WO2004026870A1 - Phenanthroline compound and organic light emitting device using same - Google Patents
Phenanthroline compound and organic light emitting device using same Download PDFInfo
- Publication number
- WO2004026870A1 WO2004026870A1 PCT/JP2003/011485 JP0311485W WO2004026870A1 WO 2004026870 A1 WO2004026870 A1 WO 2004026870A1 JP 0311485 W JP0311485 W JP 0311485W WO 2004026870 A1 WO2004026870 A1 WO 2004026870A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- unsubstituted
- group
- substituted
- hydrogen atom
- light emitting
- Prior art date
Links
- -1 Phenanthroline compound Chemical class 0.000 title claims abstract description 43
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 29
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 29
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 27
- 125000000547 substituted alkyl group Chemical group 0.000 claims abstract description 27
- 125000003107 substituted aryl group Chemical group 0.000 claims abstract description 27
- 125000005843 halogen group Chemical group 0.000 claims abstract description 25
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims abstract description 12
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 claims abstract description 12
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims abstract description 12
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 claims abstract description 12
- 150000001875 compounds Chemical group 0.000 claims description 58
- 125000003277 amino group Chemical group 0.000 claims description 18
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 17
- 150000002894 organic compounds Chemical class 0.000 claims description 13
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims 1
- 230000007774 longterm Effects 0.000 abstract description 2
- 239000010410 layer Substances 0.000 description 53
- 239000010408 film Substances 0.000 description 20
- DVLSJPCXPNKPRJ-UHFFFAOYSA-N 2-iodo-9,9-dimethylfluorene Chemical compound C1=C(I)C=C2C(C)(C)C3=CC=CC=C3C2=C1 DVLSJPCXPNKPRJ-UHFFFAOYSA-N 0.000 description 18
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- 230000015572 biosynthetic process Effects 0.000 description 16
- 239000000758 substrate Substances 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 239000000463 material Substances 0.000 description 15
- 238000000034 method Methods 0.000 description 15
- 150000005041 phenanthrolines Chemical class 0.000 description 14
- 229920005989 resin Polymers 0.000 description 11
- 239000011347 resin Substances 0.000 description 11
- 238000007738 vacuum evaporation Methods 0.000 description 11
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- 239000012044 organic layer Substances 0.000 description 8
- 238000001704 evaporation Methods 0.000 description 7
- 230000008020 evaporation Effects 0.000 description 7
- 239000011777 magnesium Substances 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 229910052749 magnesium Inorganic materials 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- 239000004411 aluminium Substances 0.000 description 5
- 229910052782 aluminium Inorganic materials 0.000 description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 239000012299 nitrogen atmosphere Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000011701 zinc Substances 0.000 description 5
- 229910052725 zinc Inorganic materials 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-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
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 239000011877 solvent mixture Substances 0.000 description 4
- 239000010409 thin film Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 229910001148 Al-Li alloy Inorganic materials 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 230000001747 exhibiting effect Effects 0.000 description 3
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical class [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- 229910044991 metal oxide Inorganic materials 0.000 description 3
- 150000004706 metal oxides Chemical class 0.000 description 3
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 239000004925 Acrylic resin Substances 0.000 description 2
- 229920000178 Acrylic resin Polymers 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 229920000547 conjugated polymer Polymers 0.000 description 2
- VPUGDVKSAQVFFS-UHFFFAOYSA-N coronene Chemical compound C1=C(C2=C34)C=CC3=CC=C(C=C3)C4=C4C3=CC=C(C=C3)C4=C2C3=C1 VPUGDVKSAQVFFS-UHFFFAOYSA-N 0.000 description 2
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000008393 encapsulating agent Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 229920005990 polystyrene resin Polymers 0.000 description 2
- 229920000123 polythiophene Polymers 0.000 description 2
- 239000011241 protective layer Substances 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 229920002050 silicone resin Polymers 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- DMDPAJOXRYGXCB-UHFFFAOYSA-N (9,9-dimethylfluoren-2-yl)boronic acid Chemical compound C1=C(B(O)O)C=C2C(C)(C)C3=CC=CC=C3C2=C1 DMDPAJOXRYGXCB-UHFFFAOYSA-N 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- DHDHJYNTEFLIHY-UHFFFAOYSA-N 4,7-diphenyl-1,10-phenanthroline Chemical compound C1=CC=CC=C1C1=CC=NC2=C1C=CC1=C(C=3C=CC=CC=3)C=CN=C21 DHDHJYNTEFLIHY-UHFFFAOYSA-N 0.000 description 1
- 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
- 229910001316 Ag alloy Inorganic materials 0.000 description 1
- SDFLTYHTFPTIGX-UHFFFAOYSA-N C[n]1c2ccccc2c2c1cccc2 Chemical compound C[n]1c2ccccc2c2c1cccc2 SDFLTYHTFPTIGX-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Natural products C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 239000004641 Diallyl-phthalate Substances 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 229910000861 Mg alloy Inorganic materials 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 1
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 238000006069 Suzuki reaction reaction Methods 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 229920001807 Urea-formaldehyde Polymers 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- QHIWVLPBUQWDMQ-UHFFFAOYSA-N butyl prop-2-enoate;methyl 2-methylprop-2-enoate;prop-2-enoic acid Chemical compound OC(=O)C=C.COC(=O)C(C)=C.CCCCOC(=O)C=C QHIWVLPBUQWDMQ-UHFFFAOYSA-N 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 229960000956 coumarin Drugs 0.000 description 1
- 235000001671 coumarin Nutrition 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Natural products CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 1
- 239000010432 diamond Substances 0.000 description 1
- 229910003460 diamond Inorganic materials 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 239000007772 electrode material Substances 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 239000007850 fluorescent dye Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- 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 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- KHUXNRRPPZOJPT-UHFFFAOYSA-N phenoxy radical Chemical group O=C1C=C[CH]C=C1 KHUXNRRPPZOJPT-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 1
- 229920000548 poly(silane) polymer Polymers 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920001230 polyarylate Polymers 0.000 description 1
- 229920005668 polycarbonate resin Polymers 0.000 description 1
- 239000004431 polycarbonate resin Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- QHGNHLZPVBIIPX-UHFFFAOYSA-N tin(ii) oxide Chemical class [Sn]=O QHGNHLZPVBIIPX-UHFFFAOYSA-N 0.000 description 1
- 125000006617 triphenylamine group Chemical group 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical class [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- 235000014692 zinc oxide Nutrition 0.000 description 1
- RNWHGQJWIACOKP-UHFFFAOYSA-N zinc;oxygen(2-) Chemical class [O-2].[Zn+2] RNWHGQJWIACOKP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- 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
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- 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
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
-
- 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
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
-
- 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
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/311—Phthalocyanine
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
- H10K85/324—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising aluminium, e.g. Alq3
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/621—Aromatic anhydride or imide compounds, e.g. perylene tetra-carboxylic dianhydride or perylene tetracarboxylic di-imide
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
Definitions
- the present invention relates to a novel organic compound and an organic light emitting device using the same.
- An organic light emitting device is a device in which a thin film containing a fluorescent organic compound or a phosphorescent organic compound is interposed between an anode and a cathode; excitons of the fluorescent compound or the phosphorescent compound are generated by injection of electrons and holes from the electrodes and a light radiated when the excitons return to the ground state is utilized.
- non-patent document 1 In a research by Eastman Kodak Company in 1987 (non-patent document 1) , there is reported a light emission of about 1,000 cd/m 2 at an applied voltage of about 10 V for a device of functionally separated two-layer structure using ITO for an anode and a magnesium/silver alloy for a cathode, respectively, an aluminium-quinolinol complex as an electron- transporting material and a light emitting material and a triphenylamine derivative as a hole transporting material.
- Related patents include patent documents 1 to 3.
- Non-patent document 3 an organic light emitting device using a conjugated polymer other than the organic light emitting device using the low- molecular materials as described above.
- light emission in a onolayer is confirmed by forming a film of polyphenylenevinylene (PPV) in a coating system.
- PPV polyphenylenevinylene
- phenanthroline compounds are used as an electron transporting material or a light emitting material by the excellent electron transporting property thereof.
- Examples of documents in which the phenanthroline compounds are reported to be used for an organic light emitting device include patent references 17 to 21, but their properties when they are used as a light emitting material or an electron transporting material are not sufficient. [Patent document 1]
- Patent document 10 Japanese Patent Application Laid-Open No. H5- 202356 (no corresponding foreign document)
- Patent document 11 Japanese Patent Application Laid-Open No. H9- 202878 (no corresponding foreign document) [Patent document 11]
- Patent document 12 Japanese Patent Application Laid-Open No. H9- 227576 (no corresponding foreign document) [Patent document 12]
- Patent document 17 Japanese Patent Application Laid-Open No. H5- 247460 (no corresponding foreign document)
- Patent document 18 Japanese Patent Application Laid-Open No. H5- 247460 (no corresponding foreign document)
- Patent document 19 Japanese Patent Application Laid-Open No. H7- 82551 (no corresponding foreign document) [Patent document 19]
- Patent document 20 Japanese Patent Application Laid-Open No. 6,010,796
- an object of the present invention to provide a novel phenanthroline compound. It is another object of the present invention to provide an organic light emitting device having a light output with an extremely high efficiency and a high luminance using a specific phenanthroline compound . It is still another object of the present invention to provide an extremely durable organic light emitting device.
- the present invention provides a phenanthroline compound represented by any one of the following general formulas [I] to [III] :
- Ri, R 2 , R 3 , R, R 5 and Re are the same or different and each is selected from a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted aralkyl group, an unsubstituted or substituted aryl group, an unsubstituted or substituted heterocyclic group, and a halogen atom; and ri and Ar 2 are the same or different and each is selected from an unsubstituted or substituted fluorenyl group, an unsubstituted or substituted fluoranthenyl group, an unsubstituted or substituted perylenyl group, and an unsubstituted or substituted carbazolyl group) ;
- R, R 3 , R 9 , Rio. Rn and R ⁇ 2 are the same or different and each is selected from a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted aralkyl group, an unsubstituted or substituted aryl group, an unsubstituted or substituted heterocyclic group, and a halogen atom; and Ar 3 and Ar are the same or different and each is selected from an unsubstituted or substituted fluorenyl group, an unsubstituted or substituted fluoranthenyl group, an unsubstituted or substituted perylenyl group, and an unsubstituted or substituted carbazolyl group) ; and
- R i3 , R i4 , R 1 5 and Rie are the same or different and each is selected from a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted aralkyl group, an unsubstituted or substituted aryl group, an unsubstituted or substituted heterocyclic group, and a halogen atom; and Ar 5 , Ar 6 , Ar 7 and Ar 8 are the same or different and each is selected from an unsubstituted or substituted fluorenyl group, an unsubstituted or substituted fluoranthenyl group, an unsubstituted or substituted perylenyl group, and an unsubstituted or substituted carbazolyl group) .
- the fluorenyl group is preferably represented by the following general formula [IV] :
- R ⁇ 7 is selected from a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted aralkyl group, an unsubstituted or substituted aryl group, an unsubstituted or substituted heterocyclic group, a substituted amino group, a cyano group, and a halogen atom; and Ris and R ⁇ 9 are the same or different and each is selected from a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted aralkyl group, an unsubstituted or substituted aryl group, and an unsubstituted or substituted heterocyclic group) .
- the fluoranthenyl group is preferably represented by the following general formula [V] :
- R 20 is selected from a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted aralkyl group, an unsubstituted or substituted aryl group, an unsubstituted or substituted heterocyclic group, a substituted amino group, a cyano group, and a halogen atom
- the perylenyl group is preferably represented by the following general formula [VI] :
- R 21 is selected from a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted aralkyl group, an unsubstituted or substituted aryl group, an unsubstituted or substituted heterocyclic group, a substituted amino group, a cyano group, and a halogen atom
- carbazolyl group is preferably represented by the following general formula [VII] :
- R 22 and R 23 are the same or different and each is selected from a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted aralkyl group, an unsubstituted or substituted aryl group, an unsubstituted or substituted heterocyclic group, a substituted amino group, a cyano group, and a halogen atom) .
