。
本发明提供了一种新颖的三并咔唑衍生物,其具有高的三线态能级,并具备有良好的空穴传输能力。在咔唑的N原子上引入缺电子基团,能提高分子的电子传输能力。另外,在氮原子上引入芳香基团也利于分子的合成,较易得到理想的化合物。且咔唑环具有良好的平面性,当多个咔唑环形成并环后,分子的平面性得到进一步的加强,这样更加利于分子间的堆积,有利于减少不必要的振动能量损失,从而实现高效的发光性能。另外,本发明的并三咔唑衍生物制备方法简单,原料易得,能够满足工业化需求。
具体实施方式
本发明的包含咔唑衍生物的有机光电器件包括基板、第一电极、有机物层、第二电极和覆盖层。优选地,该有机光电器件器件包括基板、位于该基板上的第一电极、位于该第一电极上的有机物层、位于该有机物层上的第二电极以及位于该第二电极外侧的覆盖层,其中,该第二电极外侧是指背离该第一电极的一侧。
本发明的有机层为发光层(活性层)、空穴注入层、空穴传输层、电子传输层和电子注入层中至少一层。且该有机层可由单层结构形成,也可由层叠(包括发光层、空穴注入层、空穴传输层、电子传输层和电子注入层的多层)结构形成。其中,该空穴传输层还可包括第一空穴传输层和第二空穴传输层。在本发明的有机光电器件(例如有机电激发光二极管)中,除了该发光层包含本发明的三并咔唑衍生物外,其它层均可以使用本领域公知的用于所述层的任何材料。
在本发明的发光元件中,基板材料可选用典型的有机发光元件中使用的任何基板,例如钠玻璃、无碱玻璃或透明柔性基板、不透明材料如硅或不锈钢的基板或柔性聚酰亚胺薄膜,不同基板材料具有不同的性能,且应用方向不同。本发明的空穴传输层可通过将空穴传输材料中的一种或二种以上层叠或混合的方法,或通过使用空穴传输材料和高分子粘合剂的混合物的方法来形成。空穴传输材料需要在施加了电场的电极之间高效率地传输来自正极的空穴,因此希望空穴注入效率高以及能够高效率地传输注入的空穴。因此,空穴传输材料应当具有适当的电离势及适当的能级并且具有大的空穴迁移率,进一步地,材料稳定性优异且制造及使用过程中不易产生会成为陷阱的杂质。对满足这样条件的物质,没有特别限定,例如可以是咔唑衍生物、三芳胺衍生物、联苯二胺衍生物、芴衍生物、酞菁类化合物、六腈六氮杂苯并菲类化合物、喹吖啶酮类化合物、苝衍生物、蒽醌类化合物、F4-TCNQ、聚苯胺、聚噻吩、聚乙烯咔唑等,但不限于此。
本发明的发光层材料,除了包含本发明的三并咔唑衍生物,还可包含掺杂材料(也称为客体材料)(可包含多个掺杂材料)。另外,发光层可为单一的发光层,也可为横向或纵向叠加在一起的复合发光层。对于掺杂材料的种类选择,可以为荧光材料,也可以为磷光材料;对于掺杂材料的用量选择,优选0.1~70质量%,更优选为0.1~30质量%、进一步优选为1~30质量%、更进一步优选为1~20质量%、特别优选为1~10质量%。本发明的荧光掺杂材料包括:稠合多环芳族衍生物、苯乙烯基胺衍生物、稠环胺衍生物、含硼化合物、吡咯衍生物、吲哚衍生物、咔唑衍生物等,但不限于此;本发明的磷光掺杂材料包括:重金属配合物、磷光发光性的稀土类金属配合物等,但不限于此,其中重金属配合物,例如,可以是铱配合物、铂配合物、锇配合物等;稀土类金属配合物,例如,可以是铽络合物、铕络合物等,但不限于此。本发明的电子传输材料优选具有良好的电子迁移率,同时具有合适的HOMO和LUMO能级,本发明的电子传输材料,例如,可以是金属配合物、氧杂噻唑衍生物、噁唑衍生物、二氮唑衍生物、氮杂苯衍生物、菲罗啉衍生物、二氮蒽衍生物、含硅杂环类化合物、含硼杂环类化合物、氰基类化合物、喹啉衍生物、苯并咪唑衍生物等,但不限于此。本发明的电子注入材料优选具有传输电子能力,同时具有从阴极注入电子的效应,以及具有优异的薄膜形成能力,本发明的电子注入材料,例如,可以是碱金属化合物(例如氧化锂、氟化锂、8-羟基喹啉锂、氧化锂硼、碳酸铯、8-羟基喹啉铯、硅酸钾、氟化钙、氧化钙、氟化镁、氧化镁)、芴酮、含氮五元环衍生物(例如,噁唑衍生物、恶二唑衍生物、咪唑衍生物、金属配合物);蒽醌二甲烷、联苯醌、蒽酮衍生物等,但不限于此,这些化合物可以单独使用,也可与其他材料混合使用。本发明的阴极材料优选具有低功函数,以便容易地将电子注入有机层,本发明的阴极材料例如,可以是金属(例如镁、钙、钠、钾、钛、铟、钇、锂、铝、银、锡、铅或它们的合金)或多层材料(例如LiF/Al或LiO 2 /Al)但不限于此。
