JP3591226B2 - Organic electroluminescent device material and organic electroluminescent device using the same - Google Patents
Organic electroluminescent device material and organic electroluminescent device using the same Download PDFInfo
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- JP3591226B2 JP3591226B2 JP16141897A JP16141897A JP3591226B2 JP 3591226 B2 JP3591226 B2 JP 3591226B2 JP 16141897 A JP16141897 A JP 16141897A JP 16141897 A JP16141897 A JP 16141897A JP 3591226 B2 JP3591226 B2 JP 3591226B2
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- 239000000463 material Substances 0.000 title claims description 69
- 125000003367 polycyclic group Chemical group 0.000 claims description 54
- 238000005401 electroluminescence Methods 0.000 claims description 52
- 125000002950 monocyclic group Chemical group 0.000 claims description 49
- 125000000217 alkyl group Chemical group 0.000 claims description 46
- 238000002347 injection Methods 0.000 claims description 40
- 239000007924 injection Substances 0.000 claims description 40
- 125000003277 amino group Chemical group 0.000 claims description 30
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 27
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 27
- 125000004104 aryloxy group Chemical group 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 125000004414 alkyl thio group Chemical group 0.000 claims description 14
- 125000001769 aryl amino group Chemical group 0.000 claims description 14
- 125000005110 aryl thio group Chemical group 0.000 claims description 14
- 125000005843 halogen group Chemical group 0.000 claims description 13
- 125000003282 alkyl amino group Chemical group 0.000 claims description 12
- 239000010409 thin film Substances 0.000 claims description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 150000002894 organic compounds Chemical class 0.000 claims description 8
- 125000001931 aliphatic group Chemical group 0.000 claims description 7
- 125000002947 alkylene group Chemical group 0.000 claims description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 239000010410 layer Substances 0.000 description 86
- -1 amine compound Chemical class 0.000 description 73
- 150000001875 compounds Chemical class 0.000 description 47
- 239000000758 substrate Substances 0.000 description 12
- 239000000956 alloy Substances 0.000 description 11
- 229910045601 alloy Inorganic materials 0.000 description 11
- 239000010408 film Substances 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 9
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 9
- 239000011521 glass Substances 0.000 description 9
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
- 229910052749 magnesium Inorganic materials 0.000 description 9
- 239000011777 magnesium Substances 0.000 description 9
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 9
- 239000004332 silver Substances 0.000 description 9
- 238000007740 vapor deposition Methods 0.000 description 9
- 238000000034 method Methods 0.000 description 8
- 229910052709 silver Inorganic materials 0.000 description 8
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 8
- 239000011347 resin Substances 0.000 description 7
- 229920005989 resin Polymers 0.000 description 7
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 150000003852 triazoles Chemical group 0.000 description 5
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 4
- RJGDLRCDCYRQOQ-UHFFFAOYSA-N anthrone Chemical group C1=CC=C2C(=O)C3=CC=CC=C3CC2=C1 RJGDLRCDCYRQOQ-UHFFFAOYSA-N 0.000 description 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 4
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 4
- 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 4
- 125000002883 imidazolyl group Chemical group 0.000 description 4
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- FZEYVTFCMJSGMP-UHFFFAOYSA-N acridone Chemical group C1=CC=C2C(=O)C3=CC=CC=C3NC2=C1 FZEYVTFCMJSGMP-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
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 3
- WZJYKHNJTSNBHV-UHFFFAOYSA-N benzo[h]quinoline Chemical compound C1=CN=C2C3=CC=CC=C3C=CC2=C1 WZJYKHNJTSNBHV-UHFFFAOYSA-N 0.000 description 3
- 239000004020 conductor Substances 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical group C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 125000002971 oxazolyl group Chemical group 0.000 description 3
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 3
- 229920000548 poly(silane) polymer Polymers 0.000 description 3
- 125000001725 pyrenyl group Chemical group 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 125000006617 triphenylamine group Chemical class 0.000 description 3
- 0 *C1C(*)=C(C(C2C(C3N(*)*)C(*)=C(*)C(*)C2*=C)C(O)=C([C@@]2c(c(*=C)c(*)c(*)c4*)c4C(N*)=C4C(*)=C(*)C(*)=C(*)C24)O)C3=C(*)C1* Chemical compound *C1C(*)=C(C(C2C(C3N(*)*)C(*)=C(*)C(*)C2*=C)C(O)=C([C@@]2c(c(*=C)c(*)c(*)c4*)c4C(N*)=C4C(*)=C(*)C(*)=C(*)C24)O)C3=C(*)C1* 0.000 description 2
