CN107162916B - 有机电致发光材料及其制备方法和有机电致发光器件 - Google Patents
有机电致发光材料及其制备方法和有机电致发光器件 Download PDFInfo
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- CN107162916B CN107162916B CN201710312768.6A CN201710312768A CN107162916B CN 107162916 B CN107162916 B CN 107162916B CN 201710312768 A CN201710312768 A CN 201710312768A CN 107162916 B CN107162916 B CN 107162916B
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- 239000000463 material Substances 0.000 title claims abstract description 37
- 238000002360 preparation method Methods 0.000 title abstract description 10
- 238000004519 manufacturing process Methods 0.000 claims abstract description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 78
- 150000001875 compounds Chemical class 0.000 claims description 66
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 56
- 238000006243 chemical reaction Methods 0.000 claims description 45
- 239000007787 solid Substances 0.000 claims description 32
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 27
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 20
- 239000000126 substance Substances 0.000 claims description 20
- 238000003756 stirring Methods 0.000 claims description 18
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 claims description 16
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 claims description 16
- 239000012044 organic layer Substances 0.000 claims description 15
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 14
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- 238000001914 filtration Methods 0.000 claims description 12
- 239000000243 solution Substances 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 9
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 claims description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
- 238000005406 washing Methods 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 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 claims description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 5
- 238000004440 column chromatography Methods 0.000 claims description 5
- 238000001816 cooling Methods 0.000 claims description 5
- 229910052751 metal Inorganic materials 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 5
- MBAIEZXRGAOPKH-UHFFFAOYSA-N 1,2,3,6,7,8-hexahydropyrene Chemical compound C1CCC2=CC=C3CCCC4=CC=C1C2=C43 MBAIEZXRGAOPKH-UHFFFAOYSA-N 0.000 claims description 4
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 claims description 4
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 claims description 4