本发明的有机层材料,当它们在使用时,可单独成膜形成单层结构,也可和其他材料一起混合成膜形成单层结构,或形成单独成膜的单层的层叠结构、混合成膜的单层的叠层结构、单独成膜的单层和混合成膜的单层的叠层结构,但不限于此。本发明的有机光电器件(例如有机电激发光二极管)可通过依次层叠上述结构而制造。制造方法可使用干式成膜法、湿式成膜法等公知方法,其中干式成膜法,例如,可以是真空蒸镀法、溅射法、等离子体法、离子电镀法等;湿式成膜法例如,可以是旋涂法、浸渍法、流延法、喷墨法等各种涂布法,但不限于此。本发明的有机光电器件(例如有机电激发光二极管)可广泛地应用于面板显示、照明光源、柔性OLED、电子纸、有机太阳能电池、有机感光体或有机薄膜晶体管、指示牌、信号灯等领域。
本发明的有机发光元件为有机光伏器件、有机发光器件(OLED)、有机太阳电池(OSC)、电子纸(e-paper)、有机感光体(OPC)、有机薄膜晶体管(OTFT)及有机内存器件(Organic Memory Element)、照明和显示装置。本发明通式(1)所示的三并咔唑衍生物的合成可以使用本领域公知的方法进行,例如,使用镍、钯等过渡金属的交叉偶合反应,或使用镁或锌等过渡金属的C-C、C-N偶联生成反应。上述反应,限于反应条件温和、各种官能团的选择性优越等特点,优选Suzuki,Buchwald反应。
实施例
本发明的三并咔唑衍生物用以下实施例举例说明,但并不限于这些实施例举例的三并咔唑衍生物和合成方法。
本发明实施例和对比例中采用的初始原料和溶剂购于国药,部分常用的OLED中间体类等产品购于国内的OLED中间体厂商以及各种钯催化剂和配体等购于sigma-Aldrich公司。
1HNMR数据使用JEOL(400MHz)核磁共振仪来测定;HPLC数据使用岛津LC-20AD高效液相仪来测定。
实施例和比较例中使用物质为:
(化合物1)14-苯基-5,8-双(3-苯基喹啉-2-基)-8,14-二氢-5H-吡咯[3,2-b:4,5-b']二咔唑。
(化合物5)5,8-二苯基-14-(3-苯基喹啉-2-基)-8,14-二氢-5H-吡咯[3,2-b:4,5-b']二咔唑。
(化合物11)14-苯基-5,8-二(吡啶-4-基)-8,14-二氢-5H-吡咯[3,2-b:4,5-b']二咔唑。
(化合物19)14-(萘-2-基)-5,8-双(1-苯基-1H-1,2,4-***-3-基)-8,14-二氢-5H-吡咯[3,2-b:4,5-b']二咔唑。
(化合物24)2,11-二叔丁基-5,8,14-三(吡啶-4-基)-8,14-二氢-5H-吡咯[3,2-b:4,5-b']二咔唑。
(化合物29)2,2',2'-(2,11-二叔丁基-5H-吡咯[3,2-b:4,5-b']二咔唑-5,8,14-三酰基)三(苯并[d]恶唑)。
(化合物38)5,8,14-三(吡啶-4-基)-8,14-二氢-5H-吡啶[2',3':4,5]吡咯[3,2-b]吡咯[2',3':4,5]吡咯[2,3-h]咔唑。
(化合物43)2,2',2'-(5H-吡啶基)[2',3':4,5]吡咯基[3,2-b]吡啶基[2',3':4,5]吡咯基[2,3-h]咔唑-5,8,14-三(苯并[d]恶唑)。
(化合物46)14-(异喹啉-3-基)-5,8-二(喹啉-2-基)-8,14-二氢-5H-吡啶[3',4':4,5]吡咯[3,2-b]吡咯[3',4':4,5]吡咯[2,3-h]咔唑。
(化合物54)5,8,14-三(喹啉-5-基)-8,14-二氢-5H-吡啶[3,4]:4,5]吡咯[3,2-b]吡咯[3,4]:4,5]吡咯[2,3-h]咔唑。
(化合物68)5,8,14-三(吡啶-4-基)-8,14-二氢-5H-吡咯[3,2-b:4,5-b']二咔唑-2,11-二甲腈。
(化合物88)5,8,14-三(吡嗪-2-基)-8,14-二氢-5h-吡啶[3,4]:4,5]吡咯[3,2-b]吡啶[3,4]:4,5]吡咯[2,3-h]咔唑。
(化合物93)5,8,14-三(4-(吡啶-4-基)苯基)-8,14-二氢-5H-吡啶[2',3':4,5]吡咯[3,2-b]吡咯[2',3':4,5]吡咯[2,3-h]咔唑。