- the present invention provides an organic light emitting device comprising a pair of electrodes consisting of an anode and a cathode, and a layer comprising an organic compound comprising at least one of the above-mentioned phenanthroline compounds, interposed between the pair of electrodes.
- Fig. 1 is a sectional view illustrating an example of the organic light emitting device according to the present invention
- Fig. 2 is a sectional view illustrating another example of the organic light emitting device according to the present invention
- Fig. 3 is a sectional view illustrating still another example of the organic light emitting device according to the present invention.
- Fig. 4 is a sectional view illustrating yet another example of the organic light emitting device according to the present invention.
- Fig. 5 is a sectional view illustrating yet still another example of the organic light emitting device according to the present invention.
- Fig. 6 is a sectional view illustrating yet again another example of the organic light emitting device according to the present invention.
- the phenanthroline compounds of the present invention will be first described.
- the phenanthroline compounds of the present invention are represented by the above general formulas [I] to [III], wherein a fluorenyl group is represented by the above general formula [IV], a fluoranthenyl group by the above general formula [V] , a perylenyl group by the above general formula [VI] and a carbazolyl group by the above general formula [VII] .
- the alkyl group includes methyl, ethyl, n- propyl, iso-propyl, n-butyl, ter-butyl, octyl or the like.
- the aralkyl group includes benzyl, phenethyl or the like.
- the aryl group includes phenyl, biphenyl, terphenyl or the like.
- the heterocyclic group includes thienyl, pyrolyl, pyridyl, oxazolyl, oxadiazolyl, thiazolyl, thidiazolyl, terthienyl or the like.
- the substituted amino group includes dimethylamino, diehtylamino, dibenzylamino, diphenylamino, ditolylamino, dianisolylamino or the like.
- the halogen atom includes fluorine, chlorine, bromine, iodine or the like.
- the substituent groups that the above substituent groups may have include alkyl groups such as methyl, ethyl and propyl; aralkyl groups such as benzyl and phenethyl; aryl groups such as phenyl and biphenyl; heterocyclic groups such as thienyl, pyrolyl and pyridyl; amino groups such as dimethylamino, diethylamino, dibenzylamino, diphenylamino, ditolylamino and dianisolylamino; alkoxyl groups such as methoxyl, ethoxyl, propoxyl and phenoxyl; cyano group; and halogen atoms such as fluorine, chlorine, bromine and iodine.
- the phenanthroline compound of the present invention can be synthesized by generally known methods, in which it can be obtained by the synthesis such as the Suzuki coupling method using a palladium catalyst (e.g., Chem. Rev. 1995, 95, 2457-2483) through a phenanthroline compound intermediate that is obtained by the methods, for example, described in J. Org, Chem., 16, 941-945 (1951); Tetrahedron, Lett., 36, 3489-3490 (1995) and the like.
- a palladium catalyst e.g., Chem. Rev. 1995, 95, 2457-2483
- the phenanthroline compound of the present invention has superior electron transporting property and durability to the conventional compounds and is useful as a layer comprising an organic compound of an organic light emitting device, particularly as an electron transporting layer and a light emitting layer. Moreover, the layers formed by a vacuum evaporation process or a solution coating process are difficult to be crystallized and are excellent in long-term stability.
- the organic light emitting device of the present invention comprises a pair of electrodes consisting of an anode and a cathode, and a layer comprising an organic compound comprising at least one of the phenanthroline compounds represented by the general formula [I], [II] and [III], interposed between the pair of electrodes.
- At least an electron transporting layer or a light emitting layer of the layer (s) comprised of an organic compound comprises at least one of the above-mentioned phenanthrolines .
- the phenanthroline compound represented by the above general formulas [I] to [III] is formed between the anode and the cathode by a vacuum evaporation process or a solution coating process.
- the organic layer is preferably formed in a thin film having a thickness of less than 10 ⁇ r ⁇ , preferably 0.5 ⁇ r ⁇ or less, more preferably from 0.01 to 0.5 ⁇ m.
- Figs. 1 to 6 are views illustrating preferred examples of the organic light emitting device of the present invention.
- Fig. 1 is a sectional view illustrating one example of the organic light emitting device of the present invention.
- the device of Fig. 1 has the structure in which an anode 2, a light emitting layer 3 and a cathode 4 are provided on a substrate 1 in the mentioned order.
- the structure shown in Fig. 1 is useful when employing a compound having hole transportability, electron transportability and light emitting property singularly within itself, or when employing compounds having respective characteristics in mixture.
- Fig. 2 is a sectional view illustrating another example of the organic light emitting device of the present invention.
- the device of Fig. 2 has the structure in which an anode 2, a hole transporting layer 5, an electron transporting layer 6 and a cathode 4 are provided on a substrate 1 in the mentioned order.
- the structure shown in Fig. 2 is useful when a material having a hole transportability and/or electron transportability is used for respective layers as a light emitting substance in combination with a hole transporting or electron transporting substance having no light emitting property.
- the light emitting layer comprises either the hole transporting layer 5 or the electron transporting layer 6.
- Fig. 3 is a sectional view illustrating another example of the organic light emitting device of the present invention.
- the device of Fig. 3 has the structure in which an anode 2, a hole transporting layer 5, a light emitting layer 3, an electron transporting layer 6 and a cathode 4 are provided on a substrate 1 in the mentioned order.
- the structure is to separate a carrier transporting function and a light emitting function, and is used in suitable combination with compounds having the respective properties of hole transporting property, electron transporting property and light emitting property.
- the freedom of selection of materials is extremely increased, and various compounds having different emission wavelengths can be used to allow diversification of the luminescent hue. Further, carriers or excitons can be effectively confined in the central light emitting layer 3 to improve the light emission efficiency.
- Fig. 4 is a sectional view illustrating another example of the organic light emitting device of the present invention.
- the device of Fig. 4 has the structure in which a hole injecting layer 7 is inserted to the anode 2 side as compared with the structure shown in Fig. 3.
- the structure shown in Fig. 1 is effective for improving adhesiveness of the anode 2 to the hole transporting layer 5 or improving the hole injecting property and is also effective for driving at a reduced voltage.
- Figs. 5 and 6 are sectional views illustrating other examples of the organic light emitting device of the present invention.
- the devices of Figs. 5 and 6 have the structures in which a layer (hole-blocking layer 8) for blocking holes or excitons from passing through to the cathode 4 side is inserted between the light emitting layer 3 and the electron transporting layer 6 as compared with Figs. 3 and 4.
- the structure is effective for improving the light emission efficiency by using a compound having a very high ionization potential as the hole blocking layer 8.
- Figs. 1 to 6 merely show very basic device structures, and the structures of the organic light emitting device using the compounds of the present invention are not limited thereto. It is possible to take various structures, for example, to provide an insulating layer at an interface between an electrode and an organic layer, to provide an adhesion layer or an interference layer or to compose a hole transporting layer of two layers having different ionization potentials.
- the phenanthroline compounds represented by the general formulas [I] to [III] used in the present invention are excellent in electron transporting property and durability compared with the conventional compounds, and can be used in any one of the structures shown in Figs. 1 to 6.
- the present invention uses the phenanthroline compounds represented by the general formulas [I] to [III] as constituent components for an electron transporting layer or a light emitting layer, already known hole transporting compounds, light emitting compounds or electron transporting compounds can also be used together as needed
- M Cu, Mg, AlCI, TiO, SiCI 2 , Zn , Sn, m-MTDATA MnCI, GaCI, etc
- the layers containing the phenanthroline compounds represented by the general formulas [I] to [III] and the layers containing other organic compounds are generally formed into thin films by a vacuum evaporation process or a coating process in which they are dissolved in a suitable solvent.
- a coating process it is also possible to form the film in combination with a suitable binder resin.
- the binder resin can be selected from a wide range of binder resins, and include, for example, but not limited to, polyvinylcarbazole resins, polycarbonate resins, polyester resins, polyarylate resins, polystyrene resins, acrylic resins, methacrylic resins, butyral resins, polyvinylacetal resins, diallylphthalate resins, phenol resins, epoxy resins, silicone resins, polysulfone resins, urea resins and the like. In addition, one of them or a mixture of two or more of them may be used in the form of a homopolymer or a copolymer.
- the materials for the anode preferably have a large work function, and metals such as, for example, gold, platinum, nickel, palladium, cobalt, selenium, vanadium and alloys thereof and metal oxides such as tin oxides, zinc oxides, indium tin oxides (ITO) and indium zinc oxides can be used.
- metals such as, for example, gold, platinum, nickel, palladium, cobalt, selenium, vanadium and alloys thereof and metal oxides such as tin oxides, zinc oxides, indium tin oxides (ITO) and indium zinc oxides
- metal oxides such as tin oxides, zinc oxides, indium tin oxides (ITO) and indium zinc oxides
- conductive polymers such as polyaniline, polypyrrole, polythiophene and poyphenylene sulfide can be used. These electrode materials can be used singularly or in combination.
- the materials for the cathode preferably have a small work function, and metals such as lithium, sodium, potassium, cesium, calcium, magnesium, aluminium, indium, silver, lead, tin and chrome and alloys thereof can be used. Metal oxides such as indium tin oxides (ITO) can also be used.
- the cathode may have either a one- layer structure or a multilayer structure.
- the substrate for use in the present invention includes, but not limited to, metal substrates, opaque substrates such as ceramic substrates, and transparent substrates such as glass, quartz and pla,stic sheets. Moreover, it is possible to control the color of emitted light using a color filter film, a fluorescent color conversion filter film, a dielectric reflecting film and the like for the substrate .
- a protective layer or an encapsulant layer can also be provided on the prepared device for the purpose of preventing contact with oxygen, moisture and the like.
- the protective layer includes an inorganic material film such as a diamond thin film, a metal oxide film or a metal nitride film; a polymeric film such as of fluororesin, polyparaxylene, polyethylene, silicone resin and polystyrene resin; a photo-curable resin or the like.
- the device itself can be covered with glass, a gas-impermeable film, metal or the like and packaged with a suitable encapsulant resin.
- a device having the structure shown in Fig. 3 was prepared.
- ITO indium tin oxide
- IPA isopropyl alcohol
- a chloroform solution of the compound represented by the following structural formula was applied by a spin-coating process to form a film having a thickness of 30 nm, thus forming the hole transporting layer 5.
- the Ir complex represented by the following structural formula and Exemplary Compound No. 1 as the instant phenanthroline compound (weight ratio of 5:100) were deposited by a vacuum evaporation process in a thickness of 20 nm to form the light emitting layer 3.
- the degree of the vacuum at the evaporation was 1.0 x 10 ⁇ 4 Pa and the film formation rate was 0.2-0.3 nm/sec,
- trisquinolinol aluminium was deposited by a vacuum evaporation process in a thickness of 40 nm to form the electron transporting layer 6.
- the degree of the vacuum at the evaporation was 1.0 x 10 "4 Pa and the film formation rate was 0.2-0.3 nm/sec.
- a vacuum evaporation material consisting of aluminium and lithium (lithium concentration of 1 atomic %) was used to form a metal layer film having a thickness of 50 nm on the above organic layer by a vacuum evaporation process, and further by the vacuum evaporation process an aluminium layer having a thickness of 150 nm was formed.
- the degree of the vacuum at the evaporation was 1.0 x 10 "4 Pa and the film formation rate was 1.0-1.2 nm/sec.
- the resultant structure was covered with a protective glass plate in a nitrogen atmosphere and sealed with an acrylic resin adhesive.
- the thus obtained device was applied with a DC voltage of 10 V using the ITO electrode (anode 2) as a positive electrode and the Al-Li electrode (cathode 4) as a negative electrode, the current passed through the device at a current density of 18.0 mA/cm 2 and emission of green light was observed at a luminance of 4,500 cd/m 2 .
- a device of the structure shown in Fig. 3 was prepared.
- the hole transporting layer 5 was formed on the transparent conductive supporting substrate in the same manner as in Example 1.