- UGUHFDPGDQDVGX-UHFFFAOYSA-N 1,2,3-thiadiazole Chemical group C1=CSN=N1 UGUHFDPGDQDVGX-UHFFFAOYSA-N 0.000 description 2
- 125000000355 1,3-benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 2
- DDTHMESPCBONDT-UHFFFAOYSA-N 4-(4-oxocyclohexa-2,5-dien-1-ylidene)cyclohexa-2,5-dien-1-one Chemical compound C1=CC(=O)C=CC1=C1C=CC(=O)C=C1 DDTHMESPCBONDT-UHFFFAOYSA-N 0.000 description 2
- ZZLCFHIKESPLTH-UHFFFAOYSA-N 4-Methylbiphenyl Chemical group C1=CC(C)=CC=C1C1=CC=CC=C1 ZZLCFHIKESPLTH-UHFFFAOYSA-N 0.000 description 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- RZVHIXYEVGDQDX-UHFFFAOYSA-N 9,10-anthraquinone Chemical group C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 RZVHIXYEVGDQDX-UHFFFAOYSA-N 0.000 description 2
- ZYASLTYCYTYKFC-UHFFFAOYSA-N 9-methylidenefluorene Chemical compound C1=CC=C2C(=C)C3=CC=CC=C3C2=C1 ZYASLTYCYTYKFC-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- ZTMZAVAFXOJBDQ-UHFFFAOYSA-N CC1=CC(=CC=C1)N(C2=CC=CC=C2)C3(CC=C(C=C3)C4=CC=CC=C4)NC5=CC=CC=C5 Chemical compound CC1=CC(=CC=C1)N(C2=CC=CC=C2)C3(CC=C(C=C3)C4=CC=CC=C4)NC5=CC=CC=C5 ZTMZAVAFXOJBDQ-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 2
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 description 2
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 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
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 description 2
- 229920001940 conductive 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
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical group C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 description 2
- 125000004915 dibutylamino group Chemical group C(CCC)N(CCCC)* 0.000 description 2
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000000532 dioxanyl group Chemical group 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 125000004914 dipropylamino group Chemical group C(CC)N(CCC)* 0.000 description 2
- 230000005684 electric field Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 2
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 230000006870 function Effects 0.000 description 2
- 229910052733 gallium Inorganic materials 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- 238000004020 luminiscence type Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 2
- 230000005012 migration Effects 0.000 description 2
- 238000013508 migration Methods 0.000 description 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- 125000005561 phenanthryl group Chemical group 0.000 description 2
- 229940031826 phenolate Drugs 0.000 description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 2
- 229920005668 polycarbonate resin Polymers 0.000 description 2
- 239000004431 polycarbonate resin Substances 0.000 description 2
- 229920000128 polypyrrole Polymers 0.000 description 2
- 229920000123 polythiophene Polymers 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 125000003373 pyrazinyl group Chemical group 0.000 description 2
- 125000003226 pyrazolyl group Chemical group 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 description 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 2
- 125000000168 pyrrolyl group Chemical group 0.000 description 2
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 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
- 239000002904 solvent Substances 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- 238000004544 sputter deposition Methods 0.000 description 2
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 2
- 235000021286 stilbenes Nutrition 0.000 description 2
- 125000005156 substituted alkylene group Chemical group 0.000 description 2
- 150000003536 tetrazoles Chemical class 0.000 description 2
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 2
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 2
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 2
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 2
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 description 2
- 238000007738 vacuum evaporation Methods 0.000 description 2
- UWRZIZXBOLBCON-VOTSOKGWSA-N (e)-2-phenylethenamine Chemical compound N\C=C\C1=CC=CC=C1 UWRZIZXBOLBCON-VOTSOKGWSA-N 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-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
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- UVHXEHGUEKARKZ-UHFFFAOYSA-N 1-ethenylanthracene Chemical compound C1=CC=C2C=C3C(C=C)=CC=CC3=CC2=C1 UVHXEHGUEKARKZ-UHFFFAOYSA-N 0.000 description 1
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Images
Description
【０００１】
【産業上の利用分野】
本発明は平面光源や表示に使用される有機エレクトロルミネッセンス（ＥＬ）素子に関するものである。
【０００２】
【従来の技術】
有機物質を使用したＥＬ素子は、固体発光型の安価な大面積フルカラー表示素子としての用途が有望視され、多くの開発が行われている。一般にＥＬは、発光層および該層をはさんだ一対の対向電極から構成されている。
発光は、両電極間に電界が印加されると、陰極側から電子が注入され、陽極側から正孔が注入される。さらに、この電子が発光層において正孔と再結合し、エネルギー準位が伝導帯から価電子帯に戻る際にエネルギーを光として放出する現象である。
【０００３】
従来の有機ＥＬ素子は、無機ＥＬ素子に比べて駆動電圧が高く、発光輝度や発光効率も低かった。また、特性劣化も著しく実用化には至っていなかった。
近年、１０Ｖ以下の低電圧で発光する高い蛍光量子効率を持った有機化合物を含有した薄膜を積層した有機ＥＬ素子が報告され、関心を集めている（アプライド・フィジクス・レターズ、５１巻、９１３ページ、１９８７年参照）。