(化合物145)14-(1,10-菲咯啉-2-基)-5,8-二苯基-8,14-二氢-5H-吡咯[3,2-b:4,5-b']二咔唑。
(化合物148)14-(1,10-菲咯啉-2-基)-2,5,8,11-四苯基-8,14-二氢-5H-吡咯[3,2-b:4,5-b']二咔唑。
(化合物184)14-(3-(1,8-萘啶-4-基)苯基)-5,8-二(萘-2-基)-8,14-二氢-5H-吡咯[3,2-b:4,5-b']二咔唑。
合成路线如下:
实施例1
化合物1的合成
(1)在氩气气氛下,反应容器中加入2,7-二溴-9-苯基-9H-咔唑40.1克(100mmol), (2-硝基苯基)硼酸36.7g(220mmol), [1,3-双(2,6-二-异丙基苯基)-4,5-二氢咪唑-2-亚基]氯[3-苯基烯丙基]钯(II)催化剂648毫克, 1.5M碳酸钠水液200ml(300mmol)和乙二醇二甲醚1000ml(DME),80℃加热搅拌过夜。冷却至室温,加入800ml水,固体析出,过滤,粗品通过硅胶柱层析法精制(洗脱液:乙酸乙酯/己烷),得到39.3g化合物2,7-双(2-硝基苯基)-9-苯基-9H-咔唑,收率81%,HPLC纯度99.6%。
1HNMR(DMSO):δ8.62(d,1H),8.31 (d,1H), 8.22(d,2H),8.03~8.00(m,4H) 7.91~7.89(m,3H),7.74~7.72(m,4H),7.62(m,2H), 7.58(m,1H),7.50(m,1H)
(2)在氩气气氛下,反应容器中加入2,7-双(2-硝基苯基)-9-苯基-9H-咔唑48.6克(100mmol), 用100ml氯苯溶解, 加入7.9克三苯基膦,180℃加热搅拌过夜。冷却至室温,过滤,滤液减压除去溶剂,得到的粗品通过硅胶柱层析法精制(洗脱液:乙酸乙酯/己烷),得到32.9g化合物14-苯基-8,14-二氢-5H-吡咯[3,2-b:4,5-b']二咔唑,收率78%,HPLC纯度98.6%。
1HNMR(DMSO):δ11.66(s,2H),8.19(d,2H),7.63~7.62(m,4H),7.55(s,2H), 7.50(m,4H),7.40(s,2H),7.20(m,2H)。
(3)在氩气气氛下,反应容器中加入叔丁醇钾26.9克(240mmol), [1,3-双(2,6-二-异丙基苯基)-4,5-二氢咪唑-2-亚基]氯[3-苯基烯丙基]钯(II)催化剂648毫克(1mmol%),2-溴-3-苯基喹啉62.7g(220mmol),14-苯基-8,14-二氢-5H-吡咯[3,2-b:4,5-b']二咔唑42.2克(100mmol)和1000mL乙二醇二甲醚(DME),在80℃加热搅拌15小时。反应混合物冷却到室温,加入500ml水,过滤,粗品通过硅胶柱层析法精制(洗脱液:乙酸乙酯/己烷),得到68.1克化合物1,HPLC纯度99.6%,收率82%.
1HNMR(DMSO):δ8.55 (d,2H),8.40(d,4H),7.94(d,2H),7.80(d,4H), 7.67(m,4H),7.62(m,2H),7.59~7.57(m,7H),7.50(m,2H), 7.47(s,4H), 7.35(m,2H),7.16(m,2H)。
实施例2
化合物5的合成
除了起始原料更换为2,7-二溴-9-(3-苯基喹啉-2-基)-9H咔唑以外,其他与实施例1相同
1HNMR(DMSO):δ8.62(d,2H),8.40(m,3H), 8.22(m,2H),8.03~8.00(m,4H) 7.89(m,2H),7.80(m,2H),7.74(s,2H),7.72(m,2H),7.62(m,2H), 7.59~7.57(m,2H)
除了起始原料更换为3-硝基-7-(2-硝基苯基)-2-苯基-9-(3-苯基喹啉-2-基)-9H咔唑以外,其他与实施例1相同。
1HNMR(DMSO):δ11.66(s,2H),8.40(d2H),8.19(d,2H),7.80(d,2H),7.67(m,2H),7.63(d,2H),7.59~7.57(m,3H), 7.55(s,2H),7.50(m,2H),7.40(s,2H),7.20(m,2H).