- NXQGGXCHGDYOHB-UHFFFAOYSA-L cyclopenta-1,4-dien-1-yl(diphenyl)phosphane;dichloropalladium;iron(2+) Chemical compound [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 claims description 4
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 claims description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 claims description 4
- 235000019341 magnesium sulphate Nutrition 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- ZGNPLWZYVAFUNZ-UHFFFAOYSA-N tert-butylphosphane Chemical compound CC(C)(C)P ZGNPLWZYVAFUNZ-UHFFFAOYSA-N 0.000 claims description 3
- 229910052746 lanthanum Inorganic materials 0.000 claims description 2
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 claims description 2
- 150000002739 metals Chemical class 0.000 claims description 2
- 230000001376 precipitating effect Effects 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims description 2
- 229910052723 transition metal Inorganic materials 0.000 claims description 2
- 150000003624 transition metals Chemical class 0.000 claims description 2
- 238000000034 method Methods 0.000 abstract description 4
- 230000005540 biological transmission Effects 0.000 abstract description 2
- 238000002425 crystallisation Methods 0.000 abstract description 2
- 230000008025 crystallization Effects 0.000 abstract description 2
- 238000009776 industrial production Methods 0.000 abstract description 2
- 230000008569 process Effects 0.000 abstract description 2
- 239000002994 raw material Substances 0.000 abstract description 2
- 230000015572 biosynthetic process Effects 0.000 description 20
- 238000003786 synthesis reaction Methods 0.000 description 20
- 239000010410 layer Substances 0.000 description 17
- 230000000052 comparative effect Effects 0.000 description 16
- 238000001819 mass spectrum Methods 0.000 description 11
- 238000004364 calculation method Methods 0.000 description 8
- -1 dimethylphenyl Chemical group 0.000 description 8
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 238000011156 evaluation Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 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 6
- 238000002474 experimental method Methods 0.000 description 5
- MOZHUOIQYVYEPN-UHFFFAOYSA-N 1-bromo-4-propan-2-ylbenzene Chemical compound CC(C)C1=CC=C(Br)C=C1 MOZHUOIQYVYEPN-UHFFFAOYSA-N 0.000 description 4
- LNUFLCYMSVYYNW-ZPJMAFJPSA-N [(2r,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[[(3s,5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-disulfo Chemical compound O([C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CCCC(C)C)[C@H]1O[C@H](COS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]1OS(O)(=O)=O LNUFLCYMSVYYNW-ZPJMAFJPSA-N 0.000 description 4