この方法では、金属キレート錯体を蛍光体層、アミン系化合物を正孔注入層に使用して、高輝度の緑色発光を得ており、６〜７Ｖの直流電圧で輝度は１００ｃｄ／ｍ２ 、最大発光効率は１．５ｌｍ／Ｗを達成して、実用領域に近い性能を持っている。しかしながら、現在までの有機ＥＬ素子は、構成の改善により緑色においては発光強度は改良されているが、黄色〜赤色の波長範囲では未だ十分な発光輝度は有していない。
【０００４】
有機ＥＬ素子から黄色〜赤色の波長範囲の発光を得るために、発光層をホスト材料にゲスト材料をドープして作製する技術が開示されている。例えば、発光層中にトリス（８−ヒドロキシキノリン）アルミニウム錯体をホスト材料に、クマリン色素もしくはＤＣＭ色素を蛍光性ゲスト材料としてドープした有機ＥＬ素子（ジャーナル・オブ・アプライドフィジクス、６５巻、３６１０ページ、１９８９年参照）があるが、これらの有機ＥＬ素子の発光効率は十分ではなかった。また、発光層中にトリス（８−ヒドロキシキノリン）アルミニウム錯体をホスト材料に、フタロシアニン化合物をドーピングし赤色発光の有機ＥＬ素子が開示されている（特開平０７− ２８８２８４号公報）。しかしながら、これらの有機ＥＬ素子の初期発光効率はいまだ十分でなく、また連続して発光させた場合の劣化が著しく、実用上大きな問題があった。
【０００５】
【発明が解決しようとする課題】
本発明の目的は、黄色〜赤色のスペクトル領域で発光効率が高く、発光寿命の優れた有機ＥＬ素子の提供にある。本発明者らが鋭意検討した結果、一般式［１］〜［５］で示される化合物の少なくとも一種の有機ＥＬ素子材料を少なくとも一層に使用した有機ＥＬ素子の黄色〜赤色のスペクトル領域で発光効率が高く、発光寿命も優れていることを見いだし本発明に至った。
【０００６】
【課題を解決するための手段】
即ち、本発明は、下記一般式［１］で示される有機エレクトロルミネッセンス素子材料である。
一般式［１］
【化６】
【０００７】
更に本発明は、下記一般式［２］で示される有機エレクトロルミネッセンス素子材料である。
一般式［２］
【化７】
【０００８】
更に本発明は、下記一般式［３］で示される有機エレクトロルミネッセンス素子材料である。
一般式［３］
【化８】
【０００９】
更に本発明は、下記一般式［４］で示される有機エレクトロルミネッセンス素子材料である。
一般式［４］
【化９】
【００１０】
更に本発明は、下記一般式［５］で示される有機エレクトロルミネッセンス素子材料である。
一般式［５］
【化１０】
【００１１】
更に本発明は一対の電極間に発光層を含む複数層の有機化合物薄膜を形成した有機エレクトロルミネッセンス素子において、少なくとも一層が上記記載の有機エレクトロルミネッセンス素子材料を含有する層である有機エレクトロルミネッセンス素子である。
【００１２】
更に本発明は、一対の電極間に発光層を含む複数層の有機化合物薄膜を形成した有機エレクトロルミネッセンス素子において、発光層が上記記載の有機エレクトロルミネッセンス素子材料を含有する層である有機エレクトロルミネッセンス素子である。
【００１３】更に本発明は、一対の電極間に発光層を含む複数の有機化合物薄膜を形成した有機エレクトロルミネッセンス素子において、発光層がホスト材料とドーピング材料からなり、該ドーピング材料が上記記載の有機エレクトロルミネッセンス素子材料である有機エレクトロルミネッセンス素子である。
【００１４】更に本発明は、発光層と陰極との間に１〜４層の電子注入層を形成することを特徴とする有機エレクトロルミネッセンス素子である。
【００１５】更に本発明は、発光層と陽極との間に１〜４層の正孔注入層を形成することを特徴とする有機エレクトロルミネッセンス素子である。
【００１６】
【発明の実施の形態】
一般式［１］〜［５］で表される化合物のＲ１ 〜Ｒ５６はそれぞれ独立に、水素原子、ハロゲン原子、シアノ基、ニトロ基、置換もしくは未置換のアルキル基、置換もしくは未置換のアルコキシ基、置換もしくは未置換のアリールオキシ基、置換もしくは未置換のアルキルチオ基、置換もしくは未置換のアリールチオ基、置換もしくは未置換のシクロアルキル基、置換もしくは未置換の単環基、置換もしくは未置換の縮合多環基、置換もしくは未置換のアミノ基、置換もしくは未置換のアルキルアミノ基、置換もしくは未置換のアリールアミノ基を表す。
【００１７】
本発明における一般式［１］〜［５］で表される化合物のＲ１ 〜Ｒ５６のハロゲン原子の具体例としては、塩素、臭素、ヨウ素、フッ素があり、アルキル基の具体例としては、メチル基、エチル基、プロピル基、ブチル基、ｓｅｃ−ブチル基、ｔｅｒｔ−ブチル基、ペンチル基、ヘキシル基、ヘプチル基、オクチル基、ステアリル基、トリクロロメチル基等があり、シクロアルキルの具体例としては、シクロペンタン環、シクロヘキサン環等がある。
【００１８】
本発明における一般式［１］〜［５］で表される化合物のＲ１ 〜Ｒ５６のアルコキシ基の具体例としては、メトキシ基、エトキシ基、ｎ−ブトキシ基、ｔｅｒｔ−ブトキシ基、トリクロロメトキシ基、トリフルオロエトキシ基、ペンタフルオロプロポキシ基、２，２，３，３−テトラフルオロプロポキシ基、１，１，１，３，３，３−ヘキサフルオロ−２−プロポキシ基、６−（パーフルオロエチル）ヘキシルオキシ基等があり、アリールオキシ基の具体例としては、フェノキシ基、ｐ−ニトロフェノキシ基、ｐ−ｔｅｒｔ−ブチルフェノキシ基、３−フルオロフェノキシ基、ペンタフルオロフェニル基、３−トリフルオロメチルフェノキシ基等がある。
【００１９】
本発明における一般式［１］〜［５］で表される化合物のＲ１ 〜Ｒ５６のアルキルチオ基の具体例とては、メチルチオ基、エチルチオ基、ｔｅｒｔ−ブチルチオ基、ヘキシルチオ基、オクチルチオ基、トリフルオロメチルチオ基等があり、アリールチオ基の具体例とては、フェニルチオ基、ｐ−ニトロフェニルチオ基、ｐ−ｔｅｒｔ−ブチルフェニルチオ基、３−フルオロフェニルチオ基、ペンタフルオロフェニルチオ基、３−トリフルオロメチルフェニルチオ基等がある。
【００２０】
本発明における一般式［１］〜［５］で表される化合物のＲ１ 〜Ｒ５６の単環基としてはフェニル基、チオニル基、チオフェニル基、フラニル基、ピロリル基、イミダゾリル基、ピラゾリル基、ピリジル基、ピラジニル基、ピリミジニル基、ピリダジニル基、オキサゾリル基、チアゾリル基、オキサジアゾリル基、チアジアゾリル基、イミダジアゾリル基等がある。
【００２１】
本発明における一般式［１］〜［５］で表される化合物のＲ１ 〜Ｒ５６の縮合多環基としては、ナフチル基、アントリル基、フェナントリル基、フルオレニル基、ピレニル基、インドール基、プリン基、キノリン基、イソキノリン基、シノリン基、キノキサリン基、ベンゾキノリン基、フルオレノン基、カルバゾール基、オキサゾール基、オキサジアゾール基、チアゾール基、チアジアゾール基、トリアゾール基、イミダゾール基、ベンゾオキサゾール基、ベンゾチアゾール基、ベンゾトリアゾール基、ベンゾイミダゾール基、ビスベンゾオキサゾール基、ビスベンゾチアゾール基、ビスベンゾイミダゾール基、アントロン基、ジベンゾフラン基、ジベンゾチオフェン基、アントラキノン基、アクリドン基、フェノチアジン基、ピロリジン基、ジオキサン基、モルフォリン基等がある。
【００２２】
本発明における一般式［１］〜［５］で表される化合物のＲ１ 〜Ｒ５６のアミノ基の具体例としては、アミノ基、ビス（アセトキシメチル）アミノ基、ビス（アセトキシエチル）アミノ基、ビスアセトキシプロピル）アミノ基、ビス（アセトキシブチル）アミノ基等があり、アルキルアミノ基の具体例としてはエチルアミノ基、ジエチルアミノ基、ジプロピルアミノ基、ジブチルアミノ基、ベンジルアミノ基ジベンジルアミノ基等があり、アリールアミノ基の具体例としては、フェニルアミノ基、（３−メチルフェニル）アミノ基、（４−メチルフェニル）アミノ基等があり、フェニルアミノ基の具体例としては、フェニルアミノ基、フェニルメチルアミノ基、ジフェニルアミノ基、ジトリルアミノ基、ジビフェニルアミノ基、ジ（４−メチルビフェニル）アミノ基、ジ（３−メチルフェニル）アミノ基、ジ（４−メチルフェニル）アミノ基、ナフチルフェニルアミノ基、ビス［４−（α，α’−ジメチルベンジル）フェニル］アミノ基等がある。
【００２３】
また、Ｒ１ 〜Ｒ５６の隣接する基同士で、それぞれ互いに結合して、フェニル環、ナフチル環、アントリル環、ピレニル環、カルバゾール環、ベンゾピラニル環、シクロヘキシル環等の飽和もしくは不飽和環を形成してもよい。
【００２４】
一般式［１］〜［５］の化合物のＱ１ 、Ｑ２ は、それぞれ独立に水素原子、シアノ基、置換もしくは未置換のアルキル基、置換もしくは未置換の単環基、置換もしくは未置換の縮合多環基を表す。アルキル基、単環基、縮合多環基の具体例は、前記のＲ１ 〜Ｒ５６で記述したアルキル基、単環基、縮合多環基が挙げられる。
【００２５】
一般式［１］の化合物のＡ１ 〜Ａ４ は、それぞれ独立に、置換もしくは未置換のアルキル基、置換もしくは未置換の単環基、置換もしくは未置換の縮合多環基、またはＡ１ とＡ２ 、Ａ３ とＡ４ が一体となって窒素原子を結合手とする縮合多環基を表す。アルキル基、単環基、縮合多環基の具体例は、前記のＲ１ 〜Ｒ５６で記述したアルキル基、単環基、縮合多環基が挙げられる。
【００２６】
一般式［１］の化合物のＡ１ とＡ２ 、Ａ３ とＡ４ とが一体となってカルバゾール基、フェノチアジン基、アクリドン基のような窒素原子を含む縮合多環基を形成してもよい。
【００２７】
本発明における一般式［３］および［４］で表される化合物のＸ１ 〜Ｘ４ は、それぞれ独立に、Ｏ、Ｓ、Ｃ＝Ｏ、ＣＺ１ ＝ＣＺ２ 、Ｃ≡Ｃ、ＳＯ２ 、（ＣＨ２ ）ｘ−Ｏ−（ＣＨ２ ）ｙ、置換もしくは未置換のアルキレン基、置換もしくは未置換の脂肪族環残基を表す。ここで、ｘおよびｙは、それぞれ０〜２０の正の整数を表すが、ｘ＋ｙ＝０となることはない。また、Ｚ１ およびＺ２ は、それぞれ独立に水素原子、シアノ基、置換もしくは未置換のアルキル基、置換もしくは未置換の単環基、置換もしくは未置換の縮合多環基を表す。アルキル基、単環基、縮合多環基の具体例は、前記のＲ１ 〜Ｒ５６で記述したアルキル基、単環基、縮合多環基が挙げられる。
置換もしくは未置換のアルキレン基としては炭素数１〜２０のアルキレン基もしくはその置換体、置換もしくは未置換の脂肪族環残基としては、シクロペンチル環、シクロヘキシル環、メチルシクロヘキシル環、シクロヘプチル環等の炭素数５〜７の脂肪族環の２価の残基が挙げられる。
Ｘ１ 〜Ｘ４ の置換アルキレン基または置換脂肪族環残基の置換基としてはＲ１ 〜Ｒ５６で示した置換基がある。Ｘ１ 〜Ｘ４ の置換アルキレン基として好ましいものは、２−フェニルイソプロピレン基、ジクロロメチレン基、ジフルオロメチレン基、ベンジレン基、α−フェノキシベンジレン基、α，α’−ジメチルベンジレン基、α−ベンジルオキシベンジレン基などが挙げられる。
【００２８】
本発明における一般式［５］で表される化合物のＹ１ 〜Ｙ８ は、置換もしくは未置換の炭素数１〜２０のアルキル基、置換もしくは未置換の炭素数６〜１６の単環基、縮合多環基を表す。アルキル基、単環基、縮合多環基の具体例は、前記のＲ１ 〜Ｒ５６で記述したアルキル基、単環基、縮合多環基が挙げられる。
【００２９】
