CN113861172B - 基于苯并五元杂环的双极性荧光材料及其制备方法与有机电致发光器件 - Google Patents
基于苯并五元杂环的双极性荧光材料及其制备方法与有机电致发光器件 Download PDFInfo
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- CN113861172B CN113861172B CN202111117948.1A CN202111117948A CN113861172B CN 113861172 B CN113861172 B CN 113861172B CN 202111117948 A CN202111117948 A CN 202111117948A CN 113861172 B CN113861172 B CN 113861172B
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- 239000000463 material Substances 0.000 title claims abstract description 71
- 125000000623 heterocyclic group Chemical group 0.000 title claims abstract description 15
- 125000005605 benzo group Chemical group 0.000 title claims abstract description 13
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- ASGMFNBUXDJWJJ-JLCFBVMHSA-N (1R,3R)-3-[[3-bromo-1-[4-(5-methyl-1,3,4-thiadiazol-2-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]-N,1-dimethylcyclopentane-1-carboxamide Chemical compound BrC1=NN(C2=NC(=NC=C21)N[C@H]1C[C@@](CC1)(C(=O)NC)C)C1=CC=C(C=C1)C=1SC(=NN=1)C ASGMFNBUXDJWJJ-JLCFBVMHSA-N 0.000 claims description 7
- YJLIKUSWRSEPSM-WGQQHEPDSA-N (2r,3r,4s,5r)-2-[6-amino-8-[(4-phenylphenyl)methylamino]purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1CNC1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O YJLIKUSWRSEPSM-WGQQHEPDSA-N 0.000 claims description 7
- 229940127007 Compound 39 Drugs 0.000 claims description 7
- 238000002347 injection Methods 0.000 abstract description 10
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- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 abstract description 4
- 125000000217 alkyl group Chemical group 0.000 abstract description 4
- 229910052805 deuterium Inorganic materials 0.000 abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 4
- 150000002431 hydrogen Chemical class 0.000 abstract description 4
- 239000001257 hydrogen Substances 0.000 abstract description 4
- 238000000034 method Methods 0.000 abstract description 4
- 230000002776 aggregation Effects 0.000 abstract description 3
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- 239000011669 selenium Substances 0.000 abstract description 3
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 abstract description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract description 2
- 125000004103 aminoalkyl group Chemical group 0.000 abstract description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 2
- 230000009286 beneficial effect Effects 0.000 abstract description 2
- 229910052760 oxygen Inorganic materials 0.000 abstract description 2