- 150000004770 chalcogenides Chemical class 0.000 description 4
- 229940125904 compound 1 Drugs 0.000 description 4
- 239000002019 doping agent Substances 0.000 description 4
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 229910044991 metal oxide Inorganic materials 0.000 description 3
- 150000004706 metal oxides Chemical class 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000007740 vapor deposition Methods 0.000 description 3
- VIJSPAIQWVPKQZ-BLECARSGSA-N (2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-acetamido-5-(diaminomethylideneamino)pentanoyl]amino]-4-methylpentanoyl]amino]-4,4-dimethylpentanoyl]amino]-4-methylpentanoyl]amino]propanoyl]amino]-5-(diaminomethylideneamino)pentanoic acid Chemical compound NC(=N)NCCC[C@@H](C(O)=O)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC(C)=O VIJSPAIQWVPKQZ-BLECARSGSA-N 0.000 description 2
- VUEGYUOUAAVYAS-JGGQBBKZSA-N (6ar,9s,10ar)-9-(dimethylsulfamoylamino)-7-methyl-6,6a,8,9,10,10a-hexahydro-4h-indolo[4,3-fg]quinoline Chemical compound C1=CC([C@H]2C[C@@H](CN(C)[C@@H]2C2)NS(=O)(=O)N(C)C)=C3C2=CNC3=C1 VUEGYUOUAAVYAS-JGGQBBKZSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- AVYVHIKSFXVDBG-UHFFFAOYSA-N N-benzyl-N-hydroxy-2,2-dimethylbutanamide Chemical compound C(C1=CC=CC=C1)N(C(C(CC)(C)C)=O)O AVYVHIKSFXVDBG-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- ZEEBGORNQSEQBE-UHFFFAOYSA-N [2-(3-phenylphenoxy)-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound C1(=CC(=CC=C1)OC1=NC(=CC(=C1)CN)C(F)(F)F)C1=CC=CC=C1 ZEEBGORNQSEQBE-UHFFFAOYSA-N 0.000 description 2
- ABRVLXLNVJHDRQ-UHFFFAOYSA-N [2-pyridin-3-yl-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound FC(C1=CC(=CC(=N1)C=1C=NC=CC=1)CN)(F)F ABRVLXLNVJHDRQ-UHFFFAOYSA-N 0.000 description 2
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 2
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- 230000008021 deposition Effects 0.000 description 2
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- 229910001507 metal halide Inorganic materials 0.000 description 2
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- 238000012986 modification Methods 0.000 description 2
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- 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
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 2
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- 238000006467 substitution reaction Methods 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 2
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 1