本発明におけるＱ１ 、Ｑ２ のアルキル基、単環基、縮合多環基、およびＡ１ 〜Ａ ４のアルキル基、単環基、縮合多環基、Ａ１ とＡ２ 、Ａ３ とＡ４ が一体となって窒素原子を結合手とする縮合多環基、およびＲ１ 〜Ｒ５６で示されるアルキル基、アルコキシ基、アリールオキシ基、アルキルチオ基、アリールチオ基、シクロアルキル基、単環基、縮合多環基、アミノ基、アルキルアミノ基、アリールアミノ基、およびＸ１ 〜Ｘ２ のアルキレン基、およびＹ１ 〜Ｙ８ のアルキル基、単環基、縮合多環基、Ｚ１ およびＺ２ のアルキル基、単環基、縮合多環基に置換してもよい基の代表例としては以下に示す置換基がある。
【００３０】
ハロゲン原子としては、塩素、臭素、ヨウ素、フッ素。
アルキル基としては、メチル基、エチル基、プロピル基、ブチル基、ｓｅｃ−ブチル基、ｔｅｒｔ−ブチル基、ペンチル基、ヘキシル基、ヘプチル基、オクチル基、ステアリル基、トリクロロメチル基等があり、シクロアルキルとしては、シクロペンタン環、シクロヘキサン環、１，３−シクロヘキサジエニル基、２−シクロペンテン−１−イル基、２，４−シクロペンタジエン−１−イリデニル基等がある。
【００３１】
アルコキシ基としては、メトキシ基、エトキシ基、ｎ−ブトキシ基、ｔｅｒｔ−ブトキシ基、トリクロロメトキシ基、トリフルオロエトキシ基、ペンタフルオロプロポキシ基、２，２，３，３−テトラフルオロプロポキシ基、１，１，１，３，３，３−ヘキサフルオロ−２−プロポキシ基、６−（パーフルオロエチル）ヘキシルオキシ基等があり、アリールオキシ基としては、フェノキシ基、ｐ−ニトロフェノキシ基、ｐ−ｔｅｒｔ−ブチルフェノキシ基、３−フルオロフェノキシ基、ペンタフルオロフェニル基、３−トリフルオロメチルフェノキシ基等がある。
【００３２】
アルキルチオ基としては、メチルチオ基、エチルチオ基、ｔｅｒｔ−ブチルチオ基、ヘキシルチオ基、オクチルチオ基、トリフルオロメチルチオ基等があり、アリールチオ基としては、フェニルチオ基、ｐ−ニトロフェニルチオ基、ｐ−ｔｅｒｔ−ブチルフェニルチオ基、３−フルオロフェニルチオ基、ペンタフルオロフェニルチオ基、３−トリフルオロメチルフェニルチオ基等がある。
【００３３】
アリール基としては、フェニル基、ビフェニル基、ターフェニル基、ナフチル基、アントリル基、フェナントリル基、フルオレニル基、ピレニル基等があり、複素環基としては、ピロール基、ピロリン基、ピラゾール基、ピラゾリン基、イミダゾール基、トリアゾール基、ピリジン基、ピリダジン基、ピリミジン基、ピラジン基、トリアジン基、インドール基、プリン基、キノリン基、イソキノリン基、シノリン基、キノキサリン基、ベンゾキノリン基、フルオレノン基、カルバゾール基、オキサゾール基、オキサジアゾール基、チアゾール基、チアジアゾール基、トリアゾール基、イミダゾール基、ベンゾオキサゾール基、ベンゾチアゾール基、ベンゾトリアゾール基、ベンゾイミダゾール基、ビスベンゾオキサゾール基、ビスベンゾチアゾール基、ビスベンゾイミダゾール基、アントロン基、ジベンゾフラン基、ジベンゾチオフェン基、アントラキノン基、アクリドン基、フェノチアジン基、ピロリジン基、ジオキサン基、モルフォリン基等がある。
【００３４】
アミノ基としては、アミノ基、ビス（アセトキシメチル）アミノ基、ビス（アセトキシエチル）アミノ基、ビス （アセトキシプロピル）アミノ基、ビス（アセトキシブチル）アミノ基等があり、アルキルアミノ基の具体例としてはエチルアミノ基、ジエチルアミノ基、ジプロピルアミノ基、ジブチルアミノ基、ベンジルアミノ基、ジベンジルアミノ基等があり、アリールアミノ基の具体例としては、フェニルアミノ基、（３−メチルフェニル）アミノ基、（４−メチルフェニル）アミノ基、フェニルメチルアミノ基、ジフェニルアミノ基、ビス（４−フェノキシフェニル）アミノ基、ビス（４−ビフェニル）アミノ基、ビス［４−（４−トリル）フェニル］アミノ基、ビス（３−メチルフェニル）アミノ基、ビス（４−メチルフェニル）アミノ基、ナフチルフェニルアミノ基、ビス［４−（α，α’−ジメチルベンジル）フェニル］アミノ基等がある。
【００３５】
本発明において、一般式［１］〜［５］で表される化合物は例えば次のような方法で合成することが出来る。四塩化チタン、亜鉛粉末存在下で下記一般式［６］と一般式［７］をテトラヒドロフラン中で加熱することによって得ることが出来る。以下に、本発明の化合物の代表例を表１に具体的に例示するが、本発明は以下の代表例に限定されるものではない。
【化１１】
【００３６】
【表１】
一般式［１］〜［５］で表される化合物は、１分子中にオレフィン部位（＞Ｃ＝Ｃ＜）を有している。このオレフィン部位の幾何異性体により、一般式［１］〜［５］で表される化合物はシス体、トランス体の組み合わせがあるが本発明の化合物はそのいずれであってもよく、混合したものであってもよい。
【００４８】
有機ＥＬ素子は、陽極と陰極間に一層もしくは多層の有機化合物薄膜を形成した素子である。一層型の場合、陽極と陰極との間に発光層を設けている。発光層は、発光材料を含有し、それに加えて陽極から注入した正孔もしくは陰極から注入した電子を発光材料まで輸送させるために正孔注入材料もしくは電子注入材料を含有しても良い。多層型は、（陽極／正孔注入層／発光層／陰極）、（陽極／発光層／電子注入層／陰極）、（陽極／正孔注入層／発光層／電子注入層／陰極）の多層構成で積層した有機ＥＬ素子がある。本発明の一般式［１］〜［５］で示される化合物は、固体状態において強い蛍光を持つ化合物であり電界発光性に優れているので、発光材料として発光層内で使用することができる。また、一般式［１］〜［５］の化合物は、発光層内においてドーピング材料として発光層中にて最適の割合でドーピングすることにより、高い発光効率および発光波長の最適な選択が可能である。また、一般式［１］〜［５］の化合物は、正孔もしくは電子等のキャリアを輸送することができるので、有機ＥＬ素子の正孔注入層もしくは電子注入層に使用することも可能である。
【００４９】
発光層のホスト材料に、ドーピング材料（ゲスト材料）として一般式［１］〜［５］の化合物を使用して、発光輝度が高い有機ＥＬ素子を得ることもできる。一般式［１］〜［５］の化合物は、発光層内において、ホスト材料に対して０．００１重量％〜５０重量％の範囲で含有されていることが望ましく、更には０．０１重量％〜１０重量％の範囲が効果的である。
【００５０】
一般式［１］〜［５］の化合物と併せて使用できるホスト材料としては、キノリン金属錯体、オキサジアゾール、ベンゾチアゾール金属錯体、ベンゾオキサゾール金属錯体、ベンゾイミダゾール金属錯体、トリアゾール、イミダゾール、オキサゾール、オキサジアゾール、スチルベン、ブタジエン、ベンジジン型トリフェニルアミン、スチリルアミン型トリフェニルアミン、ジアミン型トリフェニルアミンフルオレノン、ジアミノアントラセン型トリフェニルアミン、ジアミノフェナントレン型トリフェニルアミン、アントラキノジメタン、ジフェノキノン、チアジアゾール、テトラゾール、ペリレンテトラカルボン酸、フレオレニリデンメタン、アントラキノジメタン、トリフェニレン、アントロン等とそれらの誘導体、および、ポリビニルカルバゾール、ポリシラン等の導電性高分子の高分子材料等がある。以下表２に具体的に例示するが、本発明は以下の代表例に限定されるものではない。
【００５１】
【表２】
一般式［１］〜［５］と共に更なるドーピング材料を使用して発光色を変化させることも可能となる。一般式［１］〜［５］と共に使用されるドーピング材料としては、アントラセン、ナフタレン、フェナントレン、ピレン、テトラセン、コロネン、クリセン、フルオレセイン、ペリレン、フタロペリレン、ナフタロペリレン、ペリノン、フタロペリノン、ナフタロペリノン、ジフェニルブタジエン、テトラフェニルブタジエン、クマリン、オキサジアゾール、アルダジン、ビスベンゾキサゾリン、ビススチリル、ピラジン、シクロペンタジエン、キノリン金属錯体、アミノキノリン金属錯体、イミン、ジフェニルエチレン、ビニルアントラセン、ジアミノカルバゾール、ピラン、チオピラン、ポリメチン、メロシアニン、イミダゾールキレート化オキシノイド化合物、キナクリドン、ルブレン等およびそれらの誘導体があるが、これらに限定されるものではない。
【００６６】
発光層には、発光材料およびドーピング材料に加えて、必要があれば正孔注入材料や電子注入材料を使用することもできる。
【００６７】
有機ＥＬ素子は、多層構造にすることにより、クエンチングによる輝度や寿命の低下を防ぐことができる。また、必要があれば、発光材料、ドーピング材料、キャリア注入を行う正孔注入材料や電子注入材料を二種類以上組み合わせて使用することも出来る。また、正孔注入層、発光層、電子注入層は、それぞれ二層以上の層構成により形成されても良く、正孔もしくは電子が効率よく電極から注入され、層中で輸送される素子構造が選択される。
【００６８】
有機ＥＬ素子の陽極に使用される導電性材料は、４ｅＶより大きな仕事関数を持つものが好適であり、炭素、アルミニウム、バナジウム、鉄、コバルト、ニッケル、タングステン、銀、金、白金、パラジウム等およびそれらの合金、ＩＴＯ基板、ＮＥＳＡ基板と称される酸化スズ、酸化インジウム等の酸化金属、さらにはポリチオフェンやポリピロール等の有機導電性樹脂が用いられる。
陰極に使用される導電性材料は、４ｅＶより小さな仕事関数を持つものが好適であり、マグネシウム、カルシウム、錫、鉛、チタニウム、イットリウム、リチウム、ルテニウム、マンガン等およびそれらの合金が用いられる。合金としては、マグネシウム／銀、マグネシウム／インジウム、リチウム／アルミニウム等が代表例として挙げられるが、これらに限定されるものではない。合金の比率は、加熱の温度、雰囲気、真空度により制御され適切な比率が選択される。陽極および陰極は、必要があれば二層以上の層構成により形成されていても良い。
【００６９】
有機ＥＬ素子では、効率良く発光させるために、少なくとも一方は素子の発光波長領域において充分透明であることが望ましい。また、基板も透明であることが望ましい。透明電極は、上記の導電性材料を使用して、蒸着やスパッタリング等の方法で所定の透光性を確保するように設定する。発光面の電極は、光透過率を１０％以上にすることが望ましい。
基板は、機械的、熱的強度を有し、透明であれば限定されるものではないが、例示すると、ガラス基板、ポリエチレン板、ポリエーテルサルフォン板、ポリプロピレン板等の透明性樹脂があげられる。
【００７０】
本発明に係わる有機ＥＬ素子の各層の形成は、真空蒸着、スパッタリング等の乾式成膜法やスピンコーティング、ディッピング等の湿式成膜法のいずれの方法を適用することができる。膜厚は特に限定されるものではないが、各層は適切な膜厚に設定する必要がある。膜厚が厚すぎると、一定の光出力を得るために大きな印加電圧が必要になり効率が悪くなる。膜厚が薄すぎるとピンホール等が発生して、電界を印加しても充分な発光輝度が得られない。通常の膜厚は５ｎｍから１０μｍの範囲が適しているが、１０ｎｍから０．２μｍの範囲がさらに好ましい。
【００７１】湿式成膜法の場合、各層を形成する材料を、クロロホルム、テトラヒドロフラン、ジオキサン等の適切な溶媒に溶解または分散して有機化合物薄膜を形成するが、その溶媒はいずれであっても良い。また、いずれの薄膜においても、成膜性向上、膜のピンホール防止等のため適切な樹脂や添加剤を使用しても良い。