除了起始原料更换为14-(3-苯基喹啉-2-基)-8,14-二氢-5H-吡咯[3,2-b:4,5-b']二咔唑以外,其他与实施例1相同。
1HNMR(DMSO):δ8.55 (d,2H),8.40(d,4H),7.94(d,2H),7.80(d,2H), 7.62(m,4H),7.59~7.57(m,5H),7.50(m,4H), 7.47(s,4H), 7.35(m,2H),7.16(m,2H)。
实施例3
化合物11的合成
与实施例1相同。
除了溴代物更换为对溴吡啶以外,其他与实施例1相同。
1HNMR(DMSO):δ8.56 (d,4H),8.55(d,2H),7.94(d,2H),7.62(m,2H), 7.58(m,1H),7.50(d,6H),7.47(s,4H),7.35(d,2H),7.16(d,2H)。
实施例4
化合物19的合成
除了起始原料更换为2,7-二溴-9-(萘-2-基)-9H咔唑以外,其他与实施例1相同。
1HNMR (DMSO):δ8.62(d,1H),8.31 (d,1H), 8.22(d,2H),8.03~8.00(m,6H)7.91~7.89(m,3H),7.74~7.72(m,4H),7.62(m,1H),7.58(m,2H),7.50(m,1H)
除了起始原料更换为9-(萘-2-基)-2,7-双(2-硝基苯基)-9H咔唑以外,其他与实施例1相同。
1HNMR (DMSO):δ11.66(s,2H),8.19(d,2H),8.03(d,3H),7.83(s,1H),7.63
(d,2H),7.59~7.58(m,2H),7.55(s,2H),7.50(m,2H),7.40(s,2H),7.36(m,1H),7.20(m,2H).
除了起始原料更换为3-溴-1-苯基-1H-1,2,4-***和14-(萘-2-基)-8,14-二氢-5H-吡咯[3,2-b:4,5-b']二咔唑以外,其他与实施例1相同。
1HNMR (DMSO):δ9.24(s,2H),8.55 (d,2H),8.03(d,3H),7.94(m,2H),7.83(s,1H),7.67
(d,4H),7.59~7.58(m,2H),7.57(m,4H),7.52(m,2H),7.47(s,4H),7.35(d,2H),7.16(d,2H)。
实施例5
化合物24的合成
除了起始原料更换为2,7-二溴-9-(吡啶-4-基)-9H咔唑和(5-(叔丁基)-2-硝基苯基)硼酸以外,其他与实施例1相同。
1HNMR(DMSO):δ8.62(d,2H),8.56 (d,2H), 8.28(d,2H),8.22(d,2H),8.19
(s,2H),7.74(s,2H),7.67(m,2H),7.50(m,2H),1.43(s,18H).
除了起始原料更换为2,7-二(5-(叔丁基)-2-硝基苯基)-9-(吡啶-4-基)-9H咔唑以外,其他与实施例1相同。
1HNMR (DMSO):δ11.66(s,2H),8.56(d,2H),8.36(s,2H),7.62(d,2H),7.55(s,2H),
7.50(m,4H),7.40(s,2H),1.43(s,18H).
除了起始原料更换为对溴吡啶和2,11-二叔丁基-14-(吡啶-4-基)-8,14-二氢-5H-吡咯[3,2-b:4,5-b']二咔唑以外,其他与实施例1相同。
1HNMR (DMSO):δ8.95(s,2H),8.56(d,6H),7.86(d,2H),7.50(m,6H),7.47(s,6H),
7.11(d,2H),1.43(s.18H).
实施例6
化合物29的合成
除了起始原料更换为2-(2,7-二溴-9H-咔唑-9-基)苯并[d]恶唑和(5-(叔丁基)-2-硝基苯基)硼酸以外,其他与实施例1相同。
1HNMR (DMSO):δ8.62(d,2H),8.28(d,2H),8.22(d,2H),8.19(s,2H),7.74(s,2H),7.72
(m,2H),7.67(m,2H),7.39(m,2H),1.43(s,18H).
除了起始原料更换为2-(2,7-二(5-(叔丁基)-2-硝基苯基)-9H-咔唑-9-基)苯并[d]恶唑以外,其他与实施例1相同。
1HNMR (DMSO):δ11.66(s,2H),8.36(s,2H),7.72(m,2H),7.62(m,2H),7.55(s,2H),
7.50(d,2H),7.40(s,2H),7.39(m,2H),1.43(s,18H).
除了起始原料更换为2-溴苯并[d]恶唑,2-(2,11-二叔丁基-5,8-二氢-14H-吡咯[3,2-b:4,5-b']二咔唑-14-基)苯并[d]恶唑以外,其他与实施例1相同。
1HNMR (DMSO):δ8.95(s,2H),8.36(d,6H),7.86(d,2H),7.72(m,6H), 7.47(s,6H),7.39
(m,6H),7.11(d,2H),1.43(s.18H).
实施例7
化合物38的合成
除了起始原料更换为2,7-二溴-9-(吡啶-4-基)-9H咔唑和(3-硝基吡啶-2-基)硼酸以外,其他与实施例1相同。
1HNMR (DMSO):δ8.76(d,2H),8.62 (m,4H), 8.56(d,2H),8.30 (d,2H), 8.13(s,2H),
7.50(d,2H),7.27(m,2H)
除了起始原料更换为2,7-二(3-硝基吡啶-2-基)-9-(吡啶-4-基)-9H咔唑以外,其他与实施例1相同。
1HNMR(DMSO):δ11.66(s,2H),9.34(s,2H),8.56(m,2H),8.43(m,2H),7.55(s,2H),7.50
(d,2H),7.46(d,2H),7.40(s,2H).
