CN111689989B - 一种含so2多杂环化合物及其应用 - Google Patents
一种含so2多杂环化合物及其应用 Download PDFInfo
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- CN111689989B CN111689989B CN202010661829.1A CN202010661829A CN111689989B CN 111689989 B CN111689989 B CN 111689989B CN 202010661829 A CN202010661829 A CN 202010661829A CN 111689989 B CN111689989 B CN 111689989B
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 48
- 239000000463 material Substances 0.000 claims abstract description 54
- 125000000623 heterocyclic group Chemical group 0.000 claims description 18
- 125000003118 aryl group Chemical group 0.000 claims description 15
- -1 benzocarbazolyl Chemical group 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 239000000758 substrate Substances 0.000 claims description 6
- 238000002347 injection Methods 0.000 claims description 5
- 239000007924 injection Substances 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 238000006467 substitution reaction Methods 0.000 claims description 5
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
- 230000005525 hole transport Effects 0.000 claims description 4
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000005605 benzo group Chemical group 0.000 claims description 2
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
- 239000004305 biphenyl Substances 0.000 claims description 2
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 238000005286 illumination Methods 0.000 abstract description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 48
- 229910052739 hydrogen Inorganic materials 0.000 description 40
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- 238000006243 chemical reaction Methods 0.000 description 27
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 238000004440 column chromatography Methods 0.000 description 12
- 238000001704 evaporation Methods 0.000 description 12
- 239000002904 solvent Substances 0.000 description 11
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- 239000012074 organic phase Substances 0.000 description 9
- JWJQEUDGBZMPAX-UHFFFAOYSA-N (9-phenylcarbazol-3-yl)boronic acid Chemical compound C12=CC=CC=C2C2=CC(B(O)O)=CC=C2N1C1=CC=CC=C1 JWJQEUDGBZMPAX-UHFFFAOYSA-N 0.000 description 8
- 230000008020 evaporation Effects 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 125000005842 heteroatom Chemical group 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