このような樹脂としては、ポリスチレン、ポリカーボネート、ポリアリレート、ポリエステル、ポリアミド、ポリウレタン、ポリスルフォン、ポリメチルメタクリレート、ポリメチルアクリレート、セルロース等の絶縁性樹脂、ポリ−Ｎ−ビニルカルバゾール、ポリシラン等の光導電性樹脂、ポリチオフェン、ポリピロール等の導電性樹脂を挙げることができる。また、添加剤としては、酸化防止剤、紫外線吸収剤、可塑剤等を挙げることができる。
【００７２】
正孔注入材料としては、正孔を注入する能力を持ち、発光層または発光材料に対して優れた正孔注入効果を有し、発光層で生成した励起子の電子注入層または電子注入材料への移動を防止し、かつ薄膜形成能の優れた化合物が挙げられる。具体的には、フタロシアニン系化合物、ナフタロシアニン系化合物、ポルフィリン系化合物、オキサジアゾール、トリアゾール、イミダゾール、イミダゾロン、イミダゾールチオン、ピラゾリン、ピラゾロン、テトラヒドロイミダゾール、オキサゾール、オキサジアゾール、ヒドラゾン、アシルヒドラゾン、ポリアリールアルカン、スチルベン、ブタジエン、ベンジジン型トリフェニルアミン、スチリルアミン型トリフェニルアミン、ジアミン型トリフェニルアミン等と、それらの誘導体、およびポリビニルカルバゾール、ポリシラン、導電性高分子等の高分子材料等があるが、これらに限定されるものではない。
【００７３】
電子注入材料としては、電子を注入する能力を持ち、発光層または発光材料に対して優れた電子注入効果を有し、発光層で生成した励起子の正孔注入層または正孔注入材料への移動を防止し、かつ薄膜形成能の優れた化合物が挙げられる。例えば、キノリン金属錯体、オキサジアゾール、ベンゾチアゾール金属錯体、ベンゾオキサゾール金属錯体、ベンゾイミダゾール金属錯体、フルオレノン、アントラキノジメタン、ジフェノキノン、チオピランジオキシド、オキサジアゾール、チアジアゾール、テトラゾール、ペリレンテトラカルボン酸、フレオレニリデンメタン、アントラキノジメタン、アントロン等とそれらの誘導体があるが、これらに限定されるものではない。また、正孔注入材料に電子受容物質を、電子注入材料に電子供与性物質を添加して増感させることもできる。
【００７４】
本発明により得られた有機ＥＬ素子の、温度、湿度、雰囲気等に対する安定性の向上のために、素子の表面に保護層を設けたり、シリコンオイル等を封入して素子全体を保護することも可能である。
【００７５】
【実施例】
以下、本発明を実施例に基づきさらに詳細に説明する。
【００７６】
化合物（１）の合成方法
テトラヒドロフラン（ＴＨＦ）１００ｍｌをフラスコに入れアイスバスにより冷却し、四塩化チタン１２ｍｌを滴下する。その後、９−ホルミル−９’−［Ｎ，Ｎ’−ビス（４−メチルフェニル）］アミノ−アントラセン４ｇをフラスコ中に投入し、亜鉛粉末８ｇを少しずつ加える。すべて加えた後フラスコを加熱し、還流下５時間反応を行った。反応終了後、水を加え生じた沈殿をろ過し集めた。沈殿をシリカゲルでカラム精製をおこなった後、昇華精製した。ＮＭＲ、ＦＤ−ＭＳ、ＩＲによって化合物の生成を確認した。化合物（１）のＩＲスペクトル図を図１に示す。
【００７７】
実施例１
洗浄したＩＴＯ電極付きガラス板上に、Ｎ，Ｎ’ ―（３―メチルフェニル）―Ｎ，Ｎ’ ―ジフェニル―１，１―ビフェニル− ４，４―ジアミン（ＴＰＤ）を真空蒸着して、膜厚２０ｎｍの正孔注入層を得た。次いで、化合物（１）を蒸着し膜厚４０ｎｍの発光層を作成し、トリス（８−ヒドロキシキノリン）アルミニウム錯体（Ａｌｑ３）を蒸着し、膜厚３０ｎｍの電子注入層を得た。その上に、マグネシウムと銀を１０：１で混合した合金で膜厚１００ｎｍの電極を形成して有機ＥＬ素子を得た。正孔注入層および発光層は１０−６Ｔｏｒｒの真空中で、基板温度室温の条件下で蒸着した。この素子は直流電圧５Ｖで発光輝度１００ｃｄ／ｍ２ 、最大発光輝度２００００ｃｄ／ｍ２ 、５Ｖの時の発光効率２．５ｌｍ／Ｗの橙色発光が得られた。次に３ｍＡ／ｃｍ２ の電流密度で、この素子を連続して発光させた寿命試験の結果、初期輝度の１／２以上の発光が１００００時間以上保持された。
【００７８】
実施例２〜３８
発光層に、化合物（１）に換え、表３で示した化合物を使用する以外は実施例１と同様の方法で有機ＥＬ素子を作製した。この素子は表３に示す発光特性を示した。
【００７９】
【表３】
実施例３９
洗浄したＩＴＯ電極付きガラス板上に化合物（１２）を真空蒸着して膜厚１００ｎｍの発光層を作成し、その上に、マグネシウムと銀を１０：１で混合した合金で膜厚１５０ｎｍの膜厚の電極を形成して有機ＥＬ素子を得た。発光層および陰極は、１０−６Ｔｏｒｒの真空中で基板温度室温の条件下で蒸着した。この素子は直流電圧５Ｖで発光輝度３０ｃｄ／ｍ２ 、最大発光輝度１２００ｃｄ／ｍ２ 、５Ｖの時の発光効率０．３ｌｍ／Ｗの橙色発光が得られた。次に３ｍＡ／ｃｍ２ の電流密度で、この素子を連続して発光させた寿命試験の結果、初期輝度の１／２以上の発光が５０００時間以上保持された。
【００８２】
実施例４０
洗浄したＩＴＯ電極付きガラス板上に、化合物（２１）を蒸着し膜厚８０ｎｍの正孔注入層を作成し、次いで、Ａｌｑ３を蒸着し、膜厚２０ｎｍの発光層を得た。その上に、マグネシウムと銀を１０：１で混合した合金で膜厚１００ｎｍの電極を形成して有機ＥＬ素子を得た。正孔注入層および発光層は１０−６Ｔｏｒｒの真空中で、基板温度室温の条件下で蒸着した。この素子は直流電圧５Ｖで発光輝度８０ｃｄ／ｍ２ 、最大発光輝度８０００ｃｄ／ｍ２ 、５Ｖの時の発光効率１．１ｌｍ／Ｗの発光が得られた。次に３ｍＡ／ｃｍ２ の電流密度で、この素子を連続して発光させた寿命試験の結果、初期輝度の１／２以上の発光が３０００時間以上保持された。
【００８３】
実施例４１
洗浄したＩＴＯ電極付きガラス板上に、ＴＰＤを蒸着して膜厚５０ｎｍの正孔注入層を作製し、次いで、Ａｌｑ３を蒸着し、膜厚２０ｎｍの発光層を得た。化合物（２８）を蒸着し膜厚６０ｎｍの電子注入層を作成し、その上に、マグネシウムと銀を１０：１で混合した合金で膜厚１００ｎｍの電極を形成して有機ＥＬ素子を得た。正孔注入層および発光層は１０−６Ｔｏｒｒの真空中で、基板温度室温の条件下で蒸着した。この素子は直流電圧５Ｖで発光輝度１００ｃｄ／ｍ２ 、最大発光輝度６０００ｃｄ／ｍ２ 、５Ｖの時の発光効率０．９ｌｍ／Ｗの発光が得られた。次に３ｍＡ／ｃｍ２ の電流密度で、この素子を連続して発光させた寿命試験の結果、初期輝度の１／２以上の発光が３０００時間以上保持された。
【００８４】
実施例４２
洗浄したＩＴＯ電極付きガラス板上に、ＴＰＤを真空蒸着して、膜厚２０ｎｍの正孔注入層を得た。次いで、Ｎ，Ｎ’ ―（４―メチルフェニル）―Ｎ，Ｎ’ ―（４−ｎ−ブチルフェニル）―フェナントレン―９，１０―ジアミンと化合物（１）とを１００：１の重量比でを蒸着し膜厚４０ｎｍの発光層を作成し、Ａｌｑ３を蒸着し、膜厚１０ｎｍの電子注入層を得た。その上に、マグネシウムと銀を１０：１で混合した合金で膜厚１００ｎｍの電極を形成して有機ＥＬ素子を得た。正孔注入層および発光層は１０−６Ｔｏｒｒの真空中で、基板温度室温の条件下で蒸着した。この素子は直流電圧５Ｖで発光輝度１５０ｃｄ／ｍ２ 、最大発光輝度１４０００ｃｄ／ｍ２ 、５Ｖの時の発光効率２．８ｌｍ／Ｗの黄色発光が得られた。次に３ｍＡ／ｃｍ２ の電流密度で、この素子を連続して発光させた寿命試験の結果、初期輝度の１／２以上の発光が１００００時間以上保持された。
【００８５】
実施例４３
洗浄したＩＴＯ電極付きガラス板上に、４，４’，４”−トリス［Ｎ−（３−メチルフェニル）−Ｎ−フェニルアミノ］トリフェニルアミンを真空蒸着して、膜厚４０ｎｍの正孔注入層を得た。次いで、４，４’−ビス［Ｎ−（１−ナフチル）−Ｎ−フェニルアミノ］ビフェニル（α−ＮＰＤ）を真空蒸着して、膜厚１０ｎｍの第二正孔注入層を得た。さらに、化合物（１）を真空蒸着して、膜厚３０ｎｍの発光層を作成し、さらにビス（２−メチル−８−ヒドロキシキノリナト）（１−フェノラート）ガリウム錯体を真空蒸着して膜厚３０ｎｍの電子注入層を作成し、その上に、アルミニウムとリチウムを２５：１で混合した合金で膜厚１５０ｎｍの電極を形成して、有機ＥＬ素子を得た。正孔注入層および発光層は１０−６Ｔｏｒｒの真空中で、基板温度室温の条件下で蒸着した。この素子は、直流電圧５Ｖで発光輝度２１０（ｃｄ／ｍ２）、最大発光輝度２９０００（ｃｄ／ ｍ２）、発光効率２．８（ｌｍ／Ｗ）の橙色発光が得られた。
【００８６】
実施例４４〜９０
発光層に、化合物（１）に換え、表４で示した化合物を使用する以外は実施例１と同様の方法で有機ＥＬ素子を作製した。この素子は表４に示す発光特性を示した。
【００８７】
【表４】
実施例９１
洗浄したＩＴＯ電極付きガラス板上に、化合物（３）、Ａｌｑ３、ＴＰＤ、ポリカーボネート樹脂（ＰＣ−Ａ）を３：２：３：８の重量比でテトラヒドロフランに溶解させ、スピンコーティング法により膜厚１００ｎｍの発光層を得た。その上に、マグネシウムと銀を１０：１で混合した合金で膜厚１５０ｎｍの電極を形成し有機ＥＬ素子を得た。この素子は直流電圧５Ｖで発光輝度１２ｃｄ／ｍ２ 、最大発光輝度３１００ｃｄ／ｍ２ 、５Ｖの時の発光効率０．５ｌｍ／Ｗの発光が得られた。次に３ｍＡ／ｃｍ２ の電流密度で、この素子を連続して発光させた寿命試験の結果、初期輝度の１／２以上の発光が３０００時間以上保持された。
【００９０】
実施例９２
洗浄したＩＴＯ電極付きガラス板上に、α−ＮＰＤを真空蒸着して、膜厚３０ｎｍの正孔注入層を得た。次いで、ホスト材料としてのビス（２−メチル−８−ヒドロキシキノリナト）（１−フェノラート）ガリウム錯体とドーピング材料としての化合物（１）とを５０：１の重量比で蒸着して、膜厚３０ｎｍの発光層を作成し、さらに真空蒸着法により［２−（４−ｔｅｒｔ−ブチルフェニル）−５−（ビフェニル）−１，３，４−オキサジアゾール］の膜厚２０ｎｍの電子注入層を得た。その上に、マグネシウムと銀を１０：１で混合した合金で膜厚１５０ｎｍの電極を形成して有機ＥＬ素子を得た。正孔注入層、発光層、電子注入層および陰極は、１０−６Ｔｏｒｒの真空中で、基板温度室温の条件下で蒸着した。この素子は直流電圧５Ｖで発光輝度３３０ｃｄ／ｍ２ 、最大発光輝度５３０００ｃｄ／ｍ２ 、５Ｖの時の発光効率４．３ｌｍ／Ｗの黄色発光が得られた。次に３ｍＡ／ｃｍ２ の電流密度で、この素子を連続して発光させた寿命試験の結果、初期輝度の１／２以上の発光が１００００時間以上保持された。
【００９１】
実施例９３〜１０３
発光層に、ホスト材料とドーピング材料として表５で示した化合物を使用する以外は実施例２４と同様の方法で有機ＥＬ素子を作製した。この素子は表５に示す発光特性を示した。
【００９２】
【表５】
本発明の有機ＥＬ素子は発光効率、発光輝度の向上と長寿命化を達成するものであり、併せて使用される発光材料、ドーピング材料、正孔注入材料、電子注入材料、増感剤、樹脂、電極材料等および素子作製方法を限定するものではない。
【発明の効果】
本発明により、従来に比べて黄色〜赤色の波長領域で高発光効率、高輝度であり、長寿命の有機ＥＬ素子を得ることができた。
【図面の簡単な説明】
【図１】化合物（１）の赤外線吸収スペクトル図[0001]
[Industrial applications]
The present invention relates to an organic electroluminescence (EL) element used for a flat light source and a display.