除了起始原料更换为对溴吡啶和14-(吡啶-4-基)-8,14-二氢-5H-吡啶[3',4':4':4,5]吡咯[3,2-b]吡啶[3',4':4,5]吡咯[2,3-h]咔唑以外,其他与实施例1相同。
1HNMR (DMSO):δ8.56 (d,6H),8.43(m,3H),7.97(d,2H),7.55(s,2H),7.50(m,6H),
7.40(s,2H),7.22(m,2H)
实施例8
化合物43的合成
除了起始原料更换为2-(2,7-二溴-9H-咔唑-9-基)苯并[d]恶唑(3-硝基吡啶-2-基)硼酸以外,其他与实施例1相同。
1HNMR (DMSO):δ8.76(d,2H),8.62(m,2H),8.30(m,4H),8.13(s,2H),7.72(m,2H),7.39
(m,2H),7.27(m,2H).
除了起始原料更换为2-(2,7-双(3-硝基吡啶-2-基)-9H-咔唑-9-基)苯并[d]恶唑以外,其他与实施例1相同。
1HNMR (DMSO):δ11.66(s,2H),9.34(s,2H),8.43(m,2H),7.72(m,2H),7.55(s,2H),7.46
(m,2H),7.40(s,2H),7.39(m,2H).
除了起始原料更换为2-溴苯并[d]恶唑,2-(5,8-二氢-14H-吡啶[3',4':4,5]吡咯[3,2-b]吡啶[3',4':4,5]吡咯[2,3-h]咔唑-14-基)苯并[d]恶唑以外,其他与实施例1相同。
1HNMR (DMSO):δ8.43(m,2H),7.97(d,2H),7.72(m,6H),7.55(s,2H), 7.40(s,2H),7.39
(m,6H),7.22(m,2H).
实施例9
化合物46的合成
除了起始原料更换为2,7-二溴-9-(异喹啉-3-基)-9H咔唑45.2克(100mmol), (4-硝基吡啶-3-基)硼酸以外,其他与实施例1相同。
1HNMR (DMSO):δ9.50(s,2H),9.46(s,1H),8.62(d,2H),8.29(d,2H),8.22(m,2H),8.05
(d,2H),7.98(d,1H),7.74(s,2H),7.68(m,1H),7.64(m,1H),7.62(s,1H).
除了起始原料更换为9-(异喹啉-3-基)-2,7-双(4-硝基吡啶-3-基)-9H咔唑以外,其他与实施例1相同。
1HNMR (DMSO):δ11.66(s,2H),9.46(s,1H),9.34(s,2H),8.43(m,2H),7.98(d,
1H),7.68(m,1H),7.64(d,1H),7.62(s,1H),7.57(m,1H),7.55(s,2H),7.46(d,2H),7.40(s,2H).
除了起始原料更换为2-溴喹啉和14-(异喹啉-3-基)-8,14-二氢-5H-吡啶[3',4':4,5]吡咯[3,2-b]吡咯[3',4':4,5]吡咯[2,3-h]咔唑以外,其他与实施例1相同。
1HNMR(DMSO):δ9.46(s,1H),9.34(s,2H),8.43(d,2H),8.35(d,2H),8.03(d,2H),8.00(d,2H),
7.98(d,1H),7.96(d,2H),7.83(m,2H),7.68(m,1H),7.64(d,1H),7.62(s,1H),7.57(m,1H),7.53(m,2H),7.51(d,2H),7.47(s,4H).
实施例10
化合物54的合成
除了起始原料更换为2,7-二溴-9-(喹啉-5-基)-9H咔唑和(4-硝基吡啶-3-基)硼酸以外,其他与实施例1相同。
1HNMR (DMSO):δ9.50(s,2H),8.95(d,1H),8.62(d,2H),8.46(d,1H),8.29(d,2H),8.22
(m,2H),8.12(d,1H),8.05(d,2H),8.00(m,1H),7.92(d,1H),7.74(s,2H),7.63(m,1H).
除了起始原料更换为2,7-双(4-硝基吡啶-3-基)-9-(喹啉-5-基)-9H咔唑以外,其他与实施例1相同。
1HNMR (DMSO):δ11.66(s,2H),9.34(s,2H),8.95(d,1H),8.46(d,1H),8.43(d,2H),8.12
(d,1H),8.00(m,1H),7.92(d,1H),7.63(m,1H),7.55(s,2H),7.46(d,2H),7.40(s,2H).
除了起始原料更换为5-溴喹啉和14-(喹啉-5-基)-8,14-二氢-5H-吡啶[3',4':4,5]吡咯[3,2-b]吡咯[3',4':4,5]吡咯[2,3-h]咔唑以外,其他与实施例1相同。
1HNMR(DMSO):δ9.34(s,2H),8.95(d,3H),8.46(d,3H),8.35(d,2H),8.12(d,2H),8.00
(m,3H),7.92(d,3H),7.63(m,3H),7.51(d,2H),7.47(s,4H)。
实施例11
化合物68的合成
除了起始原料更换为2,7-二溴-9-(吡啶-4-基)-9H咔唑和(5-氰基-2-硝基苯基)硼酸以外,其他与实施例1相同。
1HNMR (DMSO):δ8.62(s,2H),8.56 (d,2H), 8.54(d,2H),8.22(d,2H), 8.11(s,2H),7.96
(d,2H),7.74(s,2H),7.50(d,2H).