- coumarin and trisquinolinol aluminium (polymerization ratio of 1:20) were deposited by a vacuum evaporation process in a thickness of 20 nm to form the light emitting layer 3.
- the degree of the vacuum at the evaporation was 1.0 x 10 -4 Pa and the film formation rate was 0.2-0.3 nm/sec.
- Exemplary Compound No. 3 was deposited in a thickness of 40 nm to form the electron transporting layer 6.
- the degree of the vacuum at the evaporation was 1.0 x 10 -4 Pa and the film formation rate was 0.2-0.3 nm/sec. Then, the device was sealed after the cathode 4 was formed in the same manner as in Example 1.
- a device with the structure shown in Fig. 3 was prepared.
- the hole transporting layer 5 was formed on the transparent conductive supporting substrate in the same manner as in Example 1.
- the Ir complex represented by the following structural formula and the carbazole compound represented by the following structural formula (polymerization ratio of 5:100) were deposited by a vacuum evaporation process in a thickness of 20 nm to form the light emitting layer 3
- the degree of the vacuum at the evaporation was 1.0 x 10 ⁇ 4 Pa and the film formation rate was 0.2-0.3 nm/sec.
- Exemplary Compound No. 5 was deposited in a thickness of 40 nm to form the electron transporting layer 6.
- the degree of the vacuum at the evaporation was 1.0 x 10 -4 Pa and the film formation rate was 0.2-0.3 nm/sec.
- the device was then sealed after the cathode 4 was formed in the same manner as in Example 1.
- the organic light emitting devices using the phenanthroline compounds represented by the general formulas [I] to [III] provide the emission having a high luminance at a low applied voltage and are also excellent in durability.
- the organic layers comprising the phenanthroline compounds of the present invention are excellent as an electron transporting layer as well as a light emitting layer.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Electroluminescent Light Sources (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
A novel phenanthroline compound is provided which is represented by the general formula [I]: (wherein R?1#191, R?2#191, R?3#191, R?4#191, R?5#191 and R?6#191 are the same or different and each is selected from a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted aralkyl group, an unsubstituted or substituted aryl group, an unsubstituted or substituted heterocyclic group, and a halogen atom, and Ar?1#191 and Ar?2#191 are the same or different and each is selected from an unsubstituted or substituted fluorenyl group, an unsubstituted or substituted fluoranthenyl group, an unsubstituted or substituted perylenyl group, and an unsubstituted or substituted carbazolyl group). An organic light emitting device using the phenanthroline compound is also provided that has a light output with a high efficiency and a high luminance and has a high long-term durability.
Description
DESCRIPTION
PHENANTHROLINE COMPOUND AND ORGANIC LIGHT EMITTING
DEVICE USING SAME
TECHNICAL FIELD
The present invention relates to a novel organic compound and an organic light emitting device using the same.
BACKGROUND ART
An organic light emitting device is a device in which a thin film containing a fluorescent organic compound or a phosphorescent organic compound is interposed between an anode and a cathode; excitons of the fluorescent compound or the phosphorescent compound are generated by injection of electrons and holes from the electrodes and a light radiated when the excitons return to the ground state is utilized. In a research by Eastman Kodak Company in 1987 (non-patent document 1) , there is reported a light emission of about 1,000 cd/m2 at an applied voltage of about 10 V for a device of functionally separated two-layer structure using ITO for an anode and a magnesium/silver alloy for a cathode, respectively, an aluminium-quinolinol complex as an electron- transporting material and a light emitting material
and a triphenylamine derivative as a hole transporting material. Related patents include patent documents 1 to 3.
In addition, light emission of from ultraviolet region to infrared region is possible by changing the type of the fluorescent organic compound and researches of various compounds have been conducted actively recently. For example, they are described in patent documents 4 to 11. In recent years, there have been a number of studies in which phosphorescent compounds are used as a light emitting material and an energy in a triplet state is used for an EL (electro luminescent) emission. A group of Princeton University has reported that an organic light emitting device using an iridium complex as a light emitting material exhibits a high light emission efficiency (non-patent document 2) .
Moreover, a group of Cambridge University has reported (non-patent document 3) an organic light emitting device using a conjugated polymer other than the organic light emitting device using the low- molecular materials as described above. In this report light emission in a onolayer is confirmed by forming a film of polyphenylenevinylene (PPV) in a coating system.
Related patents on organic light emitting
devices using conjugated polymers include patent documents 12 to 16.
Thus, recent progress in organic light emitting devices is remarkable, and possibilities for a wide range of applications are indicated since it is characterized in that a thin and lightweight light emitting device having a high luminance at a low applied-voltage, diversity of light emitting wavelength and high-speed response can be prepared. However, a higher-luminance light output or high conversion efficiency is required under present circumstances. In addition, there are numbers of problems in terms of durability such as variation with the elapse of time during use for a long period of time and the deterioration due to an atmospheric gas including oxygen or humidity. Moreover, the light emission of blue, green and red having a good color purity is required for applications such as a full-color display, but these issues are not sufficiently satisfied.
On the other hand, phenanthroline compounds are used as an electron transporting material or a light emitting material by the excellent electron transporting property thereof. Examples of documents in which the phenanthroline compounds are reported to be used for an organic light emitting device include patent references 17 to 21, but their properties when
they are used as a light emitting material or an electron transporting material are not sufficient. [Patent document 1]
U.S. Patent No. 4,539,507 [Patent document 2]
U.S. Patent No. 4,720,432 [Patent document 3]
U.S. Patent No. 4,885,211 [Patent document 4] U.S. Patent No. 5,151,629 [Patent document 5]
U.S. Patent No. 5,409,783 [Patent document 6]
U.S. Patent No. 5,382,477 [Patent document 7]
U.S. Patent No. 5,130,603; U.S. Patent No. 6,093,864 [Patent document 8]
U.S. Patent No. 5,227,252 [Patent document 9]
Japanese Patent Application Laid-Open No. H5- 202356 (no corresponding foreign document) [Patent document 10]
Japanese Patent Application Laid-Open No. H9- 202878 (no corresponding foreign document) [Patent document 11]
Japanese Patent Application Laid-Open No. H9-
227576 (no corresponding foreign document) [Patent document 12]
U.S. Patent No. 5,247,190 [Patent document 13] U.S. Patent No. 5,514,878 [Patent document 14]
U.S. Patent No. 5,672,678 [Patent document 15]
U.S. Patent No. 5,317,169; U.S. Patent No. 5,726,457
[Patent document 16]
Japanese Patent Application Laid-Open No. H5- 247460 (no corresponding foreign document) [Patent document 17] U.S. Patent No. 5,393,614 [Patent document 18]
Japanese Patent Application Laid-Open No. H7- 82551 (no corresponding foreign document) [Patent document 19] U.S. Patent No. 6,010,796 [Patent document 20]
Japanese Patent Application Laid-Open No. 2001- 267080 (no corresponding foreign document) [Patent document 21] Japanese Patent Application Laid-Open No. 2001- 131174 (no corresponding foreign document) [Non-patent document 1]
Appl. Phys. Lett. 51, 913 (1987) [Non-patent document 2]
Nature, 395, 151 (1998) [Non-patent document 3] Nature, 347, 539 (1990)
DISCLOSURE OF THE INVENTION
It is, therefore, an object of the present invention to provide a novel phenanthroline compound. It is another object of the present invention to provide an organic light emitting device having a light output with an extremely high efficiency and a high luminance using a specific phenanthroline compound . It is still another object of the present invention to provide an extremely durable organic light emitting device.
It is yet another object of the present invention to provide an organic light emitting device that is easily produced and can be prepared at a relatively low cost.
Specifically, the present invention provides a phenanthroline compound represented by any one of the following general formulas [I] to [III] :
(wherein Ri, R2, R3, R, R5 and Re are the same or different and each is selected from a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted aralkyl group, an unsubstituted or substituted aryl group, an unsubstituted or substituted heterocyclic group, and a halogen atom; and ri and Ar2 are the same or different and each is selected from an unsubstituted or substituted fluorenyl group, an unsubstituted or substituted fluoranthenyl group, an unsubstituted or substituted perylenyl group, and an unsubstituted or substituted carbazolyl group) ;
(wherein R, R3, R9, Rio. Rn and Rι2 are the same or different and each is selected from a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted aralkyl group, an unsubstituted or substituted aryl group, an unsubstituted or substituted heterocyclic group, and
a halogen atom; and Ar3 and Ar are the same or different and each is selected from an unsubstituted or substituted fluorenyl group, an unsubstituted or substituted fluoranthenyl group, an unsubstituted or substituted perylenyl group, and an unsubstituted or substituted carbazolyl group) ; and
(wherein Ri3, Ri4, R15 and Rie are the same or different and each is selected from a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted aralkyl group, an unsubstituted or substituted aryl group, an unsubstituted or substituted heterocyclic group, and a halogen atom; and Ar5, Ar6, Ar7 and Ar8 are the same or different and each is selected from an unsubstituted or substituted fluorenyl group, an unsubstituted or substituted fluoranthenyl group, an unsubstituted or substituted perylenyl group, and an unsubstituted or substituted carbazolyl group) . In the phenanthroline compounds of the present invention, the fluorenyl group is preferably represented by the following general formula [IV] :
(wherein Rι7 is selected from a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted aralkyl group, an unsubstituted or substituted aryl group, an unsubstituted or substituted heterocyclic group, a substituted amino group, a cyano group, and a halogen atom; and Ris and Rχ9 are the same or different and each is selected from a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted aralkyl group, an unsubstituted or substituted aryl group, and an unsubstituted or substituted heterocyclic group) . Also, the fluoranthenyl group is preferably represented by the following general formula [V] :
(wherein R20 is selected from a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted aralkyl group, an unsubstituted or substituted aryl group, an unsubstituted or substituted heterocyclic group, a substituted amino group, a cyano group, and a halogen atom) .
Also, the perylenyl group is preferably represented by the following general formula [VI] :
(wherein R21 is selected from a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted aralkyl group, an unsubstituted or substituted aryl group, an unsubstituted or substituted heterocyclic group, a substituted amino group, a cyano group, and a halogen atom) .
Also, the carbazolyl group is preferably represented by the following general formula [VII] :
(wherein R22 and R23 are the same or different and each is selected from a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted aralkyl group, an unsubstituted or substituted aryl group, an unsubstituted or substituted heterocyclic group, a substituted amino group, a cyano group, and a halogen atom) .
Further, the present invention provides an organic light emitting device comprising a pair of
electrodes consisting of an anode and a cathode, and a layer comprising an organic compound comprising at least one of the above-mentioned phenanthroline compounds, interposed between the pair of electrodes.
BRIEF DESCRIPTION OF THE DRAWINGS
Fig. 1 is a sectional view illustrating an example of the organic light emitting device according to the present invention; Fig. 2 is a sectional view illustrating another example of the organic light emitting device according to the present invention;
Fig. 3 is a sectional view illustrating still another example of the organic light emitting device according to the present invention;
Fig. 4 is a sectional view illustrating yet another example of the organic light emitting device according to the present invention;
Fig. 5 is a sectional view illustrating yet still another example of the organic light emitting device according to the present invention; and
Fig. 6 is a sectional view illustrating yet again another example of the organic light emitting device according to the present invention.
BEST MODE FOR CARRYING OUT THE INVENTION
The present invention will now be described in
detail .
The phenanthroline compounds of the present invention will be first described.
Preferably, the phenanthroline compounds of the present invention are represented by the above general formulas [I] to [III], wherein a fluorenyl group is represented by the above general formula [IV], a fluoranthenyl group by the above general formula [V] , a perylenyl group by the above general formula [VI] and a carbazolyl group by the above general formula [VII] .
Specific examples for the substituent groups in the above general formulas [I] -[VII] are shown below.
The alkyl group includes methyl, ethyl, n- propyl, iso-propyl, n-butyl, ter-butyl, octyl or the like.
The aralkyl group includes benzyl, phenethyl or the like.
