CN100334065C - Peropyrene compound, organic electroluminescent element and organic electroluminescent display - Google Patents
Peropyrene compound, organic electroluminescent element and organic electroluminescent display Download PDFInfo
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- CN100334065C CN100334065C CNB2003801022807A CN200380102280A CN100334065C CN 100334065 C CN100334065 C CN 100334065C CN B2003801022807 A CNB2003801022807 A CN B2003801022807A CN 200380102280 A CN200380102280 A CN 200380102280A CN 100334065 C CN100334065 C CN 100334065C
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- -1 Peropyrene compound Chemical class 0.000 title claims abstract description 87
- 239000000463 material Substances 0.000 claims abstract description 90
- 125000003118 aryl group Chemical group 0.000 claims abstract description 53
- 239000010409 thin film Substances 0.000 claims abstract description 47
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 claims description 102
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 claims description 57
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 39
- 229910052757 nitrogen Inorganic materials 0.000 claims description 38
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 27
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 26
- 239000010408 film Substances 0.000 claims description 23
- 150000001875 compounds Chemical class 0.000 claims description 16
- 239000011159 matrix material Substances 0.000 claims description 16
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 16
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 13
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 13
- 239000004305 biphenyl Substances 0.000 claims description 13
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 229910052760 oxygen Inorganic materials 0.000 claims description 13
- 239000001301 oxygen Substances 0.000 claims description 13
- 235000010290 biphenyl Nutrition 0.000 claims description 12
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 claims description 12
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 11
- 229910052782 aluminium Inorganic materials 0.000 claims description 11
- 238000009833 condensation Methods 0.000 claims description 11
- 230000005494 condensation Effects 0.000 claims description 11
- 239000004411 aluminium Substances 0.000 claims description 10
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 150000004982 aromatic amines Chemical class 0.000 claims description 6
- 238000005401 electroluminescence Methods 0.000 claims description 3
- 125000000609 carbazolyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 abstract description 16
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 4
- 238000004020 luminiscence type Methods 0.000 abstract description 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 150000002431 hydrogen Chemical class 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 241
- 238000000034 method Methods 0.000 description 108
- 238000000151 deposition Methods 0.000 description 27
- 239000002585 base Substances 0.000 description 24
- NPDIDUXTRAITDE-UHFFFAOYSA-N 1-methyl-3-phenylbenzene Chemical group CC1=CC=CC(C=2C=CC=CC=2)=C1 NPDIDUXTRAITDE-UHFFFAOYSA-N 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 15
- 238000001704 evaporation Methods 0.000 description 15
- 230000008020 evaporation Effects 0.000 description 15
- 238000002347 injection Methods 0.000 description 15
- 239000007924 injection Substances 0.000 description 15
- 230000000903 blocking effect Effects 0.000 description 14
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 14
- 238000004544 sputter deposition Methods 0.000 description 14
- 229910001148 Al-Li alloy Inorganic materials 0.000 description 13
- 239000011521 glass Substances 0.000 description 12
- 229910052751 metal Inorganic materials 0.000 description 12
- 239000002184 metal Substances 0.000 description 12
- 239000012530 fluid Substances 0.000 description 10
- 230000005284 excitation Effects 0.000 description 9
- 239000000758 substrate Substances 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 8
- 238000010023 transfer printing Methods 0.000 description 8
- 230000032258 transport Effects 0.000 description 8
- 238000006116 polymerization reaction Methods 0.000 description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 6
- 229910045601 alloy Inorganic materials 0.000 description 6
- 239000000956 alloy Substances 0.000 description 6
- 238000000576 coating method Methods 0.000 description 6
- 229910044991 metal oxide Inorganic materials 0.000 description 6
- 150000004706 metal oxides Chemical class 0.000 description 6
- 239000011241 protective layer Substances 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000011248 coating agent Substances 0.000 description 5
- 230000002349 favourable effect Effects 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 238000012546 transfer Methods 0.000 description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000005229 chemical vapour deposition Methods 0.000 description 4
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 238000002061 vacuum sublimation Methods 0.000 description 4
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 230000005684 electric field Effects 0.000 description 3
- 229910052737 gold Inorganic materials 0.000 description 3
- 239000010931 gold Substances 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 150000004866 oxadiazoles Chemical class 0.000 description 3
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 3
- 239000007774 positive electrode material Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
- 239000002356 single layer Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 150000003852 triazoles Chemical class 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 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 2
- SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- NSMJMUQZRGZMQC-UHFFFAOYSA-N 2-naphthalen-1-yl-1H-imidazo[4,5-f][1,10]phenanthroline Chemical compound C12=CC=CN=C2C2=NC=CC=C2C2=C1NC(C=1C3=CC=CC=C3C=CC=1)=N2 NSMJMUQZRGZMQC-UHFFFAOYSA-N 0.000 description 2
- TWPMMLHBHPYSMT-UHFFFAOYSA-N 3-methyl-n-phenylaniline Chemical compound CC1=CC=CC(NC=2C=CC=CC=2)=C1 TWPMMLHBHPYSMT-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 229910001316 Ag alloy Inorganic materials 0.000 description 2
- 229910000838 Al alloy Inorganic materials 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- 230000010748 Photoabsorption Effects 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- JFBZPFYRPYOZCQ-UHFFFAOYSA-N [Li].[Al] Chemical compound [Li].[Al] JFBZPFYRPYOZCQ-UHFFFAOYSA-N 0.000 description 2
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 2
- CUFNKYGDVFVPHO-UHFFFAOYSA-N azulene Chemical compound C1=CC=CC2=CC=CC2=C1 CUFNKYGDVFVPHO-UHFFFAOYSA-N 0.000 description 2
- 230000004888 barrier function Effects 0.000 description 2
- 125000006267 biphenyl group Chemical group 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 238000010276 construction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- QDGONURINHVBEW-UHFFFAOYSA-N dichlorodifluoroethylene Chemical group FC(F)=C(Cl)Cl QDGONURINHVBEW-UHFFFAOYSA-N 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000007429 general method Methods 0.000 description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 230000002140 halogenating effect Effects 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229910052738 indium Inorganic materials 0.000 description 2
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 2
- 239000011133 lead Substances 0.000 description 2
- 230000031700 light absorption Effects 0.000 description 2
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
- 229920000767 polyaniline Polymers 0.000 description 2
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- 239000002244 precipitate Substances 0.000 description 2
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- 125000004076 pyridyl group Chemical group 0.000 description 2
- 125000005493 quinolyl group Chemical group 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Chemical compound [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 2
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- 238000003756 stirring Methods 0.000 description 2
- ZGNPLWZYVAFUNZ-UHFFFAOYSA-N tert-butylphosphane Chemical compound CC(C)(C)P ZGNPLWZYVAFUNZ-UHFFFAOYSA-N 0.000 description 2
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- 125000001544 thienyl group Chemical group 0.000 description 2
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- 238000007738 vacuum evaporation Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- UWRZIZXBOLBCON-VOTSOKGWSA-N (e)-2-phenylethenamine Chemical compound N\C=C\C1=CC=CC=C1 UWRZIZXBOLBCON-VOTSOKGWSA-N 0.000 description 1
- VERMWGQSKPXSPZ-BUHFOSPRSA-N 1-[(e)-2-phenylethenyl]anthracene Chemical compound C=1C=CC2=CC3=CC=CC=C3C=C2C=1\C=C\C1=CC=CC=C1 VERMWGQSKPXSPZ-BUHFOSPRSA-N 0.000 description 1
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- DIVZFUBWFAOMCW-UHFFFAOYSA-N 4-n-(3-methylphenyl)-1-n,1-n-bis[4-(n-(3-methylphenyl)anilino)phenyl]-4-n-phenylbenzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 DIVZFUBWFAOMCW-UHFFFAOYSA-N 0.000 description 1
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- NSIKFNOYIGGILA-UHFFFAOYSA-N [Na].[Na].[K] Chemical compound [Na].[Na].[K] NSIKFNOYIGGILA-UHFFFAOYSA-N 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 229940111121 antirheumatic drug quinolines Drugs 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 125000003828 azulenyl group Chemical group 0.000 description 1
- 229910052728 basic metal Inorganic materials 0.000 description 1
- 150000003818 basic metals Chemical class 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 150000001716 carbazoles Chemical class 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- UUAGAQFQZIEFAH-UHFFFAOYSA-N chlorotrifluoroethylene Chemical group FC(F)=C(F)Cl UUAGAQFQZIEFAH-UHFFFAOYSA-N 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 125000000490 cinnamyl group Chemical group C(C=CC1=CC=CC=C1)* 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- OMZSGWSJDCOLKM-UHFFFAOYSA-N copper(II) sulfide Chemical compound [S-2].[Cu+2] OMZSGWSJDCOLKM-UHFFFAOYSA-N 0.000 description 1
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 1
- 125000002592 cumenyl group Chemical group C1(=C(C=CC=C1)*)C(C)C 0.000 description 1
- 229940045803 cuprous chloride Drugs 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000005281 excited state Effects 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
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000006206 glycosylation reaction Methods 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- 229920006270 hydrocarbon resin Polymers 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- MRNHPUHPBOKKQT-UHFFFAOYSA-N indium;tin;hydrate Chemical compound O.[In].[Sn] MRNHPUHPBOKKQT-UHFFFAOYSA-N 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000011229 interlayer Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000001182 laser chemical vapour deposition Methods 0.000 description 1
- 229910052745 lead Inorganic materials 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 239000010808 liquid waste Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Inorganic materials [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 229910001512 metal fluoride Inorganic materials 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002941 palladium compounds Chemical class 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 229920006287 phenoxy resin Polymers 0.000 description 1
- 239000013034 phenoxy resin Substances 0.000 description 1
- 238000005240 physical vapour deposition Methods 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 238000005268 plasma chemical vapour deposition Methods 0.000 description 1
- 238000009832 plasma treatment Methods 0.000 description 1
- 229920002493 poly(chlorotrifluoroethylene) Polymers 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 239000005023 polychlorotrifluoroethylene (PCTFE) polymer Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920006380 polyphenylene oxide Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 description 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 239000010944 silver (metal) Substances 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 238000003980 solgel method Methods 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- FJGIHZCEZAZPSP-UHFFFAOYSA-N tetrahedrane Chemical compound C12C3C1C32 FJGIHZCEZAZPSP-UHFFFAOYSA-N 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Images
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- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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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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- H10K85/00—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
- H10K85/624—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing six or more rings
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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
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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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
- H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
- H10K59/10—OLED displays
- H10K59/12—Active-matrix OLED [AMOLED] displays
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- H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
- H10K59/10—OLED displays
- H10K59/17—Passive-matrix OLED displays
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- H10K85/324—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising aluminium, e.g. Alq3
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- Luminescent Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
An organic EL element which is excellent in the luminescent efficiency, luminance, color purity, etc. of red luminescence. The organic EL element comprises a positive electrode, a negative electrode, and an organic thin film layer interposed therebetween, wherein the organic thin film layer contains as a luminescent material a peropyrene compound represented by the following structural formula (1): Structural formula (1) wherein R<1>, R<6>, R<8>, and R<13> may be the same or different and each represents a group represented by the following structural formula (2); and R<2> to R<5>, R<7>, R<9> to R<12>, and R<14> each represents hydrogen or a substituent. Structural formula (2) In the structural formula (2), R<15> and R<16> may be the same or different and each represents hydrogen, alkyl, or aryl, provided that R<15> and R<16> may be connected to each other directly or indirectly.