- 239000001301 oxygen Substances 0.000 abstract description 2
- 229910052711 selenium Inorganic materials 0.000 abstract description 2
- 229910052717 sulfur Inorganic materials 0.000 abstract description 2
- 239000011593 sulfur Substances 0.000 abstract description 2
- 229910052714 tellurium Inorganic materials 0.000 abstract description 2
- PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical compound [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 abstract description 2
- 230000003044 adaptive effect Effects 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 42
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- 230000015572 biosynthetic process Effects 0.000 description 15
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- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 14
- 229940125904 compound 1 Drugs 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 8
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 7
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
- 239000008346 aqueous phase Substances 0.000 description 7
- 239000012043 crude product Substances 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
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- 239000007858 starting material Substances 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 150000001491 aromatic compounds Chemical class 0.000 description 4
- 230000005525 hole transport Effects 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 238000010898 silica gel chromatography Methods 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
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- 238000001308 synthesis method Methods 0.000 description 3
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical group CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- -1 bromoselenophenol Chemical compound 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
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- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical group [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 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 2
- 238000011056 performance test Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- USFPINLPPFWTJW-UHFFFAOYSA-N tetraphenylphosphonium Chemical group C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 USFPINLPPFWTJW-UHFFFAOYSA-N 0.000 description 2
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 2