The aryl group includes phenyl, biphenyl, terphenyl or the like.
The heterocyclic group includes thienyl, pyrolyl, pyridyl, oxazolyl, oxadiazolyl, thiazolyl, thidiazolyl, terthienyl or the like.
The substituted amino group includes dimethylamino, diehtylamino, dibenzylamino, diphenylamino, ditolylamino, dianisolylamino or the like.
The halogen atom includes fluorine, chlorine, bromine, iodine or the like.
The substituent groups that the above substituent groups may have include alkyl groups such as methyl, ethyl and propyl; aralkyl groups such as benzyl and phenethyl; aryl groups such as phenyl and biphenyl; heterocyclic groups such as thienyl, pyrolyl and pyridyl; amino groups such as dimethylamino, diethylamino, dibenzylamino, diphenylamino, ditolylamino and dianisolylamino; alkoxyl groups such as methoxyl, ethoxyl, propoxyl and phenoxyl; cyano group; and halogen atoms such as fluorine, chlorine, bromine and iodine.
The followings are typical examples of the phenanthroline compounds of the present invention, but the present invention is not limited thereto:
[Typical Examples of Compounds of Formula [I]] (Exemplary Compound Nos. 1-16)
[Typical Examples of Compounds of Formula [II]] (Exemplary Compound Nos. 17-18)
[Typical Examples of Compounds of Formula [III] ] (Exemplary Compound Nos. 19-30)
The phenanthroline compound of the present invention can be synthesized by generally known methods, in which it can be obtained by the synthesis such as the Suzuki coupling method using a palladium catalyst (e.g., Chem. Rev. 1995, 95, 2457-2483) through a phenanthroline compound intermediate that is obtained by the methods, for example, described in J. Org, Chem., 16, 941-945 (1951); Tetrahedron, Lett., 36, 3489-3490 (1995) and the like.
The phenanthroline compound of the present invention has superior electron transporting property and durability to the conventional compounds and is useful as a layer comprising an organic compound of
an organic light emitting device, particularly as an electron transporting layer and a light emitting layer. Moreover, the layers formed by a vacuum evaporation process or a solution coating process are difficult to be crystallized and are excellent in long-term stability.
The organic light emitting device of the present invention will now be described in detail. The organic light emitting device of the present invention comprises a pair of electrodes consisting of an anode and a cathode, and a layer comprising an organic compound comprising at least one of the phenanthroline compounds represented by the general formula [I], [II] and [III], interposed between the pair of electrodes.
In the organic light emitting device of the present invention, it is preferred that at least an electron transporting layer or a light emitting layer of the layer (s) comprised of an organic compound comprises at least one of the above-mentioned phenanthrolines .
In the organic light emitting device of the present invention, the phenanthroline compound represented by the above general formulas [I] to [III] is formed between the anode and the cathode by a vacuum evaporation process or a solution coating process. The organic layer is preferably formed in a
thin film having a thickness of less than 10 μrα, preferably 0.5 μrα or less, more preferably from 0.01 to 0.5 μm.
Figs. 1 to 6 are views illustrating preferred examples of the organic light emitting device of the present invention.
Fig. 1 is a sectional view illustrating one example of the organic light emitting device of the present invention. The device of Fig. 1 has the structure in which an anode 2, a light emitting layer 3 and a cathode 4 are provided on a substrate 1 in the mentioned order. The structure shown in Fig. 1 is useful when employing a compound having hole transportability, electron transportability and light emitting property singularly within itself, or when employing compounds having respective characteristics in mixture.
Fig. 2 is a sectional view illustrating another example of the organic light emitting device of the present invention. The device of Fig. 2 has the structure in which an anode 2, a hole transporting layer 5, an electron transporting layer 6 and a cathode 4 are provided on a substrate 1 in the mentioned order. The structure shown in Fig. 2 is useful when a material having a hole transportability and/or electron transportability is used for respective layers as a light emitting substance in
combination with a hole transporting or electron transporting substance having no light emitting property. In this case, the light emitting layer comprises either the hole transporting layer 5 or the electron transporting layer 6.
Fig. 3 is a sectional view illustrating another example of the organic light emitting device of the present invention. The device of Fig. 3 has the structure in which an anode 2, a hole transporting layer 5, a light emitting layer 3, an electron transporting layer 6 and a cathode 4 are provided on a substrate 1 in the mentioned order. The structure is to separate a carrier transporting function and a light emitting function, and is used in suitable combination with compounds having the respective properties of hole transporting property, electron transporting property and light emitting property. Thus, the freedom of selection of materials is extremely increased, and various compounds having different emission wavelengths can be used to allow diversification of the luminescent hue. Further, carriers or excitons can be effectively confined in the central light emitting layer 3 to improve the light emission efficiency. Fig. 4 is a sectional view illustrating another example of the organic light emitting device of the present invention. The device of Fig. 4 has the
structure in which a hole injecting layer 7 is inserted to the anode 2 side as compared with the structure shown in Fig. 3. The structure shown in Fig. 1 is effective for improving adhesiveness of the anode 2 to the hole transporting layer 5 or improving the hole injecting property and is also effective for driving at a reduced voltage.
Figs. 5 and 6 are sectional views illustrating other examples of the organic light emitting device of the present invention. The devices of Figs. 5 and 6 have the structures in which a layer (hole-blocking layer 8) for blocking holes or excitons from passing through to the cathode 4 side is inserted between the light emitting layer 3 and the electron transporting layer 6 as compared with Figs. 3 and 4. The structure is effective for improving the light emission efficiency by using a compound having a very high ionization potential as the hole blocking layer 8. It should be noted that Figs. 1 to 6 merely show very basic device structures, and the structures of the organic light emitting device using the compounds of the present invention are not limited thereto. It is possible to take various structures, for example, to provide an insulating layer at an interface between an electrode and an organic layer, to provide an adhesion layer or an interference layer
or to compose a hole transporting layer of two layers having different ionization potentials.
The phenanthroline compounds represented by the general formulas [I] to [III] used in the present invention are excellent in electron transporting property and durability compared with the conventional compounds, and can be used in any one of the structures shown in Figs. 1 to 6.
Although the present invention uses the phenanthroline compounds represented by the general formulas [I] to [III] as constituent components for an electron transporting layer or a light emitting layer, already known hole transporting compounds, light emitting compounds or electron transporting compounds can also be used together as needed
Examples of these compounds include the followings :
[Hole Transporting Compounds]
M : Cu, Mg, AlCI, TiO, SiCI2, Zn , Sn, m-MTDATA MnCI, GaCI, etc
TPAC PDA
[Electron Transporting, Light Emitting Compounds]
M : Zn , Mg , Be M : Zn , Mg , Be
M : Zn , Mg , Be M : Zn , Mg , Be
M : Al , Ga
[Light Emitting Compounds]
Quinacridone
Coronene
Rubrene
[Light Emitting Layer Matrix Compounds/Electron Transporting Compounds]
TPD-PCA
In the organic light emitting device of the present invention, the layers containing the phenanthroline compounds represented by the general formulas [I] to [III] and the layers containing other organic compounds are generally formed into thin films by a vacuum evaporation process or a coating process in which they are dissolved in a suitable solvent. In particular, when the film is formed by a coating process, it is also possible to form the film in combination with a suitable binder resin.
The binder resin can be selected from a wide range of binder resins, and include, for example, but not limited to, polyvinylcarbazole resins, polycarbonate resins, polyester resins, polyarylate resins, polystyrene resins, acrylic resins, methacrylic resins, butyral resins, polyvinylacetal resins, diallylphthalate resins, phenol resins, epoxy resins, silicone resins, polysulfone resins, urea resins and the like. In addition, one of them or a mixture of two or more of them may be used in the form of a homopolymer or a copolymer.
The materials for the anode preferably have a large work function, and metals such as, for example, gold, platinum, nickel, palladium, cobalt, selenium, vanadium and alloys thereof and metal oxides such as tin oxides, zinc oxides, indium tin oxides (ITO) and indium zinc oxides can be used. In addition, conductive polymers such as polyaniline, polypyrrole, polythiophene and poyphenylene sulfide can be used. These electrode materials can be used singularly or in combination.
On the other hand, the materials for the cathode preferably have a small work function, and metals such as lithium, sodium, potassium, cesium, calcium, magnesium, aluminium, indium, silver, lead, tin and chrome and alloys thereof can be used. Metal oxides such as indium tin oxides (ITO) can also be
used. Moreover, the cathode may have either a one- layer structure or a multilayer structure.
The substrate for use in the present invention includes, but not limited to, metal substrates, opaque substrates such as ceramic substrates, and transparent substrates such as glass, quartz and pla,stic sheets. Moreover, it is possible to control the color of emitted light using a color filter film, a fluorescent color conversion filter film, a dielectric reflecting film and the like for the substrate .
Furthermore, a protective layer or an encapsulant layer can also be provided on the prepared device for the purpose of preventing contact with oxygen, moisture and the like. The protective layer includes an inorganic material film such as a diamond thin film, a metal oxide film or a metal nitride film; a polymeric film such as of fluororesin, polyparaxylene, polyethylene, silicone resin and polystyrene resin; a photo-curable resin or the like. Moreover, the device itself can be covered with glass, a gas-impermeable film, metal or the like and packaged with a suitable encapsulant resin. [Examples] The present invention will now be described in detail with reference to examples, but the present invention is not limited to them.
[Synthesis Example 1] [Synthesis of Exemplary Compound No . 2 ]
/ Toluene No-2
To a three-necked flask of 300 ml, 5.8 g (18.1 mmol) of 2-iodo-9, 9-dimethylfluorene [1] and 80 ml of diethyl ether were charged and 11.7 ml (18.1 mmol) of n-butyllithium (hexane solution of 15%) was dropped under stirring at -78 °C in a nitrogen atmosphere. The mixture was raised to room temperature and stirred for one hour, and then cooled to -20°C and a dispersion of 1.5 g (4.51 mmol) of bathophenanthroline [2] in 100 ml of toluene was dropped. The mixture was stirred at room temperature for 12 hours and was added with water. The organic layer was extracted with chloroform and dried with anhydrous sodium sulfate, and then purified with an alumina column (hexane/chloroform solvent mixture developer), obtaining 2.4 g (yield of 74%) of Exemplary Compound No. 2 (yellow crystal). [Synthesis Example 2] [Synthesis of Exemplary Compound No . 5]
No.5 *1) J.Org.C em., 16, 941-945 (1951)
To a three-necked flask of 500 ml, 1.0 g (2.96 mmol) of 4, 7-dibromo-l, 10-phenanthroline [3]*1', 2.8 g (11.8 mmol) of 9, 9-dimethylfluorene-2-boronic acid [4], 140 ml of toluene and 70 ml of ethanol were charged and an aqueous solution of 12 g of sodium carbonate/60 ml of water was dropped under stirring at room temperature in a nitrogen atmosphere, and then 0.17 g (0.15 mmol) of tetrakis (triphenylphosphme) palladium (0) was added. After stirring at room temperature for 30 minutes, the mixture was raised to a temperature of 77 °C and stirred for 3 hours. After the reaction, the organic layer was extracted with chloroform and dried with anhydrous sodium sulfate, and then purified with an alumina column (hexane/chloroform solvent mixture developer), obtaining 1.5 g (yield of 90%) of Exemplary Compound No. 5 (white crystal) . [Synthesis Example 3] [Synthesis of Exemplary
Compound No . 19]
No. 19
To a three-necked flask of 300 ml, 2.3 g (7.18 mmol) of 2-iodo-9, 9-dimethylfluorene [5] and 60 ml of diethyl ether were charged and .6 ml (7.18 mmol) of n-butyllithium (hexane solution of 15%) was dropped under stirring at -78 °C in a nitrogen atmosphere. The mixture was raised to room temperature and stirred for one hour, and then cooled to -20°C and a dispersion of 1.0 g (1.77 mmol) of Exemplary Compound No. 5 in 80 ml of toluene was dropped. The mixture was stirred at room temperature for 12 hours and was added with water. The organic layer was extracted with chloroform and dried with anhydrous sodium sulfate, and then purified with an alumina column (hexane/chloroform solvent mixture developer) , obtaining 1.2 g (yield of 73%) of Exemplary Compound
No. 19 (yellow crystal).
