JP2004006379A - Organic electroluminescent element - Google Patents
Organic electroluminescent element Download PDFInfo
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- JP2004006379A JP2004006379A JP2003176314A JP2003176314A JP2004006379A JP 2004006379 A JP2004006379 A JP 2004006379A JP 2003176314 A JP2003176314 A JP 2003176314A JP 2003176314 A JP2003176314 A JP 2003176314A JP 2004006379 A JP2004006379 A JP 2004006379A
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- 150000001875 compounds Chemical class 0.000 claims abstract description 36
- 239000002019 doping agent Substances 0.000 claims abstract description 23
- 238000005215 recombination Methods 0.000 claims abstract description 23
- 230000006798 recombination Effects 0.000 claims abstract description 23
- 150000002894 organic compounds Chemical class 0.000 claims abstract description 10
- 230000004044 response Effects 0.000 claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 48
- 238000002347 injection Methods 0.000 claims description 34
- 239000007924 injection Substances 0.000 claims description 34
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- 125000003118 aryl group Chemical group 0.000 claims description 18
- 125000000623 heterocyclic group Chemical group 0.000 claims description 12
- 125000003367 polycyclic group Chemical group 0.000 claims description 8
- 125000000732 arylene group Chemical group 0.000 claims description 7
- 238000005401 electroluminescence Methods 0.000 claims description 6
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 2
- 239000000126 substance Substances 0.000 abstract description 7
- 230000008859 change Effects 0.000 abstract description 4
- -1 pentalenyl group Chemical group 0.000 description 43
- 239000000463 material Substances 0.000 description 40
- 238000004519 manufacturing process Methods 0.000 description 19
- 238000000034 method Methods 0.000 description 16
- 229910052757 nitrogen Inorganic materials 0.000 description 16
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 12
- 125000003545 alkoxy group Chemical group 0.000 description 11
- 229960003540 oxyquinoline Drugs 0.000 description 11
- 229910052751 metal Inorganic materials 0.000 description 10
- 239000002184 metal Substances 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
- 239000000758 substrate Substances 0.000 description 8
- 150000002430 hydrocarbons Chemical group 0.000 description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 238000007740 vapor deposition Methods 0.000 description 7
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 6
- 239000013522 chelant Substances 0.000 description 6
- 150000004696 coordination complex Chemical class 0.000 description 6
- 238000000151 deposition Methods 0.000 description 6
- 239000010408 film Substances 0.000 description 6
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 239000004065 semiconductor Substances 0.000 description 6
- 239000010409 thin film Substances 0.000 description 6
- ZWLHKPCYGMMCFY-UHFFFAOYSA-N 1-iodoanthracene Chemical compound C1=CC=C2C=C3C(I)=CC=CC3=CC2=C1 ZWLHKPCYGMMCFY-UHFFFAOYSA-N 0.000 description 5
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 5
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 5
- 125000004104 aryloxy group Chemical group 0.000 description 5
- 230000004888 barrier function Effects 0.000 description 5
- IFVTZJHWGZSXFD-UHFFFAOYSA-N biphenylene Chemical group C1=CC=C2C3=CC=CC=C3C2=C1 IFVTZJHWGZSXFD-UHFFFAOYSA-N 0.000 description 5
- 229910052802 copper Inorganic materials 0.000 description 5
- 239000010949 copper Substances 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 229910052750 molybdenum Inorganic materials 0.000 description 5
- 239000011733 molybdenum Substances 0.000 description 5
- 125000001624 naphthyl group Chemical group 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- UHXOHPVVEHBKKT-UHFFFAOYSA-N 1-(2,2-diphenylethenyl)-4-[4-(2,2-diphenylethenyl)phenyl]benzene Chemical compound C=1C=C(C=2C=CC(C=C(C=3C=CC=CC=3)C=3C=CC=CC=3)=CC=2)C=CC=1C=C(C=1C=CC=CC=1)C1=CC=CC=C1 UHXOHPVVEHBKKT-UHFFFAOYSA-N 0.000 description 4
- FDRNXKXKFNHNCA-UHFFFAOYSA-N 4-(4-anilinophenyl)-n-phenylaniline Chemical compound C=1C=C(C=2C=CC(NC=3C=CC=CC=3)=CC=2)C=CC=1NC1=CC=CC=C1 FDRNXKXKFNHNCA-UHFFFAOYSA-N 0.000 description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 125000006267 biphenyl group Chemical group 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 230000008021 deposition Effects 0.000 description 4
- 239000007772 electrode material Substances 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- 229910052749 magnesium Inorganic materials 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 150000004982 aromatic amines Chemical class 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- YCOXTKKNXUZSKD-UHFFFAOYSA-N as-o-xylenol Natural products CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 description 3
- 150000004866 oxadiazoles Chemical class 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 125000001725 pyrenyl group Chemical group 0.000 description 3
- 230000027756 respiratory electron transport chain Effects 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 238000004528 spin coating Methods 0.000 description 3
- 229930192474 thiophene Natural products 0.000 description 3
- 230000032258 transport Effects 0.000 description 3
- YZVWKHVRBDQPMQ-UHFFFAOYSA-N 1-aminopyrene Chemical compound C1=C2C(N)=CC=C(C=C3)C2=C2C3=CC=CC2=C1 YZVWKHVRBDQPMQ-UHFFFAOYSA-N 0.000 description 2
- CWNJSSNWLUIMDP-UHFFFAOYSA-N 1-iodopyrene Chemical compound C1=C2C(I)=CC=C(C=C3)C2=C2C3=CC=CC2=C1 CWNJSSNWLUIMDP-UHFFFAOYSA-N 0.000 description 2
- WTEJYGDMCOWSLV-UHFFFAOYSA-N 1-n,1-n,6-n,6-n-tetraphenylpyrene-1,6-diamine Chemical compound C1=CC=CC=C1N(C=1C2=CC=C3C=CC(=C4C=CC(C2=C43)=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 WTEJYGDMCOWSLV-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- ARFCDUGYUGIBLG-UHFFFAOYSA-N C1=CC=C(C=C1)N(C2=CC(=CC=C2)N(C3=CC=CC=C3)C4=C5C=CC6=CC=CC7=C6C5=C(C=C7)C=C4)C8=C9C=CC1=CC=CC2=C1C9=C(C=C2)C=C8 Chemical compound C1=CC=C(C=C1)N(C2=CC(=CC=C2)N(C3=CC=CC=C3)C4=C5C=CC6=CC=CC7=C6C5=C(C=C7)C=C4)C8=C9C=CC1=CC=CC2=C1C9=C(C=C2)C=C8 ARFCDUGYUGIBLG-UHFFFAOYSA-N 0.000 description 2
- 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 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- PCYDAYVXRZGZED-UHFFFAOYSA-N N-phenyl-N-[4-[4-(N-pyren-1-ylanilino)phenyl]phenyl]pyren-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=C3C=CC=C4C=CC(C2=C43)=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=C4C=CC=C5C=CC(C3=C54)=CC=2)C=C1 PCYDAYVXRZGZED-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 150000001335 aliphatic alkanes Chemical group 0.000 description 2
- 125000005530 alkylenedioxy group Chemical group 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 125000005427 anthranyl group Chemical group 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 239000000412 dendrimer Substances 0.000 description 2
- 229920000736 dendritic polymer Polymers 0.000 description 2
- 238000009792 diffusion process Methods 0.000 description 2
- 230000005684 electric field Effects 0.000 description 2
- 125000001033 ether group Chemical group 0.000 description 2
- 230000005281 excited state Effects 0.000 description 2
- 230000005525 hole transport Effects 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 229910052744 lithium 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