Description
Technical field
The present invention relates to be suitable for Er Ben Bing perylene compound, the organic EL that uses this Er Ben Bing perylene compound and the OLED display that has adopted this organic EL used as luminescent material in organic electroluminescent (below, the be abbreviated as EL) element.
Background technology
Organic EL has characteristics such as luminous and high-speed responsive, and people wait in expectation and are applied in flat-panel monitor.Particularly since reported with since the organic film (hole transfer layer) of hole conveying property and stacked two stratotypes (cascade type) product of the organic film (electron supplying layer) of electron transport (for example referring to C.W.Tang and S.A.VanSlyke " Applied Physics communication " 51 volumes, 913 (1987)), people's care concentrates on the large area light emitting element luminous under the following low voltage of 10V.The organic EL of cascade type, as basic structure, wherein luminescent layer also can make above-mentioned hole transfer layer or above-mentioned electron supplying layer have this function concurrently as the situation in above-mentioned two stratotypes with positive pole/hole transfer layer/luminescent layer/electron supplying layer/negative pole.
Organic EL waits in expectation recently and uses in full-color display.In this full-color display, must will show blue (B), green (G), the luminous line of pixels of red (R) three primary colors is listed on the display panel, as its arrangement mode, have (a) that be suggested will show blue (B), green (G), the method that red (R) three kinds of luminous organic ELs of all kinds are arranged, (b) will be from display white light (blue (B), green (G), the colour mixture of the light of red (R)) the illuminating colour filter in the organic EL is separated into trichromatic method, and (c) utilizes the colour switching layer that sends fluorescence will show that the light that the organic EL of blue-light-emitting sends is transformed into green (G), red (R) look luminous method.
On the other hand, viewpoint from the organic EL that obtains high-luminous-efficiency, someone proposes in the material of main part as main raw, the strong pigment molecular of a small amount of fluorescence radiation that mixes is as guest materials, form the luminescent layer (for example referring to C.W.Tang, S.A.VanSlyke and C.H.Chen " applicating physical magazine " 65 volumes, 3610 (1989)) that shows high-luminous-efficiency.
But the past does not provide the organic EL that shows high-luminous-efficiency, particularly fully do not provide the organic EL (for example opening the 2000-231987 communique) that shows emitting red light, so a kind of high performance organic EL of novelty is developed in people's expectation referring to the spy.
Summary of the invention
The present invention is for solving problem in the past, and problem is to reach following purpose.The object of the invention is to provide all good organic EL of luminous efficiency, luminosity and the colour purity etc. of a kind of Er Ben Bing perylene compound that is suitable for using as red illuminating material in the organic EL, red light and the high performance OLED display that adopts this organic EL.
In order to solve above-mentioned problem, the result of processes such as inventor further investigation has following discovery.Be that specific Er Ben Bing perylene compound is suitable for using as the red illuminating material in the organic EL, use organic EL and the OLED display of this Er Ben Bing perylene compound as luminescent material, the luminous efficiency of red light, luminosity and colour purity etc. are all good, the performance height is compared the performance height with existing product.
Organic EL of the present invention has organic thin film layer between positive pole and negative pole, this organic thin film layer contains two benzene of useful following structural formula (1) expression and perylene compound as luminescent material.
Wherein, in said structure formula (1), R
1, R
6, R
8And R
13Can be identical or different mutually, the group that expression is represented with following structural formula (2).R
2～R
5, R
7, R
9～R
12And R
14Expression hydrogen atom or substituting group.
In said structure formula (2), R
15And R
16Can be identical or different mutually, expression hydrogen atom, alkyl or aryl.And R
15And R
16Can directly or indirectly connect mutually.
Organic EL of the present invention is owing to contain above-mentioned specific Er Ben Bing perylene compound as luminescent material, so the luminous efficiency of red light, luminosity and colour purity etc. are all good.
Er Ben Bing perylene compound of the present invention is with following structural formula (1) expression.
In said structure formula (1), R
1, R
6, R
8And R
13Can be identical or different mutually, group, R that expression is represented with following structural formula (2)
2～R
5, R
7, R
9～R
12And R
14Expression hydrogen atom or substituting group.
In said structure formula (2), R
15And R
16Can be identical or different mutually, expression hydrogen atom, alkyl or aryl.And R
15And R
16Can directly or indirectly connect mutually.
If Er Ben Bing perylene compound of the present invention as the luminescent material in the organic EL, then can be shown all good emitting red lights such as luminous efficiency, luminosity and colour purity.
OLED display of the present invention adopts organic EL of the present invention.OLED display of the present invention, owing to adopted organic EL of the present invention, so the luminous efficiency of emitting red light, luminosity and colour purity etc. are all good.
Description of drawings
Fig. 1 is the schematic illustration of the layer structure one routine usefulness in the explanation organic EL of the present invention.
Fig. 2 is the schematic illustration that a kind of structure example of explanation passive matrix mode OLED display (passive matrix display panel) is used.
Fig. 3 is the diagrammatic illustration figure that a kind of practical circuit is used in the explanation passive matrix mode OLED display (passive matrix display panel) shown in Figure 2.
Fig. 4 is the schematic illustration that a kind of structure example of explanation active matrix mode OLED display (active matrix panel) is used.
Fig. 5 is the diagrammatic illustration figure that a kind of practical circuit is used in the explanation active matrix mode OLED display (active matrix panel) shown in Figure 4.
Fig. 6 be synthesized 1,3,8, the IR spectrum record diagram of 10-four [N-phenyl-1-naphthyl amino] Er Ben Bing perylene.
Embodiment
＜Er Ben Bing perylene compound 〉
Er Ben Bing perylene compound of the present invention is with following structural formula (1) expression.
In said structure formula (1), R
1, R
6, R
8And R
13Can be identical or different mutually, the group that expression is represented with following structural formula (2).R
2～R
5, R
7, R
9～R
12And R
14Expression hydrogen atom or substituting group described later.
In said structure formula (2), R
15And R
16Can be identical or different mutually, expression hydrogen atom, alkyl or aryl.This alkyl or aryl also can be replaced by substituting group described later.
Be not particularly limited as above-mentioned substituting group, can suitably select according to purpose, for example can enumerate alkyl, aryl etc., these can also be substituted base and replace.Be not particularly limited as this substituting group, can in known substituting group, suitably select according to purpose.
Be not particularly limited as abovementioned alkyl, can suitably select according to purpose, for example can suitably enumerate straight chain, side chain or the cyclic alkyl of 1～10 carbonatoms, specifically can suitably enumerate methyl, ethyl, propyl group, sec.-propyl, butyl, isobutyl-, tertiary butyl, amyl group, isopentyl, hexyl, isohexyl, heptyl, different heptyl, octyl group, iso-octyl, nonyl, different nonyl, decyl, isodecyl, cyclopentyl, cyclobutyl, cyclopentyl, cyclohexyl, suberyl, ring octyl group, ring nonyl, ring decyl etc.
Be not particularly limited as above-mentioned aryl, can suitably select according to purpose, for example can enumerate monocyclic aryl, by the group of four following aromatic ring be combined intos, have the following condensation aromatic ring in five rings and carbon, oxygen, nitrogen and the group of sulphur atom sum below 50 etc.
Be not particularly limited as this monocyclic aryl, can suitably select according to purpose, for example suitably can enumerate phenyl, tolyl, xylyl, cumenyl, styryl, Lai Ji, cinnamyl, styroyl, diphenyl-methyl etc., these also can be substituted base and replace.
There is no particular restriction as the group of Fourth Ring below in conjunction with one-tenth for this aromatic ring, can suitably select according to purpose, for example can enumerate naphthyl, anthryl, phenanthryl, indenyl, Azulene base (azulenyl), benzo anthryl etc., and these also can be substituted base and replace.
Add up to group below 30 there is no particular restriction for having the following condensation aromatic ring in five rings and carbon, oxygen, nitrogen and sulphur atom, can suitably select according to purpose, for example can enumerate pyrryl, furyl, thienyl, pyridyl (ピ リ ジ Le), quinolyl, isoquinolyl, imidazolyl, pyridyl (ピ リ ジ ニ Le), pyrrolopyridinyl, thiazolyl, pyrimidyl, thienyl, indyl, quinolyl (キ ノ リ ニ Le), pyranyl, adenosyl etc., these also can be substituted base and replace.
And R
15And R
16Can directly or indirectly connect mutually.Under situation about connecting indirectly, also can be interconnection by means of at least one atom of from boron, carbon, nitrogen, oxygen, silicon, p and s, selecting.
R among the present invention in the said structure formula (1)
1, R
6, R
8And R
13(with the group of above-mentioned structural formula (2) expression) preferably uses the group that any structure formula is represented in following structural formula (3), following structural formula (4) and the following structural formula (5).