除了起始原料更换为3,3'-(9-(吡啶-4-基)-9H-咔唑-2,7-二酰基)双(4-硝基苯甲腈)以外,其他与实施例1相同。
1HNMR (DMSO):δ11.66(s,2H),8.56(m,2H),7.80(s,2H),7.76(d,2H), 7.50(d,2H),7.55
(s,2H),7.50(d,2H),7.40(s,2H),7.33(d,2H).
除了起始原料更换为4-溴吡啶34.8g(220mmol),14-(吡啶-4-基)-8,14-二氢-5H-吡咯[3,2-b:4,5-b']二咔唑-2,11-二甲腈以外,其他与实施例1相同。
1HNMR (DMSO):δ8.56 (d,6H),8.12(d,2H),7.80(s,2H),7.50(d,6H),7.47(s,4H),7.33(d,2H).
实施例12
化合物88的合成
除了起始原料更换为2,7-二溴-9-(吡嗪-2-基)-9H咔唑40.3克(100mmol), (4-硝基吡啶-3-基)硼酸以外,其他与实施例1相同。
1HNMR (DMSO):δ9.50(s,2H),8.83 (m,1H), 8.82(s,1H),8.76(d,1H), 8.62(d,2H),8.29
(d,2H),8.22(d,2H),8.05(d,2H),7.74(s,2H).
除了起始原料更换为2,7-双(4-硝基吡啶-3-基)-9-(吡嗪-2-基)-9H咔唑以外,其他与实施例1相同。
1HNMR (DMSO):δ11.66(s,2H),9.34(s,2H), 8.83 (m,1H), 8.82(s,1H),8.76(d,
1H), 8.43(d,2H),7.55(s,2H),7.46(d,2H),7.40(s,2H).
除了起始原料更换为2-溴吡嗪35.0g(220mmol),14-(吡啶-4-基)-8,14-二氢-5H-吡咯[3,2-b:4,5-b']二咔唑以外,其他与实施例1相同。
1HNMR (DMSO):δ9.34 (s,2H), 8.83 (m,3H), 8.82(s,3H),8.76(d,3H), 8.35(d,2H),
7.51(d,2H),7.47(s,4H).
实施例13
化合物93的合成
除了起始原料更换为2,7-二溴-9-(4-(吡啶-4-基)苯基)-9H咔唑47.8克(100mmol), (3-硝基吡啶-2-基)硼酸以外,其他与实施例1相同。
1HNMR (DMSO):δ8.76(d,2H),8.71 (d,2H), 8.62(s,4H),8.30(d,2H), 8.13(s,2H),8.00
(d,2H),7.92(d,2H),7.91(d,2H),7.27(d,2H).
除了起始原料更换为2,7-双(3-硝基吡啶-2-基)-9-(4-(吡啶-4-基)苯基)-9H咔唑以外,其他与实施例1相同。
1HNMR(DMSO):δ11.66(s,2H),9.34(s,2H), 8.71 (d,2H), 8.43(d,2H), 8.00(d,2H),7.92(d,2H),7.91(d,2H),7.55(s,2H),7.46(d,2H),7.40(s,2H).
除了起始原料更换为4-(4-溴苯基)吡啶51.5g(220mmol),14-(4-(吡啶-4-基)苯基)-8,14-二氢-5H-吡啶[3',4':4,5]吡咯[3,2-b]吡咯[3',4':4,5]吡咯[2,3-h]咔唑以外,其他与实施例1相同。
1HNMR(DMSO):δ8.71 (d,6H), 8.43 (d,2H),8.00(d,6H),7.97(d,2H),7.92(d,6H),7.91(d,6H),7.55(s,2H),7.46(d,2H),7.40(s,2H),7.22(d,2H)。
实施例14
化合物145的合成
除了起始原料更换为2-(2,7-二溴-9H-咔唑-9-基)-1,10-菲罗啉以外,其他与实施例1相同。
1HNMR (DMSO):δ8.80 (d,1H), 8.62 (d,2H), 8.45(d,2H),8.22(d,1H),8.14(d,1H),8.03
(d,3H),8.00(d,2H),7.89(d,2H), 7.46(d,2H),7.56(m,1H),7.47(s,4H).
除了起始原料更换为2-(2,7-双(2-硝基苯基)-9H-咔唑-9-基)-1,10-菲罗啉以外,其他与实施例1相同。
1HNMR (DMSO):δ11.66 (s,2H), 8.80 (d,1H), 8.45(d,2H),8.22(d,1H),8.19(d,
2H),8.14(d,1H),7.89(d,2H),7.63(d,2H),7.55(m,3H),7.50(m,2H),7.40(s,4H),7.20(m,2H).
除了起始原料更换为溴苯和14-(1,10-菲咯啉-2-基)-8,14-二氢-5H-吡咯[3,2-b:4,5-b']二咔唑以外,其他与实施例1相同。
1HNMR (DMSO):δ8.80 (d,1H), 8.55(d,2H),8.45(d,2H),8.03(d,1H),7.94(d,2H),7.89
(d,1H),7.62(m,4H),7.58(m,2H),7.56(m,1H),7.50(m,4H),7.47(s,4H),7.35(m,2H),7.16(m,2H).