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- 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 4
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Natural products C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 150000002894 organic compounds Chemical class 0.000 description 3
- 238000010791 quenching Methods 0.000 description 3
- 230000000171 quenching effect Effects 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
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
- ZXCFTZDZQOHUCG-UHFFFAOYSA-N [4-(12-azapentacyclo[11.8.0.02,11.03,8.016,21]henicosa-1(13),2(11),3,5,7,9,14,16,18,20-decaen-12-yl)phenyl]boronic acid Chemical compound B(C1=CC=C(C=C1)N2C3=C(C4=CC=CC=C4C=C3)C5=C2C=CC6=CC=CC=C65)(O)O ZXCFTZDZQOHUCG-UHFFFAOYSA-N 0.000 description 2
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 2
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 2
- 229910000024 caesium carbonate Inorganic materials 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- CSLSCVHILGCSTE-UHFFFAOYSA-N dibenzothiophen-2-ylboronic acid Chemical compound C1=CC=C2C3=CC(B(O)O)=CC=C3SC2=C1 CSLSCVHILGCSTE-UHFFFAOYSA-N 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000011010 flushing procedure Methods 0.000 description 2
- 239000004973 liquid crystal related substance Substances 0.000 description 2
- 238000003760 magnetic stirring Methods 0.000 description 2
- 238000010907 mechanical stirring Methods 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 229930192474 thiophene Chemical group 0.000 description 2
- 238000007738 vacuum evaporation Methods 0.000 description 2
- 238000007740 vapor deposition Methods 0.000 description 2
- FCEROUNZXZZEBY-UHFFFAOYSA-N (3-phenyl-1-benzothiophen-2-yl)boronic acid Chemical compound C1(=CC=CC=C1)C1=C(SC2=C1C=CC=C2)B(O)O FCEROUNZXZZEBY-UHFFFAOYSA-N 0.000 description 1
- JGAVTCVHDMOQTJ-UHFFFAOYSA-N (4-carbazol-9-ylphenyl)boronic acid Chemical compound C1=CC(B(O)O)=CC=C1N1C2=CC=CC=C2C2=CC=CC=C21 JGAVTCVHDMOQTJ-UHFFFAOYSA-N 0.000 description 1
- NJKCFLBYPCPLOS-UHFFFAOYSA-N (9-naphthalen-2-ylcarbazol-3-yl)boronic acid Chemical compound C12=CC=CC=C2C2=CC(B(O)O)=CC=C2N1C1=CC=C(C=CC=C2)C2=C1 NJKCFLBYPCPLOS-UHFFFAOYSA-N 0.000 description 1
- SYTBIFURTZACKR-UHFFFAOYSA-N 2-bromo-4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1Br SYTBIFURTZACKR-UHFFFAOYSA-N 0.000 description 1