R in the said structure formula (1)
1, R
6, R
8And R
13(with the group of above-mentioned structural formula (2) expression) is that described two benzene and perylene compound are 1,3,8,10-four (N, N-diphenyl amino) two benzene and perylene under the situation by the group of following structural formula (3) expression; R
1, R
6, R
8And R
13Be that described Er Ben Bing perylene compound is 1,3,8,10-four [N-phenyl-1-naphthyl amino] Er Ben Bing perylene under the situation by the group of following structural formula (4) expression; R
1, R
6, R
8And R
13Be that described Er Ben Bing perylene compound is 1,3,8,10-four [4,4 '-two (α, α-Er Jiajibianji) diphenyl amino] Er Ben Bing perylene under the situation by the group of following structural formula (5) expression.
In said structure formula (3), R
17And R
18Can be identical or different mutually, expression hydrogen atom, alkyl or aryl.Wherein as abovementioned alkyl or above-mentioned aryl, can enumerate above-mentioned those.
In said structure formula (4), R
19, R
20And R
21Can be identical or different mutually, expression hydrogen atom, alkyl or aryl.Wherein as abovementioned alkyl or above-mentioned aryl, can enumerate above-mentioned those.
In said structure formula (5), R
22, R
23, R
24And R
25Can be identical or different mutually, expression hydrogen atom, alkyl or aryl.Wherein as abovementioned alkyl or above-mentioned aryl, can enumerate above-mentioned those.
There is no particular restriction for the manufacture method of Er Ben Bing perylene compound of the present invention, can in currently known methods, suitably select according to purpose, for example can suitably enumerate " Bericht " 76 volumes 458 pages (1943) and " chemistry can will " 2013 pages (1949) and wait the method for upward putting down in writing.Promptly, at first perinaphthene ketone (ペ リ Na Off テ ノ Application) is mixed in pyridine with zinc powder, stir, reflux and under stream of nitrogen gas with behind 0 milliliter of 80% acetate of 5 hours Dropwise 5s, filtering precipitate, utilize the vacuum-sublimation device to make its dehydration distillation, obtain unsubstituted Er Ben Bing perylene.Halogenating reaction by this Er Ben Bing perylene then, synthesis example be as 1,3,8,10-four halogenated diphenyl Bing perylenes.
As the method for above-mentioned halide reaction, can suitably enumerate as " Annalen der chemie " 531 volumes and go up record for 81 pages, add the method for the halogen of four times of amounts in the 1 equivalent Er Ben Bing perylene in being dissolved in solvent.As described halogen, though chlorine, bromine, iodine etc. are favourable in the next stage reaction, the viewpoint of carrying out easily from halogenating reaction, wherein especially preferably chlorine and bromine.Then in the presence of catalyzer and alkali, by to 1,3,8,10-four halogenated diphenyl Bing perylenes and for example corresponding with required compound secondary amine heating make it reaction, can obtain required 1,3,8,10-four substituted diphenylamine Bing perylene compounds.
As described catalyzer, can use copper and even inhibition and generation compounds such as copper powder, cuprous chloride, copper sulfate, and palladium compound etc.And, can use the alkoxide of sodium such as yellow soda ash, salt of wormwood, sodium hydroxide, tert.-butoxy sodium etc. as described alkali.
Utilize above general method to make 1,3,8, under the situation of 10-four (3-methyldiphenyl base amino) Er Ben Bing perylene, at first obtain 1,3,8 by Er Ben Bing perylene and bromine reaction, the 10-tetrabromo is for Er Ben Bing perylene compound.Go up the method for record according to " Tetrahedran Letters " 39 volumes 2367 pages (1998) then, promptly, can carry out 1,3,8, the ammonia diaryl glycosylation reaction of 10-tetrabromo generation two benzene and perylene with the general method of the synthetic triarylamine of halogenated aryl.With respect to 1,3,8, the 10-tetrabromo is for Er Ben Bing perylene, add the 3-methyldiphenyl base amine of four times of amounts, tert.-butoxy sodium, 0.1% normal acid chloride and 0.4% normal three (tertiary butyl) phosphine of four times of amounts, make solvent, under 130 ℃ of temperature, make its reaction 3 hours with o-Xylol.Then after the cooling, reaction solution washes with water for several times, and above-mentioned o-Xylol is removed in distillation, remaining oily matter with methanol wash after, make resultant of reaction recrystallize in THF-methyl alcohol, obtained thick resultant.And then after utilizing the vacuum-sublimation method that above-mentioned thick resultant is made with extra care, can access purpose 1,3,8,10-four (3-methyldiphenyl base amino) two benzene and perylene.
Er Ben Bing perylene compound of the present invention can suitably use in various fields, is suitable for using as fluorescent material, is particularly suitable for using as the luminescent material in the organic EL.Wherein, in case use Er Ben Bing perylene compound of the present invention, just can obtain emitting red light as the luminescent material in the organic EL.
＜organic EL 〉
Organic EL of the present invention has organic thin film layer between positive pole and negative pole, this organic thin film layer contains the Er Ben Bing perylene compound of the invention described above, i.e. the Er Ben Bing perylene compound of said structure formula (1) expression is as luminescent material.
Wherein as mentioned above, the R in the said structure formula (1)
1, R
6, R
8And R
13(with the group of above-mentioned structural formula (2) expression) preferably uses the group that the arbitrary structures formula is represented in following structural formula (3), following structural formula (4) and the following structural formula (5).
Among the present invention,, the luminescent layer in this organic thin film layer was contained, luminescent layer electron supplying layer, the luminescent layer hole transporting layer etc. of holding concurrently of holding concurrently is contained though above-mentioned organic thin film layer contains above-mentioned two benzene and perylene compound as luminescent material.Above-mentioned luminescent layer is contained under the situation of above-mentioned Er Ben Bing perylene compound, and this luminescent layer both can be made film separately with this Er Ben Bing perylene compound and form, and also can contain other materials and form except that this Er Ben Bing perylene compound.
Among the present invention, luminescent layer in the above-mentioned organic thin film layer, luminescent layer electron supplying layer, the luminescent layer hole transporting layer etc. of holding concurrently of holding concurrently contains Er Ben Bing perylene compound of the present invention as guest materials, except that this guest materials, preferably further contain near the material of main part of light absorption wavelength that emission wavelength is in this guest materials.In addition, though described material of main part preferably contains in described luminescent layer, also can in hole transporting layer, electron supplying layer etc., contain.
And under the situation with above-mentioned guest materials and material of main part, when making organic EL luminous, described material of main part at first is excited.And since the absorbing wavelength of the emission wavelength of this material of main part and above-mentioned guest materials (Er Ben Bing perylene compound) (330～600nm) overlap, so excitation energy will move to this guest materials from this material of main part efficiently, do not make this material of main part luminous and return ground state, only there is this guest materials that becomes excited state that excitation energy is emitted with the form of red light, so the luminous efficiency of red light, luminosity and colour purity are all good.
And the general Individual existence or with under the dense situation about existing of height in film of light emitting molecule, because of interacting, produce the phenomenon that the luminous efficiency of so-called " concentration delustring " reduces between the light emitting molecule near between light emitting molecule, producing.And under the situation with above-mentioned guest materials and aforementioned body material, it itself is the above-mentioned Er Ben Bing perylene compound of above-mentioned guest materials, owing in the aforementioned body compound, disperse with low concentration, so can suppress above-mentioned " concentration delustring " effectively, be favourable from the good this point of luminous efficiency.In addition, under the situation in above-mentioned luminescent layer and with above-mentioned guest materials and aforementioned body material, because described material of main part system film is generally good, so also be favourable from the also good this point of maintenance characteristics of luminescence time system film.
There is no particular restriction for the aforementioned body material, can suitably select according to purpose, but preferred emission wavelength is near the light absorption wavelength of this material of main part, for example can suitably enumerate aryl amine derivatives by following structural formula (6) expression, the carbazole derivative of following structural formula (8) expression, the hydroxyquinoline complex compound of following structural formula (10) expression, 1 of following structural formula (12) expression, 3,6,8-tetraphenyl pyrene compound, 4 of following structural formula (14) expression, 4 '-two (2,2 '-diphenylacetylene)-1,1 '-biphenyl (DPVBi) (the main light emission wavelength=470nm), following structural formula (15) expression to six biphenyl (main light emission wavelength=400nm) and following structural formula (16) represent 9,9 '-dianthranide (main light emission wavelength=460nm) etc.
In the said structure formula (6), n represents 2～4 integer.Ar represents the aromatic group or the heterocyclic aromatic group of 2～4 valencys.R
30And R
31Can be identical or different mutually, expression univalent aryl or heterocyclic aryl.Be not particularly limited as above-mentioned univalent aryl or heterocyclic aryl, can suitably select according to purpose.
In the aryl amine derivatives of said structure formula (6) expression, preferably by the N of following structural formula (7) expression, N '-dinaphthyl-N, N '-phenylbenzene-[1,1 '-xenyl]-4,4 '-diamines (main light emission wavelength=430nm) and derivative thereof.
In the said structure formula (8), n represents 2～4 integer.Ar represents 2～4 valency groups that contain aromatic ring shown below, perhaps contains 2～4 valency groups of heterocyclic aryl.
These groups also can be replaced by non-conjugated property group, and R represents linking group, for example can suitably enumerate following group.
In the said structure formula (8), R
32And R
33Independent separately; expression hydrogen atom, halogen atom, alkyl, aralkyl, alkenyl, aryl, cyano group, amino, acyl group, carbalkoxy, carboxyl, alkoxyl group, alkyl sulphonyl, hydroxyl, amide group, aryloxy, aromatic ring alkyl or aromatic heterocyclic group, these groups can also be substituted base and further replace.
In the said structure formula (8), n represents integer, can suitably enumerate 2～4.
In the aryl amine derivatives by said structure formula (8) expression, Ar is connected aryl on the phenyl ring, R by means of singly-bound two
32And R
33Be hydrogen atom and n=2, promptly from 4 of following structural formula (9) expression, 4 '-two (9-carbazyl)-biphenyl (CBP) (main light emission wavelength=380nm) and the compound of selecting in the derivative thereof, preferred especially from the viewpoint that luminous efficiency, luminous intensity and the colour purity etc. of red light are good especially.
In said structure formula (10), M represents trivalent metal, R
34Expression hydrogen atom or alkyl.In the hydroxyquinoline complex compound of said structure formula (10) expression, preferably by the hydroxyquinoline aluminium complex (Alq) of following structural formula (11) expression (main light emission wavelength=530nm).