实施例15
化合物148的合成
除了起始原料更换为2-(2,7-二溴-9H-咔唑-9-基)-1,10-菲罗啉和(4-硝基-[1,1'-联苯]-3-基)硼酸以外,其他与实施例1相同。
1HNMR (DMSO):δ8.80(d,1H),8.45(d,2H),8.32(d,2H),8.14(d,1H),8.03(d,1H),7.99(d,2H),
7.89(s,2H),7.77(d,2H),7.75(d,4H),7.56(m,1H),7.55(s,2H),7.49(m,4H),7.41(m,2H),7.40(s,2H),
7.34(d,2H).
除了起始原料更换为2-(2,7-双(4-硝基-[1,1'-联苯]-3-基)-9H-咔唑-9-基)-1,10-菲罗啉以外,其他与实施例1相同。
1HNMR (DMSO):δ11.66(s,2H),8.80(d,1H),8.45(d,2H),8.14(d,1H),8.03(d,1H),7.99(d,2H),
7.89(s,2H),7.77(d,2H),7.75(d,4H),7.56(m,1H),7.55(s,2H),7.49(m,4H),7.41(m,2H),7.40(s,2H).
除了起始原料更换为14-(1,10-菲咯啉-2-基)-2,11-二苯基-8,14-二氢-5H-吡咯[3,2-b:4,5-b']二咔唑和2-溴苯以外,其他与实施例1相同。
1HNMR (DMSO):δ8.80(d,1H),8.45 (d,2H), 8.30(d,2H),8.14(d,3H),8.03(d,1H),7.89(d,3H),
7.75(d,4H),7.62(m,4H),7.58(m,2H),7.56(m,1H),7.50(d,4H),7.49(m,4H),7.47(s,4H),7.41(m,2H)。
实施例16
化合物184的合成
除了起始原料更换为9-(3-(1,8-萘啶-4-基)苯基)-2,7-二溴-9H-咔唑以外,其他与实施例1相同。
1HNMR (DMSO):δ8.89(d,1H),8.70(d,1H),8.62(d,2H),8.39(d,1H),8.22(m,2H),8.03(d,2H),
8.00(d,2H),7.89(m,2H),7.79(d,1H),7.74(s,2H),7.72(m,2H),7.68(m,1H),7.60(d,1H),7.47(d,1H),
7.41(m,2H).
除了起始原料更换为9-(3-(1,8-萘啶-4-基)苯基)-2,7-双(2-硝基苯基)-9H咔唑以外,其他与实施例1相同。
1HNMR (DMSO):δ11.66(s,2H),8.89(d,1H),8.70 (d,1H), 8.39(d,1H),8.21(s,1H),8.19
(d,2H),7.79(d,1H),7.68(m,1H),7.63(d,2H),7.60(d,1H),7.55(s,2H),7.50(m,2H),7.47(d,1H),
7.41(m,1H),7.40(s,2H),7.20(m,2H).
除了起始原料更换为14-(3-(1,8-萘啶-4-基)苯基)-8,14-二氢-5H-吡咯[3,2-b:4,5-b']二咔唑和2-溴萘以外,其他与实施例1相同。
1HNMR(DMSO):δ8.89(d,1H),8.70 (d,1H), 8.39(d,1H),8.21(s,1H),8.19(d,2H),8.03(m,6H),7.83(s,2H),7.79(d,2H),7.68(m,1H),7.59(m,2H),7.58(m,4H),7.50(m,2H),7.47(m,5H),7.41(m,1H),7.36(d,2H),7.20(m,2H).