- MZMZIXOCJASTPY-UHFFFAOYSA-N 2-bromo-4-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C=C1Br MZMZIXOCJASTPY-UHFFFAOYSA-N 0.000 description 1
- MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 1
- DIAWBHLTWNWYGR-UHFFFAOYSA-N 4-chloro-1-fluoro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC(Cl)=CC=C1F DIAWBHLTWNWYGR-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- MTBUMSSEAQSSQA-UHFFFAOYSA-N OB(O)C1=CC2=C(C=C1)N(C1=CC3=CC=CC=C3C=C21)C1=CC=CC=C1 Chemical compound OB(O)C1=CC2=C(C=C1)N(C1=CC3=CC=CC=C3C=C21)C1=CC=CC=C1 MTBUMSSEAQSSQA-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- ZTYPCLLZNOESMU-UHFFFAOYSA-N [4-([1]benzothiolo[3,2-b]carbazol-11-yl)phenyl]boronic acid Chemical compound B(C1=CC=C(C=C1)N2C3=CC=CC=C3C4=C2C=C5C6=CC=CC=C6SC5=C4)(O)O ZTYPCLLZNOESMU-UHFFFAOYSA-N 0.000 description 1
- JAZNSOPOXXXZQO-UHFFFAOYSA-N [N].CCO Chemical compound [N].CCO JAZNSOPOXXXZQO-UHFFFAOYSA-N 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000010549 co-Evaporation Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- 230000001808 coupling effect Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- UZVGSSNIUNSOFA-UHFFFAOYSA-N dibenzofuran-1-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O UZVGSSNIUNSOFA-UHFFFAOYSA-N 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- 239000012769 display material Substances 0.000 description 1
- 239000002019 doping agent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 238000005530 etching Methods 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- PZJSZBJLOWMDRG-UHFFFAOYSA-N furan-2-ylboronic acid Chemical compound OB(O)C1=CC=CO1 PZJSZBJLOWMDRG-UHFFFAOYSA-N 0.000 description 1
- 238000004770 highest occupied molecular orbital Methods 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- 239000002346 layers by function Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229940048181 sodium sulfide nonahydrate Drugs 0.000 description 1
- WMDLZMCDBSJMTM-UHFFFAOYSA-M sodium;sulfanide;nonahydrate Chemical compound O.O.O.O.O.O.O.O.O.[Na+].[SH-] WMDLZMCDBSJMTM-UHFFFAOYSA-M 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- FWMUJAIKEJWSSY-UHFFFAOYSA-N sulfur dichloride Chemical compound ClSCl FWMUJAIKEJWSSY-UHFFFAOYSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
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- 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