- 239000000203 mixture Substances 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- JZRYQZJSTWVBBD-UHFFFAOYSA-N pentaporphyrin i Chemical compound N1C(C=C2NC(=CC3=NC(=C4)C=C3)C=C2)=CC=C1C=C1C=CC4=N1 JZRYQZJSTWVBBD-UHFFFAOYSA-N 0.000 description 2
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000004544 sputter deposition Methods 0.000 description 2
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 2
- 125000005504 styryl group Chemical group 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 125000000101 thioether group Chemical group 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- GDTMIGSCWLYRHS-UHFFFAOYSA-K (2,6-diphenylphenoxy)-bis[(2-methylquinolin-8-yl)oxy]alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.[O-]C1=C(C=2C=CC=CC=2)C=CC=C1C1=CC=CC=C1 GDTMIGSCWLYRHS-UHFFFAOYSA-K 0.000 description 1
- UWRZIZXBOLBCON-VOTSOKGWSA-N (e)-2-phenylethenamine Chemical class N\C=C\C1=CC=CC=C1 UWRZIZXBOLBCON-VOTSOKGWSA-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
- VERMWGQSKPXSPZ-BUHFOSPRSA-N 1-[(e)-2-phenylethenyl]anthracene Chemical class C=1C=CC2=CC3=CC=CC=C3C=C2C=1\C=C\C1=CC=CC=C1 VERMWGQSKPXSPZ-BUHFOSPRSA-N 0.000 description 1
- WULZIURTBVLJRF-UHFFFAOYSA-N 1-n,3-n-diphenylbenzene-1,3-diamine Chemical compound C=1C=CC(NC=2C=CC=CC=2)=CC=1NC1=CC=CC=C1 WULZIURTBVLJRF-UHFFFAOYSA-N 0.000 description 1
- YTDHEFNWWHSXSU-UHFFFAOYSA-N 2,3,5,6-tetrachloroaniline Chemical compound NC1=C(Cl)C(Cl)=CC(Cl)=C1Cl YTDHEFNWWHSXSU-UHFFFAOYSA-N 0.000 description 1
- RZFOAVRHEGQZRV-UHFFFAOYSA-N 2,3-diphenylthiophene Chemical compound S1C=CC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 RZFOAVRHEGQZRV-UHFFFAOYSA-N 0.000 description 1
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- ZMPRRFPMMJQXPP-UHFFFAOYSA-N 2-sulfobenzoic acid Chemical group OC(=O)C1=CC=CC=C1S(O)(=O)=O ZMPRRFPMMJQXPP-UHFFFAOYSA-N 0.000 description 1
- XDASUTQDWUULOY-UHFFFAOYSA-N 3,4-diphenyl-2-thiophen-2-ylthiophene Chemical compound C1=CSC(C2=C(C(=CS2)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 XDASUTQDWUULOY-UHFFFAOYSA-N 0.000 description 1
- OGGKVJMNFFSDEV-UHFFFAOYSA-N 3-methyl-n-[4-[4-(n-(3-methylphenyl)anilino)phenyl]phenyl]-n-phenylaniline Chemical group CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 OGGKVJMNFFSDEV-UHFFFAOYSA-N 0.000 description 1
- AHDTYXOIJHCGKH-UHFFFAOYSA-N 4-[[4-(dimethylamino)-2-methylphenyl]-phenylmethyl]-n,n,3-trimethylaniline Chemical compound CC1=CC(N(C)C)=CC=C1C(C=1C(=CC(=CC=1)N(C)C)C)C1=CC=CC=C1 AHDTYXOIJHCGKH-UHFFFAOYSA-N 0.000 description 1
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 1
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 0.000 description 1
- MEIBOBDKQKIBJH-UHFFFAOYSA-N 4-methyl-n-[4-[1-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]-4-phenylcyclohexyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C1(CCC(CC1)C=1C=CC=CC=1)C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 MEIBOBDKQKIBJH-UHFFFAOYSA-N 0.000 description 1
- ZOKIJILZFXPFTO-UHFFFAOYSA-N 4-methyl-n-[4-[1-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]cyclohexyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C1(CCCCC1)C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 ZOKIJILZFXPFTO-UHFFFAOYSA-N 0.000 description 1
- DUSWRTUHJVJVRY-UHFFFAOYSA-N 4-methyl-n-[4-[2-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]propan-2-yl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C(C)(C)C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 DUSWRTUHJVJVRY-UHFFFAOYSA-N 0.000 description 1
- MVIXNQZIMMIGEL-UHFFFAOYSA-N 4-methyl-n-[4-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]phenyl]-n-(4-methylphenyl)aniline Chemical group C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 MVIXNQZIMMIGEL-UHFFFAOYSA-N 0.000 description 1
- XIQGFRHAIQHZBD-UHFFFAOYSA-N 4-methyl-n-[4-[[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]-phenylmethyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C(C=1C=CC=CC=1)C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 XIQGFRHAIQHZBD-UHFFFAOYSA-N 0.000 description 1
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 125000006189 4-phenyl benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- VJEVAXUMNMFKDT-UHFFFAOYSA-N 5,10,15,20-tetrakis(2,3,4,5,6-pentafluorophenyl)-21,23-dihydroporphyrin Chemical compound Fc1c(F)c(F)c(c(F)c1F)-c1c2ccc(n2)c(-c2c(F)c(F)c(F)c(F)c2F)c2ccc([nH]2)c(-c2c(F)c(F)c(F)c(F)c2F)c2ccc(n2)c(-c2c(F)c(F)c(F)c(F)c2F)c2ccc1[nH]2 VJEVAXUMNMFKDT-UHFFFAOYSA-N 0.000 description 1
- WPYMZALMVVFPJZ-UHFFFAOYSA-N 6,7,15,16,24,25,33,34-octamethyl-2,11,20,29,37,38,39,40-octazanonacyclo[28.6.1.13,10.112,19.121,28.04,9.013,18.022,27.031,36]tetraconta-1,3,5,7,9,11,13(18),14,16,19,21(38),22(27),23,25,28,30(37),31(36),32,34-nonadecaene Chemical compound N1=C(N=C2[C]3C=C(C)C(C)=CC3=C(N=C3C4=CC(C)=C(C)C=C4C(=N4)N3)N2)[C](C=C(C(C)=C2)C)C2=C1N=C1C2=CC(C)=C(C)C=C2C4=N1 WPYMZALMVVFPJZ-UHFFFAOYSA-N 0.000 description 1
- VIJYEGDOKCKUOL-UHFFFAOYSA-N 9-phenylcarbazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2C2=CC=CC=C21 VIJYEGDOKCKUOL-UHFFFAOYSA-N 0.000 description 1
- 229910001316 Ag alloy Inorganic materials 0.000 description 1
- 229910017090 AlO 2 Inorganic materials 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
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- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 1
- 229910000799 K alloy Inorganic materials 0.000 description 1
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- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical group CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 description 1
- DBIPWVDHKYAWSJ-UHFFFAOYSA-K [Al+3].C1(=CC(=CC=C1O)C)C(=O)[O-].CC1=NC2=C(C=CC=C2C=C1)[O-].CC1=NC2=C(C=CC=C2C=C1)[O-] Chemical compound [Al+3].C1(=CC(=CC=C1O)C)C(=O)[O-].CC1=NC2=C(C=CC=C2C=C1)[O-].CC1=NC2=C(C=CC=C2C=C1)[O-] DBIPWVDHKYAWSJ-UHFFFAOYSA-K 0.000 description 1
- ZTJGHDNXJXDLCI-UHFFFAOYSA-K [Al+3].C=1(C(=CC=CC1O)C(=O)[O-])C.CC1=NC2=C(C=CC=C2C=C1)[O-].CC1=NC2=C(C=CC=C2C=C1)[O-] Chemical compound [Al+3].C=1(C(=CC=CC1O)C(=O)[O-])C.CC1=NC2=C(C=CC=C2C=C1)[O-].CC1=NC2=C(C=CC=C2C=C1)[O-] ZTJGHDNXJXDLCI-UHFFFAOYSA-K 0.000 description 1
- GDTLRHWZBRHGEX-UHFFFAOYSA-K [Al+3].C=1(C(=CC=CC1O)C)C(=O)[O-].CC1=NC2=C(C=CC=C2C=C1)[O-].CC1=NC2=C(C=CC=C2C=C1)[O-] Chemical compound [Al+3].C=1(C(=CC=CC1O)C)C(=O)[O-].CC1=NC2=C(C=CC=C2C=C1)[O-].CC1=NC2=C(C=CC=C2C=C1)[O-] GDTLRHWZBRHGEX-UHFFFAOYSA-K 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 125000001389 aceanthrenyl group Chemical group C1(CC2=CC=CC3=CC4=CC=CC=C4C1=C23)* 0.000 description 1
- 125000004062 acenaphthenyl group Chemical group C1(CC2=CC=CC3=CC=CC1=C23)* 0.000 description 1
- 125000004054 acenaphthylenyl group Chemical group C1(=CC2=CC=CC3=CC=CC1=C23)* 0.000 description 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
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- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- HJIPNTADLUEEED-UHFFFAOYSA-K aluminum;2,6-dimethylphenolate;2-methylquinolin-8-olate Chemical compound [Al+3].CC1=CC=CC(C)=C1[O-].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21 HJIPNTADLUEEED-UHFFFAOYSA-K 0.000 description 1
- DLIRCHDELWASPG-UHFFFAOYSA-K aluminum;3,4-dimethylphenolate;2-methylquinolin-8-olate Chemical compound [Al+3].CC1=CC=C([O-])C=C1C.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21 DLIRCHDELWASPG-UHFFFAOYSA-K 0.000 description 1