[Synthesis Example 4] [Synthesis of Exemplary Compound No. 8]
[6] [71
A device having the structure shown in Fig. 3 was prepared.
On a glass substrate as the substrate 1, indium tin oxide (ITO) as the anode 2 was deposited by a sputtering process in a thickness of 120 nm, the resultant structure being used as a transparent conductive supporting substrate. This was ultrasonically cleaned with acetone and isopropyl alcohol (IPA) in this order, and dried after the cleaning by boiling with IPA. Further, it was cleaned with UV/ozone. The resultant structure was used as a transparent conductive supporting substrate,
On the transparent conductive supporting substrate, a chloroform solution of the compound represented by the following structural formula was applied by a spin-coating process to form a film having a thickness of 30 nm, thus forming the hole transporting layer 5.
In addition, the Ir complex represented by the following structural formula and Exemplary Compound
No. 1 as the instant phenanthroline compound (weight ratio of 5:100) were deposited by a vacuum evaporation process in a thickness of 20 nm to form the light emitting layer 3. As for the conditions, the degree of the vacuum at the evaporation was 1.0 x 10~4 Pa and the film formation rate was 0.2-0.3 nm/sec,
Moreover, trisquinolinol aluminium was deposited by a vacuum evaporation process in a thickness of 40 nm to form the electron transporting layer 6. As for the conditions, the degree of the vacuum at the evaporation was 1.0 x 10"4 Pa and the film formation rate was 0.2-0.3 nm/sec.
Then, as the cathode 4, a vacuum evaporation material consisting of aluminium and lithium (lithium concentration of 1 atomic %) was used to form a metal layer film having a thickness of 50 nm on the above organic layer by a vacuum evaporation process, and further by the vacuum evaporation process an aluminium layer having a thickness of 150 nm was formed. As for the conditions, the degree of the vacuum at the evaporation was 1.0 x 10"4 Pa and the
film formation rate was 1.0-1.2 nm/sec.
Furthermore, the resultant structure was covered with a protective glass plate in a nitrogen atmosphere and sealed with an acrylic resin adhesive. When the thus obtained device was applied with a DC voltage of 10 V using the ITO electrode (anode 2) as a positive electrode and the Al-Li electrode (cathode 4) as a negative electrode, the current passed through the device at a current density of 18.0 mA/cm2 and emission of green light was observed at a luminance of 4,500 cd/m2.
In addition, when the voltage was applied for 100 hours while maintaining the current density at 6.0 mA/cm2, the initial luminance of 850 cd/m2 dropped to 800 cd/m2 after 100 hours, exhibiting only a small reduction of luminance . (Examples 2 to 9)
Devices were prepared and evaluated in the same manner as in Example 1 with the exception that Exemplary Compounds shown in Table 1 below were used instead of Exemplary Compound No. 1. The results are shown in Table 1. (Comparative Examples 1 to 3)
Devices were prepared and evaluated in the same manner as in Example 1 with the exception that
Comparative Compound Nos . 1-3 shown below were used instead of Exemplary Compound No. 1. The results are
shown in Table 1
Comparative Compound No. 1
Comparative Compound No. 2
Comparative Compound No . 3
Table 1
(Example 10 )
A device of the structure shown in Fig. 3 was prepared.
The hole transporting layer 5 was formed on the transparent conductive supporting substrate in the same manner as in Example 1.
In addition, coumarin and trisquinolinol aluminium (polymerization ratio of 1:20) were deposited by a vacuum evaporation process in a thickness of 20 nm to form the light emitting layer 3. As for the conditions, the degree of the vacuum at the evaporation was 1.0 x 10-4 Pa and the film formation rate was 0.2-0.3 nm/sec.
Moreover, Exemplary Compound No. 3 was deposited in a thickness of 40 nm to form the electron transporting layer 6. As for the conditions, the degree of the vacuum at the evaporation was 1.0 x 10-4 Pa and the film formation rate was 0.2-0.3 nm/sec. Then, the device was sealed after the cathode 4 was formed in the same manner as in Example 1.
When the thus obtained device was applied with a DC voltage of 8 V using the ITO electrode (anode 2) as a positive electrode and the Al-Li electrode (cathode 4) as a negative electrode, the current passed through the device at a current density of
1,110 mA/cm2 and emission of green light was observed ■at a luminance of 95,000 cd/m2.
Furthermore, when the voltage was applied for 100 hours while maintaining the current density at 200 mA/cm2, the initial luminance of 10,000 cd/m2 dropped to 8,500 cd/m2 after 100 hours, exhibiting only a small reduction of luminance . (Examples 11 to 18)
Devices were prepared and evaluated in the same manner as in Example 10 with the exception that Exemplary Compounds shown in Table 2 were used instead of Exemplary Compound No. 3. The results are shown in Table 2. (Comparative Examples 4 to 6)
Devices were prepared and evaluated in the same manner as in Example 10 with the exception that Comparative Compound Nos. 1 to 3 were used instead of Exemplary Compound No. 3. The results are shown in Table 2.
Table 2
π
(Example 19)
A device with the structure shown in Fig. 3 was prepared.
The hole transporting layer 5 was formed on the transparent conductive supporting substrate in the same manner as in Example 1.
In addition, the Ir complex represented by the following structural formula and the carbazole compound represented by the following structural formula (polymerization ratio of 5:100) were deposited by a vacuum evaporation process in a thickness of 20 nm to form the light emitting layer 3 As for the conditions, the degree of the vacuum at the evaporation was 1.0 x 10~4 Pa and the film formation rate was 0.2-0.3 nm/sec.
When the thus obtained device was applied with a DC voltage of 10 V using the ITO electrode (anode 2) as a positive electrode and the Al-Li electrode (cathode 4) as a negative electrode, the current passed through the device at a current density of 20.0 mA/cm2 and emission of green light was observed at a luminance of 6,800 cd/m2. Furthermore, when the voltage was applied for 100 hours while maintaining the current density at 6.0 mA/cm2, the initial luminance of 1,300 cd/m2 dropped to 1,150 cd/m2 after 100 hours, exhibiting only a small reduction of luminance. (Examples 20 to 31)
Devices were prepared and evaluated in the same manner as in Example 19 with the exception that Exemplary Compounds shown in Table 3 were used instead of Exemplary Compound No. 5. The results are shown in Table 3.
(Comparative Examples 7 to 9)
Devices were prepared and evaluated in the same
manner as in Example 19 with the exception that Comparative Compound Nos. 1 to 3 were used instead of Exemplary Compound No. 5. The results are shown in Table 3.
Table 3
As described above by illustrating embodiments and examples, the organic light emitting devices using the phenanthroline compounds represented by the general formulas [I] to [III] provide the emission having a high luminance at a low applied voltage and are also excellent in durability. Particularly, the organic layers comprising the phenanthroline compounds of the present invention are excellent as an electron transporting layer as well as a light emitting layer.
Moreover, it is possible to prepare the devices by using a vacuum evaporation process, casting process or the like, and the devices having a large area can be prepared easily at a relatively low cost.
Claims
1. A phenanthroline compound represented by the general formula [I] :
(wherein Rα, R2, R3, R4, R5 and R6 are the same or different and each is selected from a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted aralkyl group, an unsubstituted or substituted aryl group, an unsubstituted or substituted heterocyclic group, and a halogen atom; and Ar_ and Ar2 are the same or different and each is selected from an unsubstituted or substituted fluorenyl group, an unsubstituted or substituted fluoranthenyl group, an unsubstituted or substituted perylenyl group, and an unsubstituted or substituted carbazolyl group) .
2. A phenanthroline compound represented by the general formula [II] :
(wherein R7, R8 , R9, R10. R11 and R12 are the same or different and each is selected from a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted aralkyl group, an unsubstituted or substituted aryl group, an unsubstituted or substituted heterocyclic group, and a halogen atom; and Ar3 and Ar4 are the same or different and each is selected from an unsubstituted or substituted fluorenyl group, an unsubstituted or substituted fluoranthenyl group, an unsubstituted or substituted perylenyl group, and an unsubstituted or substituted carbazolyl group) .
3. A phenanthroline compound represented by the general formula [III] :
(wherein Ri3, R14, Rι5 and Rχ6 are the same or different and each is selected from a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted aralkyl group, an unsubstituted or substituted aryl group, an unsubstituted or substituted heterocyclic group, and a halogen atom; and Ar5, Ar6, Ar7 and Ar8 are the same or different and each is selected from an unsubstituted or substituted fluorenyl group, an unsubstituted or substituted fluoranthenyl group, an unsubstituted or substituted perylenyl group, and an unsubstituted or substituted carbazolyl group) .
4. The phenanthroline compound according to claim 1, wherein the fluorenyl group is represented by the general formula [IV] :
5. The phenanthroline compound according to claim 2, wherein the fluorenyl group is represented by the general formula [IV] : 
(wherein Rχ7 is selected from a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted aralkyl group, an unsubstituted or substituted aryl group, an unsubstituted or substituted heterocyclic group, a substituted amino group, a cyano group, and a halogen atom; and Rι8 and Rig are the same or different and each is selected from a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted aralkyl group, an unsubstituted or substituted aryl group, and an unsubstituted or substituted heterocyclic group) .
6. The phenanthroline compound according to claim 3, wherein the fluorenyl group is represented by the general formula [IV] :
(wherein R1 is selected from a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted aralkyl group, an unsubstituted or substituted aryl group, an unsubstituted or substituted heterocyclic group, a substituted amino group, a cyano group, and a halogen atom; and R18 and Ri9 are the same or different and each is selected from a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted aralkyl group, an unsubstituted or substituted aryl group, and an unsubstituted or substituted heterocyclic group) .
7. The phenanthroline compound according to claim 1, wherein the fluoranthenyl group is represented by the general formula [V] :
(wherein R2o is selected from a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted aralkyl group, an unsubstituted or substituted aryl group, an unsubstituted or substituted heterocyclic group, a substituted amino group, a cyano group, and a halogen atom) .
8. The phenanthroline compound according to claim 2, wherein the fluoranthenyl group is represented by the general formula [V] : 
(wherein R20 is selected from a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted aralkyl group, an unsubstituted or substituted aryl group, an unsubstituted or substituted heterocyclic group, a substituted amino group, a cyano group, and a halogen atom) .
9. The phenanthroline compound according to claim 3, wherein the fluoranthenyl group is represented by the general formula [V] :
(wherein R20 is selected from a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted aralkyl group, an unsubstituted or substituted aryl group, an unsubstituted or substituted heterocyclic group, a substituted amino group, a cyano group, and a halogen atom) .
10. , The phenanthroline compound according to claim 1, wherein the perylenyl group is represented by the general formula [VI]
(wherein R2ι is selected from a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted aralkyl group, an unsubstituted or substituted aryl group, an unsubstituted or substituted heterocyclic group, a substituted amino group, a cyano group, and a halogen atom) .
11. The phenanthroline compound according to claim 2, wherein the perylenyl group is represented by the general formula [VI] :
12. The phenanthroline compound according to claim 3, wherein the perylenyl group is represented by the general formula [VI] :
(wherein R21 is selected from a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted aralkyl group, an unsubstituted or substituted aryl group, an unsubstituted or substituted heterocyclic group, a substituted amino group, a cyano group, and a halogen atom) .
13. The phenanthroline compound according to claim 1, wherein the carbazolyl group is represented by the general formula [VII] :
(wherein R22 and R23 are the same or different and each is selected from a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted aralkyl group, an unsubstituted or substituted aryl group, an unsubstituted or substituted heterocyclic group, a substituted amino group, a cyano group, and a halogen atom) .