- MXHYQOWIOCQRCN-UHFFFAOYSA-N 2,3,4,5,6-pentakis(3,6-ditert-butylcarbazol-9-yl)benzonitrile Chemical compound CC(C)(C)C1=CC2=C(C=C1)N(C1=C2C=C(C=C1)C(C)(C)C)C1=C(C#N)C(N2C3=C(C=C(C=C3)C(C)(C)C)C3=C2C=CC(=C3)C(C)(C)C)=C(N2C3=C(C=C(C=C3)C(C)(C)C)C3=C2C=CC(=C3)C(C)(C)C)C(N2C3=C(C=C(C=C3)C(C)(C)C)C3=C2C=CC(=C3)C(C)(C)C)=C1N1C2=C(C=C(C=C2)C(C)(C)C)C2=C1C=CC(=C2)C(C)(C)C MXHYQOWIOCQRCN-UHFFFAOYSA-N 0.000 description 1
- UMPSXRYVXUPCOS-UHFFFAOYSA-N 2,3-dichlorophenol Chemical compound OC1=CC=CC(Cl)=C1Cl UMPSXRYVXUPCOS-UHFFFAOYSA-N 0.000 description 1
- LILXDMFJXYAKMK-UHFFFAOYSA-N 2-bromo-1,1-diethoxyethane Chemical compound CCOC(CBr)OCC LILXDMFJXYAKMK-UHFFFAOYSA-N 0.000 description 1
- YUQUNWNSQDULTI-UHFFFAOYSA-N 2-bromobenzenethiol Chemical compound SC1=CC=CC=C1Br YUQUNWNSQDULTI-UHFFFAOYSA-N 0.000 description 1
- VADKRMSMGWJZCF-UHFFFAOYSA-N 2-bromophenol Chemical compound OC1=CC=CC=C1Br VADKRMSMGWJZCF-UHFFFAOYSA-N 0.000 description 1
- 241000235648 Pichia Species 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical group [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000011162 core material Substances 0.000 description 1
- NXQGGXCHGDYOHB-UHFFFAOYSA-L cyclopenta-1,4-dien-1-yl(diphenyl)phosphane;dichloropalladium;iron(2+) Chemical group [Fe+2].Cl[Pd]Cl.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 NXQGGXCHGDYOHB-UHFFFAOYSA-L 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- YNHIGQDRGKUECZ-UHFFFAOYSA-N dichloropalladium;triphenylphosphanium Chemical compound Cl[Pd]Cl.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-N 0.000 description 1
- 238000000295 emission spectrum Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical group [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 230000005622 photoelectricity Effects 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
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- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
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- C07D421/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having selenium, tellurium, or halogen atoms as ring hetero atoms
- C07D421/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having selenium, tellurium, or halogen atoms as ring hetero atoms containing three or more hetero rings
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- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
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- C07D517/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having selenium, tellurium, or halogen atoms as ring hetero atoms
- C07D517/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having selenium, tellurium, or halogen atoms as ring hetero atoms in which the condensed system contains two hetero rings