- BZHLLHPAFRKZAV-UHFFFAOYSA-K aluminum;3,5-dimethylphenolate;2-methylquinolin-8-olate Chemical compound [Al+3].CC1=CC(C)=CC([O-])=C1.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21 BZHLLHPAFRKZAV-UHFFFAOYSA-K 0.000 description 1
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- 125000002078 anthracen-1-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C([*])=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
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- MPCSRDRXSVSWPI-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(2-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.[O-]C1=CC=CC=C1C1=CC=CC=C1 MPCSRDRXSVSWPI-UHFFFAOYSA-K 0.000 description 1
- WDIXNURAWJTREU-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(3-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.[O-]C1=CC=CC(C=2C=CC=CC=2)=C1 WDIXNURAWJTREU-UHFFFAOYSA-K 0.000 description 1
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- CCAADOWYZMBENE-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-phenoxyalumane Chemical compound C12=NC(C)=CC=C2C=CC=C1O[Al](OC=1C2=NC(C)=CC=C2C=CC=1)OC1=CC=CC=C1 CCAADOWYZMBENE-UHFFFAOYSA-K 0.000 description 1
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- SBAUTRQODRAAMY-UHFFFAOYSA-N calcium;5-chloroquinolin-8-ol Chemical compound [Ca].C1=CN=C2C(O)=CC=C(Cl)C2=C1.C1=CN=C2C(O)=CC=C(Cl)C2=C1 SBAUTRQODRAAMY-UHFFFAOYSA-N 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
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- CTQMJYWDVABFRZ-UHFFFAOYSA-N cloxiquine Chemical compound C1=CN=C2C(O)=CC=C(Cl)C2=C1 CTQMJYWDVABFRZ-UHFFFAOYSA-N 0.000 description 1
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- HQQKMOJOCZFMSV-UHFFFAOYSA-N dilithium phthalocyanine Chemical compound [Li+].[Li+].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 HQQKMOJOCZFMSV-UHFFFAOYSA-N 0.000 description 1
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- 229910052736 halogen Inorganic materials 0.000 description 1
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- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
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- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- CSPVGJWCKNBRRB-UHFFFAOYSA-N indium;quinolin-8-ol Chemical compound [In].C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1 CSPVGJWCKNBRRB-UHFFFAOYSA-N 0.000 description 1
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- LBAIJNRSTQHDMR-UHFFFAOYSA-N magnesium phthalocyanine Chemical compound [Mg].C12=CC=CC=C2C(N=C2NC(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2N1 LBAIJNRSTQHDMR-UHFFFAOYSA-N 0.000 description 1
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- MOOHXQFFIPDLNX-UHFFFAOYSA-N magnesium;quinolin-8-ol Chemical compound [Mg].C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1 MOOHXQFFIPDLNX-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical group OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
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- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
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- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
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- JACPFCQFVIAGDN-UHFFFAOYSA-M sipc iv Chemical compound [OH-].[Si+4].CN(C)CCC[Si](C)(C)[O-].C=1C=CC=C(C(N=C2[N-]C(C3=CC=CC=C32)=N2)=N3)C=1C3=CC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 JACPFCQFVIAGDN-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 1
- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
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- 125000004149 thio group Chemical group *S* 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- 238000004506 ultrasonic cleaning Methods 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Landscapes
- Electroluminescent Light Sources (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【０００１】
【発明の属する技術分野】
本発明は有機エレクトロルミネッセンス（以下、ＥＬと略記する）素子に関し、さらに詳しくは、長時間駆動しても発光色の変化が少ないなど、長寿命を有し、かつ高効率の有機ＥＬ素子に関するものである。
【０００２】
【従来の技術】
電界発光を利用したＥＬ素子は、自己発光のため視認性が高く、かつ完全固体素子であるため、耐衝撃性に優れるなどの特徴を有することから、各種表示装置における発光素子としての利用が注目されている。
このＥＬ素子には、発光材料に無機化合物を用いてなる無機ＥＬ素子と有機化合物を用いてなる有機ＥＬ素子とがあり、このうち、有機ＥＬ素子は、印加電圧を大幅に低くしうるために、次世代の表示素子としてその実用化研究が積極的になされている。
【０００３】
ところで、この有機ＥＬ素子においては、長寿命かつ高効率の青色発光素子を開発するため、これまで青色発光材料に関する研究に力が注がれ、種々の青色発光材料、例えば高輝度，高効率のジスチリルアリーレン系青色発光材料（特許文献１），高輝度のキレート系青色発光材料（特許文献２），高輝度のジアミン系青色発光材料（特許文献３）などが開示されている。しかしながら、これらの青色発光材料は、通常陽極／正孔注入輸送層／発光層／電子注入輸送層／陰極の構成で利用され、性能が発揮されていたが、寿命の点では必ずしも満足しうるものではなく、例えば（１）駆動時間が経過するとともに、色が緑色化し、発光色が変化する、（２）初期輝度１００ｃｄ／ｍ２の時の半減寿命が１０００時間程度と短い（実用上は数千時間以上が要求される）、などの問題がある。
【０００４】
他方、本発明における蛍光性ドーパントに類似した構造を有する化合物を発光層の材料とする素子が提案されているが（特許文献４）、微量添加された蛍光性ドーパントの機能については何ら言及していない。
また、特許文献５及び特許文献６には、発光層に添加させる電荷注入補助剤であるジスチリルアリーレン系材料が開示されている。この材料は蛍光性ドーパントとしても働くものであるが、このものを用いた素子の半減寿命は１０００時間程度（初期輝度１００ｃｄ／ｍ２）と短く、改善が求められていた。
【特許文献１】
特開平２−２４７２７８号公報
【特許文献２】
特開平５−１９８３７８号公報
【特許文献３】
特開平６−２２０４３７号公報
【特許文献４】
特開平６−２２０４３７号公報
【特許文献５】
特開平６−９９５３号公報
【特許文献６】
国際公開９４−６１５７号公報
【０００５】
【発明が解決しようとする課題】
本発明は、このような従来の有機ＥＬ素子がもつ欠点を改良し、長時間駆動しても発光色の変化が少ないなど、長寿命を有し、かつ高効率の有機ＥＬ素子を提供することを目的とするものである。
【０００６】
【課題を解決するための手段】
本発明者らは、長寿命かつ高効率の有機ＥＬ素子を開発すべく鋭意研究を重ねた結果、素子の正孔と電子との結合領域又は発光領域の少なくともいずれかに、蛍光性ドーパントとして、特定の化合物を所定の割合で含有させることにより、その目的を達成しうることを見出した。本発明は、かかる知見に基づいて完成したものである。
すなわち、本発明は、正孔と電子とが再結合する再結合領域及び該再結合に応答して発光する発光領域を少なくとも有する有機化合物層と、この有機化合物層を挾持する一対の電極とを備えた有機エレクトロルミネッセンス素子において、上記再結合領域及び／又は発光領域に、蛍光性ドーパントとして、一般式（Ｉ）
【０００７】
【化３】
〔式中、Ａｒ１，Ａｒ２及びＡｒ３は、それぞれ炭素数１〜１０のアルキル基，炭素数６〜３０のアリール基又は複素環式基を示し、それらはたがいに同一でも異なっていてもよいが、その少なくとも一つは炭素数１２以上の縮合多環炭化水素基である。〕
及び一般式（ＩＩ）
【０００９】
【化４】
〔式中，Ａｒ４，Ａｒ５，Ａｒ６及びＡｒ７はそれぞれ炭素数１〜１０のアルキル基，炭素数６〜３０のアリール基又は複素環式基を示し、それらはたがいに同一でも異なっていてもよく、Ａｒ８は炭素数６〜３０のアリーレン基又は二価の複素環式基を示すが、Ａｒ４〜Ａｒ８の少なくとも一つは炭素数１２以上の縮合多環炭化水素基である。〕
で表される化合物の中から選ばれた少なくとも一種を０．１〜８重量％の割合で含有させたことを特徴とする有機ＥＬ素子を提供するものである。
【発明の実施の形態】
本発明において用いられる蛍光性ドーパントは、一般式（Ｉ）
【００１１】
【化５】
又は、一般式（ＩＩ）
【００１３】
【化６】
で表される構造を有する化合物である。
上記一般式（Ｉ）及び（ＩＩ）において、Ａｒ１〜Ａｒ７は、それぞれ炭素数１〜１０のアルキル基，炭素数６〜３０のアリール基又は複素環式基を示す。ここで、炭素数１〜１０のアルキル基の例としては、メチル基，エチル基，ｎ−プロピル基，イソプロピル基，ｎ−ブチル基，イソブチル基，ｓｅｃ−ブチル基，ｔ−ブチル基などが挙げられ、炭素数６〜３０のアリール基の例としては、フェニル基，ビフェニル基，ターフェニル基などの非縮合炭化水素基や縮合多環炭化水素基が挙げられる。該縮合多環炭化水素基としては、好ましくは環を形成する炭素数が１８以下のもの、例えばペンタレニル基，インデニル基，ナフチル基，アズレニル基，ヘプタレニル基，ビフェニレニル基，ａｓ−インダセニル基，フルオレニル基，ｓ−インダセニル基，アセナフチレニル基，プレイアデニル基，アセナフテニル基，フェナレニル基，フェナントリル基，アントリル基，フルオランテニル基，アセフェナントリレニル基，アセアントリレニル基，トリフェニレニル基，ピレニル基，クリセニル基，ナフタセニル基などが挙げられる。
【００１５】
また、複素環式基の例としては、ピリジル基，ピリミジル基，ピラジニル基，トリアジニル基，フラニル基，ピロリル基，チオフェニル基，キノリル基，クマリニル基，ベンゾフラニル基，ベンズイミダゾリル基，ベンズオキサゾリル基，ジベンゾフラニル基，ベンゾチオフェニル基，ジベンゾチオフェニル基，インドリル基，カルバゾリル基，ピラゾリル基，イミダゾリル基，オキサゾリル基，イソオキサゾリル基，チアゾリル基，インダゾリル基，ベンゾチアゾリル基，ピリダジニル基，シンノリル基，キナゾリル基，キノキサリル基，フタラジニル基，フタラジンジオニル基，フタルアミジル基，クロモニル基，ナフトラクタミル基，キノロニル基，ｏ−スルホ安息香酸イミジル基，マレイン酸イミジル基，ナフタリジニル基，ベンズイミダゾロニル基，ベンズオキサゾロニル基，ベンゾチアゾロニル基，ベンゾチアゾチオニル基，キナゾロニル基，キノキサロニル基，フタラゾニル基，ジオキソピリミジニル基，ピリドニル基，イソキノロニル基，イソキノリニル基，イソチアゾリル基，ベンズイソキサゾリル基，ベンズイソチアゾリル基，インダジロニル基，アクリジニル基，アクリドニル基，キナゾリンジオニル基，キノキサリンジオニル基，ベンゾオキサジンジオニル基，ベンゾキサジノニル基，ナフタルイミジル基などが挙げられる。
【００１６】
一方、Ａｒ８は炭素数６〜３０のアリーレン基又は二価の複素環式基を示す。ここで、炭素数６〜３０のアリーレン基又は二価の複素環式基としては、例えばＡｒ１〜Ａｒ７の説明で例示したアリール基又は複素環式から、水素原子を１個除いた二価の基を挙げることができる。また、他のアリーレン基として、ジフェニレンプロパン基，ジフェニレンメタン基などのジアリーレンアルカン基、ジフェニレンシクロヘキサン基，ジフェニレンシクロペンタン基などのジアリーレンアルカン基、ジフェニレンエーテル基などのジアリーレンエーテル基、ジフェニレンチオエーテル基などのジアリーレンチオエーテル基、Ｎ−フェニルジフェニレンアミン基，Ｎ−ナフチルジナフチレンアミン基，Ｎ−フェニルカルバゾリレン基などのＮ−アリールジアリーレンアミン基、さらにジフェニルチオフェン，ジフェニルビチオフェンの２価の基などのジアリールチオフェン又はジアリールビチオフェン基なども好ましく挙げることができる。