In said structure formula (12), R
21～R
24Can be identical or different mutually, expression hydrogen atom or substituting group.As this substituting group, for example can suitably enumerate alkyl, cycloalkyl or aryl, these groups also can be substituted base and replace.
By 1,3,6 of said structure formula (12) expression, in the 8-tetraphenyl Er Ben Bing perylene compound, R
21～R
24Be hydrogen atom, promptly by 1,3,6 of following structural formula (13) expression, 8-tetraphenyl Er Ben Bing perylene (the main light emission wavelength=440nm), preferred from the viewpoint that luminous efficiency, luminosity and the colour purity etc. of red light are good especially.
9,9 '-dianthranide
Contain the content of this Er Ben Bing perylene compound in the layer of Er Ben Bing perylene compound of described structural formula (1) expression, be preferably 0.1～50 weight %, more preferably 0.5～20 weight %.。
In a single day described content be lower than 0.1 weight %, and luminous efficiency, luminosity and colour purity etc. are often insufficient, and in case above 50 weight %, colour purity will reduce.On the other hand, if be in the above-mentioned more preferably scope, then preferred from good viewpoint such as luminous efficiency, luminosity and colour purity.
Described luminescent layer in the organic EL of the present invention, can be when applying electric field from described positive pole, injected hole such as hole injection layer and described hole transporting layer, from described negative pole, electron injecting layer and described electron supplying layer etc. inject electronics, and then provide this hole and this electronics bonded place again, by this again in conjunction with the time produce again in conjunction with energy, can have and to make the above-mentioned Er Ben Bing perylene compound (luminescent material that shows emitting red light, light emitting molecule) luminous function, except that this two benzene and perylene compound, can also contain other luminescent materials in the scope that does not hinder this emitting red light.
Above-mentioned luminescent layer can adopt known method to form, and for example can use vapour deposition method, film by wet method, MBE (molecular line extension) method, ionic fluid method, molecule layered manner, LB method, printing, transfer printing etc. suitably to form.
In these methods, though never with an organic solvent there is not low, the simple efficient viewpoint of making of liquid waste disposal problem, the cost preferred vapour deposition method that sets out, but be provided with single layer structure under the situation of above-mentioned luminescent layer, for example form under the situation of this luminescent layer also preferred film by wet method with the hole transporting layer luminescent layer form such as electron supplying layer of holding concurrently of holding concurrently.
There is no particular restriction for above-mentioned vapour deposition method, can suitably select from known method according to purpose, for example can enumerate vacuum vapour deposition, resistive heating vapour deposition method, chemical vapor deposition method, physical vapor deposition etc.Described chemical vapor deposition method for example can be enumerated plasma CVD method, laser CVD method, hot CVD method, source of the gas CVD method etc.Utilize the formation of the above-mentioned luminescent layer of above-mentioned vapour deposition method, for example by the above-mentioned Er Ben of vacuum evaporation Bing perylene compound, this luminescent layer contains under the situation of aforementioned body material except that above-mentioned Er Ben Bing perylene compound, by can suitably carrying out with vacuum evaporation while this Er Ben Bing perylene compound of evaporation and this material of main part.Under the former situation, from the easy manufacturing of the viewpoint that needn't be total to evaporation.
There is no particular restriction for above-mentioned film by wet method, can from known method, suitably select according to purpose, for example can enumerate that ink jet method, method of spin coating, kneader coating method, rod are coated with method (バ one コ one foretells), cutter is coated with method, teeming practice, dip coating, curtain Tu Fa etc.
Under the situation of above-mentioned film by wet method, can use the solution (coating etc.) that dissolves together and even disperse above-mentioned luminescent layer material and resinous principle, this resinous principle for example can be enumerated Polyvinyl carbazole, polycarbonate, polyvinyl chloride, polystyrene, polymethylmethacrylate, polyester, polysulfones, polyphenylene oxides, polyhutadiene, hydrocarbon resin, ketone resin, phenoxy resin, polymeric amide, ethyl cellulose, vinyl acetate, ABS resin, urethane, melamine resin, unsaturated polyester resin, Synolac, Resins, epoxy, silicone resin etc.
Formation with the above-mentioned luminescent layer of above-mentioned film by wet method, for example use the solution (coating fluid) (coating, drying) that the above-mentioned resin material of above-mentioned Er Ben Bing perylene compound and use is in case of necessity made in solvent, when this luminescent layer contains under the situation of aforementioned body material outside above-mentioned Er Ben Bing perylene compound, use is dissolved in solution (coating fluid) (coating, drying) in the solvent with this Er Ben Bing perylene compound, this material of main part and the above-mentioned resin material that uses in case of necessity, can suitably carry out.
Preferred 1～50 nanometer of the thickness of above-mentioned luminescent layer, more preferably 3～20 nanometers.
The thickness of above-mentioned luminescent layer, in case be in the above-mentioned preferable range, because this organic EL can make luminous efficiency, luminosity and the colour purity etc. of luminous red light abundant, if be in the above-mentioned more preferably numerical range, will be more remarkable but favourable because of above-mentioned advantage then.
Organic EL of the present invention has the organic thin film layer that comprises luminescent layer between positive pole and negative pole, can also have other layers such as protective layer as required.
Above-mentioned organic thin film layer has above-mentioned luminescent layer at least, and in case of necessity hole injection layer can also be arranged, hole transporting layer, hole blocking layer, electron supplying layer etc.
-anodal-
There is no particular restriction as above-mentioned positive pole, can suitably select as required, but preferably to this organic thin film layer, working as above-mentioned organic thin film layer particularly only has under the situation of above-mentioned luminescent layer, this organic thin film layer also has under the situation of above-mentioned hole transporting layer, this organic thin film layer further has under the situation of above-mentioned hole injection layer, can be respectively to the electrode of this luminescent layer with this hole transporting layer and this hole injection layer supply hole (current carrier).
There is no particular restriction as above-mentioned positive electrode material, can suitably select as required, for example can enumerate metal, alloy, metal oxide, electric conductivity compound and composition thereof etc., and preferred work function is in the above material of 4eV in these materials.
Specific examples as above-mentioned positive electrode material, can enumerate stannic oxide, zinc oxide, Indium sesquioxide, tin indium oxide conductive metal oxides such as (ITO), metals such as gold and silver, chromium, nickel, the mixture of these metals and conductive metal oxide or sandwich, inorganic conductive such as cupric iodide, cupric sulfide material, sandwich of organic conductive material such as polyaniline, Polythiophene, polypyrrole and these materials and ITO etc.These materials can be used alone or two or more and usefulness.In these materials, preferred conductive metal oxide is from the preferred especially ITO of viewpoints such as productivity, high conductivity and the transparency.
Be not particularly limited for above-mentioned anodal thickness, can suitably select according to material etc., but preferred 1～5000 nanometer, more preferably 20～2000 nanometers.
Above-mentioned positive pole forms on substrates such as glass such as soda glass, non-alkali glass, transparent resin usually.
Use under the situation of above-mentioned glass as substrate, the few viewpoint of the ion of stripping from this glass, has been coated with the above-mentioned soda glass of top coats such as silicon oxide at preferred above-mentioned non-alkali glass.
Keep the required thickness of physical strength just not have special restriction as long as the thickness of aforesaid substrate has, adopt under the situation of glass as base material, be generally more than 0.2 millimeter, preferred more than 0.7 millimeter.
Above-mentioned positive pole for example adopts vapour deposition method, film by wet method, electronic beam method, sputtering method, active sputtering method, MBE (molecular line extension) method, ionic fluid method, ionic depositing method, plasma polymerization method (high frequency excitation ionic depositing method), molecule layered manner, LB method, print process, transfer printing, chemical reaction method (sol-gel method etc.) to be coated with the method etc. of the dispersion thing of this ITO, can suitably form.
Above-mentioned positive pole is handled by washing and other, and the driving voltage of this organic EL is reduced, and also can improve luminous efficiency.Handle as above-mentioned other, for example working as above-mentioned positive electrode material is under the situation of ITO, can suitably enumerate UV-ozonize, plasma treatment etc.
-negative pole-
There is no particular restriction for above-mentioned negative pole, can suitably select as required, but preferably can be to this organic thin film layer, the concrete above-mentioned organic thin film layer of working as only has under the situation of above-mentioned luminescent layer, this organic thin film layer also has under the situation of above-mentioned electron supplying layer, this organic thin film layer further has under the situation of above-mentioned electron injecting layer, and this luminescent layer and this electron supplying layer and this electron injecting layer are supplied with the electrode of electronics respectively.
There is no particular restriction for above-mentioned negative material, can suitably select according to the adherence of above-mentioned electron supplying layer, above-mentioned luminescent layer etc. and this negative pole adjacent layers and even molecule, ionization potential, stability etc., for example can enumerate metal, alloy, metal oxide, electric conductivity compound and composition thereof etc.
The specific examples of above-mentioned negative material can be enumerated rare earth metal, its alloys etc. such as basic metal (for example Li, Na, K, Cs etc.), alkaline-earth metal (for example Mg, Ca etc.), gold and silver, lead, aluminium, sodium-potassium-sodium alloy or its hybrid metal, lithium-aluminium alloy or its hybrid metal, magnesium-silver alloys or its hybrid metal, indium, ytterbium.
These materials can be used alone or two or more and usefulness.Preferred work function is in the following material of 4eV, more preferably aluminium, lithium-aluminium alloy or its hybrid metal, magnesium-silver alloys or its hybrid metal etc. in these materials.
Thickness as above-mentioned negative pole is not particularly limited, can suitably select according to this negative material etc., but preferred 1～10000 nanometer, more preferably 20～200 nanometers.
Above-mentioned negative pole for example can adopt above-mentioned methods such as vapour deposition method, film by wet method, electronic beam method, sputtering method, active sputtering method, MBE (molecular line extension) method, ionic fluid method, ionic depositing method, plasma polymerization method (high frequency excitation ionic depositing method), molecule layered manner, LB method, print process, transfer printing suitably to form.
And with under the situation of two or more materials as above-mentioned negative material, both evaporation this two or more materials simultaneously formed alloy electrode etc., alloy formation alloy electrode that also can the evaporation prepared beforehand etc.
The resistance value of above-mentioned positive pole and negative pole hangs down, and preferably is in below hundreds of Ω/.
-hole injection layer-
There is no particular restriction for above-mentioned hole injection layer, can suitably select as required, has from the input horizon of above-mentioned anodal injected hole function when still for example preferably applying electric field.