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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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- H—ELECTRICITY
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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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- 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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- H10K85/649—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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- 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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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
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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
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
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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
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- 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
- C09K2211/1033—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with oxygen
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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
- C09K2211/1037—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with sulfur
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- C09K2211/10—Non-macromolecular compounds
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Abstract
本发明属于有机电致发光显示技术领域,具体涉及一种新型含SO2多杂环化合物及其在有机电致发光器件中的应用。本发明提供的新型含SO2多杂环化合物的结构如式(I)所示。这类化合物具有良好的热稳定性,将其应用于OLED器件中,作为绿光主体材料使用,可以有效地提升器件的光电性能。含有所述含SO2多杂环化合物的OLED器件可以应用于显示或者照明领域。
Description
技术领域
本发明属于有机电致发光显示技术领域,具体涉及一种新型含SO2多杂环结构的有机材料,及其在有机电致发光(OLED)器件中的应用。
背景技术
有机电致发光(OLED)材料在信息显示材料、有机光电子材料等领域中的应用具有极大的研究价值和美好的应用前景。随着多媒体信息技术的发展,对平板显示器件性能的要求越来越高。目前主要的显示技术有等离子显示器件、场发射显示器件和有机电致发光显示器件(OLED)。其中,OLED具有自身发光、低电压直流驱动、全固化、视角宽、颜色丰富等一系列优点,与液晶显示器件相比,OLED不需要背光源,视角更宽,功耗低,其响应速度是液晶显示器件的1000倍,因此,OLED具有更广阔的应用前景。
自OLED第一次被报道以来,许多学者致力于研究怎样提高器件效率和稳定性。Forrest和Thompson研究组发现过渡金属配合物能应用于Ph OLEDs(phosphorescentOLEDs),磷光材料存在很强的自旋轨道耦合作用,能同时利用单线态和三线态激子,使磷光电致发光器件内量子效率在理论上达到了100%。然而,磷光材料激发态寿命较长,当三线态激子浓度较高时容易形成三线态-三线态凐灭和三线态-极化子间凐灭。所以常常将磷光材料作为客体参入到主体材料中,以此来降低自身的浓度淬灭现象。因此,在磷光有机电致发光器件(Phosphorescent OLEDs,Ph OLEDs)中选择合适的主体材料也是一件重要的事。主体材料必备特性:(1)拥有高于客体染料的三线态能级;(2)具有较好的载流子迁移率且能与相邻层能级匹配;(3)具有高的热稳定性和成膜稳定性。