該Ａｒ１，Ａｒ２及びＡｒ３は、たがいに同一でも異なっていてもよいが、その少なくとも一つは炭素数１２以上の縮合多環炭化水素基であることが必要である。またＡｒ４，Ａｒ５，Ａｒ６及びＡｒ７はたがいに同一でも異なっていてもよいが、Ａｒ４〜Ａｒ８の少なくとも一つは炭素数１２以上の縮合多環炭化水素基であることが必要である。
【００１７】
さらに、該Ａｒ１〜Ａｒ８は適当な置換基が導入されていてもよく、この置換基としては、例えば（１）ハロゲン原子（Ｆ，Ｃｌ，Ｂｒ，Ｉ），シアノ基，ニトロ基，（２）アルキル基，（３）アルコキシ基，（４）アリールオキシ基，（５）アルキル又はアリールメルカプト基，（６）−ＮＲ１Ｒ２（Ｒ１及びＲ２はそれぞれ水素原子，アルキル基又はアリール基を示し、それらはたがいに同一でも異なっていてもよい。）で表される置換若しくは無置換アミノ基，（７）アルキレンジオキシ基，アルキレンジチオ基などを挙げることができる。ここで、（２）のアルキル基としては、炭素数１〜２０、特に１〜１２の直鎖状又は分岐鎖状のものが好ましく、また、このアルキル基は、さらにハロゲン原子（Ｆ，Ｃｌ，Ｂｒ，Ｉ），水酸基，シアノ基，炭素数１〜１２のアルコキシ基，フェニル基又は炭素数１〜１２のアルキル基やアルコキシ基で置換されたフェニル基を含有していてもよい。このようなアルキル基の例としては、メチル基，エチル基，ｎ−プロピル基，イソプロピル基，ｔ−ブチル基，ｓｅｃ−ブチル基，ｎ−ブチル基，イソブチル基，トリフルオロメチル基，２−ヒドロキシエチル基，２−シアノエチル基，２−エトキシエチル基，２−メトキシエチル基，ベンジル基，４−クロロベンジル基，４−メチルベンジル基，４−メトキシベンジル基，４−フェニルベンジル基などが挙げられる。
【００１８】
（３）のアルコキシ基（−ＯＲ３）としては、Ｒ３として上記（２）で例示したアルキル基を有するものを挙げることができ、具体的には、メトキシ基，エトキシ基，ｎ−プロポキシ基，イソプロポキシ基，ｔ−ブトキシ基，ｎ−ブトキシ基，ｓｅｃ−ブトキシ基，イソブトキシ基，２−ヒドロキシエトキシ基，２−シアノエトキシ基，ベンジルオキシ基，４−メチルベンジルオキシ基，トリフルオロメトキシ基などが挙げられる。（４）のアリールオキシ基（−ＯＡｒ）としては、Ａｒとして無置換又はハロゲン原子（Ｆ，Ｃｌ，Ｂｒ，Ｉ），炭素数１〜４のアルキル基若しくはアルコキシ基などが置換されたフェニル基やナフチル基を有するものを好ましく挙げることができ、具体的にはフェノキシ基，１−ナフチルオキシ基，２−ナフチルオキシ基，４−メチルフェノキシ基，４−メトキシフェノキシ基，４−クロロフェノキシ基，６−メチル−２−ナフチルオキシ基などが挙げられる。また、（５）のアルキル又はアリールメルカプト基（−ＳＲ４）としては、Ｒ４として上記（２）で例示したアルキル基又は（４）で例示したフェニル基やナフチル基などを有するものを挙げることができ、具体的には、メチルチオ基，エチルチオ基，フェニルチオ基，ｐ−メチルフェニルチオ基などが挙げられる。
【００１９】
さらに、（６）の−ＮＲ１Ｒ２で示される基としては、Ｒ１及びＲ２がそれぞれ水素原子，アルキル基又はアリール基であるものが挙げられる。ここで、アルキル基としては、上記（２）で例示したものを挙げることができ、またアリール基としては、無置換又はハロゲン原子（Ｆ，Ｃｌ，Ｂｒ，Ｉ），炭素数１〜４のアルキル基若しくはアルコキシ基などが置換されたフェニル基，ビフェニル基，ナフチル基，ピレニル基，アントラニル基などを挙げることができる。該Ｒ１及びＲ２はたがいに同一でも異なっていてもよく、またたがいに結合して環構造を形成していてもよい。具体的には、アミノ基，ジエチルアミノ基，Ｎ−メチル−Ｎ−フェニルアミノ基，Ｎ，Ｎ−ジフェニルアミノ基，Ｎ，Ｎ−ジ−（ｐ−トリル）アミノ基，ジベンジルアミノ基，ピペリジノ基，モルホリノ基，ユロリジル基などが挙げられる。（７）のアルキレンジオキシ基，アルキレンジチオ基としては、例えばメチレンジオキシ基，メチレンジチオ基などが挙げられる。
【００２０】
前記一般式（Ｉ），（ＩＩ）で表される化合物としては、例えば次に示す構造のものを挙げることができる。
【００２１】
【化７】
【化８】
【化９】
【化１０】
【化１１】
【化１２】
【化１３】
【化１４】
本発明においては、蛍光性ドーパントとして、これらの化合物を一種用いてもよく、二種以上を組み合わせて用いてもよい。
なお、本発明における蛍光性ドーパントとは、有機ＥＬ素子の再結合領域又は発光領域において、正孔と電子の再結合に応答して光を発する化合物のことであり、再結合領域又は発光領域を形成する物質（ホスト材料）に微量含有させるものである。ここで、再結合領域とは、素子中にあって、正孔と電子とが出会い、結合して励起状態を形成する場所のことである。また、発光領域とは、再結合領域で形成された励起状態は、場合によっては移動し、拡散するが、その拡散する範囲を指定する場所のことである。
【００３０】
本発明においては、上記蛍光性ドーパントは、再結合領域及び発光領域の少なくともいずれか、即ち、再結合領域のみに、発光領域のみに、あるいは両領域に、０．１〜８重量％の割合で含有させることが必要である。この含有量が０．１重量％未満では蛍光性ドーパントの効果が充分に発揮されず、本発明の目的が達せられない。一方、８重量％を超えると蛍光性ドーパント間の会合により、消失現象が生じ、充分に効果が発揮されない場合がある。素子の長寿命化及び高効率化の点から、蛍光性ドーパントの好ましい含有量は０．３〜４重量％の範囲であり、特に０．８〜３重量％の範囲が好適である。
この蛍光性ドーパントを、再結合領域又は発光領域に含有させる方法については特に制限はないが、例えば再結合領域又は発光領域を形成する材料（ホスト材料）との共蒸着法を採用するのが好ましい。この方法においては、ホスト材料と蛍光性ドーパントを、それぞれが収容された別々のボートから真空蒸着し、再結合領域や発光領域を形成する。
本発明の有機ＥＬ素子においては、有機化合物層として、再結合領域及び発光領域を少なくとも有するものが用いられる。この再結合領域及び発光領域は、通常発光層に存在するため、本発明においては、有機化合物層として発光層のみを用いてもよいが、必要に応じ、発光層以外に、例えば正孔注入層，電子注入層，有機半導体層，電子障壁層，付着改善層なども用いることができる。
【００３１】
次に、本発明の有機ＥＬ素子の代表的な構成例を示す。もちろん、これに限定されるものではない。
▲１▼陽極／正孔注入層／発光層／陰極
▲２▼陽極／正孔注入層／発光層／電子注入層／陰極
▲３▼陽極／発光層／電子注入層／陰極
▲４▼陽極／有機半導体層／発光層／陰極
▲５▼陽極／有機半導体層／電子障壁層／発光層／陰極
▲６▼陽極／正孔注入層／発光層／付着改善層／陰極
これらの中で、通常▲２▼の構成が好ましく用いられる。
【００３２】
本発明の素子における再結合領域及び発光領域は、前記したように通常発光層に存在する。したがって、蛍光性ドーパントは、通常発光層に含有される。しかし、場合によっては、他の層、例えば正孔注入層，電子注入層，有機半導体層，電子障壁層，付着改善層なども、再結合や発光に関与することがある。この場合、これらの層にも含有させるのが好ましい。
【００３３】
本発明の有機ＥＬ素子は、上記有機化合物層が一対の電極、すなわち陽極と陰極とによって挾持された構造を有しており、該陽極としては、仕事関数の大きい（４ｅＶ以上）金属，合金，電気伝導性化合物及びこれらの混合物を電極物質とするものが好ましく用いられる。このような電極物質の具体例としては、Ａｕなどの金属，ＣｕＩ，ＩＴＯ，ＳｎＯ２，ＺｎＯなどの誘電性透明材料が挙げられる。該陽極は、これらの電極物質を蒸着やスパッタリングなどの方法により、薄膜を形成させることにより作製することができる。この電極より発光を取り出す場合には、透過率を１０％より大きくすることが望ましく、また、電極としてのシート抵抗は数百Ω／□以下が好ましい。さらに膜厚は材料にもよるが、通常１０ｎｍ〜１μｍ，特に１０〜２００ｎｍの範囲が好ましい。
【００３４】
一方、陰極としては、仕事関数の小さい（４ｅＶ以下）金属，合金，電気伝導性化合物及びこれらの混合物を電極物質とするものが用いられる。このような電極物質の具体例としては、ナトリウム，ナトリウム−カリウム合金，マグネシウム，リチウム，マグネシウム・銀合金，Ａｌ／ＡｌＯ２，インジウム，希土類金属などが挙げられる。該陰極はこれらの電極物質を蒸着やスパッタリングなどの方法により、薄膜を形成させることにより、作製することができる。また、電極としてのシート抵抗は数百Ω／□以下が好ましく、膜厚は通常１０ｎｍ〜１μｍ，特に５０〜２００ｎｍの範囲が好ましい。なお、本発明の素子においては、特に規定しないが、該陽極又は陰極のいずれか一方が透明若しくは半透明であることが発光を透過し、取り出す効率がよいので好ましい。
【００３５】
本発明の素子における発光層においては、発光材料（ホスト材料）として、一般式（ＩＩＩ）
【００３６】
【化１５】
で表されるジスチリルアリーレン系化合物が好ましく用いられる。この化合物は、特開平２−２４７２７８号公報に開示されている。
【００３８】
上記一般式（ＩＩＩ）において、Ｙ１〜Ｙ４はそれぞれ水素原子，炭素数１〜６のアルキル基，炭素数１〜６のアルコキシ基，炭素数７〜８のアラルキル基，置換あるいは無置換の炭素数６〜１８のアリール基，置換あるいは無置換のシクロヘキシル基，置換あるいは無置換の炭素数６〜１８のアリールオキシ基，炭素数１〜６のアルコキシ基を示す。ここで、置換基は炭素数１〜６のアルキル基，炭素数１〜６のアルコキシ基，炭素数７〜８のアラルキル基，炭素数６〜１８のアリールオキシ基，炭素数１〜６のアシル基，炭素数１〜６のアシルオキシ基，カルボキシル基，スチリル基，炭素数６〜２０のアリールカルボニル基，炭素数６〜２０のアリールオキシカルボニル基，炭素数１〜６のアルコキシカルボニル基，ビニル基，アニリノカルボニル基，カルバモイル基，フェニル基，ニトロ基，水酸基あるいはハロゲンを示す。これらの置換基は単一でも複数でもよい。また、Ｙ１〜Ｙ４は同一でも、また互いに異なっていてもよく、Ｙ１とＹ２及びＹ３とＹ４は互いに置換している基と結合して、置換あるいは無置換の飽和五員環又は置換あるいは無置換の飽和六員環を形成してもよい。Ａｒ９は置換あるいは無置換の炭素数６〜２０のアリーレン基を表し、単一置換されていても、複数置換されていてもよく、また結合部位は、オルト，パラ，メタいずれでもよい。但し、Ａｒ９が無置換フェニレン基の場合、Ｙ１〜Ｙ４はそれぞれ炭素数１〜６のアルコキシ基，炭素数７〜８のアラルキル基，置換あるいは無置換のナフチル基，ビフェニル基，シクロヘキシル基，アリールオキシ基より選ばれたものである。 このようなジスチリルアリーレン系化合物としては、例えば、
【００３９】
【化１６】
【化１７】
【化１８】
【化１９】
などが挙げられる。
【００４４】
また、別の好ましい発光材料（ホスト材料）として、８−ヒドロキシキノリン、又はその誘導体の金属錯体を挙げることができる。具体的には、オキシン（一般に８−キノリノールまたは８−ヒドロキシキノリン）のキレートを含む金属キレートオキシノイド化合物である。このような化合物は高水準の性能を示し、容易に薄膜形態に成形される。このオキシノイド化合物の例は下記構造式を満たすものである。
【００４５】
【化２０】
（式中、Ｍｔは金属を表し、ｎは１〜３の整数であり、Ｚはそのそれぞれの位置が独立であって、少なくとも２以上の縮合芳香族環を完成させるために必要な原子を示す。）
ここで、Ｍｔで表される金属は、一価，二価又は三価の金属とすることができるものであり、例えばリチウム，ナトリウム，カリウムなどのアルカリ金属、マグネシウムやカルシウムなどのアルカリ土類金属、あるいはホウ素又はアルミニウムなどの土類金属である。
一般に有用なキレート化合物であると知られている一価，二価又は三価の金属はいずれも使用することができる。
【００４７】
また、Ｚは、少なくとも２以上の縮合芳香族環の一方がアゾール又はアジンからなる複素環を形成させる原子を示す。ここで、もし必要であれば、上記縮合芳香族環に他の異なる環を付加することが可能である。また、機能上の改善がないまま嵩ばった分子を付加することを回避するため、Ｚで示される原子の数は１８以下に維持することが好ましい。
さらに、具体的にキレート化オキシノイド化合物を例示すると、トリス（８−キノリノール）アルミニウム，ビス（８−キノリノール）マグネシウム，ビス（ベンゾ−８−キノリノール）亜鉛，ビス（２−メチル−８−キノリラート）アルミニウムオキシド，トリス（８−キノリノール）インジウム，トリス（５−メチル−８−キノリノール）アルミニウム，８−キノリノールリチウム，トリス（５−クロロ−８−キノリノール）ガリウム，ビス（５−クロロ−８−キノリノール）カルシウム，５，７−ジクロル−８−キノリノールアルミニウム，トリス（５，７−ジブロモ−８−ヒドロキシキノリノール）アルミニウムなどがある。
【００４８】
さらに、特開平５−１９８３７８号公報に記載されているフェノラート置換８−ヒドロキシキノリンの金属錯体は、青色発光材料として、好ましいものでる。このフェノラート置換８−ヒドロキシキノリンの金属錯体の具体例としては、ビス（２−メチル−８−キノリノラート）（フェノラート）アルミニウム（ＩＩＩ），ビス（２−メチル−８−キノリノラート）（ｏ−クレゾラート）アルミニウム（ＩＩＩ），ビス（２−メチル−８−キノリノラート）（ｍ−クレゾラート）アルミニウム（ＩＩＩ），ビス（２−メチル−８−キノリノラート）（ｐ−クレゾラート）アルミニウム（ＩＩＩ），ビス（２−メチル−８−キノリノラート）（ｏ−フェニルフェノラート）アルミニウム（ＩＩＩ），ビス（２−メチル−８−キノリノラート）（ｍ−フェニルフェノラート）アルミニウム（ＩＩＩ），ビス（２−メチル−８−キノリノラート）（ｐ−フェニルフェノラート）アルミニウム（ＩＩＩ），ビス（２−メチル−８−キノリノラート）（２，３−ジメチルフェノラート）アルミニウム（ＩＩＩ），ビス（２−メチル−８−キノリノラート）（２，６−ジメチルフェノラート）アルミニウム（ＩＩＩ），ビス（２−メチル−８−キノリノラート）（３，４−ジメチルフェノラート）アルミニウム（ＩＩＩ），ビス（２−メチル−８−キノリノラート）（３，５−ジメチルフェノラート）アルミニウム（ＩＩＩ），ビス（２−メチル−８−キノリノラート）（３，５−ジ−ｔ−ブチルフェノラート）アルミニウム（ＩＩＩ），ビス（２−メチル−８−キノリノラート）（２，６−ジフェニルフェノラート）アルミニウム（ＩＩＩ），ビス（２−メチル−８−キノリノラート）（２，４，６−トリフェニルフェノラート）アルミニウム（ＩＩＩ）などが挙げられる。
これらの発光材料は一種用いてもよく、二種以上を組み合わせて用いてもよい。
【００４９】
本発明の素子における発光層の形成方法としては、例えば蒸着法，スピンコート法，キャスト法，ＬＢ法などの公知の方法により薄膜化することにより形成することができるが、特に分子堆積膜であることが好ましい。ここで、分子堆積膜とは、該化合物の気相状態から沈着され形成された薄膜や、該化合物の溶融状態又は液相状態から固体化され形成された膜のことである。通常、この分子堆積膜はＬＢ法により形成された薄膜（分子累積膜）と凝集構造，高次構造の相違や、それに起因する機能的な相違により区別することができる。
また、この発光層は樹脂などの結着材と共に溶剤に溶かして溶液とした後、これをスピンコート法などにより薄膜化して形成することができる。
このようにして形成された発光層の膜厚については特に制限はなく、適宜状況に応じて選ぶことができるが、好ましくは１ｎｍ〜１０μｍ、特に好ましくは５ｎｍ〜５μｍの範囲がよい。
【００５０】
次に、正孔注入層は、必ずしも本発明の素子に必要なものではないが、発光性能の向上のために用いた方が好ましいものである。この正孔注入層は、発光層への正孔注入を助ける層であって、正孔移動度が大きく、イオン化エネルギーが、通常５．５ｅＶ以下と小さい。このような正孔注入層としては、より低い電界で正孔を発光層に輸送する材料が好ましく、さらに正孔の移動度が、例えば１０４〜１０６Ｖ／ｃｍの電界印加時に、少なくとも１０−６ｃｍ２／Ｖ・秒であればなお好ましい。
このような正孔注入材料については、前記の好ましい性質を有するものであれば特に制限はなく、従来、光導伝材料において、正孔の電荷輸送材として慣用されているものやＥＬ素子の正孔注入層に使用される公知のものの中から任意のものを選択して用いることができる。
【００５１】