There is no particular restriction for the material of above-mentioned hole injection layer, can suitably select as required, for example can suitably enumerate an array of stars formula amine of representing with following formula (4,4 ', 4 "-three [3-aminomethyl phenyl (phenyl) amino] triphenylamine: m-MTDATA), CuPc, polyaniline etc.
The thickness of above-mentioned hole injection layer can suitably be selected as required, but about for example preferred 1～100 nanometer, more preferably 5～50 nanometers.
Above-mentioned hole injection layer for example can adopt above-mentioned methods such as vapour deposition method, film by wet method, electronic beam method, sputtering method, active sputtering method, MBE (molecular line extension) method, ionic fluid method, ionic depositing method, plasma polymerization method (high frequency excitation ionic depositing method), molecule layered manner, LB method, print process, transfer printing suitably to form.
-hole transporting layer-
There is no particular restriction for above-mentioned hole transporting layer, can suitably select as required, has when still for example preferably applying electric field from above-mentioned anodal transfer layer of carrying the function in hole.
Material for above-mentioned hole transporting layer, there is no particular restriction, can suitably select as required, for example can suitably enumerate aromatic amine compound, carbazole, imidazoles, triazole, oxazole, oxadiazoles, poly-aromatic yl paraffin, pyrazoline, pyrazolone, to the phenyl diamines, arylamines, the amino cinnamophenone that replaces, the styryl anthracene, Fluorenone, hydrazone, stibene, silazane, styryl amine, aromatics dimethime compound, metal servant quinoline based compound, poly-silicomethane based compound, poly-(N-vinylcarbazole), the aniline based copolymer, thiophene oligomers and polymkeric substance, electroconductive polymer oligopolymer and polymkeric substance such as Polythiophene, carbon film etc.Wherein in case with these cavity conveying layer materials and above-mentioned luminescent layer material mixing system film, just can form the hole transporting layer luminescent layer of holding concurrently.
These compounds can be used alone or two or more and usefulness, preferred aromatic amine compound in these materials, the TPD that specifically more preferably is expressed from the next (N, N '-phenylbenzene-N, N '-two (3-aminomethyl phenyl)-[1,1 '-xenyl]-4,4 '-diamines), the NPD (N, N '-dinaphthyl-N, the N '-phenylbenzene-[1 that are expressed from the next, 1 '-xenyl]-4,4 '-diamines) etc.
The thickness of above-mentioned hole transporting layer can suitably be selected as required, is generally about 1～500 nanometer preferred 10～100 nanometers.
Above-mentioned hole transporting layer for example can adopt above-mentioned methods such as vapour deposition method, film by wet method, electronic beam method, sputtering method, active sputtering method, MBE (molecular line extension) method, ionic fluid method, ionic depositing method, plasma polymerization method (high frequency excitation ionic depositing method), molecule layered manner, LB method, print process, transfer printing suitably to form.
-hole blocking layer-
There is no particular restriction for above-mentioned hole blocking layer, can suitably select as required, for example preferred to have the blocking layer of barrier functionality from above-mentioned anodal injected holes.
There is no particular restriction for the material of above-mentioned hole blocking layer, can suitably select as required.
In a single day above-mentioned organic EL has above-mentioned hole blocking layer, carry the hole of coming to be stopped by this hole blocking layer from positive pole, make the electronics that transports from negative pole arrive above-mentioned luminescent layer through this hole blocking layer, because electronics produces in this luminescent layer with the hole and efficiently combines again, so can prevent combining again between the above-mentioned hole and above-mentioned electronics in the organic thin film layer beyond this luminescent layer, thereby can efficiently obtain luminous from as the above-mentioned Er Ben Bing perylene compound of purpose luminescent material, on colour purity etc., be favourable.
Preferably above-mentioned hole blocking layer is configured between above-mentioned luminescent layer and the above-mentioned electron supplying layer.
The thickness of above-mentioned hole blocking layer is not particularly limited, and can suitably select as required, is generally about 1～500 nanometer preferred 10～50 nanometers.
Above-mentioned hole blocking layer both can be made single layer structure, thereby can be stepped construction.
Above-mentioned hole blocking layer for example can adopt above-mentioned methods such as vapour deposition method, film by wet method, electronic beam method, sputtering method, active sputtering method, MBE (molecular line extension) method, ionic fluid method, ionic depositing method, plasma polymerization method (high frequency excitation ionic depositing method), molecule layered manner, LB method, print process, transfer printing suitably to form.
-electron supplying layer-
There is no particular restriction for above-mentioned electron supplying layer, and can suitably select as required, but for example preferably have the function that transports from the electronics of above-mentioned negative pole, and to have the transfer layer of any function the barrier functionality from above-mentioned anodal injected holes.
There is no particular restriction as the material of above-mentioned electron supplying layer, can suitably select as required, for example can suitably enumerate above-mentioned hydroxyquinoline aluminium complex quinolines such as (Alq), oxadiazoles derivative, triazole derivative, phenanthroline derivative, perylene derivative, pyridine derivate, pyrimidine derivatives, quinoline room quinoline derivant, phenylbenzene quinone derivative, nitro substituted fluorene derivative etc.Wherein in case with these electron transport layer materials and above-mentioned luminescent layer material mixing system film, just can form the electron supplying layer luminescent layer of holding concurrently, and again with above-mentioned hole transporting layer material mixing system film, just can form the electron supplying layer hole transporting layer luminescent layer of holding concurrently of holding concurrently, can use polymkeric substance such as Polyvinyl carbazole, polycarbonate this moment.
The thickness of above-mentioned electron supplying layer is not particularly limited, and can suitably select as required, for example is generally about 1～500 nanometer preferred 10～50 nanometers.
Above-mentioned electron supplying layer both can be made single layer structure, also can be stepped construction
In this case, the electron transport materials of using as this electron supplying layer adjacent with above-mentioned luminescent layer, from the light-emitting zone the organic EL is limited to above-mentioned luminescent layer, prevent from the luminous viewpoint of the residue of above-mentioned electron supplying layer, preferably adopt the photoabsorption end electron transport materials shorter than above-mentioned Er Ben Ji perylene compound wavelength.As the photoabsorption end electron transport materials shorter than above-mentioned Er Ben Ji perylene compound wavelength, for example can enumerate phenanthroline derivative, oxadiazoles derivative, triazole derivative etc., compound shown below is suitable for.
2-(4-tert-butyl-phenyl)-5-(4-xenyl)-1,3, the 4-oxadiazoles
3-phenyl-4-(1-naphthyl)-5-phenyl-1,2, the 4-triazole
3-(4-tert-butyl-phenyl)-4-phenyl-5-(4 '-xenyl)-1,2, the 4-triazole
Above-mentioned electron supplying layer for example can adopt above-mentioned methods such as vapour deposition method, film by wet method, electronic beam method, sputtering method, active sputtering method, MBE (molecular line extension) method, ionic fluid method, ionic depositing method, plasma polymerization method (high frequency excitation ionic depositing method), molecule layered manner, LB method, print process, transfer printing suitably to form.
-other layers-
Organic EL of the present invention, other layers that can suitably select as required as described other layers, for example can suitably be enumerated protective layer etc.
Be not particularly limited for above-mentioned protective layer, can suitably select as required, for example preferably have and to suppress molecule and even the material that moisture content and oxygen etc. promote the organic EL deterioration, immerse the protective layer of the function in the organic EL.
The material of above-mentioned protective layer for example can be enumerated metals such as In, Sn, Pb, Au, Cu, Ag, Al, Ti, Ni, MgO, SiO, SiO
2, Al
2O
3, GeO, NiO, CaO, BaO, Fe
2O
3, Y
2O
3, TiO
2Deng metal oxide, nitride such as SiN, SiNxOy, MgF
2, LiF, AlF
3, CaF
2Deng metal fluoride, the multipolymer of polyethylene, polypropylene, polymethylmethacrylate, polyimide, urethane, tetrafluoroethylene, polychlorotrifluoroethylene, poly-dichloro difluoroethylene, a chlorotrifluoroethylene and dichloro difluoroethylene, make water-absorbent material more than 1% of the multipolymer that the monomer mixture copolymerization that contains tetrafluoroethylene and at least a oligopolymer obtains, the fluorinated copolymer that on the copolymerization main chain, has ring texture, water-intake rate, the moisture resistance material of water-intake rate below 0.1% etc.
Above-mentioned protective layer for example can adopt above-mentioned methods such as vapour deposition method, film by wet method, electronic beam method, sputtering method, active sputtering method, MBE (molecular line extension) method, ionic fluid method, ionic depositing method, plasma polymerization method (high frequency excitation ionic depositing method), molecule layered manner, LB method, print process, transfer printing suitably to form.
There is no particular restriction for the structure of organic EL of the present invention, can suitably select as required, but as its layer structure, for example can enumerate following (1)～(13) and plant layer structure, i.e. (1) positive pole/hole injection layer/hole transporting layer/luminescent layer/electron supplying layer/electron injecting layer/negative pole, (2) positive pole/hole injection layer/hole transporting layer/luminescent layer/electron supplying layer/negative pole, (3) positive pole/hole transporting layer/luminescent layer/electron supplying layer/electron injecting layer/negative pole, (4) positive pole/hole transporting layer/luminescent layer/electron supplying layer/negative pole, (5) positive pole/hole injection layer/hole transporting layer/luminescent layer electron supplying layer/electron injecting layer/negative pole of holding concurrently, (6) positive pole/hole injection layer/hole transporting layer/luminescent layer electron supplying layer/negative pole of holding concurrently, (7) positive pole/hole transporting layer/luminescent layer electron supplying layer/electron injecting layer/negative pole of holding concurrently, (8) positive pole/hole transporting layer/luminescent layer electron supplying layer/negative pole of holding concurrently, (9) positive pole/hole injection layer/hole transporting layer luminescent layer/electron supplying layer/electron injecting layer/negative pole (10) positive pole/hole injection layer/hole transporting layer luminescent layer/electron supplying layer/negative pole of holding concurrently of holding concurrently, (11) positive pole/hole transporting layer luminescent layer/electron supplying layer/electron injecting layer/negative pole of holding concurrently, (12) positive pole/hole transporting layer luminescent layer/electron supplying layer/negative pole of holding concurrently, (13) positive pole/hole transporting layer luminescent layer electron supplying layer/negative pole etc. of holding concurrently of holding concurrently.