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- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- UHXOHPVVEHBKKT-UHFFFAOYSA-N 1-(2,2-diphenylethenyl)-4-[4-(2,2-diphenylethenyl)phenyl]benzene Chemical compound C=1C=C(C=2C=CC(C=C(C=3C=CC=CC=3)C=3C=CC=CC=3)=CC=2)C=CC=1C=C(C=1C=CC=CC=1)C1=CC=CC=C1 UHXOHPVVEHBKKT-UHFFFAOYSA-N 0.000 description 1
- HLBOAQSKBNNHMW-UHFFFAOYSA-N 3-(3-methoxyphenyl)pyridine Chemical compound COC1=CC=CC(C=2C=NC=CC=2)=C1 HLBOAQSKBNNHMW-UHFFFAOYSA-N 0.000 description 1
- BGAJNPLDJJBRHK-UHFFFAOYSA-N 3-[2-[5-(3-chloro-4-propan-2-yloxyphenyl)-1,3,4-thiadiazol-2-yl]-3-methyl-6,7-dihydro-4h-pyrazolo[4,3-c]pyridin-5-yl]propanoic acid Chemical compound C1=C(Cl)C(OC(C)C)=CC=C1C1=NN=C(N2C(=C3CN(CCC(O)=O)CCC3=N2)C)S1 BGAJNPLDJJBRHK-UHFFFAOYSA-N 0.000 description 1
- IAOZGTYMBWFZBE-UHFFFAOYSA-N 3-tert-butylperylene Chemical group C=12C3=CC=CC2=CC=CC=1C1=CC=CC2=C1C3=CC=C2C(C)(C)C IAOZGTYMBWFZBE-UHFFFAOYSA-N 0.000 description 1
- JQUCWIWWWKZNCS-LESHARBVSA-N C(C1=CC=CC=C1)(=O)NC=1SC[C@H]2[C@@](N1)(CO[C@H](C2)C)C=2SC=C(N2)NC(=O)C2=NC=C(C=C2)OC(F)F Chemical compound C(C1=CC=CC=C1)(=O)NC=1SC[C@H]2[C@@](N1)(CO[C@H](C2)C)C=2SC=C(N2)NC(=O)C2=NC=C(C=C2)OC(F)F JQUCWIWWWKZNCS-LESHARBVSA-N 0.000 description 1
- KOPBYBDAPCDYFK-UHFFFAOYSA-N Cs2O Inorganic materials [O-2].[Cs+].[Cs+] KOPBYBDAPCDYFK-UHFFFAOYSA-N 0.000 description 1
- FUJCRWPEOMXPAD-UHFFFAOYSA-N Li2O Inorganic materials [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- QOVYHDHLFPKQQG-NDEPHWFRSA-N N[C@@H](CCC(=O)N1CCC(CC1)NC1=C2C=CC=CC2=NC(NCC2=CN(CCCNCCCNC3CCCCC3)N=N2)=N1)C(O)=O Chemical compound N[C@@H](CCC(=O)N1CCC(CC1)NC1=C2C=CC=CC2=NC(NCC2=CN(CCCNCCCNC3CCCCC3)N=N2)=N1)C(O)=O QOVYHDHLFPKQQG-NDEPHWFRSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
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- 239000007983 Tris buffer Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
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- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 229940125773 compound 10 Drugs 0.000 description 1
- 150000001908 cumenes Chemical class 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 1
- AKUNKIJLSDQFLS-UHFFFAOYSA-M dicesium;hydroxide Chemical compound [OH-].[Cs+].[Cs+] AKUNKIJLSDQFLS-UHFFFAOYSA-M 0.000 description 1
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- 239000012153 distilled water Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
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- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- RWGFKTVRMDUZSP-UHFFFAOYSA-N isopropyl-benzene Natural products CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Inorganic materials [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 229910001635 magnesium fluoride Inorganic materials 0.000 description 1