器件实施方案
发光材料器件的评价
器件实施例和对比例中所用的各有机层化合物如下所示:
实施例17
本发明有机光电器件的基本结构模型为:
ITO/HAT-CN (10 nm)/TAPC (40 nm)/TCTA(10 nm)/EML(本发明的化合物):RD(Ir配合物)=94:6 (40nm)/ETL(30nm)/LiF(1nm)/Al(80nm)。
本发明有机光电器件的制造方法:
(1)依次用丙酮、乙醇和蒸馏水对透明阳极氧化铟锡(ITO)20(10Ω/sq)玻璃基板进行超声清洗,再用臭氧等离子处理15分钟。
(2)在真空气相蒸镀设备的衬底固定器上安装ITO衬底后,控制体系压力在10-6托,接着向ITO衬底上依次蒸镀厚度为10nm的HAT-CN,40nm的TAPC和10nm的TCTA。
(3)在上述TCTA上蒸镀厚度为40nm的发光层(EML),其中本发明化合物1与RD的质量比为94:6。
(4)在上述发光层上蒸镀厚度为30nm的电子传输层(ETL)材料。
(5)在上述电子传输层上蒸镀厚度为1nm的LiF作为电子注入层。
(6)最后在上述电子注入层上蒸镀厚度为80nm的Al作为阴极,且利用玻璃封装盖对器件进行封装。
器件测试结果见表1。
实施例18
本实施例中器件的制造与实施例17相同,除了发光层(EML)主体材料为化合物5。器件测试结果见表1。
实施例19
本实施例中器件的制造与实施例17相同,除了发光层(EML)主体材料为化合物11。器件测试结果见表1。
实施例20
本实施例中器件的制造与实施例17相同,除了发光层(EML)主体材料为化合物19。器件测试结果见表1。
实施例21
本实施例中器件的制造与实施例17相同,除了发光层(EML)主体材料为化合物24。器件测试结果见表1。
实施例22
本实施例中器件的制造与实施例17相同,除了发光层(EML)主体材料为化合物29。器件测试结果见表1。
实施例23
本实施例中器件的制造与实施例17相同,除了发光层(EML)主体材料为化合物38。器件测试结果见表1。
实施例24
本实施例中器件的制造与实施例17相同,除了发光层(EML)主体材料为化合物43。器件测试结果见表1。
实施例25
本实施例中器件的制造与实施例17相同,除了发光层(EML)主体材料为化合物46。器件测试结果见表1。
实施例26
本实施例中器件的制造与实施例17相同,除了发光层(EML)主体材料为化合物54。器件测试结果见表1。
实施例27
本实施例中器件的制造与实施例17相同,除了发光层(EML)主体材料为化合物68。器件测试结果见表1。
实施例28
本实施例中器件的制造与实施例17相同,除了发光层(EML)主体材料为化合物88。器件测试结果见表1。
实施例29
本实施例中器件的制造与实施例17相同,除了发光层(EML)主体材料为化合物93。器件测试结果见表1。
实施例30
本实施例中器件的制造与实施例17相同,除了发光层(EML)主体材料为化合物145。器件测试结果见表1。
实施例31
本实施例中器件的制造与实施例17相同,除了发光层(EML)主体材料为化合物148。器件测试结果见表1。
实施例32
本实施例中器件的制造与实施例17相同,除了发光层(EML)主体材料为化合物184。器件测试结果见表1。
对比例1
本实施例中器件的制造与实施例17相同,除了发光层(EML)主体材料为化合物RH-01。器件测试结果见表1。
对比例2
本实施例中器件的制造与实施例17相同,除了发光层(EML)主体材料为化合物RH-02。器件测试结果见表1。
表1显示了实施例17-32及对比例1-2中器件的性能测试结果
表1
上述实施例和对比例中的器件结构除了发光层不同外,其它均一致,基于RH-01和RH-02的器件性能为参考,包含本发明的三并咔唑衍生物的器件的电流效率有了显著提升,同时其寿命也有所提升。综上所述,本发明的新颖的咔唑衍生物在有机光电器件上具有有较大的应用价值。
以上描述了本发明的基本原理、主要特征和本发明的优点。本行业的技术人员应该了解,本发明不受上述实施例的限制,上述实施例和说明书中描述的只是说明本发明的原理,在不脱离本发明精神和范围的前提下本发明还会有各种变化和改进,这些变化和改进都落入要求保护的本发明范围内。本发明要求保护范围由所附的权利要求书及其等同物界定。
Claims (6)
1.三并咔唑衍生物,其具有下列式(1)所示的结构:
X1-X8各自独立地选自CR或N原子,其中R选自氢、氘、卤素、氰基、取代或未取代的烷基、环烷基、杂烷基杂环烷基或芳基或杂芳基;
X1-X8彼此相同或不同,其中当X1-X8均不为N原子时,R1、R2和R3不全相同或全部不相同;
L1、L2和L3各自独立地为单键或取代或未取代的芳基;
R1、R2和R3各自独立地选自取代或未取代的C6~C30芳基、取代或未取代的C4~C30杂芳基或与邻近的原子键合成环;
R4和R5各自独立地选自氢、取代或未取代的 C1-C15烷基、取代或未取代的C6~C30芳基或取代或未取代的C4~C30杂芳基;
其中,R1、R2和R3中至少一者选自如下取代或未取代的基团,
其中,R6-R10各自独立地选自氢、取代或未取代的 C1-C15烷基、取代或未取代的C6~C30芳基或取代或未取代的C4~C30杂芳基;
并且当R1为上述S-44,且R2和R3不为上述S-44时,L1为单键;
当R2为上述S-44,且R1和R3不为上述S-44时,L2为单键;
当R3为上述S-44,且R1和R2不为上述S-44时,L3为单键。
3.有机光电器件,其包括阴极层、阳极层和有机层,
其中,所述有机层为空穴注入层、空穴传输层、发光层、电子注入层或电子传输层中至少一层,其中,所述有机层包含权利要求1或2所述的三并咔唑衍生物。
4.根据权利要求3所述的有机光电器件,其中所述有机层为发光层,所述发光层中还包含掺杂剂,其中所述三并咔唑衍生物与所述掺杂剂的质量比为1:99~99:1。
5.根据权利要求3所述的有机光电器件,其中所述有机光电器件为有机光伏器件、有机发光器件、有机太阳电池、电子纸、有机感光体、有机薄膜晶体管或有机内存器件。
6.显示或照明装置,其包括权利要求3所述的有机光电器件。
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