該正孔注入材料としては、例えばトリアゾール誘導体（米国特許第３，１１２，１９７号明細書等参照），オキサジアゾール誘導体（米国特許第３，１８９，４４７号明細書等参照），イミダゾール誘導体（特公昭３７−１６０９６号公報等参照），ポリアリールアルカン誘導体（米国特許第３，６１５，４０２号明細書，同３，８２０，９８９号明細書，同３，５４２，５４４号明細書，特公昭４５−５５５号公報，同５１−１０９８３号公報，特開昭５１−９３２２４号公報，同５５−１７１０５号公報，同５６−４１４８号公報，同５５−１０８６６７号公報，同５５−１５６９５３号公報，同５６−３６６５６号公報等参照），ピラゾリン誘導体およびピラゾロン誘導体（米国特許第３，１８０，７２９号明細書，同４，２７８，７４６号明細書，特開昭５５−８８０６４号公報，同５５−８８０６５号公報，同４９−１０５５３７号公報，同５５−５１０８６号公報，同５６−８００５１号公報，同５６−８８１４１号公報，同５７−４５５４５号公報，同５４−１１２６３７号公報，同５５−７４５４６号公報等参照），フェニレンジアミン誘導体（米国特許第３，６１５，４０４号明細書，特公昭５１−１０１０５号公報，同４６−３７１２号公報，同４７−２５３３６号公報，特開昭５４−５３４３５号公報，同５４−１１０５３６号公報，同５４−１１９９２５号公報等参照），アリールアミン誘導体（米国特許第３，５６７，４５０号明細書，同３，１８０，７０３号明細書，同３，２４０，５９７号明細書，同３，６５８，５２０号明細書，同４，２３２，１０３号明細書，同４，１７５，９６１号明細書，同４，０１２，３７６号明細書，特公昭４９−３５７０２号公報，同３９−２７５７７号公報，特開昭５５−１４４２５０号公報，同５６−１１９１３２号公報，同５６−２２４３７号公報，西独特許第１，１１０，５１８号明細書等参照），アミノ置換カルコン誘導体（米国特許第３，５２６，５０１号明細書等参照），オキサゾール誘導体（米国特許第３，２５７，２０３号明細書などに記載のもの），スチリルアントラセン誘導体（特開昭５６−４６２３４号公報等参照），フルオレノン誘導体（特開昭５４−１１０８３７号公報等参照），ヒドラゾン誘導体（米国特許第３，７１７，４６２号明細書，特開昭５４−５９１４３号公報，同５５−５２０６３号公報，同５５−５２０６４号公報，同５５−４６７６０号公報，同５５−８５４９５号公報，同５７−１１３５０号公報，同５７−１４８７４９号公報等参照），スチルベン誘導体（特開昭６１−２１０３６３号公報，同６１−２２８４５１号公報，同６１−１４６４２号公報，同６１−７２２５５号公報，同６２−４７６４６号公報，同６２−３６６７４号公報，同６２−１０６５２号公報，同６２−３０２５５号公報，同６０−９３４４５号公報，同６０−９４４６２号公報，同６０−１７４７４９号公報，同６０−１７５０５２号公報等参照）などを挙げることができる。
さらに、シラザン誘導体（米国特許第４，９５０，９５０号明細書），ポリシラン系（特開平２−２０４９９６号公報），アニリン系共重合体（特開平２−２８２２６３号公報），導電性高分子オリゴマー（特開平１−２１１３９９号公報），特に含チオフェンオリゴマーなどが挙げられる。
【００５２】
本発明においては、これらの化合物を正孔注入材料として使用することができるが、次に示すポリフィリン化合物（特開昭６３−２９５６９６５号公報などに記載のもの）、芳香族第三級アミン化合物およびスチリルアミン化合物（米国特許第４，１２７，４１２号明細書，特開昭５３−２７０３３号公報，同５４−５８４４５号公報，同５４−１４９６３４号公報，同５４−６４２９９号公報，同５５−７９４５０号公報，同５５−１４４２５０号公報，同５６−１１９１３２号公報，同６１−２９５５５８号公報，同６１−９８３５３号公報，同６３−２９５６９５号公報等参照），特に該芳香族第三級アミン化合物を用いることが好ましい。
【００５３】
該ポリフィリン化合物の代表例としては、ポルフィン，１，１０，１５，２０−テトラフェニル−２１Ｈ，２３Ｈ−ポルフィン銅（ＩＩ）；１，１０，１５，２０−テトラフェニル２１Ｈ，２３Ｈ−ポルフィン亜鉛（ＩＩ）；５，１０，１５，２０−テトラキス（ペンタフルオロフェニル）−２１Ｈ，２３Ｈ−ポルフィン；シリコンフタロシアニンオキシド；アルミニウムフタロシアニンクロリド；フタロシアニン（無金属）；ジリチウムフタロシアニン；銅テトラメチルフタロシアニン；銅フタロシアニン；クロムフタロシアニン；亜鉛フタロシアニン；鉛フタロシアニン；チタニウムフタロシアニンオキシド；マグネシウムフタロシアニン；銅オクタメチルフタロシアニンなどが挙げられる。
【００５４】
また該芳香族第三級アミン化合物及びスチリルアミン化合物の代表例としては、Ｎ，Ｎ，Ｎ’，Ｎ’−テトラフェニル−４，４’−ジアミノフェニル，Ｎ，Ｎ’−ジフェニル−Ｎ，Ｎ’−ジ（３−メチルフェニル）−４，４’−ジアミノビフェニル，２，２−ビス（４−ジ−ｐ−トリルアミノフェニル）プロパン，１，１−ビス（４−ジ−ｐ−トリルアミノフェニル）シクロヘキサン，Ｎ，Ｎ，Ｎ’，Ｎ’−テトラ−ｐ−トリル−４，４’−ジアミノビフェニル，１，１−ビス（４−ジ−ｐ−トリルアミノフェニル）−４−フェニルシクロヘキサン，ビス（４−ジメチルアミノ−２−メチルフェニル）フェニルメタン，ビス（４−ジ−ｐ−トリルアミノフェニル）フェニルメタン，Ｎ，Ｎ’−ジフェニル−Ｎ，Ｎ’−ジ（４−メトキシフェニル）−４，４’−ジアミノビフェニル，Ｎ，Ｎ，Ｎ’，Ｎ’−テトラフェニル−４，４’−ジアミノジフェニルエーテル，４，４’−ビス（ジフェニルアミノ）クオードリフェニル，Ｎ，Ｎ，Ｎ−トリ（Ｐ−トリル）アミン，４−（ジ−ｐ−トリルアミノ）−４’−〔４（ジ−ｐ−トリルアミノ）スチリル〕スチルベン，４−Ｎ，Ｎ−ジフェニルアミノ−（２−ジフェニルビニル）ベンゼン，３−メトキシ−４’−Ｎ，Ｎ−ジフェニルアミノスチルベンゼン，Ｎ−フェニルカルバゾール，芳香族ジメチリディン系化合物などが挙げられる。
【００５５】
本発明のＥＬ素子における該正孔注入層は、上記化合物を、例えば真空蒸着法，スピンコート法，ＬＢ法などの公知の薄膜法により製膜して形成することができる。この正孔注入層の膜厚は、特に制限はないが、通常は５ｎｍ〜５μｍである。この正孔注入層は、上記正孔注入材料一種又は二種以上からなる一層で構成されていてもよいし、あるいは、前記正孔注入層とは別種の化合物からなる正孔注入層を積層したものであってもよい。
また、有機半導体層は、発光層への正孔注入又は電子注入を助ける層であって、１０−１０Ｓ／ｃｍ以上の導電率を有するものが好適である。このような有機半導体層の材料としては、含チオフェンオリゴマーや含アリールアミンオリゴマーなどの導電性オリゴマー、含アリールアミンデンドリマーなどの導電性デンドリマーなどを用いることができる。具体的には、
【００５６】
【化２１】
【化２２】
などが挙げられる。
さらに、電子障壁層は、電子を発光層内に閉じ込める役割をもつ層であって、発光層と陽極との間に設けられ、正孔輸送性に優れることが望ましい。このような電子障壁層の材料としては、例えば
【００５９】
【化２３】
【化２４】
【化２５】
などを挙げることができる。
【００６３】
一方、電子注入層は、発光層への電子の注入を助ける層であって、電子移動度が大きく、また付着改善層は、この電子注入層の中で、特に陰極との付着が良い材料からなる層である。電子注入層に用いられる材料としては、例えば８−ヒドロキシキノリン又はその誘導体の金属錯体、あるいはオキサジアゾール誘導体が好ましく挙げられる。また、付着改善層に用いられる材料としては、特に８−ヒドロキシキノリン又はその誘導体の金属錯体が好適である。
上記８−ヒドロキシキノリン又はその誘導体の金属錯体の具体例としては、オキシン（一般に８−キノリノール又は８−ヒドロキシキノリン）のキレートを含む金属キレートオキシノイド化合物が挙げられる。
【００６４】
一方、オキサジアゾール誘導体としては、一般式（ＩＶ）及び（Ｖ）
【００６５】
【化２６】
（式中Ａｒ１０〜Ａｒ１３はそれぞれ置換又は無置換のアリール基を示し、Ａｒ１０とＡｒ１１及びＡｒ１２とＡｒ１３はそれぞれにおいてたがいに同一であっても異なっていてもよく、Ａｒ１４は置換又は無置換のアリーレン基を示す。）
で表される電子伝達化合物が挙げられる。ここで、アリール基としてはフェニル基，ビフェニル基，アントラニル基，ペリレニル基，ピレニル基などが挙げられ、アリーレン基としてはフェニレン基，ナフチレン基，ビフェニレン基，アントラセニレン基，ペリレニレン基，ピレニレン基などが挙げられる。また、置換基としては炭素数１〜１０のアルキル基、炭素数１〜１０のアルコキシ基又はシアノ基などが挙げられる。この電子伝達化合物は、薄膜形成性のものが好ましい。
上記電子伝達化合物の具体例としては、
【００６７】
【化２７】
などが挙げられる。
【００６９】
【実施例】
次に、本発明を実施例によりさらに詳しく説明するが、本発明はこれらの例によってなんら限定されるものではない。
【００７０】
製造例１ Ｋ−１の製造
３００ミリリットルの三つ口フラスコに、Ｎ，Ｎ’−ジフェニル−４，４’−ベンジジン（東京化成社製）２ｇ；１−ヨードアントラセン（ナード研究所社製）５ｇ，無水炭酸カリウム１０ｇ及び銅１ｇを入れ、ジメチルスルホキシド（ＤＭＳＯ）２００ミリリットルに溶解し、２００℃で８時間加熱し、攪拌した。
反応終了後、無機物をろ別し、溶媒を減圧下で留去したのち、残渣をシリカゲル（広島和光社製）を充填したカラムでトルエンを展開溶媒として精製したところ、黄色粉末１．８ｇを得た。
このものは、ＮＭＲ及びＦＤ−ＭＳ（フィールドディフュージョンマススペクトル）の測定より、Ｎ，Ｎ’−ジ−（アントラセン−１−イル）−Ｎ，Ｎ’−ジフェニル−４，４’−ベンジジン（Ｋ−１）と同定した。
【００７１】
製造例２ Ｋ−２の製造
製造例１において、１−ヨードアントラセンの代わりに１−ヨードピレン（ナード研究所社製）を用いた以外は、製造例１と同様に反応し、精製したところ、黄色粉末１．５ｇを得た。
このものは、ＮＭＲ及びＦＤ−ＭＳの測定より、Ｎ，Ｎ’−ジ−（ピレン−１−イル）−Ｎ，Ｎ’−ジフェニル−４，４’−ベンジジン（Ｋ−２）と同定した。
【００７２】
製造例３ Ｋ−３の製造
製造例１において、Ｎ，Ｎ’−ジフェニルベンジジンの代わりに１，６−ジアミノピレン（東京化成社製）を用い、かつ１−ヨードアントラセンの代わりにヨードベンゼン（東京化成社製）２０ｇを用いた以外は、製造例１と同様に反応し、精製したところ、黄色粉末１．４ｇを得た。
このものは、ＮＭＲ及びＦＤ−ＭＳの測定より、Ｎ，Ｎ，Ｎ’，Ｎ’−テトラフェニル−１，６−ジアミノピレン（Ｋ−３）と同定した。
【００７３】
製造例４ Ｋ−４の製造
製造例１において、Ｎ，Ｎ’−ジフェニルベンジジンの代わりにＮ，Ｎ’−ジフェニル−１，３−フェニレンジアミン（ナード研究所社製）を用い、かつ１−ヨードアントラセンの代わりに１−ヨードピレン（ナード研究所社製）を用いた以外は、製造例１と同様に反応し、精製したところ、黄色粉末１．５ｇを得た。
このものは、ＮＭＲ及びＦＤ−ＭＳの測定より、Ｎ，Ｎ’−ジ−（ピレン−１−イル）−Ｎ，Ｎ’−ジフェニル−１，３−フェニレンジアミン（Ｋ−４）と同定した。
【００７４】
製造例５ Ｋ−５の製造
製造例１において、Ｎ，Ｎ’−ジフェニルベンジジンの代わりに１−アミノピレンを用い、かつ１−ヨードアントラセンの代わりにヨードベンゼン１０ｇを用いた以外は、製造例１と同様に反応し、精製したところ、黄色粉末１．９ｇを得た。
このものは、ＮＭＲとＦＤ−ＭＳの測定より、Ｎ，Ｎ’−ジフェニル−１−アミノピレン（Ｋ−５）と同定した。
【００７５】
製造例６ Ｋ−６の製造
３００ミリリットルの三つ口フラスコに、１−アミノアントラセン（アルドリッチ社製）２ｇ；２，５−ビス−（４−ヨードフェニル−１−イル）−チオフェン（ナード研究所社製）２ｇ，無水炭酸カリウム１０ｇ及び銅１ｇを入れ、ＤＭＳＯ２００ミリリットルに溶解し、２００℃で８時間加熱攪拌した。
反応終了後、無機物をろ別し、減圧下で溶媒を留去したのち、残渣を、シリカゲル（広島和光社製）を充填したカラムでトルエンを展開溶媒として精製し、黄色粉末１．７ｇを得た。
次に、３００ミリリットルの三つ口フラスコに、この黄色粉末１．５ｇ，ヨードベンゼン１０ｇ，無水炭酸カリウム１０ｇ及び銅１ｇを入れ、ＤＭＳＯに溶解し、２００℃で８時間加熱攪拌した。
反応終了後、無機物をろ別し、減圧下で溶媒を留去したのち、残渣を、シリカゲル（広島和光社製）を充填したカラムでトルエンを展開溶媒として精製し、黄色粉末０．６８ｇを得た。
このものは、ＮＭＲ及びＦＤ−ＭＳの測定より、２，５−ビス−（４−〔Ｎ−（アントラセン−１−イル）−Ｎ−フェニル〕アミノフェニル）チオフェン（Ｋ−６）と同定した。
【００７６】
実施例１〜６及び比較例１
２５ｍｍ×７５ｍｍ×１．１ｍｍのガラス基板上に、ＩＴＯを蒸着法にて１００ｎｍの厚さで製膜したもの（ジオマティック社製）を透明支持基板とした。なお、この基板は、イソプロピルアルコール中で５分間超音波洗浄後、窒素を吹きつけて乾燥し、ＵＶオゾン洗浄（ＵＶ３００，サムコインターナショナル社製）を３０分間行ったものである。
この透明支持基板を市販の蒸着装置（日本真空技術（株）製）の基板ホルダ ーに固定し、モリブデン製抵抗加熱ボートにＭＴＤＡＴＡ２００ｍｇを入れ、他のモリブデン製抵抗加熱ボートにＤＰＶＢｉ２００ｍｇを入れ、別のモリブデン製抵抗加熱ボートに正孔輸送材であるＮＰＤ２００ｍｇを入れ、さらに他のモリブデン製抵抗加熱ボートに第１表に示す種類の蛍光性ドーパント〔化合物（Ａ）〕２００ｍｇを入れ、真空槽を１×１０−４Ｐａまで減圧した。その後ＭＴＤＡＴＡの入った前記ボートを２１５〜２２０℃まで加熱し、蒸着速度０．１〜０．３ｎｍ／秒で透明支持基板上に蒸着して、膜厚６０ｎｍの正孔注入層を製膜させた。
次に、真空槽より基板を取り出すことなく、ＮＰＤの入ったボートを加熱し、膜厚２０ｎｍの正孔輸送層を正孔注入層の上に製膜した。このとき、基板の温度は室温であった。これを真空槽より取り出すことなく、ＮＰＤ層上にＤＰＶＢｉをホスト材料として４０ｎｍ積層した。このとき同時に化合物（Ａ）のボートを加熱し、発光層に化合物（Ａ）を混合した。このときの蒸着速度はＤＰＶＢｉの蒸着速度（第１表に示す（Ｂ））に対して、化合物（Ａ）の蒸着速度を（Ｃ）（第１表に示す）とした。したがって、混合比〔ホスト材料に対する化合物（Ａ）の割合〕は（Ｄ）（第１表に示す）となった。
その後、真空槽を大気圧に戻し、新たにモリブデン製抵抗加熱ボートに電子注入層の材料である８−ヒドロキシキノリン・アルミニウム錯体を入れ、さらにモリブデン製抵抗加熱ボートにマグネシウムリボン１ｇを入れ、タングステン製バスケットに銀ワイヤーを５００ｍｇ入れて、真空槽を１×１０−４Ｐａまで減圧した。
次いで、蒸着速度０．０１〜０．０３ｎｍ／秒で８−ヒドロキシキノリン・アルミニウム錯体を蒸着し電子注入層を２０ｎｍ形成した。さらに、銀を蒸着速度０．１ｎｍ／秒，マグネシウムを蒸着速度１．４ｎｍ／秒で同時蒸着して銀：マグネシウム混合電極を陰極とした。膜厚は１５０ｎｍであった。
得られた素子に、電圧８Ｖを印加し、電流量，素子の輝度を測定して発光効率を算出した。得られた結果を第２表に示す。
なお、ＭＴＤＡＴＡ，ＤＰＶＢｉ及びＮＰＤの構造は次のとおりである。
【００７７】
【化２８】
【表１】
【表２】
以上の結果、本発明の素子は、蛍光性ドーパントとしてペリレン（特開平５−１９８３７８号公報記載の蛍光性ドーパント）を用いた比較例１のものに比べて、発光効率が優れていることが分かる。
次に各素子を初期輝度３００ｃｄ／ｍ２にて乾燥窒素雰囲気下で駆動し、半減寿命（初期輝度が半分になる時間）を求めた。結果を第３表に示す。尚、初期輝度１００ｃｄ／ｍ２で試験した結果は、第３表の約３．５倍程度の寿命が得られている。従って、本発明の素子は初期輝度１００ｃｄ／ｍ２の条件では２５００時間〜１１００時間の寿命が得られるものである。
【００８１】
【表３】
第３表から分かるように、本発明の素子は、比較例１のものに比べて寿命が大幅に改善されている。
【００８３】
比較例２
蛍光性ドーパント〔化合物（Ａ）〕として、ＰＡＶＴＰ（国際特許公開９４−６１５７号記載の蛍光性ドーパント）を用いた以外は、実施例１と同様にして素子を作製し、初期輝度３００ｃｄ／ｍ２で半減寿命を求めたところ、半減寿命は３００時間であり、本発明の素子に比べて寿命が短く、劣っていた。尚、初期輝度１００ｃｄ／ｍ２の時での試験結果は半減寿命１０００時間であった。
なお、ＰＡＶＴＰの構造を次に示す。
【００８４】
【化２９】
【発明の効果】
本発明の有機ＥＬ素子は、正孔と電子とが再結合する再結合領域又は該再結合に応答して発光する発光領域の少なくともいずれかに、特定の構造の蛍光性ドーパントを含有させたものであって、長時間駆動しても発光色の変化が少ないなど、長寿命を有し、かつ発光効率が高く、例えば情報産業機器のディスプレイなどに好適に用いられる。[0001]
TECHNICAL FIELD OF THE INVENTION
The present invention relates to an organic electroluminescence (hereinafter abbreviated as EL) device, and more particularly, to a long-life and high-efficiency organic EL device having little change in emission color even when driven for a long time. It is.