目前OLED显示和照明得到了广泛的商业化应用,客户终端的对OLED屏体光电要求的不断提升,为了应对这类需求,除了在OLED面板制程工艺上的精益求精,能够满足更高器件指标的OLED材料的开发就显得尤为重要。因此,开发稳定高效的主体材料,从而降低驱动电压,提高器件发光效率,具有很重要的实际应用价值。
发明内容
本发明的目的在于提供具有较高的三线态能级、具有较好的载流子迁移率且能与相邻能级匹配,具有较高的热稳定性和成膜稳定性的OLED主体材料,以及这种有机材料在OLED器件中的应用。
具体而言,本发明发现一类新型的可用于有机电致发光器件的含SO2多杂环结构化合物。该系列化合物的母核具有拉电子效应,与具有给电子能力的咔唑、呋喃、噻吩等五元杂环基团相连,可以作为绿光主体材料使用,同时具有良好的热稳定性,能够很好地应用于OLED器件中。该系列化合物用通式(Ⅰ)表示,将其应用于OLED器件中,可达到上述目的。
第一方面,本发明提供一种新型含SO2多杂环化合物,其具有式(I)所示结构:
所述式(I)中,
R1~R12各自独立地任意选自氢原子、卤原子、直链或含支链的烷基、环烷基、氨基、烷胺基、取代或未被取代的含有苯环和/或芳杂环的芳香基团,且R1~R12中至少有一个基团为含五元杂环的芳香基团。
优选地,所述R1~R12中,至少有一个基团为取代或未被取代的含五元杂环的芳香基团,所述取代或未被取代的含五元杂环的芳香基团含有至少一个五元杂环,优选为含有一个、两个或三个五元杂环;所述五元杂环含有至少一个杂原子,优选为含有一个、两个或三个杂原子;所述杂原子任意地选自N原子、S原子和O原子;当所述取代或未被取代的含五元杂环的芳香基团中含有多个杂原子时,各个杂原子可以彼此相同,可以部分相同,也可以各不相同。
作为本发明的优选方案,所述取代或未被取代的含五元杂环的芳香基团选自:取代或未被取代的咔唑基、取代或未取代的苯并咔唑基、取代或未取代的菲并咔唑基、取代或未被取代的吲哚并吲哚基、取代或未被取代的噻吩基、取代或未被取代的苯并噻吩基、取代或未被取代的苯并呋喃基、取代或未取代的萘并呋喃基。
作为本发明的优选方案,所述取代的含五元杂环的芳香基团中,取代基可以任意选自:苯基、萘基、联苯基、苯并基、萘并基、菲并基、吲哚并基(如N-苯代吲哚并基)、苯并噻吩并基、苯并呋喃并基。取代基的个数为1~5、优选为1~3的整数。
作为本发明的优选方案,所述取代或未被取代的含五元杂环的芳香基团选自:
优选地,所述取代或未被取代的含五元杂环的芳香基团选自:
更优选地,所述取代或未被取代的含五元杂环的芳香基团选自:
在上述各取代基团中,“---”表示取代位。
作为本发明的优选方案,本发明提供以下结构所示的化合物:
上述有机化合物以含SO2多杂环结构为母核,该母核结构具有良好的热稳定性,同时具有合适的HOMO和LUMO能级以及Eg,通过在母核结构中的合适位置引入具有较强给电子能力的基团,即通过在结构中引入具有较强给电子能力的咔唑、呋喃、噻吩等五元杂环结构,获得了一类新型结构OLED材料。将其应用于OLED器件中,作为绿光主体材料使用,可以有效地提升器件的光电性能。该器件可以应用于显示或者照明领域。
第二方面,本发明提供式(I)所示的有机化合物在制备有机电致发光器件中的应用。优选地,本发明提供所述有机化合物在有机电致发光器件中作为电致发光层的发光主体材料的应用;进一步优选地,所述电致发光材料为绿光主体材料。所述电致发光层的厚度可以为10~50nm,优选为20~40nm。
第三方面,本发明提供一种有机电致发光器件,所述有机电致发光器件包括含有本发明所述的化合物的电致发光层。
作为本发明的优选方案,所述有机电致发光器件由下至上依次包括透明基片、阳极层、空穴传输层、电致发光层(包含本发明所述的化合物作为绿光主体材料)、电子传输层、电子注入层和阴极层。优选地,所述电致发光层的厚度为10~50nm,优选为20~40nm。
第四方面,本发明提供了一种显示装置,包括所述有机电致发光器件。
第五方面,本发明提供了一种照明装置,包括所述有机电致发光器件。
本发明提供的新型OLED材料以含SO2多杂环结构化合物为母核,通过在母核结构中引入给电子基团,获得了一类具有较高的三线态能级、较好的载流子迁移率且能与相邻能级匹配,具有较高的热稳定性和成膜稳定性的新型OLED材料。该类材料可以被应用在有机电致发光领域,作为绿光主体材料使用,可以有效提高器件的光电性能。
具体实施方式
以下实施例用于说明本发明,但不用来限制本发明的范围,凡其他未脱离本发明所揭示的精神下所完成的等效改变或修饰,均应包含在所属权利要求范围内。
根据本发明提供的制备方法,本领域技术人员可采用已知的常见手段来实现,如进一步选择合适的催化剂、溶剂,确定适宜的反应温度、时间、物料比等,本发明对此不作特别限定。如无特别说明,制备过程中使用的溶剂、催化剂、碱等原料均可以通过公开商业途径或者本领域已知的方法合成得到。
实施例1中间体M1的合成
合成路线如下:
包括如下具体步骤:
(1)在配有机械搅拌的2L三口瓶中,加入4-氯-1-氟-2-硝基苯(17.5g,0.1mol)、2-溴-4-氯苯胺(30.8g,0.15mol),搅拌,氩气保护,升温至180℃,保温反应30小时以上,在反应过程中,反应液颜色逐渐变成红色,最后逐渐变成深红色。反应结束后,分离有机相,萃取,干燥,柱层析,旋干溶剂,得到30g橙红色固体M-01,收率83%。
(2)在配有机械搅拌的1L三口瓶中,加入M-01(36.0g,0.1mol)、九水合硫化钠(96g,0.4mol)、乙醇(200mL)、水(100mL),氮气保护,加热至回流,回流反应3小时,结束反应。分离有机相,萃取,干燥,柱层析,旋干溶剂,得26.5g白色固体M-02,收率80%。