- LVKCSZQWLOVUGB-UHFFFAOYSA-M magnesium;propane;bromide Chemical compound [Mg+2].[Br-].C[CH-]C LVKCSZQWLOVUGB-UHFFFAOYSA-M 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 1
- ZTLUNQYQSIQSFK-UHFFFAOYSA-N n-[4-(4-aminophenyl)phenyl]naphthalen-1-amine Chemical compound C1=CC(N)=CC=C1C(C=C1)=CC=C1NC1=CC=CC2=CC=CC=C12 ZTLUNQYQSIQSFK-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
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Abstract
本发明涉及一种有机电致发光材料及其制备方法和有机电致发光器件,涉及发光材料领域。本发明的目的是提供一种发光效率高、器件寿命好、具有适当的色坐标的新型结构的有机电致发光材料及其制备方法和有机电致发光器件。本发明提供的有机电致发光材料具有高的电子传达效率,从而能够在制造器件时防止结晶,并能够很容易地形成层,由此改善了器件的电流特性。本发明提供的有机电致发光材料的制备方法,原料易得,工艺简单,适合于工业化生产。
Description
技术领域
本发明涉及发光材料领域,具体涉及一种有机电致发光材料及其制备方法和有机电致发光器件。
背景技术
电致发光器件(electroluminescence device:EL device)作为自发光型显示器件,它具有可视角度宽、对比度好,以及应答速度快的优点。1987年,柯达(Eastman Kodak)公司首次开发了利用低分子芳香二胺和铝络合物作为发光层材料的有机电致发光器件。有机电致发光器件中决定发光效率、寿命和性能的最重要的因素是发光材料。
目前已经产业化的蓝色发光材料有DPVBi、二萘蒽(dinaphthylanthracen)、4-t-丁基二萘嵌苯(tetra(t-butyl)perlyene)等。上述材料的发光效率达到6Lm/W、器件寿命达到30,000h,但因会发生驱动时间引起的色纯度低的问题,导致应用在面板的时候寿命只能达到几千小时。而蓝色发光材料的发射波长向长波方向移动,会使效率方面提高很多,但色坐标满足不了要求,所以不适合于高品位的面板中。此外还有效率和热稳定性方面存在一些问题,因而急需研制一种色纯度、效率、热稳定性方面均能满足要求的新材料。
发明内容
本发明的目的是:提供一种发光效率高、器件寿命好、具有适当的色坐标的新型结构的有机电致发光材料及其制备方法和有机电致发光器件。
为了实现上述目的,本发明的技术方案具体如下:
一种有机电致发光材料,其化学结构式如下:
式中:Ar1和Ar2各自独立地选自苯基、碳原子数为6-18的取代苯基、碳原子数为12-17的芳族杂环基或碳原子数为10-25的稠环芳烃,所述的Ar1和Ar2还可通过碳碳键成环;R为氢、碳原子数为1-8的烷基、环丙基、环戊基、苯基、二甲基苯基、甲基苯基、奈基、菲基、乙基苯基、二苯并呋喃基、咔唑基、三甲基硅基、二苯并噻吩基、三联苯基或取代胺基,n为0或1。
在上述技术方案中,Ar1和Ar2各自独立地选自碳原子数为9-12的取代苯基、碳原子数为15的芳族杂环基或碳原子数为14-18的稠环芳烃。
在上述技术方案中,R为甲基、乙基、异丙基、叔丁基、异丁基、叔戊基或2-乙基己基。
在上述技术方案中,所述有机电致发光材料为下列结构中的任意一种:
一种有机电致发光材料的制备方法,包括以下步骤:
(1)取1,2,3,6,7,8-六氢芘、N-溴代丁二酰亚胺和二氯甲烷,常温搅拌,反应结束以后减压过滤得到固体,得到的固体用甲醇洗涤得到化合物Ⅰ;
(2)在氮气条件下,取化合物Ⅰ、化合物Ⅱ及叔丁醇钠,用甲醇溶解,滴加三(二亚苄基丙酮)双钯和叔丁基膦,搅拌反应,反应结束以后向反应物里加甲醇得到固体化合物,固体化合物过滤重新溶解在氯苯里,加活性炭和硫酸镁,继续搅拌,过滤溶剂以后利用氯苯和甲醇重结晶得到化合物Ⅲ;
(3)取化合物Ⅲ、2,3-二氯-5,6-二氰基-1,4-苯醌(DDQ),用甲苯溶解,搅拌反应,反应结束以后反应液冷却进行过滤,浓缩溶剂,用二氯甲烷重结晶得到化合物Ⅳ,其合成路线如下:
(4)取化合物Ⅳ、N-溴代丁二酰亚胺和二氯甲烷,用甲醇溶解以后,常温搅拌反应,反应结束以后析出生成物,通过减压过滤得到固体,再用甲醇洗涤得到化合物Ⅴ;
(5)在氮气条件下,取化合物Ⅴ、[1,1'-双(二苯基膦基)二茂铁]二氯化钯、化合物Ⅵ、四氢呋喃和二氧六环,搅拌反应,反应结束以后反应液冷却后用水和二氯甲烷分离有机层,有机层浓缩以后用己烷进行柱层析,得到的固体重结晶、甲醇洗涤得到化学式1所示的有机电致发光材料,其合成路线如下:
一种有机电致发光器件,包括第一电极、第二电极和设置于所述第一电极与第二电极之间的有机层;所述有机层包括化学式1所示的有机电致发光材料。
在上述技术方案中,所述有机层还包括由Ⅰ主族、Ⅱ主族、Ⅳ主族、Ⅴ主族转移金属、镧和d-转移元素中的一个以上的金属或其金属络合物。
上述有机层可以包括发光层和电子形成层。
另外,上述有机层是包含一个以上的上述有机电致材料以外还包含蓝色、红色或黄色发光化合物的有机发光层同时形成白色有机电致发光器件。
本发明的有机电致发光器件中至少安置一面电极中另一面内表面硫族化物(chalcogenide)、卤化金属层及金属氧化物层中选择的一层以上。
具体的说有机发光层的阳极表面硅、铝及硫族化物(chalcogenide)(包括氧化物)层,另外发光体层侧的阴极表面安置卤素金属层或金属氧化物。从这些实施得到驱动的稳定性。上述硅、铝及硫族化物理想实例是有SiOX(1≤X≤2),AlOX(1≤X≤1.5),SiON或SiAlON,卤化金属的理想实例是有LiF,MgF2,CaF2,氟化稀土类金属,金属氧化物的理想例是有Cs2O,Li2O,MgO,SrO,BaO,CaO。