- C07D517/04—Ortho-condensed systems
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- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
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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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- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
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- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
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Abstract
本发明公开基于苯并五元杂环的双极性荧光材料及其制备方法与有机电致发光器件,所述双极性荧光材料具有以下所示结构:或其中,X、Y独立地选自氧、硫、硒、碲或氮烷基;R1‑R4独立地选自氢、氘或烷基链;EG1‑EG4为电性基团,所述EG1‑EG4中至少两个分别选自荧光基团和与所述荧光基团极性平衡的辅助基团,在此之外独立地选自氢、氘或烷基链。本发明通过辅助极性基团的引入可以有效的改善材料本身的单极性特性,平衡电荷注入。另外,在基本不影响发光区域结构的前提下扭曲材料结构,减弱材料堆叠作用,降低荧光体聚集淬灭效应,提高器件稳定性和适配掺杂浓度,有利于大规模生产过程中的调控和良品率提升。
Description
技术领域
本发明涉及有机光电领域,尤其涉及一种基于苯并五元杂环的双极性荧光材料及其制备方法与有机电致发光器件。
背景技术
与传统无机发光二极管相比,有机发光二极管(Organic Light-Emitting Diode,OLED)具有视角宽、响应速度快、色彩还原度高以及柔性显示等诸多优点。有机发光器件在汽车显示、智能手机、电视、照明和穿戴设备等方面有着广泛的应用。
发光材料是学界和产业界重点发展的OLED核心材料。当前发光材料以低效率的普通荧光材料,使用贵金属的磷光材料和寿命较短的TADF材料为主。
当前普遍采用的普通荧光或TADF材料多为含N、O等富电子杂原子的共轭结构,大多数为P型客体材料,空穴传输性能优于电子传输性能,具有单极性特性。其单极性特性导致器件必须使用N型主体材料以平衡电荷注入,这也是发光材料必须使用主客体掺杂的其中一原因。
发明内容
鉴于上述现有技术的不足,本发明的目的在于提供一种基于苯并五元杂环的双极性荧光材料及其制备方法与有机电致发光器件,旨在解决现有发光材料为单极性材料,导致器件发光效率较低的问题。
本发明的技术方案如下:
本发明的第一方面,提供一种基于苯并五元杂环的双极性荧光材料,其中,所述双极性荧光材料具有以下所示结构:
其中,X、Y独立地选自氧(O)、硫(S)、硒(Se)、碲(Te)或氮烷基(NR)等;
R1-R4独立地选自氢、氘或烷基链;
EG1-EG4为电性基团,所述EG1-EG4中至少两个分别选自荧光基团和与所述荧光基团极性平衡的辅助基团,在此之外可以独立地选自氢、氘或烷基链。
其中,所述电性基团是指具有一定的电荷给予-接受能力的基团。所述极性平衡是指,对于荧光基团与辅助基团,二者传递的载流子相反,而速率大致相近。
优选的,所述荧光基团选自如下结构中的一种:
其中,表示连接位点。
具有上述荧光基团的双极性荧光材料,其荧光量子产率更高。优选的,所述辅助基团选自如下结构中的一种:
其中,表示连接位点。
优选的,所述双极性荧光材料选自如下结构中的一种:
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本发明的第二方面,提供一种如上所述的基于苯并五元杂环的双极性荧光材料的制备方法,其制备路线如下所示:
制备方法包括以下步骤:
步骤1、将原料a与原料b溶于第一溶剂中,在第一预定反应条件下反应,得到第一中间产物;
步骤2、将所述第一中间产物与EG1溶于第一溶剂中,在第二预定反应条件下反应,得到第二中间产物;
步骤3、将所述第二中间产物与液溴溶于第二溶剂中,在第三预定反应条件下反应,得到第三中间产物;
步骤4、将所述第三中间产物与EG2溶于第一溶剂中,在第四预定反应条件下反应,得到具有结构式1-42的双极性荧光材料。
优选的,所述第一预定反应条件为:反应温度为100-110℃,反应时间为12小时。
优选的,上述步骤1具体包括:在无水无氧条件下,将原料a(如溴代苯酚、溴代苯硫酚、溴代苯硒酚等)与原料b(即溴代乙醛缩二乙醇)、碳酸钾溶于第一溶剂中,100℃下反应12小时,反应后加入磷酸水溶液继续搅拌2小时,搅拌后混合液经提取,色谱柱分离得到第一中间产物。
优选的,所述第二预定反应条件为:反应温度为100-110℃,反应时间为24小时,且反应在催化剂下进行,所述催化剂可以为三(二亚苄基丙酮)二钯。
优选的,上述步骤2具体包括:在无水无氧条件下,将所述第一中间产物与具有EG1荧光基团的芳香化合物溶于第一溶剂中,在100-110℃下反应24小时,反应后溶液经提取,色谱柱分离得到第二中间产物。
优选的,所述第三预定反应条件为:反应温度为室温(指的是16-25℃),反应时间为12小时。
优选的,上述步骤3具体包括:将所述第二中间产物与液溴溶于第二溶剂中,在室温(指的是16-25℃)下反应12小时,反应后溶液经提取,色谱柱分离得到第三中间产物。