(3)在配有机械搅拌的1L三口瓶中,加入M-02(33.0g,0.1mol)和丙酮300mL,完全溶解,加入KOH(11.2g,0.2mol)溶于(50mL)水的溶液,然后向反应瓶中缓慢滴加2-溴-4-氯苯甲酰氯(25.2g,0.1mol),反应瓶中逐渐有固体析出,滴加完毕后常温反应2小时,反应结束。调至中性,分离有机相,萃取,干燥,柱层析,旋干溶剂,得到43.8g白色固体M-03,收率79%。
(4)1L三口瓶中加入M-03(54.8g,0.1mol),加入乙二醇醚200mL,氮气保护,逐渐加热至回流,固体逐渐溶解,磁力搅拌,保温反应3小时,反应结束。分离有机相,萃取,干燥,柱层析,旋干溶剂,得到40g淡红色固体M-04,收率76%。
(5)在氮气保护下,2L三口瓶中加入M-04(53.0g,0.1mol)和THF 800mL,冷却至-78℃,在搅拌下缓慢滴加正丁基锂(100mL,0.25mol),滴加时间约30mins,滴完用50mL THF冲淋滴液漏斗,保温1.5小时得到M-05的反应液。在-78℃的低温体系中,缓慢滴加二氯化硫(16mL,0.25mol),然后用少量THF冲洗滴液漏斗,加完后保温1小时,然后缓慢升温至室温,在室温下搅拌反应4小时,反应结束。调至中性,分离有机相,萃取,干燥,柱层析,旋干溶剂,得到26.6g白色固体中间体M-06,收率66%。
(6)2L三口瓶中加入M-06(40.2g,0.1mol)和600mL二氯甲烷,开动搅拌,缓慢滴加(40mL,0.4mol,30%)过氧化氢水溶液,室温反应2小时,反应结束,加入100mL饱和碳酸氢钠水溶液,搅拌分液,旋干得白色固体,二氯甲烷柱层析,过柱液旋干溶剂得39.1g白色固体母核中间体M1,收率90%。
产物MS(m/e):433.95;元素分析(C19H9Cl3N2O2S):理论值C:52.38%,H:2.08%,N:6.43%;实测值C:52.14%,H:1.96%,N:6.21%。
实施例2中间体M2的合成
产物MS(m/e):399.98;元素分析(C19H10Cl2N2O2S):理论值C:56.87%,H:2.51%,N:6.98%;实测值C:56.66%,H:2.27%,N:6.74%。
实施例3中间体M3的合成
产物MS(m/e):399.98;元素分析(C19H10Cl2N2O2S):理论值C:56.87%,H:2.51%,N:6.98%;实测值C:56.63%,H:2.28%,N:6.72%。
实施例4中间体M4的合成
产物MS(m/e):399.98;元素分析(C19H10Cl2N2O2S):理论值C:56.87%,H:2.51%,N:6.98%;实测值C:56.63%,H:2.28%,N:6.72%。
实施例5中间体M5的合成
产物MS(m/e):366.02;元素分析(C19H11ClN2O2S):理论值C:62.21%,H:3.02%,N:7.64%;实测值C:62.01%,H:2.87%,N:7.40%。
实施例6中间体M6的合成
产物MS(m/e):366.02;元素分析(C19H11ClN2O2S):理论值C:62.21%,H:3.02%,N:7.64%;实测值C:62.01%,H:2.87%,N:7.41%。
实施例7中间体M7的合成
产物MS(m/e):366.02;元素分析(C19H11ClN2O2S):理论值C:62.21%,H:3.02%,N:7.64%;实测值C:62.03%,H:2.89%,N:7.42%。
实施例8中间体M8的合成
产物MS(m/e):399.98;元素分析(C19H10Cl2N2O2S):理论值C:56.87%,H:2.51%,N:6.98%;实测值C:56.63%,H:2.28%,N:6.72%。
实施例9中间体M9的合成
合成路线如下:
包括如下具体步骤:
(1)中间体M9-04的合成:
(2)中间体M9-06的合成:在N2保护下,2L三口瓶中加入M9-04(58.8g,0.1mol),500ml无水THF,搅拌下用液氮乙醇浴将反应体系冷却到-78℃,然后在此温度下缓慢加入70ml正丁基锂的1.6M己烷溶液(0.11mol),滴加完全后,在此温度下保温15分钟,然后加入升华硫粉(3.2g,0.1mol),加完后在-78℃下搅拌反应1小时,然后反应体系缓慢升温到-20℃,并保持30分钟。接着将反应体系继续冷却到-78℃,并加入CuCl(10g,0.1mol),在此温度下保温30分钟,然后撤去冷浴,使反应体系自然升到室温,搅拌2h,接着加热反应体系至回流,反应2h。冷却到室温,缓慢加入饱和氯化铵溶液,加入乙酸乙酯250ml,分离有机相,水相用乙酸乙酯萃取3遍,合并有机相,无水氯化镁干燥,旋干溶剂,柱色谱分离,得到中间体M9-06共19.0g,白色固体,收率约46%。
(3)中间体M9的合成:
1L三口瓶中加入M9-06(41.2g,0.1mol)和300mL二氯甲烷,开动搅拌,缓慢滴加(40mL,0.4mol,30%)过氧化氢水溶液,室温反应2小时,反应结束,加入100mL饱和碳酸氢钠水溶液,搅拌分液,旋干得白色固体,二氯甲烷柱层析,过柱液旋干溶剂得40.0g白色固体母核中间体M9,收率90%。
产物MS(m/e):443.93;元素分析(C19H10BrClN2O2S):理论值C:51.20%,H:2.26%,N:6.29%;实测值C:50.99%,H:2.06%,N:6.01%。
实施例10中间体M10的合成
产物MS(m/e):443.93;元素分析(C19H10BrClN2O2S):理论值C:51.20%,H:2.26%,N:6.29%;实测值C:50.96%,H:2.02%,N:6.03%。