In addition, have when organic EL element under the situation of above-mentioned hole blocking layer, in described (1)～(13), can suitably enumerate the layer structure that disposes this hole blocking layer at above-mentioned luminescent layer and above-mentioned electron transport interlayer.
In these layers structure, if with (4) positive pole/hole transporting layer/luminescent layer/electron supplying layer/negative pole diagram, then as shown in Figure 1, organic EL 10 has the layer structure of the positive pole 14 (for example ITO electrode) that forms that stacks gradually, hole transporting layer 16, luminescent layer 18, electron supplying layer 20, negative pole 22 (for example Al-Li electrode) on glass substrate 12.Wherein anodal 14 (for example ITO electrodes) are interconnection by means of power supply with negative pole 22 (for example Al-Li electrode).Form the organic thin film layer 24 that emitting red light is used by hole transporting layer 16, luminescent layer 18 and electron supplying layer 20.
The peak luminous wavelength of organic EL of the present invention, preferred 580～700nm.
The luminous efficiency of organic EL of the present invention, ruddiness is sent in expectation below 10V, preferably sends ruddiness below 7V, more preferably sends ruddiness below 5V.
Light emission luminance of the present invention applies and preferably is in 100cd/m under the 10V voltage condition
2More than, more preferably 500cd/m
2More than, preferably be in 1000cd/m
2More than.
Organic EL of the present invention, for example can suitably be used for computer, Vehicular display device, open-air indicating meter, household electrical appliance, office instrument, household electrical appliances with the various fields headed by equipment, the indicating meter that relates to traffic, clock and watch indicating meter, calendar date display, window of tube, the stereo set etc., but be specially adapted on following organic EI indicating meter of the present invention.
＜OLED display 〉
OLED display of the present invention is not particularly limited except that the organic EL that has adopted the invention described above, can suitably adopt known configurations.
Above-mentioned OLED display both can be red monochromatic luminous indicating meter, also can be multicolor luminous indicating meter, can also be the indicating meter of panchromatic mode.
As the method for above-mentioned OLED display being made the panchromatic mode indicating meter, for example as going up record " indicating meter monthly magazine " in September, 2000 numbers 33～37 pages, known have on substrate configuration to send the colour switching method etc. that is transformed into redness (R) and green (G) with the three-colour light-emitting method of the organic EL of the corresponding light of three primary colors (blue (B), green (G), red (R)) of color, white light that the organic EL of white luminous usefulness is produced by colour filter respectively.Among the present invention,,, be particularly suitable for adopting the three-colour light-emitting method so can suitably adopt three-colour light-emitting method and colour switching method because the organic EL of the invention described above that adopts is that emitting red light is used.
Utilize under the situation of above-mentioned three-colour light-emitting manufactured panchromatic mode indicating meter, except the organic EL of the invention described above of using as emitting red light, the organic EL that must have organic EL that green emitting uses and blue-light-emitting to use.
There is no particular restriction as organic EL that above-mentioned green emitting is used, can suitably select those from known, can suitably enumerate layer structure for example and be the element of ITO (positive pole)/above-mentioned Alq/Al-Li of above-mentioned NPD/ (negative pole) etc.
There is no particular restriction as organic EL that blue-light-emitting is used, can suitably select those from known, can suitably enumerate layer structure for example and be the element of ITO (positive pole)/above-mentioned Alq/Al-Li of the above-mentioned DPVBi/ of above-mentioned NPD/ (negative pole) etc.
There is no particular restriction for the form of above-mentioned OLED display, can suitably select as required, for example can suitably enumerate at " Nikkei electron " No.765 on March 13rd, 2000, the passive matrix display panel of 55～62 pages of last records, active array type display panel etc.
The structure of above-mentioned passive matrix display panel, for example as shown in Figure 2, on glass substrate 12, banded anodal 14 (for example ITO electrodes) with configuration parallel to each other, have organic thin film layer 28 parallel successively and that use at the organic thin film layer of using with the anodal 14 zonal emitting red lights that dispose on the orthogonal direction substantially 24, organic thin film layer 26 that blue-light-emitting is used and green emitting on anodal 14, the organic thin film layer 28 that the organic thin film layer of using at emitting red light 24, organic thin film layer 26 and the green emitting that blue-light-emitting is used are used all has the negative pole 22 identical with its shape.
In the above-mentioned passive matrix display panel, for example as shown in Figure 3, intersect to form circuit with the direction of keeping straight on substantially mutually with the negative line 32 that constitutes by most negative poles 22 by most anodal 14 electrode lines that constitute 30.Be in the locational emitting red light in each point of crossing with, blue-light-emitting with and the organic thin film layer 24,26,28 used of green emitting play a part pixel, correspondingly with each pixel have most organic ELs 34.In the above-mentioned passive matrix display panel, in case with a positive pole 14 in 36 pairs of electrode lines 30 of constant current power supply, apply electric current with a negative pole 22 in the negative line 32, be on the locational organic EL thin film layer in this point of crossing and just be applied in electric current this moment, makes this locational organic EL thin film layer luminous.By controlling the luminous of this pixel cell, can form full-colour image easily.
Above-mentioned active matrix panel, for example as shown in Figure 4, on glass substrate 12, form sweep trace latticedly, data line and electric current supplying wire, have and form latticed sweep trace and be connected and be configured in TFT circuit 40 in each mesh, can drive and be configured in positive pole 14 (for example ITO electrode) in each mesh with TFT circuit 40, on anodal 14, has the organic thin film layer 24 that the zonal emitting red light of configuration parallel to each other is successively used, the organic thin film layer 28 that organic thin film layer 26 that blue-light-emitting is used and green emitting are used, the organic thin film layer of using at emitting red light 24, the organic thin film layer 28 that organic thin film layer 26 that blue-light-emitting is used and green emitting are used has and disposes with its negative poles 22 that all cover.The organic thin film layer 28 that the organic thin film layer 24 that emitting red light is used, the organic thin film layer 26 that blue-light-emitting is used and green emitting are used has hole transporting layer 16, luminescent layer 18 and electron supplying layer 20 respectively.
In the above-mentioned active matrix panel, for example as shown in Figure 5, the sweep trace 46 of most settings parallel to each other, the data line 42 of most settings parallel to each other and electric current supplying wire 44 mutually orthogonals form grid, form on each grid with switch and are connected to form circuit with driving with TFT50 with TFT48.In case apply electric current from driving circuit 38, just can be on each grid driving switch with TFT48 and driving TFT50.And the organic thin film layer 24,26,28 that the emitting red light of each grid is used, blue-light-emitting is used and green emitting is used plays a part pixel, in this active matrix panel, in case apply electric current with of the sweep trace 46 of 38 pairs of landscape configuration of driving circuit and the electric current supplying wire 44 of vertically configuration, just can drive this moment and be in the locational switch TFT48 in this point of crossing, drive to drive thereupon and use TFT50, make this locational organic EL 52 luminous.By controlling the luminous of this pixel cell, can form full-colour image easily.
OLED panel of the present invention for example can suitably be used for computer, Vehicular display device, open-air indicating meter, household electrical appliance, office instrument, household electrical appliances with the various fields headed by equipment, the indicating meter that relates to traffic, clock and watch indicating meter, calendar date display, window of tube, the stereo set etc.
Embodiments of the invention below are described, but the present invention is not subjected to any restriction of these embodiment.
(embodiment 1)
-1,3,8,10-four (3-methyldiphenyl base amine) Er Ben Bing perylene synthetic-
Shown in the following note route, perinaphthene ketone is mixed (note synthetic route I down) in pyridine with zinc powder, stir, reflux and under stream of nitrogen gas, behind 0 milliliter of 80% acetate of 5 hours Dropwise 5s, filtering precipitate (note synthetic route II down), utilize the vacuum-sublimation device to make its dehydration distillation, obtain unsubstituted Er Ben Bing perylene (note synthetic route III down).
Then the bromo-reaction by Er Ben Bing perylene (referring under remember route), for example synthetic 1,3,8, the 10-tetrabromo is for Er Ben Bing perylene (note synthetic route IV down).Wherein said bromo-reaction, as 81 pages of " Annalen derchemie " 531 volumes go up record like that, be that the mode of the elemental bromine that is dissolved in the four times of amounts of 1 equivalent Er Ben Bing perylene adding in the solvent is carried out.
Shown in the following then note route, for synthetic 1,3,8, the 10-tetrabromo adds the 3-methyldiphenyl base amine of four times of amounts, tert.-butoxy sodium, 0.1% normal acid chloride and 0.4% normal three (tertiary butyl) phosphine of four times of amounts for Er Ben Bing perylene, make solvent with o-Xylol, under 130 ℃ of temperature, make its reaction 3 hours.After the cooling, reaction solution washes with water for several times, and o-Xylol is removed in distillation.Remaining oily matter with methanol wash after, make resultant of reaction recrystallize in THF-methyl alcohol, obtained thick resultant.After utilizing the vacuum-sublimation method should thick resultant refining, have synthesized as 1,3,8 of object 10-four (3-methyldiphenyl base amino) Er Ben Bing perylene.
Wherein 1,3,8,10-four (3-methyldiphenyl base amino) Er Ben Bing perylene has R in the said structure formula (1)
1, R
6, R
8And R
13Identical mutually, be the group of representing with following structural formula; R
2～R
5, R
7, R
9～R
12And R
14It is the structure of hydrogen atom.
(embodiment 2)
-1,3,8,10-four [N-phenyl-1-naphthyl amino] Er Ben Bing perylene synthetic-
In embodiment 1, except replace 3 methyl diphenylamine with the N-phenyl-1-naphthylamine, synthesized 1,3,8 similarly to Example 1,10-four [N-phenyl-1-naphthyl amino] Er Ben Bing perylene.Wherein 1,3,8,10-four [N-phenyl-1-naphthyl amino] Er Ben Bing perylene is R in the said structure formula (1)
1～R
4Be by the compound of remembering the group that structural formula is represented down.
In addition, about synthetic 1,3,8, mass spectrum, ultimate analysis and the IR analytical results of 10-four [N-phenyl-1-naphthyl amino] Er Ben Bing perylene illustrate as follows.