优选的,所述第四预定反应条件为:反应温度为100-110℃,反应时间为24小时,且反应在催化剂下进行,所述催化剂为四三苯基膦钯。
优选的,上述步骤4具体包括:在无水无氧条件下,将所述第三中间产物与具有EG2辅助基团的芳香化合物溶于第一溶剂中,在100-110℃下反应24小时,反应后溶液经提取,色谱柱分离得到具有上述结构式1-42的双极性荧光材料。
本发明的第三方面,提供一种如上所述的基于苯并五元杂环的双极性荧光材料的制备方法,其制备路线如下所示:
制备方法包括以下步骤:
步骤1、制备第四中间产物;
步骤2、将所述第四中间产物与原料c溶于第三溶剂中,在第五预定反应条件下反应,得到第五中间产物;
步骤3、将所述第五中间产物溶于第四溶剂中,在第六预定反应条件下反应,得到第六中间产物;
步骤4、将所述第六中间产物与具有EG2辅助基团的芳香化合物溶于第一溶剂中,在第七预定反应条件下反应,得到具有结构式43-105的双极性荧光材料。
上述步骤1中,第四中间产物的制备路线如下所示:
优选的,所述第五预定反应条件为:反应温度为70-100℃,反应时间为12小时。
优选的,上述步骤2具体包括:将所述第三中间产物与原料c(如二氯苯酚、二氯苯硫酚、二氯苯硒酚等)溶于第三溶剂中,加入碳酸钾,在70-100℃下反应12小时,反应后溶液经提取,色谱柱分离得到第四中间产物。
优选的,所述第六预定反应条件为:反应温度为140-160℃,反应时间为16-24小时,且反应在催化剂下进行,所述催化剂为[1,1'-双(二苯基膦基)二茂铁]二氯化钯。
优选的,上述步骤3具体包括:将所述第四中间产物溶于第四溶剂中,在150℃下反应24小时,反应后溶液经提取,色谱柱分离得到第五中间产物。
优选的,所述第七预定反应条件为:反应温度为100-110℃,反应时间为24小时,且反应在催化剂下进行,所述催化剂为四三苯基膦钯。
优选的,上述步骤4具体包括:将所述第五中间产物与具有EG2辅助基团的芳香化合物溶于第一溶剂中,在100-110℃下反应24小时,反应后溶液经提取,色谱柱分离得到具有结构式43-105的双极性荧光材料。
优选的,第一溶剂为分子筛脱水的甲苯,第二溶剂为二氯甲烷,第三溶剂为N,N-二甲基甲酰胺,第四溶剂为N,N-二甲基乙酰胺。
本发明的第四方面,提供一种有机电致发光器件,包括发光层,其中,所述发光层包括本发明所述的基于苯并五元杂环的双极性荧光材料。
本发明中,所述发光层包括主体材料和客体材料。优选的,所述发光层由主体材料和客体材料共掺杂形成,其中客体材料选用本发明所述的基于苯并五元杂环的双极性荧光材料。优选的,所述主体材料与所述客体材料的质量比为85:15-97:3。
优选的,所述有机电致发光器件从上到下依次包括阴极,电子注入层,电子传输层,发光层,空穴传输层,空穴注入层,阳极。
有益效果:本发明通过辅助极性基团的引入可以有效的改善材料本身的单极性特性,平衡电荷注入。另外,在基本不影响荧光基团发光特性的前提下扭曲材料结构,增大材料分子间距,减弱材料堆叠作用,降低荧光体聚集淬灭效应,提高器件稳定性,改善苛刻的低掺杂浓度要求,有利于大规模生产过程中的调控和良品率提升。其作为有机电致发光器件的发光材料具有对主体材料普适性好,发光效率高,色纯度高和寿命长等优点。
附图说明
图1是实施例4中有机电致发光器件的电流密度-电压曲线。
图2是实施例4中有机电致发光器件的外量子效率-电流密度曲线。
具体实施方式
本发明提供一种基于苯并五元杂环的双极性荧光材料及其制备方法与有机电致发光器件,为使本发明的目的、技术方案及效果更加清楚、明确,以下对本发明进一步详细说明。应当理解,此处所描述的具体实施例仅仅用以解释本发明,并不用于限定本发明。
实施例中未注明具体实验步骤或条件的,按照本领域内的文献所描述的常规实验步骤或条件即可进行。所用试剂或仪器未注明生产厂商的,均为可通过市购获得的常规产品。
实施例中未提及合成方法的化合物均为通过商业途径获得的原料产品。实施例中所用溶剂和试剂均可从国内化工市场购买,例如购买自国药集团试剂公司,安耐吉公司,阿拉丁公司,上海毕得医药公司等。另外,本领域技术人员也可以通过公知方法合成。
实施例1
本实施例提供一种基于苯并五元杂环的双极性荧光材料,该材料为化合物1,化合物1的合成路线如下所示:
化合物1的合成方法具体包括以下步骤:
中间体1的合成:取原料1(1.73g,10mmol)、原料2(2.36g,12mmol)、碳酸钾(4.14g)和甲苯(50mL)放入圆底烧瓶中,100℃下反应12小时,加入50mL磷酸水溶液,继续搅拌2小时,使用三氯甲烷萃取,水相用60mL乙酸乙酯萃取三次,合并有机相,无水硫酸钠干燥,粗产物以硅胶柱层析(石油醚/乙酸乙酯为6/1(体积比))纯化得到中间体1(0.83克,产率42%)。
中间体2的合成:取200mL双颈圆底烧瓶,上接球形冷凝管,干燥后充入氮气,分别加入中间体1(1.97克,10mmol),原料3(2.00克,12mmol),三(二亚苄基丙酮)二钯(183毫克,0.2mmol),三叔丁基膦(45毫克,0.22mmol),叔丁醇钠(2.88克,30mmol),甲苯(60mL)。加热回流24小时,冷却至室温,将溶液倒入水中,使用三氯甲烷萃取,水相用乙酸乙酯萃取三次,合并有机相,无水硫酸钠干燥,粗产物以硅胶柱层析(石油醚/乙酸乙酯为4/1(体积比))纯化得到中间体2(2.41克,产率85%)。
中间体3的合成:取中间体2(2.83g,10mmol)、液溴(0.66mL,12mmol)和二氯甲烷(50mL,简写为DCM)放入圆底烧瓶中,室温下搅拌12小时,反应结束后加入硫代硫酸钠溶液淬灭,使用三氯甲烷萃取,水相用乙酸乙酯萃取三次,合并有机相,无水硫酸钠干燥,粗产物以硅胶柱层析(石油醚/乙酸乙酯为8/1(体积比))纯化得到中间体3(3.51克,产率97%)。