实施例11化合物I-12的合成
合成路线如下:
2L三口瓶,配磁力搅拌,氮气置换后依次加入M1(43.4g,0.1mol)、(9-苯基-9H-咔唑-3-基)硼酸(86.1g,0.3mol)、碳酸铯(117g,0.36mol)和二氧六环800ml,开动搅拌。再次氮气置换后加入(2.2g,11mmol)三叔丁基膦和(4.1g,4.5mmol)三(二亚苄基丙酮)二钯。加完后,加热升温,控温80-90℃反应4个小时,反应结束后降温。调至中性,分离有机相,萃取,干燥,柱层析,旋干溶剂,得到80.2g浅黄色固体,收率约76%。
产物MS(m/e):1055.33;元素分析(C73H45N5O2S):理论值C:83.01%,H:4.29%,N:6.63%;实测值C:82.79%,H:4.03%,N:6.41%。
实施例12化合物I-20的合成
合成路线如下:
用M2代替M1,(4-(9H-咔唑-9-基)苯基)硼酸代替(9-苯基-9H-咔唑-3-基)硼酸,选择合适的物料比,其他原料和步骤均和实施例11相同,得到64.5g淡黄色固体,收率约79%。
产物MS(m/e):814.24;元素分析(C55H34N4O2S):理论值C:81.06%,H:4.21%,N:6.87%;实测值C:80.86%,H:4.00%,N:6.61%。
实施例13化合物I-33的合成
合成路线如下:
用M3代替M1,(9-(萘-2-基)-9H-咔唑-3-基)硼酸代替(9-苯基-9H-咔唑-3-基)硼酸,选择合适的物料比,其他原料和步骤均和实施例11相同,得76.8g浅黄色固体,收率约84%。
产物MS(m/e):914.27;元素分析(C63H38N4O2S):理论值C:82.69%,H:4.19%,N:6.12%;实测值C:82.43%,H:4.00%,N:5.96%。
实施例14化合物I-46的合成
合成路线如下:
用M4代替M1,(5-苯基-5H-苯并[b]咔唑-2-基)硼酸代替(9-苯基-9H-咔唑-3-基)硼酸,选择合适的物料比,其他原料和步骤均和实施例11相同,得71.5g浅黄色固体,收率约78%。
产物MS(m/e):914.27;元素分析(C63H38N4O2S):理论值C:82.69%,H:4.19%,N:6.12%;实测值C:82.44%,H:3.98%,N:5.96%。
实施例15化合物I-59的合成
合成路线如下:
用M5代替M1,(4-(7H-二苯并[c,g]咔唑-7-基)苯基)硼酸代替(9-苯基-9H-咔唑-3-基)硼酸,选择合适的物料比,其他原料和步骤均和实施例11相同,得47.8g浅黄色固体,收率约71%。
产物MS(m/e):673.18;元素分析(C45H27N3O2S):理论值C:80.22%,H:4.04%,N:6.24%;实测值C:80.01%,H:3.79%,N:6.02%。
实施例16化合物I-73的合成
合成路线如下:
用M6代替M1,(4-(10-苯基吲哚[3,2-b]吲哚-5(10H)-基)苯基)硼酸代替(9-苯基-9H-咔唑-3-基)硼酸,选择合适的物料比,其他原料和步骤均和实施例11相同,得51.6g浅黄色固体,收率约75%。
产物MS(m/e):688.19;元素分析(C45H28N4O2S):理论值C:78.47%,H:4.10%,N:8.13%;实测值C:78.22%,H:3.86%,N:7.91%。
实施例17化合物I-85的合成
合成路线如下:
用M7代替M1,(4-(11H-苯并[4,5]噻吩并[3,2-b]咔唑-11-基)苯基)硼酸代替(9-苯基-9H-咔唑-3-基)硼酸,选择合适的物料比,其他原料和步骤均和实施例11相同,得55.0g浅黄色固体,收率约81%。
产物MS(m/e):679.14;元素分析(C43H25N3O2S2):理论值C:75.97%,H:3.71%,N:6.18%;实测值C:75.69%,H:3.52%,N:5.98%。
实施例18化合物I-98的合成
合成路线如下:
用M8代替M1,(3-苯基苯并[b]噻吩-2-基)硼酸代替(9-苯基-9H-咔唑-3-基)硼酸,选择合适的物料比,其他原料和步骤均和实施例11相同,得59.8g浅黄色固体,收率约80%。
产物MS(m/e):748.13;元素分析(C47H28N2O2S3):理论值C:75.38%,H:3.77%,N:3.74%;实测值C:75.10%,H:3.52%,N:3.51%。
实施例19化合物I-138的合成
合成路线如下:
包括如下具体步骤:
在1L的三口瓶中,加入M9(44.4g,0.1mol)、(4-(7H-二苯并[c,g]咔唑-7-基)苯基)硼酸(38.7g,0.1mol)、碳酸钠(21.2g,0.2mol)、甲苯150mL、乙醇150mL、水150mL,反应体系用氮气置换保护后加入Pd(PPh3)4(11.5g,10mmol)。加热回流反应(体系内温度约78℃)3小时,停止反应。减蒸掉溶剂,二氯甲烷萃取,无水硫酸镁干燥,过滤,石油醚/乙酸乙酯(2:1)柱层析,旋干溶剂,乙酸乙酯打浆,过滤得58.0g浅黄色固体I-138-1,收率约82%。
1L三口瓶,配磁力搅拌,氮气置换后依次加入I-138-1(70.7g,0.1mol)、二苯并[b,d]噻吩-2-基硼酸(22.8g,0.1mol)、碳酸铯(39g,0.12mol)和二氧六环400ml,开动搅拌。再次氮气置换后加入(0.8g,4mmol)三叔丁基膦和(1.4g,1.5mmol)三(二亚苄基丙酮)二钯。加完后,加热升温,控温80-90℃反应4个小时,反应结束后降温。调至中性,分离有机相,萃取,干燥,柱层析,旋干溶剂,得到得64.1g浅黄色固体I-138,收率约75%。