[0002]
[Prior art]
EL devices using electroluminescence emit light with high visibility due to self-emission, and have characteristics such as excellent impact resistance because they are completely solid devices. Therefore, their use as light emitting devices in various display devices attracts attention. Have been.
This EL element includes an inorganic EL element using an inorganic compound as a light emitting material and an organic EL element using an organic compound. Among these, the organic EL element is used because the applied voltage can be significantly reduced. Practical research is being actively conducted on the next-generation display element.
[0003]
By the way, in this organic EL device, in order to develop a long-life and high-efficiency blue light-emitting device, research on a blue light-emitting material has been focused on so far, and various blue light-emitting materials, for example, a high-brightness and high-efficiency light-emitting device have been developed. Distyrylarylene-based blue light-emitting materials (Patent Document 1), high-luminance chelate-based blue light-emitting materials (Patent Document 2), and high-luminance diamine-based blue light-emitting materials (Patent Document 3) are disclosed. However, these blue light-emitting materials have usually been used in the structure of anode / hole injection / transport layer / light-emitting layer / electron injection / transport layer / cathode and have exhibited their performance, but they are not necessarily satisfactory in terms of life. Instead, for example, (1) the color turns green and the emission color changes as the drive time elapses, and (2) the initial luminance is 100 cd / m2. 2 In this case, the half life is as short as about 1000 hours (several thousands hours or more are required in practice).
[0004]
On the other hand, an element using a compound having a structure similar to the fluorescent dopant in the present invention as a material of the light emitting layer has been proposed (Patent Document 4), but does not mention the function of the fluorescent dopant added in a small amount. Absent.
Patent Documents 5 and 6 disclose a distyryl arylene-based material that is a charge injection auxiliary added to a light emitting layer. Although this material also functions as a fluorescent dopant, the half-life of an element using this material is about 1000 hours (initial luminance of 100 cd / m2). 2 ) And it was short and needed to be improved.
[Patent Document 1]
JP-A-2-247278
[Patent Document 2]
JP-A-5-198338
[Patent Document 3]
JP-A-6-22037
[Patent Document 4]
JP-A-6-22037
[Patent Document 5]
JP-A-6-9953
[Patent Document 6]
International Publication No. 94-6157
[0005]
[Problems to be solved by the invention]
An object of the present invention is to improve the drawbacks of the conventional organic EL element and provide a highly efficient organic EL element having a long life, such as a small change in emission color even when driven for a long time. The purpose is.
[0006]
[Means for Solving the Problems]
The present inventors have conducted intensive studies to develop a long-life and high-efficiency organic EL device, and as a result, as a fluorescent dopant, in at least one of a hole-electron bonding region and a light-emitting region of the device. It has been found that the object can be achieved by including a specific compound in a predetermined ratio. The present invention has been completed based on such findings.
That is, the present invention provides an organic compound layer having at least a recombination region where holes and electrons recombine and a light emitting region which emits light in response to the recombination, and a pair of electrodes sandwiching the organic compound layer. In the organic electroluminescence device provided, the above-mentioned recombination region and / or light-emitting region is represented by the following general formula (I) as a fluorescent dopant:
[0007]
Embedded image
[Wherein, Ar 1 , Ar 2 And Ar 3 Represents an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 30 carbon atoms or a heterocyclic group, which may be the same or different, and at least one of them has 12 or more carbon atoms. Is a fused polycyclic hydrocarbon group. ]
And general formula (II)
[0009]
Embedded image
[Wherein, Ar 4 , Ar 5 , Ar 6 And Ar 7 Represents an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 30 carbon atoms or a heterocyclic group, which may be the same or different; 8 Represents an arylene group having 6 to 30 carbon atoms or a divalent heterocyclic group; 4 ~ Ar 8 At least one is a fused polycyclic hydrocarbon group having 12 or more carbon atoms. ]
And at least one compound selected from the group consisting of compounds represented by the formula (1) in a ratio of 0.1 to 8% by weight.
BEST MODE FOR CARRYING OUT THE INVENTION
The fluorescent dopant used in the present invention has the general formula (I)
[0011]
Embedded image
Or the general formula (II)
[0013]
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Is a compound having a structure represented by
In the above general formulas (I) and (II), Ar 1 ~ Ar 7 Represents an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 30 carbon atoms, or a heterocyclic group, respectively. Here, examples of the alkyl group having 1 to 10 carbon atoms include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group and a t-butyl group. Examples of the aryl group having 6 to 30 carbon atoms include a non-condensed hydrocarbon group such as a phenyl group, a biphenyl group, and a terphenyl group and a condensed polycyclic hydrocarbon group. The fused polycyclic hydrocarbon group preferably has 18 or less carbon atoms forming a ring, for example, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, a biphenylenyl group, an as-indacenyl group, a fluorenyl group , S-indacenyl, acenaphthylenyl, preyadenyl, acenaphthenyl, phenalenyl, phenanthryl, anthryl, fluoranthenyl, acephenanthrenyl, aceanthrenyl, triphenylenyl, pyrenyl, chrysenyl , Naphthacenyl group and the like.
[0015]
Examples of the heterocyclic group include a pyridyl group, a pyrimidyl group, a pyrazinyl group, a triazinyl group, a furanyl group, a pyrrolyl group, a thiophenyl group, a quinolyl group, a coumarinyl group, a benzofuranyl group, a benzimidazolyl group, and a benzoxazolyl group. , Dibenzofuranyl, benzothiophenyl, dibenzothiophenyl, indolyl, carbazolyl, pyrazolyl, imidazolyl, oxazolyl, isoxazolyl, thiazolyl, indazolyl, benzothiazolyl, pyridazinyl, cinnolyl, quinazolyl Group, quinoxalyl group, phthalazinyl group, phthalazinionyl group, phthalamidyl group, chromonyl group, naphthactamyl group, quinolonyl group, imidyl o-sulfobenzoate group, imidyl maleate group, naphthalidinyl group, benz Midazolonyl group, benzoxazolonyl group, benzothiazolonyl group, benzothiazothonyl group, quinazolonyl group, quinoxalonyl group, phthalazonyl group, dioxopyrimidinyl group, pyridonyl group, isoquinolonyl group, isoquinolinyl group, isothiazolyl group, benzisoxa Examples include a zolyl group, a benzisothiazolyl group, an indazilonyl group, an acridinyl group, an acrylonyl group, a quinazolindionyl group, a quinoxalinedionyl group, a benzoxazinionyl group, a benzoxazinonyl group, and a naphthalimidyl group.
[0016]
On the other hand, Ar 8 Represents an arylene group having 6 to 30 carbon atoms or a divalent heterocyclic group. Here, as the arylene group having 6 to 30 carbon atoms or the divalent heterocyclic group, for example, Ar 1 ~ Ar 7 And a divalent group in which one hydrogen atom has been removed from the aryl group or heterocyclic group exemplified in the description. Other arylene groups include diarylene alkane groups such as diphenylene propane group and diphenylene methane group, diarylene alkane groups such as diphenylene cyclohexane group, diphenylene cyclopentane group, and diarylene ether groups such as diphenylene ether group. , A diarylene thioether group such as a diphenylene thioether group, an N-aryl diarylene amine group such as an N-phenyldiphenyleneamine group, an N-naphthyldinaphthyleneamine group, an N-phenylcarbazolylen group, and further diphenylthiophene And diarylthiophene or diarylbithiophene groups such as divalent groups of diphenylbithiophene.
The Ar 1 , Ar 2 And Ar 3 May be the same or different, but at least one of them must be a condensed polycyclic hydrocarbon group having 12 or more carbon atoms. Ar 4 , Ar 5 , Ar 6 And Ar 7 Although they may be the same or different, Ar 4 ~ Ar 8 Must be a fused polycyclic hydrocarbon group having 12 or more carbon atoms.
[0017]
Further, the Ar 1 ~ Ar 8 May have an appropriate substituent introduced therein. Examples of the substituent include (1) a halogen atom (F, Cl, Br, I), a cyano group, a nitro group, (2) an alkyl group, and (3) Alkoxy group, (4) aryloxy group, (5) alkyl or arylmercapto group, (6) -NR 1 R 2 (R 1 And R 2 Represents a hydrogen atom, an alkyl group or an aryl group, which may be the same or different. Or (7) an alkylenedioxy group, an alkylenedithio group and the like. Here, the alkyl group of (2) is preferably a straight-chain or branched-chain alkyl group having 1 to 20, particularly 1 to 12 carbon atoms, and the alkyl group further has a halogen atom (F, Cl, Br, I), a hydroxyl group, a cyano group, an alkoxy group having 1 to 12 carbon atoms, a phenyl group, or a phenyl group substituted with an alkyl group or an alkoxy group having 1 to 12 carbon atoms. Examples of such alkyl groups include methyl, ethyl, n-propyl, isopropyl, t-butyl, sec-butyl, n-butyl, isobutyl, trifluoromethyl, 2-hydroxy Examples include an ethyl group, a 2-cyanoethyl group, a 2-ethoxyethyl group, a 2-methoxyethyl group, a benzyl group, a 4-chlorobenzyl group, a 4-methylbenzyl group, a 4-methoxybenzyl group, and a 4-phenylbenzyl group. .
[0018]
The alkoxy group (-OR) of (3) 3 ) Is R 3 Examples thereof include those having an alkyl group exemplified in the above (2), and specifically, methoxy group, ethoxy group, n-propoxy group, isopropoxy group, t-butoxy group, n-butoxy group, sec -Butoxy, isobutoxy, 2-hydroxyethoxy, 2-cyanoethoxy, benzyloxy, 4-methylbenzyloxy, trifluoromethoxy and the like. As the aryloxy group (—OAr) of (4), Ar is unsubstituted or substituted with a halogen atom (F, Cl, Br, I), an alkyl group having 1 to 4 carbon atoms or an alkoxy group, or the like. Preferred are those having a naphthyl group. Specific examples include phenoxy, 1-naphthyloxy, 2-naphthyloxy, 4-methylphenoxy, 4-methoxyphenoxy, 4-chlorophenoxy, -Methyl-2-naphthyloxy group and the like. Further, the alkyl or aryl mercapto group of (5) (-SR 4 ) Is R 4 Examples thereof include those having an alkyl group exemplified in the above (2) or a phenyl group or a naphthyl group exemplified in the above (4), and specifically, a methylthio group, an ethylthio group, a phenylthio group, a p-methylphenyl And a thio group.
[0019]
Further, -NR of (6) 1 R 2 The group represented by 1 And R 2 Is a hydrogen atom, an alkyl group or an aryl group. Here, examples of the alkyl group include those exemplified in the above (2), and examples of the aryl group include unsubstituted or halogen atoms (F, Cl, Br, I) and alkyl groups having 1 to 4 carbon atoms. Examples thereof include a phenyl group, a biphenyl group, a naphthyl group, a pyrenyl group, and an anthranyl group substituted with a group or an alkoxy group. The R 1 And R 2 They may be the same or different, and may combine with each other to form a ring structure. Specifically, amino group, diethylamino group, N-methyl-N-phenylamino group, N, N-diphenylamino group, N, N-di- (p-tolyl) amino group, dibenzylamino group, piperidino group , A morpholino group, a eurololidyl group and the like. Examples of the alkylenedioxy group and alkylenedithio group (7) include a methylenedioxy group and a methylenedithio group.
[0020]
Examples of the compounds represented by the general formulas (I) and (II) include those having the following structures.
[0021]
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In the present invention, one kind of these compounds may be used as the fluorescent dopant, or two or more kinds thereof may be used in combination.
Note that the fluorescent dopant in the present invention is a compound that emits light in response to recombination of holes and electrons in a recombination region or a light-emitting region of an organic EL device. A small amount is contained in the substance (host material) to be formed. Here, the recombination region is a place in the device where holes and electrons meet and combine to form an excited state. In addition, the light emitting region is a place where the excited state formed in the recombination region moves and diffuses in some cases, but designates a range of the diffusion.
[0030]
In the present invention, the fluorescent dopant is contained in at least one of the recombination region and the light-emitting region, that is, only in the recombination region, only in the light-emitting region, or in both regions at a ratio of 0.1 to 8% by weight. It is necessary to contain it. When the content is less than 0.1% by weight, the effect of the fluorescent dopant is not sufficiently exhibited, and the object of the present invention cannot be achieved. On the other hand, if it exceeds 8% by weight, the disappearance phenomenon occurs due to association between the fluorescent dopants, and the effect may not be sufficiently exhibited. From the viewpoint of extending the life of the device and increasing the efficiency, the preferable content of the fluorescent dopant is in the range of 0.3 to 4% by weight, and particularly preferably in the range of 0.8 to 3% by weight.
There is no particular limitation on the method for incorporating this fluorescent dopant into the recombination region or the light-emitting region, but it is preferable to employ, for example, a co-evaporation method with a material (host material) forming the recombination region or the light-emitting region. . In this method, a host material and a fluorescent dopant are vacuum-deposited from separate boats each containing a host material to form a recombination region or a light-emitting region.