[0002]
[Prior art]
2. Description of the Related Art An EL element using an organic substance is expected to be used as a solid-state light-emitting inexpensive large-area full-color display element, and many developments have been made. In general, an EL is composed of a light emitting layer and a pair of counter electrodes sandwiching the light emitting layer.
In light emission, when an electric field is applied between both electrodes, electrons are injected from the cathode side, and holes are injected from the anode side. In addition, the electrons recombine with holes in the light emitting layer, and emit energy as light when the energy level returns from the conduction band to the valence band.
[0003]
The conventional organic EL element has a higher driving voltage and lower light emission luminance and light emission efficiency than the inorganic EL element. In addition, the characteristics deteriorated remarkably, and practical use has not been achieved.
In recent years, an organic EL device formed by laminating a thin film containing an organic compound having a high fluorescence quantum efficiency and emitting light at a low voltage of 10 V or less has been reported and attracted attention (Applied Physics Letters, vol. 51, p. 913). 1987).
In this method, high-luminance green light emission is obtained by using a metal chelate complex for a phosphor layer and an amine compound for a hole injection layer, and the luminance is 100 cd / m 2 at a DC voltage of 6 to 7 V. 2 And a maximum luminous efficiency of 1.5 lm / W, which is close to the practical range. However, organic EL devices up to now have improved light emission intensity in green due to the improved structure, but do not yet have sufficient light emission luminance in the yellow to red wavelength range.
[0004]
There is disclosed a technique in which a light emitting layer is formed by doping a host material with a guest material in order to obtain light emission in a yellow to red wavelength range from an organic EL element. For example, an organic EL device in which a light emitting layer is doped with a tris (8-hydroxyquinoline) aluminum complex as a host material and a coumarin dye or a DCM dye as a fluorescent guest material (Journal of Applied Physics, Vol. 65, p. 3610) 1989), but the luminous efficiency of these organic EL devices was not sufficient. Further, an organic EL device emitting red light by doping a phthalocyanine compound with a tris (8-hydroxyquinoline) aluminum complex as a host material in a light emitting layer has been disclosed (Japanese Patent Application Laid-Open No. 07-288284). However, the initial luminous efficiencies of these organic EL devices are not yet sufficient, and when they emit light continuously, the deterioration is remarkable, which poses a serious problem in practical use.
[0005]
[Problems to be solved by the invention]
An object of the present invention is to provide an organic EL device having high luminous efficiency in a yellow to red spectral region and excellent luminous life. As a result of intensive studies by the present inventors, it has been found that the luminous efficiency in the yellow to red spectral region of an organic EL device using at least one organic EL device material of the compounds represented by the general formulas [1] to [5]. And the luminescent lifetime was excellent, and the present invention was achieved.
[0006]
[Means for Solving the Problems]
That is, the present invention is an organic electroluminescent device material represented by the following general formula [1].
General formula [1]
Embedded image
[0007]
Further, the present invention is an organic electroluminescent device material represented by the following general formula [2].
General formula [2]
Embedded image
[0008]
Furthermore, the present invention is an organic electroluminescent device material represented by the following general formula [3].
General formula [3]
Embedded image
[0009]
Further, the present invention is an organic electroluminescent device material represented by the following general formula [4].
General formula [4]
Embedded image
[0010]
Further, the present invention is an organic electroluminescent device material represented by the following general formula [5].
General formula [5]
Embedded image
[0011]
Furthermore, the present invention relates to an organic electroluminescence device in which a plurality of organic compound thin films including a light-emitting layer are formed between a pair of electrodes, wherein at least one layer is a layer containing the organic electroluminescence device material described above. is there.
[0012]
Furthermore, the present invention provides an organic electroluminescent device in which a plurality of organic compound thin films including a light emitting layer are formed between a pair of electrodes, wherein the light emitting layer is a layer containing the organic electroluminescent device material described above. It is.
Further, the present invention provides In an organic electroluminescent element formed with a plurality of organic compound thin films including a light emitting layer between a pair of electrodes, The light emitting layer is a host material and a doping material, and the doping material is the organic electroluminescence device material described above.
Further, the present invention provides a light-emitting layer cathode And an organic electroluminescence device characterized in that one to four electron injection layers are formed between the two.
Further, the present invention provides a light-emitting layer anode And an organic electroluminescence device characterized in that one to four hole injection layers are formed between the two.
[0016]
BEST MODE FOR CARRYING OUT THE INVENTION
R of the compound represented by the general formulas [1] to [5] 1 ~ R 56 Are each independently a hydrogen atom, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkylthio group, Substituted or unsubstituted arylthio group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted monocyclic group, substituted or unsubstituted fused polycyclic group, substituted or unsubstituted amino group, substituted or unsubstituted alkyl group Represents an amino group or a substituted or unsubstituted arylamino group.
[0017]
R of the compound represented by the general formulas [1] to [5] in the present invention 1 ~ R 56 Specific examples of the halogen atom include chlorine, bromine, iodine, and fluorine, and specific examples of the alkyl group include methyl, ethyl, propyl, butyl, sec-butyl, tert-butyl, and pentyl. Group, hexyl group, heptyl group, octyl group, stearyl group, trichloromethyl group and the like, and specific examples of cycloalkyl include a cyclopentane ring and a cyclohexane ring.
[0018]
R of the compound represented by the general formulas [1] to [5] in the present invention 1 ~ R 56 Examples of the alkoxy group include methoxy, ethoxy, n-butoxy, tert-butoxy, trichloromethoxy, trifluoroethoxy, pentafluoropropoxy, 2,2,3,3-tetrafluoropropoxy Group, 1,1,1,3,3,3-hexafluoro-2-propoxy group, 6- (perfluoroethyl) hexyloxy group and the like. Specific examples of the aryloxy group include a phenoxy group and a p- Examples include a nitrophenoxy group, a p-tert-butylphenoxy group, a 3-fluorophenoxy group, a pentafluorophenyl group, and a 3-trifluoromethylphenoxy group.
[0019]
R of the compound represented by the general formulas [1] to [5] in the present invention 1 ~ R 56 Specific examples of the alkylthio group include methylthio group, ethylthio group, tert-butylthio group, hexylthio group, octylthio group, and trifluoromethylthio group. Specific examples of the arylthio group include phenylthio group and p-nitro group. Examples include a phenylthio group, a p-tert-butylphenylthio group, a 3-fluorophenylthio group, a pentafluorophenylthio group, and a 3-trifluoromethylphenylthio group.
[0020]
R of the compound represented by the general formulas [1] to [5] in the present invention 1 ~ R 56 Examples of the monocyclic group include phenyl, thionyl, thiophenyl, furanyl, pyrrolyl, imidazolyl, pyrazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, oxazolyl, thiazolyl, oxadiazolyl, and thiadiazolyl. And imidadiazolyl groups.
[0021]
R of the compound represented by the general formulas [1] to [5] in the present invention 1 ~ R 56 Examples of condensed polycyclic groups include naphthyl, anthryl, phenanthryl, fluorenyl, pyrenyl, indole, purine, quinoline, isoquinoline, sinoline, quinoxaline, benzoquinoline, fluorenone, and carbazole groups. , Oxazole group, oxadiazole group, thiazole group, thiadiazole group, triazole group, imidazole group, benzoxazole group, benzothiazole group, benzotriazole group, benzimidazole group, bisbenzooxazole group, bisbenzothiazole group, bisbenzimidazole Group, anthrone group, dibenzofuran group, dibenzothiophene group, anthraquinone group, acridone group, phenothiazine group, pyrrolidine group, dioxane group, morpholine group and the like.
[0022]
R of the compound represented by the general formulas [1] to [5] in the present invention 1 ~ R 56 Specific examples of the amino group include amino group, bis (acetoxymethyl) amino group, bis (acetoxyethyl) amino group, bisacetoxypropyl) amino group, bis (acetoxybutyl) amino group and the like. Specific examples include an ethylamino group, a diethylamino group, a dipropylamino group, a dibutylamino group, a benzylamino group and a dibenzylamino group. Specific examples of the arylamino group include a phenylamino group and (3-methylphenyl) Examples include an amino group and a (4-methylphenyl) amino group. Specific examples of the phenylamino group include a phenylamino group, a phenylmethylamino group, a diphenylamino group, a ditolylamino group, a dibiphenylamino group, and a di (4-methyl Biphenyl) amino group, di (3-methylphenyl) amino group, di (4 Methylphenyl) amino group, naphthylphenylamino group, a bis [4- (α, α'- dimethylbenzyl) phenyl] amino group.
[0023]
Also, R 1 ~ R 56 May be bonded to each other to form a saturated or unsaturated ring such as a phenyl ring, a naphthyl ring, an anthryl ring, a pyrenyl ring, a carbazole ring, a benzopyranyl ring, and a cyclohexyl ring.
[0024]
Q of the compounds of the general formulas [1] to [5] 1 , Q 2 Each independently represents a hydrogen atom, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted monocyclic group, or a substituted or unsubstituted fused polycyclic group. Specific examples of the alkyl group, the monocyclic group, and the condensed polycyclic group include the above-mentioned R 1 ~ R 56 And the monocyclic group and the condensed polycyclic group described in the above.