另外,本发明的有机电致发光器件中,至少包括电子传输化合物、掺杂材料和空穴传输化合物中的一种或多种混合。
本发明的有益效果是:
本发明提供的有机电致发光材料具有高的电子传达效率,从而能够在制造器件时防止结晶,并能够很容易地形成层,由此改善了器件的电流特性。
本发明提供的有机电致发光材料的制备方法,原料易得,工艺简单,适合于工业化生产。
具体实施方式
为了详细理解本发明,对本发明的代表化合物举例说明及它的制造方法及说明器件的发光特性。
通过以下实施例具体说明本发明的有机电致发光器件用化合物及包含它的有机电致发光器件的制造方法。但这仅仅是举例而不是用于限定本发明的范围。
[合成例1]化合物1的合成
向反应容器里加1,2,3,6,7,8-六氢芘(10g,48mmol),N-溴代丁二酰亚胺(21.4g,120mmol),二氯甲烷250mL,乙腈250mL以后常温搅拌24小时。反应结束以后减压过滤得到固体,得到的固体用甲醇洗涤得到化合物1-1(12.3g,收率70%)。质谱为363,理论计算值为363.95。
在氮气条件下,向反应容器里加化合物1-17.25g(19.8mmol),二苯胺(7.37g,43.56mmol)及叔丁醇钠(3.2g,33.7mmol),用160mL甲醇溶解,滴加三(二亚苄基丙酮)双钯(0.454g,0.5mmol)和叔丁基膦(0.6g,1.49mmol),110℃条件下搅拌12小时。反应结束以后向反应物里加甲醇得到固体化合物,固体化合物过滤重新溶解在氯苯溶剂里。加活性炭和硫酸镁搅拌。溶剂过滤以后利用氯苯和甲醇重结晶得到化合物1-2(8.06g,收率75%),质谱为542,理论计算值为542.27。
向反应容器里加化合物1-2(15g,27.64mmol)、DDQ、甲苯350mL以后90℃条件下搅拌3小时。反应液冷却进行过滤以后,浓缩溶剂,用二氯甲烷重结晶化合物1(12.6g,收率85%),质谱为536,理论计算值为536.23。
按照化合物1的合成,将二苯胺替换成
[合成例2]化合物10的合成
向反应容器里加化合物1(23g,42.86mmol),N-溴代丁二酰亚胺(16.78g,94.3mmol),二氯甲烷(DCM)360mL,甲醇360mL以后常温搅拌24小时。反应结束以后析出的生成物通过减压过滤得到固体,再用甲醇溶剂洗涤得到化合物1-3(23.8g,收率80%),质谱为692,理论计算值为692.05。
在氮气条件下,向反应容器里加化合物1-3(20.0g,28.8mmol),[1,1'-双(二苯基膦基)二茂铁]二氯化钯(0.10g),环戊基溴化镁/四氢呋喃(1M,165mL),二氧六环(150mL)以后,90℃条件下搅拌12小时。反应液冷却以后用水和二氯甲烷分离有机层,有机层浓缩以后用己烷进行柱层析,得到的固体重结晶以后甲醇洗涤得到化合物10(7.75g,收率40%),质谱为672,理论计算值为672.35。
[合成例3]化合物18的合成
在氮气条件下,向反应容器里加邻氨基联苯(10.0g,59.1mmol)、1-溴-4-异丙基苯(11.77g,59.1mmol)、三(二亚苄基丙酮)二钯(0.1g),三叔丁基膦(15%,0.3g),叔丁醇钠(1.8g),甲苯(300mL)以后60℃条件下搅拌12小时。反应液冷却以后硅胶滤斗过滤,溶液浓缩以后二氯甲烷和己烷进行柱层析得到化合物F-18(11.50g,收率68%)。
化合物1-1(10.88g,29.7mmol),化合物F-1818.77g(65.34mmol)及叔丁醇钠(4.8g,50.55mmol)溶解在甲苯(350mL)以后,滴加三(二亚苄基丙酮)二钯(0.82g,0.75mmol)和三叔丁基膦(0.9g,2.24mmol)。反应液在氮气条件下与110℃条件下加热搅拌12小时。反应结束以后反应物加甲醇得到固体,固体过滤重新溶解在氯苯中以后,加活性炭和硫酸镁搅拌。溶液过滤以后重结晶得到目标化合物18-1(19.7g,收率85%)。质谱为778,理论计算值为778.43。
向反应容器里加化合物18-1(21.5g,27.64mmol)、2,3-二氯-5,6-二氰基-1,4-苯醌(7.53g,33.2mmol)、甲苯(500mL),以后90℃条件下加热3小时。反应液冷却以后硅胶滤斗过滤,浓缩溶剂用二氯甲烷和甲醇重结晶得到化合物18-2(19.2g,收率90%),质谱为773,理论计算值为773.02。
向反应容器里加化合物18-2(16.57g,21.43mmol)、N-溴代丁二酰亚胺(8.4g,47.1mmol)、二氯甲烷(360mL),甲醇(360mL)以后常温搅拌24小时。反应结束以后析出固体减压过滤得到固体物质,固体物质用甲醇洗涤得到化合物18-3(16.96g,收率85%),质谱为928,理论计算值为928.20。
在氮气条件下,向反应容器里加化合物18-3(20.0g,21.5mmol)、[1,1’-双(二苯基膦基)二茂铁]二氯化钯(2.0g)、溶解在四氢呋喃的异丙基溴化镁(1M,300mL)、二氧六环(300mL)以后,90℃条件下搅拌12小时。反应液冷却以后用水和二氯甲烷进行层分离以后浓缩有机层,得到的固体进行重结晶以后用甲醇洗涤得到化合物18(10.10g,收率55%),质谱为856,理论计算值为856.48。
[合成例4]化合物51的合成
向反应容器里加化合物1-3(22.4g,32.24mmol)、苯硼酸(8.64g,70.9mmol)、碳酸钾(6.7g,48.51mmol)以后溶解在1,4-二氧六环(670mL)里。油浴温度调节70~80℃以后,加四(三苯基膦)钯1.12g(0.98mmol)和水(67mL),在氮气条件下回流搅拌24小时。反应结束以后常温里冷却得到固体化物质。固体物质过滤以后加丙酮和水通过回流搅拌洗涤产物。用甲苯/丙酮重结晶得到化合物51(9.1g,41.33%),质谱为688,理论计算值为688.29。
[合成例5]化合物71的合成