＜mass spectrum result 〉
As C
90H
58N
4, (with C12, H:1 is 1194 N:14) to the molecular weight calculated value
Mass spectral molecular weight peaks: 1194,1195
＜results of elemental analyses 〉
As C
90H
58N
4,
Calculated value: C:90.42%, H:4.89%, N:4.69%
Trial value: C:90.18%, H:5.43%, N:4.38%
＜IR analytical results 〉
Utilize synthetic 1,3,8, the IR spectrogram that 10-four [N-phenyl-1-naphthyl amino] the KBr lozenge method of Er Ben Bing perylene obtains is shown among Fig. 6.
(embodiment 3)
-1,3,8,10-four [4,4 ' two (α, α-Er Jiajibianji) diphenyl amino] Er Ben Bing perylene synthetic-
In embodiment 1, [beyond 4,4 ' two (α, α-Er Jiajibianji) diphenylamine replacement 3 methyl diphenylamine, synthesized 1,3,8 similarly to Example 1,10-four [4,4 ' two (α, α-Er Jiajibianji) diphenyl amino] Er Ben Bing perylene except using.Wherein 1,3,8,10-four [4,4 ' two (α, α-Er Jiajibianji) diphenyl amino] Er Ben Bing perylene is R in the said structure formula (1)
1～R
4Be by the compound of remembering the group that structural formula is represented down.
(embodiment 4)
The making of-organic EL-
Prepared in accordance with the following methods in the luminescent layer and used with embodiment 1 synthetic 1,3,8,10-four (3-methyldiphenyl base amino) Er Ben Bing perylene is as the cascade type organic EL of luminescent material.That is, utilize water, acetone and Virahol that the glass substrate that has formed as anodal ITO electrode is carried out ultrasonic washing, after the UV ozonize, with vacuum deposition apparatus (vacuum tightness=1 * 10
-6Torr (1.3 * 10
-4Pa), substrate temperature=room temperature), on this ITO positive pole, cover N, N '-dinaphthyl-N, N '-phenylbenzene-[1,1 '-xenyl]-4,4 '-diamines (NPD) as the thickness 50nm of hole transporting layer.Then at this N, N '-dinaphthyl-N, N '-phenylbenzene-[1,1 '-xenyl]-4, on the hole transporting layer that 4 '-diamines (NPD) forms, evaporation covers 1,3,8 of 30nm thickness, 10-four (3-methyldiphenyl base amino) Er Ben Bing perylene luminescent layer.And then the hydroxyquinoline aluminium complex (Alq) that evaporation covers 20nm thickness on this luminescent layer is as electron supplying layer, and the Al-Li alloy (Li content=0.5 weight %) of evaporation thickness 50nm is as negative pole on the electron supplying layer that this hydroxyquinoline aluminium complex (Alq) forms.By making organic EL with upper type.
In a single day apply voltage on ITO electrode (positive pole) and Al-Li alloy (negative pole) in the organic EL of making, in this organic EL, just observed emitting red light at the above voltage of 5V, observing luminosity when applying 10V voltage is 1350cd/m
2Highly purified emitting red light.
(embodiment 5)
The making of-organic EL-
In embodiment 4, except making 1,3,8,10-four (3-methyldiphenyl base amino) Er Ben Bing perylene and N, N '-dinaphthyl-N, N '-phenylbenzene-[1,1 '-xenyl]-4,4 '-diamines (NPD), with with respect to 1,3,8,10-four (3-methyldiphenyl base amino) Er Ben Bing perylene 1 this NPD is 99 evaporation rate ratio, evaporation forms beyond the luminescent layer simultaneously, has made organic EL similarly to Example 4.
In a single day apply voltage on ITO electrode (positive pole) and Al-Li alloy (negative pole) in the organic EL of making, then in this organic EL, just observed emitting red light at the above voltage of 5V, observing luminosity when applying 10V voltage is 1820cd/m
2Highly purified emitting red light.
(embodiment 6)
The making of-organic EL-
In embodiment 4, except making 1,3,8,10-four (3-methyldiphenyl base amino) Er Ben Bing perylene and 4,4 '-two (9-carbazyl) biphenyl (CBP) are with respect to 1,3,8,10-four (3-methyldiphenyl base amino) Er Ben Bing perylene 1 this CBP is 99 evaporation rate ratio, and evaporation forms beyond the luminescent layer simultaneously, has made organic EL similarly to Example 4.
In the organic EL of making, in case on ITO electrode (positive pole) and Al-Li alloy (negative pole), apply voltage, then in this organic EL, just observed emitting red light at the above voltage of 5V, observing luminosity when applying 10V voltage is 1890cd/m
2Highly purified emitting red light.
(embodiment 7)
The making of-organic EL-
In embodiment 4, except making 1,3,8,10-four (3-methyldiphenyl base amino) two benzene and perylene and hydroxyquinoline aluminium complex (Alq), with with respect to 1,3,8,10-four (3-methyldiphenyl base amino) Er Ben Bing perylene 1Alq is 99 evaporation rate ratio, evaporation forms beyond the luminescent layer simultaneously, has made organic EL similarly to Example 4.
In the organic EL of making, in case on ITO electrode (positive pole) and Al-Li alloy (negative pole), apply voltage, then in this organic EL, just observed emitting red light at the above voltage of 5V, observing luminosity when applying 10V voltage is 2040cd/m
2Highly purified emitting red light.
(embodiment 8)
The making of-organic EL-
In embodiment 4, except using embodiment 2 synthetic 1,3,8,10-four [N-phenyl-1-naphthyl amino] Er Ben Bing perylene replaces embodiment 1 synthetic 1,3,8, beyond 10-four (3-methyldiphenyl base amino) the Er Ben Bing perylene, made organic EL similarly to Example 4.
In the organic EL of making ,-the dawn applies voltage on ITO electrode (positive pole) and Al-Li alloy (negative pole), then in this organic EL, has just observed emitting red light at the above voltage of 5V, and observing luminosity when applying 10V voltage is 1480cd/m
2Highly purified emitting red light.
(embodiment 9)
The making of-organic EL-
In embodiment 8, except making 1,3,8,10-four [N-phenyl-1-naphthyl amino] two benzene and perylene and hydroxyquinoline aluminium complex (Alq), with with respect to 1,3,8,10-four [N-phenyl-1-naphthyl amino] Er Ben Bing perylene 1Alq is 99 evaporation rate ratio, evaporation forms beyond the luminescent layer simultaneously, has made organic EL similarly to Example 8.
In the organic EL of making, in case on ITO electrode (positive pole) and Al-Li alloy (negative pole), apply voltage, then in this organic EL, just observed emitting red light at the above voltage of 5V, observing luminosity when applying 10V voltage is 2030cd/m
2Highly purified emitting red light.
(embodiment 10)
The making of-organic EL-
In embodiment 8, except not establishing hole transporting layer, and with this 1,3,8,10-four [N-phenyl-1-naphthyl amino] Er Ben Bing perylene forms hole transporting layer and holds concurrently beyond the luminescent layer, has made organic EL similarly to Example 8.
In the organic EL of making, in case on ITO electrode (positive pole) and Al-Li alloy (negative pole), apply voltage, then in this organic EL, just observed emitting red light at the above voltage of 5V, observing luminosity when applying 10V voltage is 1440cd/m
2Highly purified emitting red light.
(embodiment 11)
The making of-organic EL-
In embodiment 9, except using embodiment 3 synthetic 1,3,8,10-four [4,4 '-two (α, α-Er Jiajibianji) diphenyl amino] Er Ben Bing perylene replaces 1,3,8, beyond 10-four [N-phenyl-1-naphthyl amino] the Er Ben Bing perylene, made organic EL similarly to Example 9.
In case to applying voltage on ITO electrode (positive pole) in the organic EL of making and the Al-Li alloy (negative pole), then in this organic EL, just observed emitting red light at the above voltage of 5V, observing luminosity when applying 10V voltage is 2100cd/m
2Highly purified emitting red light.
The possibility of utilizing on the industry
Can provide a kind of problem that can solve in the past according to the present invention, can provide to be suitable for organic EL unit Be used as the Er Ben Bing perylene compound of red illuminating material in the part, the luminous efficiency of emitting red light, luminosity and Colour purities etc. are good organic EL all, and uses the high performance organic of this organic EL The EL display.
Claims (17)
1. an organic electroluminescent device is characterized in that, has organic thin film layer between positive pole and negative pole, and this organic thin film layer contains two benzene of useful following structural formula (1) expression and perylene compound as luminescent material;
Structural formula (1)
In said structure formula (1), R
2～R
5, R
7, R
9～R
12And R
14The expression hydrogen atom;
In said structure formula (1), R
1, R
6, R
8And R
13Be group with following structural formula (3) expression, promptly 1,3,8,10-four (N, N-diphenyl amino) Er Ben Bing perylene; Or with the group of following structural formula (4) expression, promptly 1,3,8,10-four (N-phenyl-1-naphthyl amino) Er Ben Bing perylene; Or with the group of following structural formula (5) expression, promptly 1,3,8,10-four [4,4 '-two (α, α-Er Jiajibianji) diphenyl amino] Er Ben Bing perylene;
Structural formula (3)
In said structure formula (3), R
17And R
18Can be identical or different mutually, expression hydrogen atom, carbonatoms are 1～10 straight chain, side chain or cyclic alkyl or are selected from by the group of monocyclic aryl, four following aromatic ring be combined intos, have the aryl that the following condensation aromatic ring in five rings and carbon, oxygen, nitrogen and sulphur atom add up to the group that the group below 50 forms;
Structural formula (4)
In said structure formula (4), R
19, R
20And R
21Can be identical or different mutually, expression hydrogen atom, carbonatoms are 1～10 straight chain, side chain or cyclic alkyl or are selected from by the group of monocyclic aryl, four following aromatic ring be combined intos, have the aryl that the following condensation aromatic ring in five rings and carbon, oxygen, nitrogen and sulphur atom add up to the group that the group below 50 forms;
Structural formula (5)
In said structure formula (5), R
22, R
23, R
24And R
25Can be identical or different mutually, expression hydrogen atom, carbonatoms are 1～10 straight chain, side chain or cyclic alkyl or are selected from by the group of monocyclic aryl, four following aromatic ring be combined intos, have the aryl that the following condensation aromatic ring in five rings and carbon, oxygen, nitrogen and sulphur atom add up to the group that the group below 50 forms.