14. The phenanthroline compound according to claim 2, wherein the carbazolyl group is represented by the general formula [VII] :
15. The phenanthroline compound according to claim 3, wherein the carbazolyl group is represented by the general formula [VII] :
(wherein R22 and R23 are the same or different and each is selected from a hydrogen atom, an unsubstituted or, substituted alkyl group, an unsubstituted or substituted aralkyl group, an unsubstituted or substituted aryl group, an unsubstituted or substituted heterocyclic group, a substituted amino group, a cyano group, and a halogen atom) .
16. An organic light emitting device comprising a pair of electrodes consisting of an anode and a cathode, and a layer comprising an organic compound comprising the phenanthroline compound set forth in claim 1, interposed between the pair of electrodes.
17. An organic light emitting device comprising a pair of electrodes consisting of an anode and a cathode, and a layer comprising an organic compound comprising the phenanthroline compound set forth in claim 2, interposed between the pair of electrodes .
18. An organic light emitting device comprising a pair of electrodes consisting of an anode and a cathode, and a layer comprising an organic compound comprising the phenanthroline compound set forth in claim 3, interposed between the pair of electrodes .
19. The organic light emitting device according to claim 18, wherein the layer comprising the organic compound comprising the phenanthroline compound functions as an electron transporting layer or a light emitting layer.
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU2003260955A AU2003260955A1 (en) | 2002-09-19 | 2003-09-09 | Phenanthroline compound and organic light emitting device using same |
| US10/527,192 US7550594B2 (en) | 2002-09-19 | 2003-09-09 | Phenanthroline compound and organic light emitting device using same |
| US12/436,507 US7982213B2 (en) | 2002-09-19 | 2009-05-06 | Phenanthroline compound and organic light emitting device using same |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JPNO.2002-272408 | 2002-09-19 | ||
| JP2002272408A JP4261855B2 (en) | 2002-09-19 | 2002-09-19 | Phenanthroline compound and organic light emitting device using the same |
Related Child Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US10527192 A-371-Of-International | 2003-09-09 | ||
| US12/436,507 Division US7982213B2 (en) | 2002-09-19 | 2009-05-06 | Phenanthroline compound and organic light emitting device using same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2004026870A1 true WO2004026870A1 (en) | 2004-04-01 |
Family
ID=32024930
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/JP2003/011485 WO2004026870A1 (en) | 2002-09-19 | 2003-09-09 | Phenanthroline compound and organic light emitting device using same |
Country Status (4)
| Country | Link |
|---|---|
| US (2) | US7550594B2 (en) |
| JP (1) | JP4261855B2 (en) |
| AU (1) | AU2003260955A1 (en) |
| WO (1) | WO2004026870A1 (en) |
Cited By (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007064484A2 (en) * | 2005-11-30 | 2007-06-07 | Eastman Kodak Company | Electroluminescent device containing a phenanthroline derivative |
| US7517596B2 (en) * | 2004-11-29 | 2009-04-14 | Canon Kabushiki Kaisha | Phenanthroline compound and light-emitting device |
| EP2072517A1 (en) * | 2007-12-21 | 2009-06-24 | Novaled AG | Asymmetric phenanthrolins, method for their manufacture and doped organic semiconductor material containing them |
| CN100566489C (en) * | 2004-12-01 | 2009-12-02 | 株式会社半导体能源研究所 | Light-emitting component, light-emitting device and electronic equipment |
| EP2161272A1 (en) | 2008-09-05 | 2010-03-10 | Basf Se | Phenanthrolines |
| US7750340B2 (en) * | 2003-04-30 | 2010-07-06 | Canon Kabushiki Kaisha | Light-emitting device |
| US7750159B2 (en) | 2004-07-07 | 2010-07-06 | Semiconductor Energy Laboratory Co., Ltd. | Phenanthroline derivative and light emitting element and light emitting device using the same |
| US7833634B2 (en) * | 2005-06-21 | 2010-11-16 | Canon Kabushiki Kaisha | 1,8-naphthyridine compound and organic light-emitting device using the same |
| WO2011030566A1 (en) * | 2009-09-14 | 2011-03-17 | Eisai R&D Management Co., Ltd. | Phenanthroline derivatives and their use as ligands |
| WO2011046182A1 (en) | 2009-10-16 | 2011-04-21 | 出光興産株式会社 | Fluorene-containing aromatic compound, material for organic electroluminescent element, and organic electroluminescent element using same |
| US7931975B2 (en) | 2008-11-07 | 2011-04-26 | Global Oled Technology Llc | Electroluminescent device containing a flouranthene compound |
| WO2012124310A1 (en) | 2011-03-11 | 2012-09-20 | B.R.A.H.M.S Gmbh | Rare earth metal complex having phenanthroline compound as ligand |
| EP2299508A3 (en) * | 2004-11-24 | 2014-04-23 | The Trustees of Princeton University | Organic photosensitive optoelectronic device having a phenanthroline exciton blocking layer |
| US8748013B2 (en) | 2003-03-20 | 2014-06-10 | Semiconductor Energy Laboratory Co., Ltd. | Electroluminescent device |
| US8962155B2 (en) | 2007-11-02 | 2015-02-24 | Toray Industries, Inc. | Light emitting device based on a pyrromethene compound |
| CN104603137A (en) * | 2012-09-12 | 2015-05-06 | 出光兴产株式会社 | Novel compound, material for organic electroluminescent element, and electronic device |
| WO2015064969A2 (en) * | 2013-10-29 | 2015-05-07 | 덕산네오룩스 주식회사 | Compound for organic electroluminescent device, organic electroluminescent device using same, and electronic device using said organic electroluminescent device |
| US9153790B2 (en) | 2009-05-22 | 2015-10-06 | Idemitsu Kosan Co., Ltd. | Organic electroluminescent device |
| CN105646480A (en) * | 2014-11-28 | 2016-06-08 | 机光科技股份有限公司 | Phenanthroline-bsaed compound and use thereof |
| US9666826B2 (en) | 2005-11-30 | 2017-05-30 | Global Oled Technology Llc | Electroluminescent device including an anthracene derivative |
| CN107207503A (en) * | 2015-01-29 | 2017-09-26 | 东丽株式会社 | Phenanthroline derivative, the electronic installation containing it, light-emitting component and photo-electric conversion element |
| CN111574505A (en) * | 2020-05-22 | 2020-08-25 | 西安瑞联新材料股份有限公司 | Compound with benzo [ c ] cinnoline as receptor and application thereof |
| CN116514778A (en) * | 2023-06-26 | 2023-08-01 | 季华实验室 | Organic electronic transmission material and organic electroluminescent device |
| EP4223744A1 (en) * | 2022-02-08 | 2023-08-09 | Gwangju Institute of Science and Technology | Novel phenanthroline-based compound and optoelectronic device comprising the same |
Families Citing this family (118)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4427947B2 (en) * | 2002-11-18 | 2010-03-10 | コニカミノルタホールディングス株式会社 | Organic electroluminescence element and display device |
| JP4707082B2 (en) * | 2002-11-26 | 2011-06-22 | コニカミノルタホールディングス株式会社 | Organic electroluminescence element and display device |
| JP4356463B2 (en) * | 2004-01-29 | 2009-11-04 | ソニー株式会社 | Organic light emitting material and organic electroluminescent device |
| JP4533015B2 (en) * | 2004-06-15 | 2010-08-25 | キヤノン株式会社 | Compound and organic electroluminescence device using the same |
| JP2006128624A (en) * | 2004-09-29 | 2006-05-18 | Canon Inc | Light emitting element |
| JP4478555B2 (en) * | 2004-11-30 | 2010-06-09 | キヤノン株式会社 | Metal complex, light emitting element and image display device |
| TWI321968B (en) | 2005-07-15 | 2010-03-11 | Lg Chemical Ltd | Organic light meitting device and method for manufacturing the same |
| JP4770699B2 (en) * | 2005-12-16 | 2011-09-14 | ソニー株式会社 | Display element |
| JP2007308477A (en) * | 2006-04-20 | 2007-11-29 | Canon Inc | Compound and organic light-emitting device |
| JP4227628B2 (en) * | 2006-04-25 | 2009-02-18 | キヤノン株式会社 | Compound and organic light emitting device |
| US7754348B2 (en) * | 2007-04-25 | 2010-07-13 | Luminescene Technology Corp. | Phenanthroline compound and organic light emitting device using the same |
| JP5159164B2 (en) * | 2007-05-14 | 2013-03-06 | キヤノン株式会社 | Benzo [ghi] fluoranthene derivative and organic light-emitting device using the same |
| US8431242B2 (en) | 2007-10-26 | 2013-04-30 | Global Oled Technology, Llc. | OLED device with certain fluoranthene host |
| US8076009B2 (en) * | 2007-10-26 | 2011-12-13 | Global Oled Technology, Llc. | OLED device with fluoranthene electron transport materials |
| US8420229B2 (en) * | 2007-10-26 | 2013-04-16 | Global OLED Technologies LLC | OLED device with certain fluoranthene light-emitting dopants |
| US8129039B2 (en) * | 2007-10-26 | 2012-03-06 | Global Oled Technology, Llc | Phosphorescent OLED device with certain fluoranthene host |
| US20090110956A1 (en) * | 2007-10-26 | 2009-04-30 | Begley William J | Oled device with electron transport material combination |
| EP2213639B1 (en) * | 2007-11-19 | 2016-04-13 | Idemitsu Kosan Co., Ltd. | Monobenzochrysene derivatives and their use in materials for organic electroluminescent devices |
| US8686403B2 (en) | 2008-01-18 | 2014-04-01 | Lg Chem Ltd. | Organic luminescent device including a first electrode, two or more organic layers and a second electrode and a production method for the same |
| JP4830127B2 (en) * | 2008-03-22 | 2011-12-07 | コニカミノルタホールディングス株式会社 | Organic electroluminescence element and display device |
| JP4830126B2 (en) * | 2008-03-22 | 2011-12-07 | コニカミノルタホールディングス株式会社 | Organic electroluminescence element and display device |
| JP2011521414A (en) | 2008-05-16 | 2011-07-21 | エルジー・ケム・リミテッド | Multilayer organic light emitting device |
| JP2012504847A (en) | 2008-10-01 | 2012-02-23 | エルジー・ケム・リミテッド | ORGANIC LIGHT EMITTING ELEMENT AND MANUFACTURING METHOD THEREOF |
| EP2206716A1 (en) * | 2008-11-27 | 2010-07-14 | Solvay S.A. | Host material for light-emitting diodes |
| US8088500B2 (en) * | 2008-11-12 | 2012-01-03 | Global Oled Technology Llc | OLED device with fluoranthene electron injection materials |
| US7968215B2 (en) * | 2008-12-09 | 2011-06-28 | Global Oled Technology Llc | OLED device with cyclobutene electron injection materials |
| WO2010075379A2 (en) * | 2008-12-22 | 2010-07-01 | E. I. Du Pont De Nemours And Company | Electronic device including phenanthroline derivative |
| US8216697B2 (en) * | 2009-02-13 | 2012-07-10 | Global Oled Technology Llc | OLED with fluoranthene-macrocyclic materials |
| JP5349105B2 (en) * | 2009-03-25 | 2013-11-20 | 株式会社東芝 | Organic electroluminescence device |
| US20100244677A1 (en) * | 2009-03-31 | 2010-09-30 | Begley William J | Oled device containing a silyl-fluoranthene derivative |
| JP5171734B2 (en) * | 2009-06-04 | 2013-03-27 | 株式会社半導体エネルギー研究所 | Electroluminescent device and light emitting device |
| KR101450959B1 (en) | 2010-01-15 | 2014-10-15 | 이데미쓰 고산 가부시키가이샤 | Nitrogenated heterocyclic ring derivative and organic electroluminescent element comprising same |
| JP5757615B2 (en) * | 2011-03-10 | 2015-07-29 | 国立研究開発法人物質・材料研究機構 | Organic / metal hybrid polymer comprising a metal having a coordination number of 4 and a bisphenanthroline derivative, a ligand thereof, and a production method thereof |
| KR102059328B1 (en) * | 2011-09-09 | 2020-02-20 | 이데미쓰 고산 가부시키가이샤 | Organic electroluminescence element |
| JP2013110224A (en) * | 2011-11-18 | 2013-06-06 | Mitsubishi Chemicals Corp | Photoelectric conversion element, solar cell, and solar cell module |