在氮气条件下,向反应容器里加化合物1-3(13.7g,19.75mmol)、二苯胺(7.35g,43.5mmol)、甲苯(105mL)以后常温搅拌。加三(二亚苄基丙酮)二钯(0.75g,0.79mmol)、叔丁醇钠(2.85g,29.63mmol)、三叔丁基膦(0.77ml,1.58mmol),回流搅拌6小时。反应结束以后常温冷却,过滤固体。固体溶解二氯甲烷中以后过滤。过滤后的固体放到甲苯(175m)里加热溶解以后,常温冷却过滤固体,用柱层析(二氯甲烷:己烷=1:1)得到化合物71(13.94g,81%),质谱为870,理论计算值为870.37。
[合成例6-14]
化合物11的合成路线如下:
化合物75合成路线如下:
[合成例15]化合物92的合成
参照合成例1,中间体1-1的合成,加入1,2,3,6,7,8-六氢芘1.2倍量的N-溴代丁二酰亚胺,得到化合物92-1,参照中间体1-2及化合物1的合成,用相同的实验方法制备得到化合物92。
[其他化合物合成例]
参照合成例1-14的合成方法,合成化合物2-9、化合物12-17、化合物19-42、化合物44、化合物46、化合物47、化合物49、化合物50、化合物52-61、化合物65-70、化合物72-74、化合物76-84、化合物86-91。
有机电致发光器件的制备及评价
荧光蓝色掺杂
比较例1
下面化学式a表示的化合物a使用蓝色荧光主体,化学式b表示的化合物b使用蓝色荧光掺杂、2-TNATA(4,4',4”-三[2-萘基苯基氨基]三苯基胺)使用空穴注入物质、α-NPD(N,N'-二苯基-N,N'-(1-萘基)-1,1'-联苯-4,4'-二胺)使用空穴传输物质、制备下面结构的有机发光器件。ITO/2-TNATA(80nm)/α-NPD(30nm)/化合物a+化合物b(30nm)/Alq3(30nm)/LiF(0.5nm)/Al(60nm)。阳极是康宁(Corning)公司的15Ω/cm2 ITO玻璃基板切断50mmx 50mm x0.7mm大小以后丙酮、异丙醇、蒸馏水中各进行15分超音波洗涤,再进行30分UV臭氧洗涤以后使用。上述基板上蒸镀空穴注入层2-TANATA(80nm)、蒸镀空穴传输层α-NPD(30nm)、蒸镀发光层化学式a和化学式b(5%掺杂)(30nm)、蒸镀电子传输层Alq3(30nm)、蒸镀电子注入层LiF(0.5nm)、蒸镀阴极Al(60nm)。按表1的所示制备有机电致发光器件,这是比较样品1。
比较例2
比较例1的化学式b替代化学式c以外,其他步骤同比较例1同样的方法制备器件。
比较例3
比较例1的化学式b替代化学式d以外,用比较例1同样的方法制备器件。
比较例4
比较例1的化学式b替代化学式f以外,用比较例1同样的方法制备器件。
实施例1~20
上述比较例1中,发光层荧光掺杂化合物b替代上述合成例制备的化合物使用蓝色荧光掺杂以外,采用与上述比较例1同样的方法制备ITO/2-TNATA(80nm)/α-NPD(30nm)/[化合物a+蓝光荧光掺杂化合物中一个(5%)](30nm)/Alq3(30nm)/LiF(0.5nm)/Al(60nm)的有机电致发光器件,得样品1~20。
评价例1:比较样品1,2,3,4及样品1~20发光特性评价。
比较样品1~4及样品1~20使用Keithley sourcemeter“2400”,KONIKA MINOLTA“CS-2000”仪器评价发光亮度,发光效率,发光峰,评价结果见表1。上述示例发光峰蓝光448~463nm范围。
表1
上述表1结果能看出:本发明提供的有机电致发光材料制备的器件样品1~20跟比较样品1~4比较,具有更好的发光性能。
评价例2:比较样品1~4及示例1~20的寿命特性评价
比较样品1~4及示例1~20利用ENC technology公司的LTS-1004AC寿命测试装置3000nit为基准测试达到97%时间结果见表2。
表2
上述表2结果能看出:本发明提供的有机电致发光材料制备的器件样品1~20跟比较样品1~4比较,具有更好的发光性能。
显然,上述实施例仅仅是为清楚地说明所作的举例,而并非对实施方式的限定。对于所属领域的普通技术人员来说,在上述说明的基础上还可以做出其它不同形式的变化或变动。这里无需也无法对所有的实施方式予以穷举。而由此所引伸出的显而易见的变化或变动仍处于本发明创造的保护范围之中。
Claims (4)
2.权利要求1所述的有机电致发光材料的制备方法,其特征在于,包括以下步骤:
(1)取1,2,3,6,7,8-六氢芘、N-溴代丁二酰亚胺和乙腈、二氯甲烷,常温搅拌,反应结束以后减压过滤得到固体,得到的固体用甲醇洗涤得到化合物Ⅰ;
(2)在氮气条件下,取化合物Ⅰ、化合物Ⅱ及叔丁醇钠,用甲醇溶解,滴加三(二亚苄基丙酮)双钯和叔丁基膦,搅拌反应,反应结束以后向反应物里加甲醇得到固体化合物,固体化合物过滤重新溶解在氯苯里,加活性炭和硫酸镁,继续搅拌,过滤溶剂以后利用氯苯和甲醇重结晶得到化合物Ⅲ;
(3)取化合物Ⅲ、2,3-二氯-5,6-二氰基-1,4-苯醌,用甲苯溶解,搅拌反应,反应结束以后反应液冷却进行过滤,浓缩溶剂,用二氯甲烷重结晶得到化合物Ⅳ,其合成路线如下:
(4)取化合物Ⅳ、N-溴代丁二酰亚胺和二氯甲烷,用甲醇溶解以后,常温搅拌反应,反应结束以后析出生成物,通过减压过滤得到固体,再用甲醇洗涤得到化合物Ⅴ;
(5)在氮气条件下,取化合物Ⅴ、[1,1'-双(二苯基膦基)二茂铁]二氯化钯、化合物Ⅵ、四氢呋喃和二氧六环,搅拌反应,反应结束以后反应液冷却后用水和二氯甲烷分离有机层,有机层浓缩以后用己烷进行柱层析,得到的固体重结晶、甲醇洗涤得到化学式1所示的有机电致发光材料,其合成路线如下:
3.一种有机电致发光器件,包括第一电极、第二电极和设置于所述第一电极与第二电极之间的有机层;其特征在于,所述有机层包括权利要求1所示结构的有机电致发光材料。
4.根据权利要求3所述的有机电致发光器件,其特征在于,所述有机层还包括由Ⅰ主族、Ⅱ主族、Ⅳ主族、Ⅴ主族转移金属、镧和d-转移元素中的一个以上的金属或其金属络合物。
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