[0025]
A of the compound of the general formula [1] 1 ~ A 4 Is each independently a substituted or unsubstituted alkyl group, a substituted or unsubstituted monocyclic group, a substituted or unsubstituted fused polycyclic group, or A 1 And A 2 , A 3 And A 4 Represents a condensed polycyclic group having a nitrogen atom as a bond. Specific examples of the alkyl group, the monocyclic group, and the condensed polycyclic group include the above-mentioned R 1 ~ R 56 And the monocyclic group and the condensed polycyclic group described in the above.
[0026]
A of the compound of the general formula [1] 1 And A 2 , A 3 And A 4 May be combined with each other to form a condensed polycyclic group containing a nitrogen atom such as a carbazole group, a phenothiazine group, or an acridone group.
[0027]
X of the compound represented by the general formulas [3] and [4] in the present invention 1 ~ X 4 Is independently O, S, C = O, CZ 1 = CZ 2 , C≡C, SO 2 , (CH 2 ) X-O- (CH 2 ) Y represents a substituted or unsubstituted alkylene group or a substituted or unsubstituted aliphatic ring residue. Here, x and y each represent a positive integer of 0 to 20; however, x + y = 0 does not occur. Also, Z 1 And Z 2 Each independently represents a hydrogen atom, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted monocyclic group, or a substituted or unsubstituted fused polycyclic group. Specific examples of the alkyl group, the monocyclic group, and the condensed polycyclic group include the above-mentioned R 1 ~ R 56 And the monocyclic group and the condensed polycyclic group described in the above.
As a substituted or unsubstituted alkylene group, an alkylene group having 1 to 20 carbon atoms or a substituted product thereof, as a substituted or unsubstituted aliphatic ring residue, a cyclopentyl ring, a cyclohexyl ring, a methylcyclohexyl ring, a cycloheptyl ring, etc. Examples thereof include a divalent residue of an aliphatic ring having 5 to 7 carbon atoms.
X 1 ~ X 4 Is a substituted alkylene group or a substituent of a substituted aliphatic ring residue of R 1 ~ R 56 There are substituents indicated by. X 1 ~ X 4 Preferred as the substituted alkylene group are 2-phenylisopropylene, dichloromethylene, difluoromethylene, benzylene, α-phenoxybenzylene, α, α′-dimethylbenzylene, α-benzyloxybenzylene. And the like.
[0028]
Y of the compound represented by the general formula [5] in the present invention 1 ~ Y 8 Represents a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted monocyclic group having 6 to 16 carbon atoms, or a condensed polycyclic group. Specific examples of the alkyl group, the monocyclic group, and the condensed polycyclic group include the above-mentioned R 1 ~ R 56 And the monocyclic group and the condensed polycyclic group described in the above.
[0029]
Q in the present invention 1 , Q 2 An alkyl group, a monocyclic group, a condensed polycyclic group, and A 1 ~ A 4 Alkyl group, monocyclic group, fused polycyclic group, A 1 And A 2 , A 3 And A 4 Is integrated with a condensed polycyclic group having a nitrogen atom as a bond, and R 1 ~ R 56 , An alkyl group, an alkoxy group, an aryloxy group, an alkylthio group, an arylthio group, a cycloalkyl group, a monocyclic group, a condensed polycyclic group, an amino group, an alkylamino group, an arylamino group, and X 1 ~ X 2 An alkylene group, and Y 1 ~ Y 8 Alkyl group, monocyclic group, fused polycyclic group, Z 1 And Z 2 Representative examples of the group which may be substituted with an alkyl group, a monocyclic group or a condensed polycyclic group include the following substituents.
[0030]
Halogen atoms include chlorine, bromine, iodine and fluorine.
Examples of the alkyl group include a methyl group, an ethyl group, a propyl group, a butyl group, a sec-butyl group, a tert-butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a stearyl group, and a trichloromethyl group. Examples of the alkyl include a cyclopentane ring, a cyclohexane ring, a 1,3-cyclohexadienyl group, a 2-cyclopenten-1-yl group, and a 2,4-cyclopentadiene-1-ylenyl group.
[0031]
Examples of the alkoxy group include a methoxy group, an ethoxy group, an n-butoxy group, a tert-butoxy group, a trichloromethoxy group, a trifluoroethoxy group, a pentafluoropropoxy group, a 2,2,3,3-tetrafluoropropoxy group, There are a 1,1,3,3,3-hexafluoro-2-propoxy group, a 6- (perfluoroethyl) hexyloxy group and the like, and examples of the aryloxy group include a phenoxy group, a p-nitrophenoxy group, and a p-tert. -Butylphenoxy group, 3-fluorophenoxy group, pentafluorophenyl group, 3-trifluoromethylphenoxy group and the like.
[0032]
Examples of the alkylthio group include a methylthio group, an ethylthio group, a tert-butylthio group, a hexylthio group, an octylthio group, and a trifluoromethylthio group. Examples of the arylthio group include a phenylthio group, a p-nitrophenylthio group, and a p-tert-butyl group. Examples include a phenylthio group, a 3-fluorophenylthio group, a pentafluorophenylthio group, and a 3-trifluoromethylphenylthio group.
[0033]
Examples of the aryl group include a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthryl group, a phenanthryl group, a fluorenyl group, and a pyrenyl group.Examples of the heterocyclic group include a pyrrole group, a pyrroline group, a pyrazole group, and a pyrazoline group. , Imidazole group, triazole group, pyridine group, pyridazine group, pyrimidine group, pyrazine group, triazine group, indole group, purine group, quinoline group, isoquinoline group, sinoline group, quinoxaline group, benzoquinoline group, fluorenone group, carbazole group, Oxazole group, oxadiazole group, thiazole group, thiadiazole group, triazole group, imidazole group, benzoxazole group, benzothiazole group, benzotriazole group, benzimidazole group, bisbenzoxazole group, bisbenzothia Lumpur group, bisbenzoimidazole group, anthrone group, dibenzofuran group, a dibenzothiophene group, anthraquinone group, acridone group, a phenothiazine group, a pyrrolidine group, dioxane group, a morpholine group.
[0034]
Examples of the amino group include an amino group, a bis (acetoxymethyl) amino group, a bis (acetoxyethyl) amino group, ( Examples include an acetoxypropyl) amino group and a bis (acetoxybutyl) amino group. Specific examples of the alkylamino group include an ethylamino group, a diethylamino group, a dipropylamino group, a dibutylamino group, and a benzylamino group. , Examples of the arylamino group include a phenylamino group, a (3-methylphenyl) amino group, a (4-methylphenyl) amino group, a phenylmethylamino group, a diphenylamino group, and a bis ( 4-phenoxyphenyl) amino group, bis (4-biphenyl) amino group, bis [4- (4-tolyl) phenyl] amino group, bis (3-methylphenyl) amino group, bis (4-methylphenyl) amino group , A naphthylphenylamino group, a bis [4- (α, α'-dimethylbenzyl) phenyl] amino group and the like.
[0035]
In the present invention, the compounds represented by the general formulas [1] to [5] can be synthesized, for example, by the following method. It can be obtained by heating the following general formulas [6] and [7] in tetrahydrofuran in the presence of titanium tetrachloride and zinc powder. Hereinafter, typical examples of the compound of the present invention are specifically shown in Table 1, but the present invention is not limited to the following typical examples.
Embedded image
[0036]
[Table 1]
The compounds represented by the general formulas [1] to [5] are contained in one molecule. Oh It has a refining site (> C = C <). According to the geometric isomer of the olefin moiety, the general formula [1] ~ [5] The compound represented by the formula has a combination of a cis-form and a trans-form, but the compound of the present invention may be any of them and may be a mixture thereof.
[0048]
An organic EL device is a single or multilayer organic EL device between an anode and a cathode. Compound This is an element with a thin film formed. In the case of a single layer type, a light emitting layer is provided between the anode and the cathode. The light-emitting layer contains a light-emitting material and may further contain a hole-injection material or an electron-injection material for transporting holes injected from an anode or electrons injected from a cathode to the light-emitting material. The multilayer type includes (anode / hole injection layer / emission layer / cathode), (anode / emission layer / electron injection layer / cathode), and (anode / hole injection layer / emission layer / electron injection layer / cathode) There is an organic EL element stacked in a configuration. The compounds represented by the general formulas [1] to [5] of the present invention are compounds having strong fluorescence in a solid state and have excellent electroluminescence properties, and thus can be used in a light emitting layer as a light emitting material. Further, by doping the compounds of the general formulas [1] to [5] as a doping material in the light emitting layer at an optimum ratio in the light emitting layer, it is possible to select a high light emitting efficiency and an optimum light emitting wavelength. . Further, the compounds represented by the general formulas [1] to [5] can transport carriers such as holes or electrons, and thus can be used for a hole injection layer or an electron injection layer of an organic EL device. .
[0049]
An organic EL device having high emission luminance can be obtained by using a compound represented by any one of the general formulas [1] to [5] as a doping material (guest material) as a host material of the light emitting layer. The compounds of the general formulas [1] to [5] are desirably contained in the light emitting layer in a range of 0.001% by weight to 50% by weight relative to the host material, and more preferably 0.01% by weight. A range of from 10 to 10% by weight is effective.
[0050]
Examples of the host material that can be used in combination with the compounds of the general formulas [1] to [5] include a quinoline metal complex, oxadiazole, benzothiazole metal complex, benzoxazole metal complex, benzimidazole metal complex, triazole, imidazole, oxazole, Oxadiazole, stilbene, butadiene, benzidine triphenylamine, styrylamine triphenylamine, diamine triphenylamine fluorenone, diaminoanthracene triphenylamine, diaminophenanthrene triphenylamine, anthraquinodimethane, diphenoquinone, thiadiazole , Tetrazole, perylenetetracarboxylic acid, fluorenylidenemethane, anthraquinodimethane, triphenylene, anthrone, etc. and their derivatives, and polyvinylidene Carbazole, polymeric materials such conductive polymers polysilane. The specific examples are shown in Table 2 below, but the present invention is not limited to the following representative examples.