In the organic EL device of the present invention, an organic compound layer having at least a recombination region and a light-emitting region is used. Since the recombination region and the light-emitting region are usually present in the light-emitting layer, in the present invention, only the light-emitting layer may be used as the organic compound layer. , An electron injection layer, an organic semiconductor layer, an electron barrier layer, an adhesion improving layer, and the like.
[0031]
Next, a typical configuration example of the organic EL device of the present invention will be described. Of course, it is not limited to this.
(1) Anode / hole injection layer / light-emitting layer / cathode
(2) anode / hole injection layer / light-emitting layer / electron injection layer / cathode
(3) anode / light-emitting layer / electron injection layer / cathode
(4) anode / organic semiconductor layer / light-emitting layer / cathode
(5) Anode / organic semiconductor layer / electron barrier layer / light emitting layer / cathode
(6) anode / hole injection layer / light-emitting layer / adhesion improving layer / cathode
Of these, the configuration (2) is preferably used.
[0032]
The recombination region and the light emitting region in the device of the present invention usually exist in the light emitting layer as described above. Therefore, the fluorescent dopant is usually contained in the light emitting layer. However, in some cases, other layers, such as a hole injection layer, an electron injection layer, an organic semiconductor layer, an electron barrier layer, and an adhesion improving layer, may also contribute to recombination and light emission. In this case, it is preferable that these layers are also contained.
[0033]
The organic EL device of the present invention has a structure in which the organic compound layer is sandwiched between a pair of electrodes, that is, an anode and a cathode. As the anode, a metal, alloy, or the like having a large work function (4 eV or more) is used. Those using an electrically conductive compound and a mixture thereof as an electrode material are preferably used. Specific examples of such an electrode material include metals such as Au, CuI, ITO, and SnO. 2 , ZnO and the like. The anode can be produced by forming a thin film from these electrode substances by a method such as vapor deposition or sputtering. When light is extracted from this electrode, the transmittance is desirably greater than 10%, and the sheet resistance of the electrode is preferably several hundred Ω / □ or less. Further, although the film thickness depends on the material, it is preferably in the range of usually 10 nm to 1 μm, particularly preferably 10 to 200 nm.
[0034]
On the other hand, as the cathode, a metal, an alloy, an electrically conductive compound or a mixture thereof having a low work function (4 eV or less) as an electrode material is used. Specific examples of such an electrode material include sodium, sodium-potassium alloy, magnesium, lithium, magnesium-silver alloy, Al / AlO 2 , Indium, rare earth metals and the like. The cathode can be manufactured by forming a thin film from these electrode substances by a method such as evaporation or sputtering. Further, the sheet resistance as an electrode is preferably several hundreds Ω / □ or less, and the film thickness is usually 10 nm to 1 μm, particularly preferably 50 to 200 nm. In the element of the present invention, although not particularly specified, it is preferable that either the anode or the cathode is transparent or translucent, because the efficiency of transmitting and extracting light is high.
[0035]
In the light emitting layer of the device of the present invention, a light emitting material (host material) represented by the general formula (III)
[0036]
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A distyryl arylene compound represented by the following formula is preferably used. This compound is disclosed in JP-A-2-247278.
[0038]
In the above general formula (III), Y 1 ~ Y 4 Is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an aralkyl group having 7 to 8 carbon atoms, a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, substituted or unsubstituted A substituted or unsubstituted aryloxy group having 6 to 18 carbon atoms and an alkoxy group having 1 to 6 carbon atoms. Here, the substituent is an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an aralkyl group having 7 to 8 carbon atoms, an aryloxy group having 6 to 18 carbon atoms, an acyl having 1 to 6 carbon atoms. Group, acyloxy group having 1 to 6 carbon atoms, carboxyl group, styryl group, arylcarbonyl group having 6 to 20 carbon atoms, aryloxycarbonyl group having 6 to 20 carbon atoms, alkoxycarbonyl group having 1 to 6 carbon atoms, vinyl group , Anilinocarbonyl group, carbamoyl group, phenyl group, nitro group, hydroxyl group or halogen. These substituents may be single or plural. Also, Y 1 ~ Y 4 May be the same or different from each other, and Y 1 And Y 2 And Y 3 And Y 4 And may be bonded to mutually substituted groups to form a substituted or unsubstituted saturated 5-membered ring or a substituted or unsubstituted saturated 6-membered ring. Ar 9 Represents a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, which may be monosubstituted or plurally substituted, and the binding site may be any of ortho, para and meta. Where Ar 9 Is an unsubstituted phenylene group, 1 ~ Y 4 Is selected from an alkoxy group having 1 to 6 carbon atoms, an aralkyl group having 7 to 8 carbon atoms, a substituted or unsubstituted naphthyl group, a biphenyl group, a cyclohexyl group, and an aryloxy group. Such distyryl arylene compounds include, for example,
[0039]
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And the like.
[0044]
Another preferable light-emitting material (host material) includes a metal complex of 8-hydroxyquinoline or a derivative thereof. Specifically, it is a metal chelate oxinoid compound containing a chelate of oxine (generally 8-quinolinol or 8-hydroxyquinoline). Such compounds exhibit a high level of performance and are easily formed into thin film form. Examples of the oxinoid compound satisfy the following structural formula.
[0045]
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(In the formula, Mt represents a metal, n is an integer of 1 to 3, and Z is an independent atom, and represents an atom necessary for completing at least two or more fused aromatic rings. .)
Here, the metal represented by Mt can be a monovalent, divalent or trivalent metal, for example, an alkali metal such as lithium, sodium and potassium, and an alkaline earth metal such as magnesium and calcium. Or an earth metal such as boron or aluminum.
Any of the monovalent, divalent or trivalent metals generally known to be useful chelate compounds can be used.
[0047]
Z represents an atom in which at least one of two or more fused aromatic rings forms a heterocyclic ring composed of azole or azine. Here, if necessary, another different ring can be added to the fused aromatic ring. Further, in order to avoid adding bulky molecules without improving the function, it is preferable to keep the number of atoms represented by Z at 18 or less.
Further, specific examples of chelated oxinoid compounds include tris (8-quinolinol) aluminum, bis (8-quinolinol) magnesium, bis (benzo-8-quinolinol) zinc, bis (2-methyl-8-quinolinolate) aluminum Oxide, tris (8-quinolinol) indium, tris (5-methyl-8-quinolinol) aluminum, 8-quinolinollithium, tris (5-chloro-8-quinolinol) gallium, bis (5-chloro-8-quinolinol) calcium , 5,7-dichloro-8-quinolinol aluminum, tris (5,7-dibromo-8-hydroxyquinolinol) aluminum and the like.
[0048]
Furthermore, a metal complex of phenolate-substituted 8-hydroxyquinoline described in JP-A-5-198338 is preferable as a blue light-emitting material. Specific examples of the metal complex of the phenolate-substituted 8-hydroxyquinoline include bis (2-methyl-8-quinolinolate) (phenolate) aluminum (III), bis (2-methyl-8-quinolinolate) (o-cresolate) aluminum (III), bis (2-methyl-8-quinolinolate) (m-cresolate) aluminum (III), bis (2-methyl-8-quinolinolate) (p-cresolate) aluminum (III), bis (2-methyl- 8-quinolinolate) (o-phenylphenolate) aluminum (III), bis (2-methyl-8-quinolinolate) (m-phenylphenolate) aluminum (III), bis (2-methyl-8-quinolinolate) (p -Phenylphenolate) aluminum (III), (2-methyl-8-quinolinolate) (2,3-dimethylphenolate) aluminum (III), bis (2-methyl-8-quinolinolate) (2,6-dimethylphenolate) aluminum (III), bis (2 -Methyl-8-quinolinolate) (3,4-dimethylphenolate) aluminum (III), bis (2-methyl-8-quinolinolate) (3,5-dimethylphenolate) aluminum (III), bis (2-methyl -8-quinolinolate) (3,5-di-t-butylphenolate) aluminum (III), bis (2-methyl-8-quinolinolate) (2,6-diphenylphenolate) aluminum (III), bis (2 -Methyl-8-quinolinolate) (2,4,6-triphenylphenolate) aluminum (II ), And the like.
These light emitting materials may be used alone or in combination of two or more.
[0049]
As a method for forming the light emitting layer in the device of the present invention, for example, the light emitting layer can be formed by thinning by a known method such as a vapor deposition method, a spin coating method, a casting method, and an LB method. Is preferred. Here, the molecular deposition film refers to a thin film formed by depositing the compound from a gaseous state or a film formed by solidifying the compound from a molten state or a liquid state. Usually, the molecular deposited film can be distinguished from a thin film (molecule accumulation film) formed by the LB method by a difference in an aggregated structure and a higher-order structure and a functional difference caused by the difference.
Further, the light emitting layer can be formed by dissolving in a solvent together with a binder such as a resin to form a solution, and then thinning the solution by spin coating or the like.
The thickness of the light emitting layer formed in this manner is not particularly limited and can be appropriately selected depending on the situation, but is preferably in the range of 1 nm to 10 μm, and particularly preferably in the range of 5 nm to 5 μm.
[0050]
Next, the hole injection layer is not always necessary for the device of the present invention, but is preferably used for improving light emitting performance. This hole injection layer is a layer that assists hole injection into the light emitting layer, has a high hole mobility, and a small ionization energy of usually 5.5 eV or less. As such a hole injecting layer, a material that transports holes to the light emitting layer with a lower electric field is preferable. 4 -10 6 When an electric field of V / cm is applied, at least 10 -6 cm 2 / V · sec is more preferable.
Such a hole injecting material is not particularly limited as long as it has the above-mentioned preferable properties. Conventionally, in a photoconductive material, a material commonly used as a hole charge transporting material or a hole in an EL element has been used. Any one of known ones used for the injection layer can be selected and used.
[0051]
Examples of the hole injection material include a triazole derivative (see US Pat. No. 3,112,197), an oxadiazole derivative (see US Pat. No. 3,189,447, etc.), and an imidazole derivative (see US Pat. No. 3,189,447). JP-B-37-16096, etc.), polyarylalkane derivatives (U.S. Pat. Nos. 3,615,402, 3,820,989, and 3,542,544) JP-A-45-555, JP-A-51-10983, JP-A-51-93224, JP-A-55-17105, JP-A-56-4148, JP-A-55-108667, JP-A-55-156953, No. 56-36656, pyrazoline derivatives and pyrazolone derivatives (U.S. Pat. Nos. 3,180,729 and 4,278,7). 6, JP-A-55-88064, JP-A-55-88065, JP-A-49-105537, JP-A-55-51086, JP-A-56-80051, JP-A-56-88141, Nos. 57-45545, 54-112637 and 55-74546; phenylenediamine derivatives (U.S. Pat. No. 3,615,404; JP-B-51-10105; Nos. 3712, 47-25336, JP-A-54-53435, JP-A-54-110536, JP-A-54-119925, etc., and arylamine derivatives (US Pat. No. 3,567,450). Specification, 3,180,703, 3,240,597, 3,658,520, 4,232, No. 03, No. 4,175,961, No. 4,012,376, JP-B-49-35702, JP-A-39-27577, JP-A-55-144250, and JP-A-55-144250. JP-A-56-119132, JP-A-56-22437, West German Patent No. 1,110,518, etc.), amino-substituted chalcone derivatives (see U.S. Pat. No. 3,526,501), oxazole derivatives (See, for example, U.S. Pat. No. 3,257,203), styryl anthracene derivatives (see JP-A-56-46234, etc.), fluorenone derivatives (see JP-A-54-110837, etc.), Hydrazone derivatives (US Pat. No. 3,717,462, JP-A-54-59143, JP-A-55-52063, and JP-A-55-52064). JP-A-55-46760, JP-A-55-85495, JP-A-57-1350, and JP-A-57-148749, etc.), stilbene derivatives (JP-A-61-210363, JP-A-61-228451). JP-A-61-14642, JP-A-61-72255, JP-A-62-47646, JP-A-62-36674, JP-A-62-10652, JP-A-62-30255, and JP-A-60-93445. JP-A-60-94462, JP-A-60-174747, JP-A-60-175052, etc.).
Furthermore, silazane derivatives (U.S. Pat. No. 4,950,950), polysilanes (JP-A-2-204996), aniline-based copolymers (JP-A-2-282263), and conductive polymer oligomers (Japanese Unexamined Patent Publication (Kokai) No. 1-211399), and especially thiophene-containing oligomers.
[0052]
In the present invention, these compounds can be used as a hole injecting material, and the following porphyrin compounds (those described in JP-A-63-2959695 and the like), aromatic tertiary amine compounds and Styrylamine compounds (U.S. Pat. No. 4,127,412, JP-A-53-27033, JP-A-54-58445, JP-A-54-149634, JP-A-54-64299, and JP-A-55-79450). JP-A-55-144250, JP-A-56-119132, JP-A-61-295558, JP-A-61-98353, JP-A-63-295695, etc.), especially the aromatic tertiary amine compound. It is preferable to use
[0053]
Representative examples of the porphyrin compound include porphine, 1,10,15,20-tetraphenyl-21H, 23H-porphine copper (II); 1,10,15,20-tetraphenyl 21H, 23H-porphine zinc (II) 5,10,15,20-tetrakis (pentafluorophenyl) -21H, 23H-porphine; silicon phthalocyanine oxide; aluminum phthalocyanine chloride; phthalocyanine (metal-free); dilithium phthalocyanine; copper tetramethyl phthalocyanine; copper phthalocyanine; Phthalocyanine; zinc phthalocyanine; lead phthalocyanine; titanium phthalocyanine oxide; magnesium phthalocyanine; copper octamethylphthalocyanine.