产物MS(m/e):823.21;元素分析(C57H33N3O2S2):理论值C:79.98%,H:3.89%,N:4.91%;实测值C:79.73%,H:3.62%,N:4.69%。
实施例20化合物I-139的合成
合成路线如下:
用M10代替M9,(4-(10-苯基吲哚[3,2-b]吲哚-5(10H)-基)苯基)硼酸代替(4-(7H-二苯并[c,g]咔唑-7-基)苯基)硼酸,二苯并[b,d]呋喃-2-基硼酸代替二苯并[b,d]噻吩-2-基硼酸,选择合适的物料比,其他原料和步骤均和实施例19相同,得59.8g浅黄色固体I-139,收率约70%。
产物MS(m/e):854.24;元素分析(C57H34N4O3S):理论值C:80.07%,H:4.01%,N:6.55%;实测值C:79.78%,H:3.86%,N:6.32%。
依据实施例1~实施例20的技术方案,只需要简单替换对应的原料,不改变任何实质性操作,可以合成I-1~I-140的其他化合物。
实施例21用本发明化合物作绿光主体材料
本实施例提供了一组OLED绿光器件,器件的结构为:
ITO/HATCN(1nm)/HT01(40nm)/NPB(25nm)/EML(30nm)(含实施例11-20所提供的任一化合物)/Bphen(35nm)/LiF(1nm)/Al。
各功能层材料分子结构如下:
本发明的OLED绿光器件OLED-1的制备过程为:
(1)将表面涂覆了ITO透明导电薄膜的玻璃基板在清洗液中超声清洗,在去离子水中超声处理,在丙酮∶乙醇混合溶剂(体积比1∶1)混合溶液中超声除油,在洁净环境下烘烤至完全去除水分,用紫外灯进行刻蚀和臭氧处理,并用低能阳离子束轰击表面;
(2)把上述带有阳极的玻璃基片置于真空腔内,抽真空至1×10-5~9×10-3Pa,在上述阳极层膜上真空蒸镀HATCN作为第一空穴注入层,蒸镀速率为0.1nm/s,蒸镀总膜厚为1nm;接着蒸镀第二空穴注入层HT01,蒸镀速率为0.1nm/s,厚度为40nm;然后蒸镀空穴传输层NPB,蒸镀速率为0.1nm/s,蒸镀膜厚为25nm;
(3)在空穴传输层之上真空蒸镀EML作为器件的发光层,EML包括本发明的绿光主体材料(I-12)和染料材料,利用多源共蒸的方法,将作为发光层的主体材料放置在真空气相沉积设备的小室中,将作为掺杂剂的Ir(ppy)3放置在真空气相沉积设备的另一室中,调节主体材料蒸镀速率为0.1nm/s,Ir(ppy)3的浓度为10%,蒸镀总膜厚为30nm;
(4)在发光层上真空蒸镀Bphen形成膜厚为35nm的电子传输层,其蒸镀速率为0.1nm/s;
(5)在电子传输层上依次真空蒸镀厚度为1nm的LiF作为电子注入层,厚度为150nm的Al层作为器件的阴极。
按照与上相同的步骤,仅将步骤(3)中的I-12分别替换为I-20、I-33、I-46、I-59、I-73、I-85、I-98、I-138以及I-139,作为绿光主体材料使用,分别得到本发明提供的OLED-2~OLED-10。
按照与上相同的步骤,仅将步骤(3)中的I-12替换为CBP(对比化合物),得到本发明提供的对比例OLED-11。所述CBP的结构具体为:
本发明对上述所得器件OLED-1~OLED-11的性能进行检测,检测结果如表1所示。
表1:OLED器件性能检测结果
由上可知,利用本发明提供的式(I)所示有机材料制备成的器件OLED-1~OLED-10的电流效率偏高,且在亮度相同的条件下,工作电压明显比CBP作为主体材料的器件OLED-11偏低,是性能良好的绿光主体材料。
虽然,上文中已经用一般性说明、具体实施方式及试验,对本发明作了详尽的描述,但在本发明基础上,可以对之作一些修改或改进,这对本领域技术人员而言是显而易见的。因此,在不偏离本发明精神的基础上所做的这些修改或改进,均属于本发明要求保护的范围。
Claims (10)
1.式(I)所示的化合物:
其中,
R1~R12各自独立地任意选自氢原子、卤原子、直链或含支链的烷基、环烷基、氨基、烷胺基、取代或未被取代的含五元杂环的芳香基团,且R1~R12中至少有一个基团为取代或未被取代的含五元杂环的芳香基团;
其中,所述取代或未被取代的含五元杂环的芳香基团选自:取代或未被取代的咔唑基、取代或未取代的苯并咔唑基、取代或未取代的菲并咔唑基、取代或未被取代的吲哚并吲哚基、取代或未被取代的噻吩基、取代或未被取代的苯并噻吩基、取代或未被取代的苯并呋喃基、取代或未取代的萘并呋喃基;
所述取代的含五元杂环的芳香基团中,取代基任意选自:苯基、萘基、联苯基、苯并基、萘并基、菲并基、N-苯代吲哚并基、苯并噻吩并基、苯并呋喃并基;取代基的个数为1~5的整数。
5.权利要求1-4任一项所述的化合物在制备有机电致发光器件中的应用。
6.根据权利要求5所述的应用,其特征在于,所述的化合物在有机电致发光器件中作为电致发光层的发光主体材料的应用。
7.一种有机电致发光器件,其中,所述有机电致发光器件包括含有权利要求1-4任一项所述的化合物的电致发光层。
8.根据权利要求7所述的有机电致发光器件,其特征在于,所述有机电致发光器件由下至上依次包括透明基片、阳极层、空穴传输层、含有权利要求1-4任一项所述的化合物的电致发光层、电子传输层、电子注入层和阴极层。
9.一种显示装置,其中,所述显示装置包括权利要求7或8所述的有机电致发光器件。
10.一种照明装置,其中,所述照明装置包括权利要求7或8所述的有机电致发光器件。
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