| KR101722027B1 (en) * | 2012-05-03 | 2017-04-03 | 삼성디스플레이 주식회사 | A condensed-cyclic compound and an organic light emitting diode comprising the same |
| WO2013180542A1 (en) | 2012-05-31 | 2013-12-05 | 주식회사 엘지화학 | Stacked organic light emitting diode |
| CN104508855B (en) | 2012-05-31 | 2017-06-23 | 乐金显示有限公司 | Organic light emitting diode |
| TWI599086B (en) | 2012-05-31 | 2017-09-11 | 樂金顯示科技股份有限公司 | Organic electroluminescent device |
| US9859517B2 (en) * | 2012-09-07 | 2018-01-02 | Nitto Denko Corporation | White organic light-emitting diode |
| KR102120894B1 (en) | 2013-05-03 | 2020-06-10 | 삼성디스플레이 주식회사 | Organic light emitting device |
| CN104854724B (en) | 2013-06-07 | 2018-09-28 | 乐金显示有限公司 | Organic light emitting diode |
| US9929361B2 (en) | 2015-02-16 | 2018-03-27 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11056657B2 (en) | 2015-02-27 | 2021-07-06 | University Display Corporation | Organic electroluminescent materials and devices |
| US9768390B2 (en) | 2015-03-26 | 2017-09-19 | Feng-wen Yen | Phenanthroline derivative for organic electroluminescent device |
| US9692003B2 (en) * | 2015-04-15 | 2017-06-27 | Feng-wen Yen | Phenanthroline derivative and use thereof |
| US9859510B2 (en) | 2015-05-15 | 2018-01-02 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10418568B2 (en) | 2015-06-01 | 2019-09-17 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11127905B2 (en) | 2015-07-29 | 2021-09-21 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10672996B2 (en) | 2015-09-03 | 2020-06-02 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US20170229663A1 (en) | 2016-02-09 | 2017-08-10 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10236456B2 (en) | 2016-04-11 | 2019-03-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11482683B2 (en) | 2016-06-20 | 2022-10-25 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10862054B2 (en) | 2016-06-20 | 2020-12-08 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10672997B2 (en) | 2016-06-20 | 2020-06-02 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10608186B2 (en) | 2016-09-14 | 2020-03-31 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10680187B2 (en) | 2016-09-23 | 2020-06-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11196010B2 (en) | 2016-10-03 | 2021-12-07 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11011709B2 (en) | 2016-10-07 | 2021-05-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US20180130956A1 (en) | 2016-11-09 | 2018-05-10 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10680188B2 (en) | 2016-11-11 | 2020-06-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11780865B2 (en) | 2017-01-09 | 2023-10-10 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10844085B2 (en) | 2017-03-29 | 2020-11-24 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US10944060B2 (en) | 2017-05-11 | 2021-03-09 | Universal Display Corporation | Organic electroluminescent materials and devices |
| KR102536248B1 (en) | 2017-06-21 | 2023-05-25 | 삼성디스플레이 주식회사 | Heterocyclic compound and organic light emitting device comprising the same |
| US12098157B2 (en) | 2017-06-23 | 2024-09-24 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11228010B2 (en) | 2017-07-26 | 2022-01-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
| KR102415376B1 (en) | 2017-08-04 | 2022-07-01 | 삼성디스플레이 주식회사 | Condensed-cyclic compound and organic light emitting device comprising the same |
| US11744142B2 (en) | 2017-08-10 | 2023-08-29 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US20190161504A1 (en) | 2017-11-28 | 2019-05-30 | University Of Southern California | Carbene compounds and organic electroluminescent devices |
| EP3492480B1 (en) | 2017-11-29 | 2021-10-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11937503B2 (en) | 2017-11-30 | 2024-03-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11542289B2 (en) | 2018-01-26 | 2023-01-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
| KR101926770B1 (en) * | 2018-03-05 | 2018-12-07 | 주식회사 진웅산업 | Phenanthroline compound and organic light emitting element comprising the same |
| KR102536246B1 (en) | 2018-03-23 | 2023-05-25 | 삼성디스플레이 주식회사 | Heterocyclic compound and organic light emitting device comprising the same |
| US20200075870A1 (en) | 2018-08-22 | 2020-03-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11737349B2 (en) | 2018-12-12 | 2023-08-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US11780829B2 (en) | 2019-01-30 | 2023-10-10 | The University Of Southern California | Organic electroluminescent materials and devices |
| US20200251664A1 (en) | 2019-02-01 | 2020-08-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
| JP2020158491A (en) | 2019-03-26 | 2020-10-01 | ユニバーサル ディスプレイ コーポレイション | Organic electroluminescent materials and devices |
| CN110144213A (en) * | 2019-05-31 | 2019-08-20 | 北京诚志永华显示科技有限公司 | Electroluminescent organic material, organic electroluminescence device |
| US20210032278A1 (en) | 2019-07-30 | 2021-02-04 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US20210047354A1 (en) | 2019-08-16 | 2021-02-18 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US20210135130A1 (en) | 2019-11-04 | 2021-05-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US20210217969A1 (en) | 2020-01-06 | 2021-07-15 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US20220336759A1 (en) | 2020-01-28 | 2022-10-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
| EP3937268A1 (en) | 2020-07-10 | 2022-01-12 | Universal Display Corporation | Plasmonic oleds and vertical dipole emitters |
| US20220158096A1 (en) | 2020-11-16 | 2022-05-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US20220162243A1 (en) | 2020-11-24 | 2022-05-26 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US20220165967A1 (en) | 2020-11-24 | 2022-05-26 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US20220271241A1 (en) | 2021-02-03 | 2022-08-25 | Universal Display Corporation | Organic electroluminescent materials and devices |
| EP4059915A3 (en) | 2021-02-26 | 2022-12-28 | Universal Display Corporation | Organic electroluminescent materials and devices |
| EP4060758A3 (en) | 2021-02-26 | 2023-03-29 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US20220298192A1 (en) | 2021-03-05 | 2022-09-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US20220298190A1 (en) | 2021-03-12 | 2022-09-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US20220298193A1 (en) | 2021-03-15 | 2022-09-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US20220340607A1 (en) | 2021-04-05 | 2022-10-27 | Universal Display Corporation | Organic electroluminescent materials and devices |
| EP4075531A1 (en) | 2021-04-13 | 2022-10-19 | Universal Display Corporation | Plasmonic oleds and vertical dipole emitters |
| US20220352478A1 (en) | 2021-04-14 | 2022-11-03 | Universal Display Corporation | Organic eletroluminescent materials and devices |
| US20230006149A1 (en) | 2021-04-23 | 2023-01-05 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US20220407020A1 (en) | 2021-04-23 | 2022-12-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US20230133787A1 (en) | 2021-06-08 | 2023-05-04 | University Of Southern California | Molecular Alignment of Homoleptic Iridium Phosphors |
| EP4151699A1 (en) | 2021-09-17 | 2023-03-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US20240343970A1 (en) | 2021-12-16 | 2024-10-17 | Universal Display Corporation | Organic electroluminescent materials and devices |
| EP4231804A3 (en) | 2022-02-16 | 2023-09-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US20230292592A1 (en) | 2022-03-09 | 2023-09-14 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US20230337516A1 (en) | 2022-04-18 | 2023-10-19 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US20230389421A1 (en) | 2022-05-24 | 2023-11-30 | Universal Display Corporation | Organic electroluminescent materials and devices |
| EP4293001A1 (en) | 2022-06-08 | 2023-12-20 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US20240016051A1 (en) | 2022-06-28 | 2024-01-11 | Universal Display Corporation | Organic electroluminescent materials and devices |
| WO2024034301A1 (en) * | 2022-08-09 | 2024-02-15 | 株式会社日本触媒 | Phenanthroline compound, and organic thin film and organic semiconductor element using same |
| US20240107880A1 (en) | 2022-08-17 | 2024-03-28 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US20240188319A1 (en) | 2022-10-27 | 2024-06-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US20240188316A1 (en) | 2022-10-27 | 2024-06-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US20240188419A1 (en) | 2022-10-27 | 2024-06-06 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US20240180025A1 (en) | 2022-10-27 | 2024-05-30 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US20240196730A1 (en) | 2022-10-27 | 2024-06-13 | Universal Display Corporation | Organic electroluminescent materials and devices |
| US20240247017A1 (en) | 2022-12-14 | 2024-07-25 | Universal Display Corporation | Organic electroluminescent materials and devices |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1097980A2 (en) * | 1999-11-02 | 2001-05-09 | Sony Corporation | Bathophenanthroline compound and process for preparing same |
| EP1097981A2 (en) * | 1999-11-02 | 2001-05-09 | Sony Corporation | Organic electroluminescent device |
| JP2001267080A (en) * | 2000-01-14 | 2001-09-28 | Toray Ind Inc | Light emission element |
| JP2002050481A (en) * | 2000-08-04 | 2002-02-15 | Toray Ind Inc | Light emission element |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4539507A (en) * | 1983-03-25 | 1985-09-03 | Eastman Kodak Company | Organic electroluminescent devices having improved power conversion efficiencies |
| US4720432A (en) * | 1987-02-11 | 1988-01-19 | Eastman Kodak Company | Electroluminescent device with organic luminescent medium |
| US4885211A (en) * | 1987-02-11 | 1989-12-05 | Eastman Kodak Company | Electroluminescent device with improved cathode |
| US5130603A (en) * | 1989-03-20 | 1992-07-14 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device |
| GB8909011D0 (en) * | 1989-04-20 | 1989-06-07 | Friend Richard H | Electroluminescent devices |
| JP2815472B2 (en) * | 1990-01-22 | 1998-10-27 | パイオニア株式会社 | EL device |
| DE69110922T2 (en) * | 1990-02-23 | 1995-12-07 | Sumitomo Chemical Co | Organic electroluminescent device. |
| GB9018698D0 (en) * | 1990-08-24 | 1990-10-10 | Lynxvale Ltd | Semiconductive copolymers for use in electroluminescent devices |
| US5382477A (en) * | 1991-02-27 | 1995-01-17 | Sanyo Electric Co., Ltd. | Organic electroluminescent element and process for producing the same |
| US5151629A (en) * | 1991-08-01 | 1992-09-29 | Eastman Kodak Company | Blue emitting internal junction organic electroluminescent device (I) |
| JPH05202356A (en) | 1991-09-11 | 1993-08-10 | Pioneer Electron Corp | Organic electroluminescence element |
| JP3328731B2 (en) | 1991-12-05 | 2002-09-30 | 住友化学工業株式会社 | Organic electroluminescence device |
| US5393614A (en) * | 1992-04-03 | 1995-02-28 | Pioneer Electronic Corporation | Organic electroluminescence device |
| US5514878A (en) * | 1994-03-18 | 1996-05-07 | Holmes; Andrew B. | Polymers for electroluminescent devices |
| JPH0782551A (en) | 1993-09-09 | 1995-03-28 | Nisshinbo Ind Inc | Organic electroluminescent element |
| US5409783A (en) * | 1994-02-24 | 1995-04-25 | Eastman Kodak Company | Red-emitting organic electroluminescent device |