2. according to the described organic electroluminescent device of claim 1, wherein, organic thin film layer has luminescent layer, and this luminescent layer contains Er Ben Bing perylene compound as luminescent material.
3. according to the described organic electroluminescent device of claim 1, wherein, organic thin film layer has the hole transporting layer luminescent layer of holding concurrently, and this hole transporting layer luminescent layer of holding concurrently contains Er Ben Bing perylene compound as luminescent material.
4. according to the described organic electroluminescent device of claim 2, wherein, organic thin film layer further has hole transporting layer and electron supplying layer, and luminescent layer is by hole transporting layer and electron supplying layer clamping.
5. according to the described organic electroluminescent device of claim 2, wherein, luminescent layer is to become film formed separately by two benzene of structural formula (1) expression and perylene compound.
6. according to the described organic electroluminescent device of claim 2, wherein, luminescent layer contains the N that is selected from by following structural formula (7) expression, N '-dinaphthyl-N, N '-phenylbenzene-[1,1 '-xenyl]-4, the aryl amine derivatives of the group that 4 '-diamines (NPD) and derivative thereof are formed;
Structural formula (7).
7. according to the described organic electroluminescent device of claim 3, wherein, the hole transporting layer luminescent layer of holding concurrently contains the N that is selected from by following structural formula (7) expression, N '-dinaphthyl-N, N '-phenylbenzene-[1,1 '-xenyl]-4, the aryl amine derivatives of the group that 4 '-diamines (NPD) and derivative thereof are formed;
Structural formula (7).
8. according to the described organic electroluminescent device of claim 2, wherein, luminescent layer contains the carbazole derivative that is selected from the group of being made up of 4,4 '-two (9-carbazyl) biphenyl (CBP) and the derivative thereof of following structural formula (9) expression;
Structural formula (9).
9. according to the described organic electroluminescent device of claim 3, wherein, the hole transporting layer luminescent layer of holding concurrently contains the carbazole derivative that is selected from the group of being made up of 4,4 '-two (9-carbazyl) biphenyl (CBP) and the derivative thereof of following structural formula (9) expression;
Structural formula (9).
10. according to the described organic electroluminescent device of claim 2, wherein, luminescent layer contains the hydroxyquinoline complex compound by the hydroxyquinoline aluminium complex (Alq) of following structural formula (11) expression;
Structural formula (11).
11. according to the described organic electroluminescent device of claim 3, wherein, the hole transporting layer luminescent layer of holding concurrently contains hydroxyquinoline complex compound by the hydroxyquinoline aluminium complex (Alq) of following structural formula (11) expression;
Structural formula (11).
12. according to the described organic electroluminescent device of claim 2, wherein, the electron transport materials that is contained in electron supplying layer is the 2 (BCP) by following structural formula (12) expression;
Structural formula (12).
13. the application of the described organic electroluminescent device of claim 1 in emitting red light.
14. benzene and perylene compound is characterized in that, with following structural formula (1) expression;
Structural formula (1);
In said structure formula (1), R
2～R
5, R
7, R
9～R
12And R
14The expression hydrogen atom;
In said structure formula (1), R
1, R
6, R
8And R
13Be group with following structural formula (3) expression, promptly 1,3,8,10-four (N, N-diphenyl amino) Er Ben Bing perylene; Or with the group of following structural formula (4) expression, promptly 1,3,8,10-four (N-phenyl-1-naphthyl amino) Er Ben Bing perylene; Or with the group of following structural formula (5) expression, promptly 1,3,8,10-four [4,4 '-two (α, α-Er Jiajibianji) diphenyl amino] Er Ben Bing perylene;
Structural formula (3);
In said structure formula (3), R
17And R
18Can be identical or different mutually, expression hydrogen atom, carbonatoms are 1～10 straight chain, side chain or cyclic alkyl or are selected from by the group of monocyclic aryl, four following aromatic ring be combined intos, have the aryl that the following condensation aromatic ring in five rings and carbon, oxygen, nitrogen and sulphur atom add up to the group that the group below 50 forms;
Structural formula (4);
In said structure formula (4), R
19, R
20And R
21Can be identical or different mutually, expression hydrogen atom, carbonatoms are 1～10 straight chain, side chain or cyclic alkyl or are selected from by the group of monocyclic aryl, four following aromatic ring be combined intos, have the aryl that the following condensation aromatic ring in five rings and carbon, oxygen, nitrogen and sulphur atom add up to the group that the group below 50 forms;
Structural formula (5);
In said structure formula (5), R
22, R
23, R
24And R
25Can be identical or different mutually, expression hydrogen atom, carbonatoms are 1～10 straight chain, side chain or cyclic alkyl or are selected from by the group of monocyclic aryl, four following aromatic ring be combined intos, have the aryl that the following condensation aromatic ring in five rings and carbon, oxygen, nitrogen and sulphur atom add up to the group that the group below 50 forms.
15. the described Er Ben of claim 14 Bing perylene compound is as the application in the luminescent material in the organic electroluminescent device.
16. display of organic electroluminescence, it is characterized in that, adopt organic electroluminescent device, this organic electroluminescent device has organic thin film layer between positive pole and negative pole, and this organic thin film layer contains two benzene of useful following structural formula (1) expression and perylene compound as luminescent material;
Structural formula (1)
In said structure formula (1), R
2～R
5, R
7, R
9～R
12And R
14The expression hydrogen atom;
In said structure formula (1), R
1, R
6, R
8And R
13Be group with following structural formula (3) expression, promptly 1,3,8,10-four (N, N-diphenyl amino) Er Ben Bing perylene; Or with the group of following structural formula (4) expression, promptly 1,3,8,10-four (N-phenyl-1-naphthyl amino) Er Ben Bing perylene; Or with the group of following structural formula (5) expression, promptly 1,3,8,10-four [4,4 '-two (α, α-Er Jiajibianji) diphenyl amino] Er Ben Bing perylene;
Structural formula (3);
In said structure formula (3), R
17And R
18Can be identical or different mutually, expression hydrogen atom, carbonatoms are 1～10 straight chain, side chain or cyclic alkyl or are selected from by the group of monocyclic aryl, four following aromatic ring be combined intos, have the aryl that the following condensation aromatic ring in five rings and carbon, oxygen, nitrogen and sulphur atom add up to the group that the group below 50 forms;
Structural formula (4);
In said structure formula (4), R
19, R
20And R
21Can be identical or different mutually, expression hydrogen atom, carbonatoms are 1～10 straight chain, side chain or cyclic alkyl or are selected from by the group of monocyclic aryl, four following aromatic ring be combined intos, have the aryl that the following condensation aromatic ring in five rings and carbon, oxygen, nitrogen and sulphur atom add up to the group that the group below 50 forms;
Structural formula (5);
In said structure formula (5), R
22, R
23, R
24And R
25Can be identical or different mutually, expression hydrogen atom, carbonatoms are 1～10 straight chain, side chain or cyclic alkyl or are selected from by the group of monocyclic aryl, four following aromatic ring be combined intos, have the aryl that the following condensation aromatic ring in five rings and carbon, oxygen, nitrogen and sulphur atom add up to the group that the group below 50 forms.
17. according to the described display of organic electroluminescence of claim 16, it is in passive matrix display panel and the active array type display panel any one.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2002330533A JP2004161691A (en) | 2002-11-14 | 2002-11-14 | Peropyrene compound, organic el element and organic el display |
| JP330533/2002 | 2002-11-14 |
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| Publication Number | Publication Date |
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| CN1708474A CN1708474A (en) | 2005-12-14 |
| CN100334065C true CN100334065C (en) | 2007-08-29 |
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| CNB2003801022807A Expired - Lifetime CN100334065C (en) | 2002-11-14 | 2003-11-06 | Peropyrene compound, organic electroluminescent element and organic electroluminescent display |
Country Status (4)
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| JP (1) | JP2004161691A (en) |
| CN (1) | CN100334065C (en) |
| TW (1) | TWI239791B (en) |
| WO (1) | WO2004043901A1 (en) |
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| KR100681473B1 (en) | 2005-11-18 | 2007-02-09 | 이수화학 주식회사 | Hexabenzocoronenes derivatives for organic electroluminescent materials |
| JP5478819B2 (en) | 2007-11-02 | 2014-04-23 | キヤノン株式会社 | Fused polycyclic compound and organic light emitting device using the same |
| KR102647809B1 (en) | 2015-03-19 | 2024-03-15 | 네바다 리서치 & 이노베이션 코포레이션 | Aryl compounds and polymers and methods of making and using them |
| CN106608828A (en) * | 2015-10-22 | 2017-05-03 | 上海和辉光电有限公司 | Benzoperylene derivative for organic light-emitting material |
| EP3762363A4 (en) * | 2018-03-05 | 2022-02-23 | Nevada Research & Innovation Corporation | Polycyclic aromatic compounds and methods for making and using the same |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2000231987A (en) * | 1999-02-10 | 2000-08-22 | Fujitsu Ltd | Organic electroluminescent element and display device using it |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| DE3005299A1 (en) * | 1980-02-13 | 1981-08-20 | Basf Ag, 6700 Ludwigshafen | METHOD FOR THE PRODUCTION OF ELECTRICALLY CONDUCTIVE POLYAROMATS AND THEIR USE IN ELECTROTECHNICS AND FOR THE ANTISTATIC EQUIPMENT OF PLASTICS |
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2002
- 2002-11-14 JP JP2002330533A patent/JP2004161691A/en active Pending
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2003
- 2003-11-06 WO PCT/JP2003/014137 patent/WO2004043901A1/en active Application Filing
- 2003-11-06 CN CNB2003801022807A patent/CN100334065C/en not_active Expired - Lifetime
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| JP2000231987A (en) * | 1999-02-10 | 2000-08-22 | Fujitsu Ltd | Organic electroluminescent element and display device using it |
Also Published As
| Publication number | Publication date |
|---|---|
| TW200420188A (en) | 2004-10-01 |
| TWI239791B (en) | 2005-09-11 |
| CN1708474A (en) | 2005-12-14 |
| WO2004043901A1 (en) | 2004-05-27 |
| JP2004161691A (en) | 2004-06-10 |
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