化合物1的合成:取200mL双颈圆底烧瓶,上接球形冷凝管,干燥后充入氮气,分别加入中间体3(3.62克,10mmol),原料4(2.44克,20mmol),四三苯基膦钯(183毫克,0.2mmol),2mol/L的碳酸钾水溶液(10mL),甲苯(100mL)。加热回流24小时,冷却至室温,将溶液倒入水中,使用三氯甲烷萃取,水相用乙酸乙酯萃取三次,合并有机相,无水硫酸钠干燥,粗产物以硅胶柱层析(石油醚/乙酸乙酯为3/1(体积比))纯化得到化合物1(2.74克,产率76%)。
实施例2
本实施例提供一种基于苯并五元杂环的双极性荧光材料,该材料为化合物39,化合物39的合成路线如下所示:
化合物39的合成方法具体包括以下步骤:
中间体1的合成:同化合物1中所述,区别在于使用原料1(2.36克,10mmol),得到中间体1(1.17克,产率45%)。
中间体2的合成:取200mL双颈圆底烧瓶,上接球形冷凝管,干燥后充入氮气,分别加入中间体1(3.62克,10mmol),原料3(5.57克,12mmol),四三苯基膦钯(183毫克,0.2mmol),2mol/L的碳酸钾水溶液(10mL),甲苯(100mL)。加热回流24小时,冷却至室温,将溶液倒入水中,使用三氯甲烷萃取,水相用乙酸乙酯萃取三次,合并有机相,无水硫酸钠干燥,粗产物以硅胶柱层析(石油醚/乙酸乙酯为5/1(体积比))纯化得到中间体2(4.80克,产率80%)。
中间体3的合成:同化合物1中所述。
化合物39的合成:同化合物1中所述,区别在于使用原料4(6.82克,20mmol),得到化合物39(6.44克,产率72%)。
实施例3
本实施例提供一种基于苯并五元杂环的双极性荧光材料,该材料为化合物48,化合物48的合成路线如下所示:
化合物48的合成方法具体包括以下步骤:
中间体1的合成:同化合物1中所述,区别在于使用原料1(1.73克,10mmol),得到中间体1(0.77克,产率39%)。
中间体2的合成:同化合物1中所述,区别在于使用原料3(2.51克,12mmol),得到中间体2(2.86克,产率88%)。
中间体3的合成:同化合物1中所述,产率98%。
中间体4的合成:取中间体3(4.04g,10mmol)、原料4(2.15g,12mmol)、碳酸钾(4.14g)和DMF(50mL)放入圆底烧瓶中,70℃下反应12小时,冷却至室温,将溶液倒入水中,使用三氯甲烷萃取,水相用乙酸乙酯萃取三次,合并有机相,无水硫酸钠干燥,粗产物以硅胶柱层析(石油醚/乙酸乙酯为8/1(体积比))纯化得到中间体4(3.26克,产率65%)。
中间体5的合成:取200mL双颈圆底烧瓶,上接球形冷凝管,干燥后充入氮气,分别加入中间体4(5.02克,10mmol),二(三苯基膦)二氯化钯(140毫克,0.2mmol),乙酸钠(2.46克,30mmol),N,N-二甲基乙酰胺(60mL)。150℃下反应24小时,冷却至室温,将溶液倒入水中,使用三氯甲烷萃取,水相用乙酸乙酯萃取三次,合并有机相,无水硫酸钠干燥,粗产物以硅胶柱层析(石油醚/乙酸乙酯为4/1(体积比))纯化得到中间体5(4.29克,产率92%)。
化合物48的合成:同化合物1的合成,区别在于使用原料5(3.46克,20mmol),得到化合物48(3.91克,产率70%)。
实施例4
本实施例提供一种有机电致发光器件,从上至下依次为层叠设置的金属阴极、电子注入层、电子传输层、发光层、空穴传输层、空穴注入层、阳极以及玻璃基板。
其中,金属阴极选用铝;
电子注入层选用氟化锂;
电子传输层选用具有如下结构的化合物LET003;
发光层由主体材料和客体材料共掺杂形成,其中主体材料选用具有以下结构的化合物mCBP,客体材料选用实施例1合成得到的化合物1,主体材料与客体材料的质量比为85:15;
空穴传输层选用具有如下结构的化合物NPB;
空穴注入层选用具有如下结构的化合物HATCN;
阳极选用氧化铟锡。
本实施例中器件性能测试结果如下:
图1是本实施例中有机电致发光器件的电流密度-电压曲线。
图2是本实施例中有机电致发光器件的外量子效率-电流密度曲线。
实施例5
本实施例提供一种有机电致发光器件,与实施例4中提供的有机电致发光器件的区别仅在于:发光层中客体材料选用实施例2合成的化合物39。
实施例6
本实施例提供一种有机电致发光器件,与实施例4中提供的有机电致发光器件的区别仅在于:发光层中客体材料选用实施例3合成的化合物48。
对比例1
本对比例提供一种有机电致发光器件,与实施例4中提供的有机电致发光器件的区别仅在于:发光层中客体材料选用5TCzBN(2,3,4,5,6-五(3,6-二叔丁基-9H-咔唑-9-基)苯甲腈)。
对实施例4-6和对比例1的器件性能进行测试,测试结果见下表1。
表1、采用不同发光材料的器件性能测试结果
从上表1可知,与目前商业化的蓝光热激活延迟荧光材料5TCzBN相比,实施例中制备的器件具有效率高,发光光谱窄,寿命长等优点。
综上所述,本发明通过辅助极性基团的引入可以有效的改善材料本身的单极性特性,平衡电荷注入。另外,在基本不影响荧光基团发光特性的前提下扭曲材料结构,增大材料分子间距,减弱材料堆叠作用,降低荧光体聚集淬灭效应,提高器件稳定性,改善苛刻的低掺杂浓度要求,有利于大规模生产过程中的调控和良品率提升。其作为有机电致发光器件的发光材料具有对主体材料普适性好,发光效率高,色纯度高和寿命长等优点。
应当理解的是,本发明的应用不限于上述的举例,对本领域普通技术人员来说,可以根据上述说明加以改进或变换,所有这些改进和变换都应属于本发明所附权利要求的保护范围。
Claims (3)
1.一种有机电致发光器件,包括发光层,其特征在于,所述发光层由主体材料和客体材料共掺杂形成,主体材料与客体材料的质量比为85:15;其中,所述客体材料为基于苯并五元杂环的双极性荧光材料,选自如下结构中的一种:、/>。
2.根据权利要求1所述的有机电致发光器件,其特征在于,化合物39的制备路线如下所示:
。
3.根据权利要求1所述的有机电致发光器件,其特征在于,化合物48的制备路线如下所示:
。
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