| JPH09202878A (en) | 1996-01-25 | 1997-08-05 | Nippon Telegr & Teleph Corp <Ntt> | Near ultraviolet or ultraviolet region light-emission element |
| JPH09227576A (en) | 1996-02-23 | 1997-09-02 | Sony Corp | Metallic multinuclear complex, its production and optical element |
| JPH1079297A (en) * | 1996-07-09 | 1998-03-24 | Sony Corp | Electroluminescent element |
| CA2341268C (en) | 1998-07-22 | 2010-10-12 | Id-Lelystad, Instituut Voor Dierhouderij En Diergezondheid B.V. | Streptococcus suis vaccines and diagnostic tests |
| WO2003076549A1 (en) * | 2002-03-08 | 2003-09-18 | Canon Kabushiki Kaisha | Electroluminescent element containing metal coordination compound |
-
2002
- 2002-09-19 JP JP2002272408A patent/JP4261855B2/en not_active Expired - Fee Related
-
2003
- 2003-09-09 US US10/527,192 patent/US7550594B2/en active Active
- 2003-09-09 AU AU2003260955A patent/AU2003260955A1/en not_active Abandoned
- 2003-09-09 WO PCT/JP2003/011485 patent/WO2004026870A1/en active Application Filing
-
2009
- 2009-05-06 US US12/436,507 patent/US7982213B2/en not_active Expired - Fee Related
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1097980A2 (en) * | 1999-11-02 | 2001-05-09 | Sony Corporation | Bathophenanthroline compound and process for preparing same |
| EP1097981A2 (en) * | 1999-11-02 | 2001-05-09 | Sony Corporation | Organic electroluminescent device |
| JP2001267080A (en) * | 2000-01-14 | 2001-09-28 | Toray Ind Inc | Light emission element |
| JP2002050481A (en) * | 2000-08-04 | 2002-02-15 | Toray Ind Inc | Light emission element |
Non-Patent Citations (1)
| Title |
|---|
| ITO, T: "Synthesis of phenanthroline delivatives and their application to organic EL devices.", POLYMER PREPRINTS, JAPAN, vol. 51, no. 11, 18 September 2002 (2002-09-18), pages 2859 - 2860, XP002974180 * |
Cited By (41)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8748013B2 (en) | 2003-03-20 | 2014-06-10 | Semiconductor Energy Laboratory Co., Ltd. | Electroluminescent device |
| US7750340B2 (en) * | 2003-04-30 | 2010-07-06 | Canon Kabushiki Kaisha | Light-emitting device |
| US7820478B2 (en) | 2003-04-30 | 2010-10-26 | Canon Kabushiki Kaisha | Light-emitting device |
| US7750159B2 (en) | 2004-07-07 | 2010-07-06 | Semiconductor Energy Laboratory Co., Ltd. | Phenanthroline derivative and light emitting element and light emitting device using the same |
| EP2299508A3 (en) * | 2004-11-24 | 2014-04-23 | The Trustees of Princeton University | Organic photosensitive optoelectronic device having a phenanthroline exciton blocking layer |
| US7517596B2 (en) * | 2004-11-29 | 2009-04-14 | Canon Kabushiki Kaisha | Phenanthroline compound and light-emitting device |
| CN100566489C (en) * | 2004-12-01 | 2009-12-02 | 株式会社半导体能源研究所 | Light-emitting component, light-emitting device and electronic equipment |
| US7833634B2 (en) * | 2005-06-21 | 2010-11-16 | Canon Kabushiki Kaisha | 1,8-naphthyridine compound and organic light-emitting device using the same |
| US9666826B2 (en) | 2005-11-30 | 2017-05-30 | Global Oled Technology Llc | Electroluminescent device including an anthracene derivative |
| WO2007064484A3 (en) * | 2005-11-30 | 2007-11-15 | Eastman Kodak Co | Electroluminescent device containing a phenanthroline derivative |
| WO2007064484A2 (en) * | 2005-11-30 | 2007-06-07 | Eastman Kodak Company | Electroluminescent device containing a phenanthroline derivative |
| US8962155B2 (en) | 2007-11-02 | 2015-02-24 | Toray Industries, Inc. | Light emitting device based on a pyrromethene compound |
| WO2009083197A2 (en) * | 2007-12-21 | 2009-07-09 | Novaled Ag | Asymmetric phenanthrolines, preparation process therefore and doped organic semiconductor material containing them |
| EP2072517A1 (en) * | 2007-12-21 | 2009-06-24 | Novaled AG | Asymmetric phenanthrolins, method for their manufacture and doped organic semiconductor material containing them |
| WO2009083197A3 (en) * | 2007-12-21 | 2009-11-12 | Novaled Ag | Asymmetric phenanthrolines, preparation process therefore and doped organic semiconductor material containing them |
| EP2161272A1 (en) | 2008-09-05 | 2010-03-10 | Basf Se | Phenanthrolines |
| US7931975B2 (en) | 2008-11-07 | 2011-04-26 | Global Oled Technology Llc | Electroluminescent device containing a flouranthene compound |
| US9153790B2 (en) | 2009-05-22 | 2015-10-06 | Idemitsu Kosan Co., Ltd. | Organic electroluminescent device |
| US8648194B2 (en) | 2009-09-14 | 2014-02-11 | B.R.A.H.M.S Gmbh | Compounds having phenanthroline structure |
| CN102666534A (en) * | 2009-09-14 | 2012-09-12 | B.R.A.H.M.S有限公司 | Phenanthroline derivatives and their use as ligands |
| CN102666534B (en) * | 2009-09-14 | 2015-01-07 | B.R.A.H.M.S有限公司 | Novel compound with phenanthroline structure |
| WO2011030566A1 (en) * | 2009-09-14 | 2011-03-17 | Eisai R&D Management Co., Ltd. | Phenanthroline derivatives and their use as ligands |
| CN102471320A (en) * | 2009-10-16 | 2012-05-23 | 出光兴产株式会社 | Fluorene-containing aromatic compound, material for organic electroluminescent element, and organic electroluminescent element using same |
| WO2011046182A1 (en) | 2009-10-16 | 2011-04-21 | 出光興産株式会社 | Fluorene-containing aromatic compound, material for organic electroluminescent element, and organic electroluminescent element using same |
| US9266851B2 (en) | 2009-10-16 | 2016-02-23 | Idemitsu Kosan Co., Ltd. | Fluorene-containing aromatic compound, material for organic electroluminescent element, and organic electroluminescent element using same |
| US9187690B2 (en) | 2011-03-11 | 2015-11-17 | B.R.A.H.M.S. Gmbh | Rare earth metal complex having phenanthroline compound as ligand |
| WO2012124310A1 (en) | 2011-03-11 | 2012-09-20 | B.R.A.H.M.S Gmbh | Rare earth metal complex having phenanthroline compound as ligand |
| CN103534262A (en) * | 2011-03-11 | 2014-01-22 | B.R.A.H.M.S有限公司 | Rare earth metal complex having phenanthroline compound as ligand |
| CN104603137A (en) * | 2012-09-12 | 2015-05-06 | 出光兴产株式会社 | Novel compound, material for organic electroluminescent element, and electronic device |
| US9871206B2 (en) | 2012-09-12 | 2018-01-16 | Idemitsu Kosan Co., Ltd. | Compound, organic electroluminescence device material, organic electroluminescence device and electronic device |
| US10510964B2 (en) | 2012-09-12 | 2019-12-17 | Idemitsu Kosan Co., Ltd. | Compound, organic electroluminescence device material, organic electroluminescence device and electronic device |
| WO2015064969A2 (en) * | 2013-10-29 | 2015-05-07 | 덕산네오룩스 주식회사 | Compound for organic electroluminescent device, organic electroluminescent device using same, and electronic device using said organic electroluminescent device |
| WO2015064969A3 (en) * | 2013-10-29 | 2015-06-25 | 덕산네오룩스 주식회사 | Compound for organic electroluminescent device, organic electroluminescent device using same, and electronic device using said organic electroluminescent device |
| CN105646480B (en) * | 2014-11-28 | 2018-11-16 | 机光科技股份有限公司 | Coffee quinoline class compound and application thereof |
| CN105646480A (en) * | 2014-11-28 | 2016-06-08 | 机光科技股份有限公司 | Phenanthroline-bsaed compound and use thereof |
| CN107207503A (en) * | 2015-01-29 | 2017-09-26 | 东丽株式会社 | Phenanthroline derivative, the electronic installation containing it, light-emitting component and photo-electric conversion element |
| EP3252052A4 (en) * | 2015-01-29 | 2018-06-27 | Toray Industries, Inc. | Phenanthroline derivative, electronic device containing same, light emitting element, and photoelectric conversion element |
| TWI680130B (en) * | 2015-01-29 | 2019-12-21 | 日商東麗股份有限公司 | Phoroline derivatives, electronic devices containing them, light emitting elements, photoelectric conversion elements, and image sensors |
| CN111574505A (en) * | 2020-05-22 | 2020-08-25 | 西安瑞联新材料股份有限公司 | Compound with benzo [ c ] cinnoline as receptor and application thereof |
| EP4223744A1 (en) * | 2022-02-08 | 2023-08-09 | Gwangju Institute of Science and Technology | Novel phenanthroline-based compound and optoelectronic device comprising the same |
| CN116514778A (en) * | 2023-06-26 | 2023-08-01 | 季华实验室 | Organic electronic transmission material and organic electroluminescent device |
Also Published As
| Publication number | Publication date |
|---|---|
| US7550594B2 (en) | 2009-06-23 |
| US20060097227A1 (en) | 2006-05-11 |
| US7982213B2 (en) | 2011-07-19 |
| JP4261855B2 (en) | 2009-04-30 |
| JP2004107263A (en) | 2004-04-08 |
| AU2003260955A1 (en) | 2004-04-08 |
| US20090218940A1 (en) | 2009-09-03 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US7550594B2 (en) | Phenanthroline compound and organic light emitting device using same | |
| JP4336483B2 (en) | Diazafluorene compound and organic light-emitting device using the same | |
| JP4065547B2 (en) | Fluorene compound and organic light emitting device using the same | |
| JP3848224B2 (en) | Spiro compound and organic light emitting device using the same | |
| JP3902993B2 (en) | Fluorene compound and organic light emitting device using the same | |
| JP4585750B2 (en) | Fused polycyclic compound and organic light emitting device using the same | |
| JP4865258B2 (en) | 1,8-naphthyridine compound and organic light-emitting device using the same | |
| JP3870102B2 (en) | Organic light emitting device | |
| US7749617B2 (en) | Organic compound and organic light-emitting device | |
| JP2003105332A (en) | Organic light-emitting element | |
| JP4336537B2 (en) | Organic light emitting device | |
| JP2003109765A (en) | Organic light emitting element | |
| JP4065552B2 (en) | Organic light emitting device | |
| JP4035499B2 (en) | Organic light emitting device | |
| JP2007001879A (en) | 1, 9, 10-anthridine compound and organic light emitting device using the same | |
| JP4423022B2 (en) | 2,1-Benzisothiazole compound and organic light emitting device using the same | |
| JP5072896B2 (en) | Diazafluorene compound, organic light-emitting device and organic light-emitting device using the same | |
| JP4566962B2 (en) | Organic light emitting device | |
| JP2002069063A (en) | Furoxan compound and organic light emitting element using the same |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| AK | Designated states |
Kind code of ref document: A1 Designated state(s): AE AG AL AM AT AU AZ BA BB BG BR BY BZ CA CH CN CO CR CU CZ DE DK DM DZ EC EE EG ES FI GB GD GE GH GM HR HU ID IL IN IS KE KG KP KR KZ LC LK LR LS LT LU LV MA MD MG MK MN MW MX MZ NI NO NZ OM PG PH PL PT RO RU SC SD SE SG SK SL SY TJ TM TN TR TT TZ UA UG US UZ VC VN YU ZA ZM ZW |
|
| AL | Designated countries for regional patents |
Kind code of ref document: A1 Designated state(s): GH GM KE LS MW MZ SD SL SZ TZ UG ZM ZW AM AZ BY KG KZ MD RU TJ TM AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IT LU MC NL PT RO SE SI SK TR BF BJ CF CG CI CM GA GN GQ GW ML MR NE SN TD TG |
|
| 121 | Ep: the epo has been informed by wipo that ep was designated in this application | ||
| DFPE | Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101) | ||
| ENP | Entry into the national phase |
Ref document number: 2006097227 Country of ref document: US Kind code of ref document: A1 |
|
| WWE | Wipo information: entry into national phase |
Ref document number: 10527192 Country of ref document: US |
|
| 122 | Ep: pct application non-entry in european phase | ||
| WWP | Wipo information: published in national office |
Ref document number: 10527192 Country of ref document: US |