[0054]
Representative examples of the aromatic tertiary amine compound and styrylamine compound include N, N, N ', N'-tetraphenyl-4,4'-diaminophenyl, N, N'-diphenyl-N, N '-Di (3-methylphenyl) -4,4'-diaminobiphenyl, 2,2-bis (4-di-p-tolylaminophenyl) propane, 1,1-bis (4-di-p-tolylamino Phenyl) cyclohexane, N, N, N ′, N′-tetra-p-tolyl-4,4′-diaminobiphenyl, 1,1-bis (4-di-p-tolylaminophenyl) -4-phenylcyclohexane, Bis (4-dimethylamino-2-methylphenyl) phenylmethane, bis (4-di-p-tolylaminophenyl) phenylmethane, N, N'-diphenyl-N, N'-di (4-methoxyphenyl)- 4,4'- Aminobiphenyl, N, N, N ', N'-tetraphenyl-4,4'-diaminodiphenyl ether, 4,4'-bis (diphenylamino) quadriphenyl, N, N, N-tri (P-tolyl) Amine, 4- (di-p-tolylamino) -4 '-[4 (di-p-tolylamino) styryl] stilbene, 4-N, N-diphenylamino- (2-diphenylvinyl) benzene, 3-methoxy-4 '-N, N-diphenylaminostilbenzene, N-phenylcarbazole, aromatic dimethylidin compounds and the like.
[0055]
The hole injection layer in the EL device of the present invention can be formed by forming the above compound by a known thin film method such as a vacuum evaporation method, a spin coating method, and an LB method. The thickness of the hole injection layer is not particularly limited, but is usually 5 nm to 5 μm. This hole injection layer may be composed of one or more layers of the above-described hole injection material, or may have a hole injection layer made of a compound different from the hole injection layer. It may be something.
The organic semiconductor layer is a layer that assists hole injection or electron injection into the light emitting layer, -10 Those having a conductivity of S / cm or more are suitable. As a material of such an organic semiconductor layer, a conductive oligomer such as a thiophene-containing oligomer or an arylamine-containing oligomer, or a conductive dendrimer such as an arylamine-containing dendrimer can be used. In particular,
[0056]
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And the like.
Further, the electron barrier layer is a layer having a role of confining electrons in the light emitting layer, is provided between the light emitting layer and the anode, and desirably has excellent hole transportability. As a material of such an electron barrier layer, for example,
[0059]
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And the like.
[0063]
On the other hand, the electron injection layer is a layer that assists the injection of electrons into the light emitting layer, has a high electron mobility, and the adhesion improving layer is made of a material that has a good adhesion to the cathode, particularly in the electron injection layer. Layer. Preferred examples of the material used for the electron injection layer include a metal complex of 8-hydroxyquinoline or a derivative thereof, or an oxadiazole derivative. As a material used for the adhesion improving layer, a metal complex of 8-hydroxyquinoline or a derivative thereof is particularly preferable.
Specific examples of the metal complex of 8-hydroxyquinoline or a derivative thereof include a metal chelate oxinoid compound containing a chelate of oxine (generally, 8-quinolinol or 8-hydroxyquinoline).
[0064]
On the other hand, as oxadiazole derivatives, general formulas (IV) and (V)
[0065]
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(Where Ar 10 ~ Ar 13 Each represents a substituted or unsubstituted aryl group; 10 And Ar 11 And Ar 12 And Ar 13 May be the same or different in each case, and Ar 14 Represents a substituted or unsubstituted arylene group. )
The electron transfer compound represented by these is mentioned. Here, the aryl group includes a phenyl group, a biphenyl group, an anthranyl group, a perylenyl group, a pyrenyl group, and the like. Can be Examples of the substituent include an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, and a cyano group. The electron transfer compound is preferably a thin film-forming compound.
Specific examples of the electron transfer compound,
[0067]
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And the like.
[0069]
【Example】
Next, the present invention will be described in more detail with reference to examples, but the present invention is not limited to these examples.
[0070]
Production Example 1 Production of K-1
In a 300 ml three-necked flask, 2 g of N, N'-diphenyl-4,4'-benzidine (manufactured by Tokyo Kasei); 5 g of 1-iodoanthracene (manufactured by Nard Institute), 10 g of anhydrous potassium carbonate and 1 g of copper Was dissolved in 200 ml of dimethyl sulfoxide (DMSO), heated at 200 ° C. for 8 hours, and stirred.
After completion of the reaction, the inorganic substance was filtered off, the solvent was distilled off under reduced pressure, and the residue was purified with a column packed with silica gel (manufactured by Hiroshima Wako) using toluene as a developing solvent to obtain 1.8 g of a yellow powder. Was.
This product was analyzed by NMR and FD-MS (field diffusion mass spectrum) to find that N, N′-di- (anthracen-1-yl) -N, N′-diphenyl-4,4′-benzidine (K- 1).
[0071]
Production Example 2 Production of K-2
In Production Example 1, the reaction was carried out in the same manner as in Production Example 1 except that 1-iodopyrene (manufactured by Nard Institute) was used instead of 1-iodoanthracene, and 1.5 g of a yellow powder was obtained.
This was identified as N, N'-di- (pyren-1-yl) -N, N'-diphenyl-4,4'-benzidine (K-2) by NMR and FD-MS measurements.
[0072]
Production Example 3 Production of K-3
In Production Example 1, 1,6-diaminopyrene (manufactured by Tokyo Kasei) was used instead of N, N'-diphenylbenzidine, and 20 g of iodobenzene (manufactured by Tokyo Kasei) was used instead of 1-iodoanthracene. Except for the above, the reaction and purification were carried out in the same manner as in Production Example 1 to obtain 1.4 g of a yellow powder.
This was identified as N, N, N ', N'-tetraphenyl-1,6-diaminopyrene (K-3) by NMR and FD-MS measurements.
[0073]
Production Example 4 Production of K-4
In Production Example 1, N, N'-diphenyl-1,3-phenylenediamine (manufactured by Nard Institute) was used in place of N, N'-diphenylbenzidine, and 1-iodopyrene (instead of 1-iodoanthracene) was used. The reaction and purification were carried out in the same manner as in Production Example 1 except that NARD Laboratory Co., Ltd. was used, to obtain 1.5 g of a yellow powder.
This was identified as N, N′-di- (pyren-1-yl) -N, N′-diphenyl-1,3-phenylenediamine (K-4) by NMR and FD-MS measurements.
[0074]
Production Example 5 Production of K-5
The reaction and purification were carried out in the same manner as in Production Example 1 except that 1-aminopyrene was used instead of N, N'-diphenylbenzidine and 10 g of iodobenzene was used instead of 1-iodoanthracene. As a result, 1.9 g of a yellow powder was obtained.
This was identified as N, N'-diphenyl-1-aminopyrene (K-5) by NMR and FD-MS measurements.
[0075]
Production Example 6 Production of K-6
In a 300 ml three-necked flask, 2 g of 1-aminoanthracene (manufactured by Aldrich); 2 g of 2,5-bis- (4-iodophenyl-1-yl) -thiophene (manufactured by Nard Institute), anhydrous potassium carbonate 10 g and 1 g of copper were added, dissolved in 200 ml of DMSO, and heated and stirred at 200 ° C. for 8 hours.
After completion of the reaction, the inorganic substance was filtered off, and the solvent was distilled off under reduced pressure. The residue was purified with a column packed with silica gel (manufactured by Hiroshima Wako) using toluene as a developing solvent to obtain 1.7 g of a yellow powder. Was.
Next, 1.5 g of this yellow powder, 10 g of iodobenzene, 10 g of anhydrous potassium carbonate and 1 g of copper were put into a 300 ml three-necked flask, dissolved in DMSO, and heated and stirred at 200 ° C. for 8 hours.
After completion of the reaction, the inorganic substance was filtered off and the solvent was distilled off under reduced pressure. The residue was purified by a column packed with silica gel (manufactured by Hiroshima Wako) using toluene as a developing solvent to obtain 0.68 g of a yellow powder. Was.
This was identified as 2,5-bis- (4- [N- (anthracen-1-yl) -N-phenyl] aminophenyl) thiophene (K-6) by NMR and FD-MS measurements.
[0076]
Examples 1 to 6 and Comparative Example 1
A transparent support substrate was formed by depositing ITO with a thickness of 100 nm on a glass substrate of 25 mm × 75 mm × 1.1 mm by a vapor deposition method. The substrate was subjected to ultrasonic cleaning in isopropyl alcohol for 5 minutes, dried by blowing nitrogen, and then subjected to UV ozone cleaning (UV300, manufactured by Samco International) for 30 minutes.
This transparent support substrate was fixed to a substrate holder of a commercially available vapor deposition device (manufactured by Japan Vacuum Technology Co., Ltd.), 200 mg of MTDATA was put into a molybdenum resistance heating boat, 200 mg of DPVBi was put into another molybdenum resistance heating boat, and another A molybdenum resistance heating boat was charged with 200 mg of NPD as a hole transport material, and another molybdenum resistance heating boat was charged with 200 mg of a fluorescent dopant [compound (A)] of the type shown in Table 1, and the vacuum chamber was 1 × 10 -4 The pressure was reduced to Pa. Thereafter, the boat containing MTDATA was heated to 215 to 220 ° C., and was vapor-deposited on a transparent support substrate at a vapor deposition rate of 0.1 to 0.3 nm / sec to form a 60-nm-thick hole injection layer. .
Next, without removing the substrate from the vacuum chamber, the boat containing the NPD was heated to form a 20 nm-thick hole transport layer on the hole injection layer. At this time, the temperature of the substrate was room temperature. This was stacked on the NPD layer with a thickness of 40 nm using DPVBi as a host material without taking it out of the vacuum chamber. At this time, the boat of the compound (A) was heated at the same time, and the compound (A) was mixed into the light emitting layer. At this time, the deposition rate of the compound (A) was set to (C) (shown in Table 1) with respect to the deposition rate of DPVBi ((B) shown in Table 1). Therefore, the mixing ratio [the ratio of the compound (A) to the host material] was (D) (shown in Table 1).
After that, the vacuum chamber was returned to the atmospheric pressure, and a new molybdenum resistance heating boat was charged with 8-hydroxyquinoline / aluminum complex, which is a material for the electron injection layer. Put 500 mg of silver wire in the basket and set the vacuum tank to 1 × 10 -4 The pressure was reduced to Pa.
Next, an 8-hydroxyquinoline / aluminum complex was deposited at a deposition rate of 0.01 to 0.03 nm / sec to form an electron injection layer of 20 nm. Further, silver was vapor-deposited at a vapor deposition rate of 0.1 nm / sec and magnesium was vapor-deposited at a vapor deposition rate of 1.4 nm / sec, and a silver: magnesium mixed electrode was used as a cathode. The thickness was 150 nm.
A voltage of 8 V was applied to the obtained device, and the amount of current and the luminance of the device were measured to calculate the luminous efficiency. Table 2 shows the obtained results.
The structures of MTDATA, DPVBi and NPD are as follows.
[0077]
Embedded image
[Table 1]
[Table 2]
From the above results, it can be seen that the device of the present invention is superior in luminous efficiency to that of Comparative Example 1 using perylene (fluorescent dopant described in JP-A-5-198338) as the fluorescent dopant. .
Next, each element was set to an initial luminance of 300 cd / m. 2 Was driven in a dry nitrogen atmosphere to obtain a half-life (time during which the initial luminance becomes half). The results are shown in Table 3. Note that the initial luminance is 100 cd / m. 2 As a result, the life was about 3.5 times as long as that in Table 3. Therefore, the device of the present invention has an initial luminance of 100 cd / m 2. 2 Under the conditions described above, a life of 2500 hours to 1100 hours can be obtained.
[0081]
[Table 3]
As can be seen from Table 3, the life of the device of the present invention is significantly improved as compared with that of Comparative Example 1.
[0083]
Comparative Example 2
A device was prepared in the same manner as in Example 1, except that PAVTP (fluorescent dopant described in International Patent Publication No. 94-6157) was used as the fluorescent dopant [compound (A)], and an initial luminance of 300 cd / m2 was obtained. 2 The half-life was determined to be 300 hours. The half-life was 300 hours, which was shorter and inferior to the device of the present invention. Note that the initial luminance is 100 cd / m. 2 The test result at that time was a half life of 1000 hours.
The structure of PAVTP is shown below.
[0084]
Embedded image
【The invention's effect】
The organic EL device of the present invention has a structure in which at least one of a recombination region where holes and electrons recombine or a light-emitting region which emits light in response to the recombination contains a fluorescent dopant having a specific structure. It has a long life and high luminous efficiency, such as little change in emission color even when driven for a long time, and is suitably used for, for example, displays of information industry equipment.
Claims (3)
及び一般式（ＩＩ）
で表される化合物の中から選ばれた少なくとも一種を０．１〜８重量％の割合で含有させたことを特徴とする有機エレクトロルミネッセンス素子。An organic electroluminescent device including an organic compound layer having at least a recombination region where holes and electrons recombine, a light emitting region emitting light in response to the recombination, and a pair of electrodes sandwiching the organic compound layer. In the above formula, the compound represented by the general formula (I)
And general formula (II)
An organic electroluminescence device characterized in that at least one selected from the compounds represented by formula (1) is contained at a ratio of 0.1 to 8% by weight.
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| JP2003176314A JP2004006379A (en) | 2003-06-20 | 2003-06-20 | Organic electroluminescent element |
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