[0051]
[Table 2]
It is also possible to change the emission color by using a further doping material together with the general formulas [1] to [5]. Examples of the doping material used in combination with the general formulas [1] to [5] include anthracene, naphthalene, phenanthrene, pyrene, tetracene, coronene, chrysene, fluorescein, perylene, phthaloperylene, naphthaloperylene, perinone, phthaloperinone, naphthaloperinone, diphenylbutadiene, and tetraphenylene. Phenylbutadiene, coumarin, oxadiazole, aldazine, bisbenzoxazoline, bisstyryl, pyrazine, cyclopentadiene, quinoline metal complex, aminoquinoline metal complex, imine, diphenylethylene, vinylanthracene, diaminocarbazole, pyran, thiopyran, polymethine, merocyanine , Imidazole chelated oxinoid compounds, quinacridone, rubrene, and the like, and derivatives thereof, but are not limited thereto. Not intended to be.
[0066]
For the light emitting layer, a hole injection material or an electron injection material can be used, if necessary, in addition to the light emitting material and the doping material.
[0067]
When the organic EL element has a multilayer structure, it is possible to prevent a decrease in luminance and life due to quenching. If necessary, a combination of two or more kinds of light emitting materials, doping materials, hole injection materials for carrier injection, and electron injection materials can be used. Further, each of the hole injection layer, the light emitting layer and the electron injection layer may be formed in a layer structure of two or more layers, and an element structure in which holes or electrons are efficiently injected from the electrode and transported in the layer. Selected.
[0068]
The conductive material used for the anode of the organic EL element preferably has a work function greater than 4 eV, and includes carbon, aluminum, vanadium, iron, cobalt, nickel, tungsten, silver, gold, platinum, palladium, and the like. These alloys, metal oxides such as tin oxide and indium oxide called ITO substrates and NESA substrates, and organic conductive resins such as polythiophene and polypyrrole are used.
The conductive material used for the cathode preferably has a work function of less than 4 eV, and magnesium, calcium, tin, lead, titanium, yttrium, lithium, ruthenium, manganese and the like and alloys thereof are used. Representative examples of the alloy include magnesium / silver, magnesium / indium, lithium / aluminum, and the like, but are not limited thereto. The ratio of the alloy is controlled by the heating temperature, atmosphere, and degree of vacuum, and an appropriate ratio is selected. The anode and the cathode may be formed of two or more layers if necessary.
[0069]
In an organic EL device, at least one of them is desirably sufficiently transparent in an emission wavelength region of the device in order to emit light efficiently. Further, it is desirable that the substrate is also transparent. The transparent electrode is set so as to secure a predetermined translucency by a method such as vapor deposition or sputtering using the above conductive material. It is desirable that the electrode on the light emitting surface has a light transmittance of 10% or more.
The substrate is not limited as long as it has mechanical and thermal strength and is transparent, but examples thereof include a glass substrate, a transparent resin such as a polyethylene plate, a polyether sulfone plate, and a polypropylene plate. .
[0070]
Each layer of the organic EL device according to the present invention can be formed by any of dry film forming methods such as vacuum evaporation and sputtering and wet film forming methods such as spin coating and dipping. The thickness is not particularly limited, but each layer needs to be set to an appropriate thickness. When the film thickness is too large, a large applied voltage is required to obtain a constant light output, and the efficiency is deteriorated. If the film thickness is too small, pinholes or the like are generated, and sufficient light emission luminance cannot be obtained even when an electric field is applied. The normal film thickness is suitably in the range of 5 nm to 10 μm, but is more preferably in the range of 10 nm to 0.2 μm.
In the case of the wet film forming method, the material for forming each layer is dissolved or dispersed in an appropriate solvent such as chloroform, tetrahydrofuran, dioxane or the like. Organic compounds A thin film is formed, and any solvent may be used. In any of the thin films, a suitable resin or additive may be used to improve film forming properties, prevent pinholes in the film, and the like.
Examples of such a resin include insulating resins such as polystyrene, polycarbonate, polyarylate, polyester, polyamide, polyurethane, polysulfone, polymethyl methacrylate, polymethyl acrylate, and cellulose; and photoconductive materials such as poly-N-vinyl carbazole and polysilane. And conductive resins such as polythiophene and polypyrrole. Examples of the additive include an antioxidant, an ultraviolet absorber, and a plasticizer.
[0072]
The hole injecting material has the ability to inject holes, has an excellent hole injecting effect on the light emitting layer or the light emitting material, and excites generated in the light emitting layer into the electron injecting layer or the electron injecting material. And a compound that prevents the migration of a compound and has an excellent ability to form a thin film. Specifically, phthalocyanine compounds, naphthalocyanine compounds, porphyrin compounds, oxadiazole, triazole, imidazole, imidazolone, imidazolethione, pyrazoline, pyrazolone, tetrahydroimidazole, oxazole, oxadiazole, hydrazone, acylhydrazone, poly There are arylalkanes, stilbenes, butadienes, benzidine-type triphenylamines, styrylamine-type triphenylamines, diamine-type triphenylamines, and derivatives thereof, and polymer materials such as polyvinylcarbazole, polysilane, and conductive polymers. However, the present invention is not limited to these.
[0073]
The electron injecting material has the ability to inject electrons, has an excellent electron injecting effect on the light emitting layer or the light emitting material, and excites generated in the light emitting layer into the hole injecting layer or the hole injecting material. Compounds that prevent migration and have excellent thin film forming ability can be used. For example, quinoline metal complex, oxadiazole, benzothiazole metal complex, benzoxazole metal complex, benzimidazole metal complex, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxadiazole, thiadiazole, tetrazole, perylenetetracarbon Examples include, but are not limited to, acids, fluorenylidenemethane, anthraquinodimethane, anthrone, and derivatives thereof. In addition, an electron accepting substance may be added to the hole injecting material, and an electron donating substance may be added to the electron injecting material for sensitization.
[0074]
In order to improve the stability of the organic EL device obtained according to the present invention with respect to temperature, humidity, atmosphere, etc., a protective layer may be provided on the surface of the device, or silicon oil or the like may be sealed to protect the entire device. It is possible.
[0075]
【Example】
Hereinafter, the present invention will be described in more detail with reference to Examples.
[0076]
Method for synthesizing compound (1)
Tetrahydrofuran ( THF ) 100 ml is placed in a flask, cooled by an ice bath, and 12 ml of titanium tetrachloride is added dropwise. Then, 9-formyl-9 '-[N , [N'-bis (4-methylphenyl)] amino-anthracene is charged into a flask, and 8 g of zinc powder is added little by little. After adding all, heat the flask, Return The reaction was carried out for 5 hours under flow. After completion of the reaction, water was added, and the resulting precipitate was collected by filtration. The precipitate was subjected to column purification using silica gel, and then to sublimation purification. The formation of the compound was confirmed by NMR, FD-MS, and IR. FIG. 1 shows an IR spectrum of the compound (1).
[0077]
Example 1
N, N '-(3-methylphenyl) -N, N'-diphenyl-1,1-biphenyl-4,4-diamine (TPD) is vacuum-deposited on the cleaned glass plate with the ITO electrode to form a film. A hole injection layer having a thickness of 20 nm was obtained. Next, the compound (1) was vapor-deposited to form a light-emitting layer having a thickness of 40 nm, and tris (8-hydroxyquinoline) aluminum complex (Alq3) was vapor-deposited to obtain a 30-nm-thick electron injection layer. An electrode having a thickness of 100 nm was formed thereon using an alloy in which magnesium and silver were mixed at a ratio of 10: 1 to obtain an organic EL device. The hole injection layer and the light emitting layer are 10 -6 Vapor deposition was performed in a Torr vacuum at a substrate temperature of room temperature. This device emits light at a luminance of 100 cd / m at a DC voltage of 5 V. 2 , Maximum emission luminance 20,000 cd / m 2 Orange light emission with a luminous efficiency of 2.5 lm / W at 5 V was obtained. Next, 3 mA / cm 2 As a result of a life test in which the device was continuously lit at a current density of, light emission of １ ／ or more of the initial luminance was maintained for 10000 hours or more.
[0078]
Examples 2-38
An organic EL device was produced in the same manner as in Example 1 except that the compounds shown in Table 3 were used in the light emitting layer instead of the compound (1). This device exhibited the emission characteristics shown in Table 3.
[0079]
[Table 3]
Example 39
A compound (12) was vacuum-deposited on the washed glass plate with an ITO electrode to form a 100-nm-thick light-emitting layer, and a 150-nm-thick alloy of magnesium and silver mixed at a ratio of 10: 1 was formed thereon. Was formed to obtain an organic EL device. The light emitting layer and the cathode are 10 -6 Vapor deposition was performed at a substrate temperature of room temperature in a vacuum of Torr. This device has a light emission luminance of 30 cd / m at a DC voltage of 5 V 2 ,
[0082]
Example 40
The compound (21) was vapor-deposited on the washed glass plate with an ITO electrode to form a hole injection layer having a thickness of 80 nm, and then Alq3 was vapor-deposited to obtain a light-emitting layer having a thickness of 20 nm. An electrode having a thickness of 100 nm was formed thereon using an alloy in which magnesium and silver were mixed at a ratio of 10: 1 to obtain an organic EL device. The hole injection layer and the light emitting layer are 10 -6 Vapor deposition was performed in a Torr vacuum at a substrate temperature of room temperature. This device has a luminance of 80 cd / m at a DC voltage of 5 V. 2 , Maximum emission luminance 8000 cd / m 2 Light emission with a luminous efficiency of 1.1 lm / W at 5 V was obtained. Next, 3 mA / cm 2 As a result of a life test in which the device was continuously lit at a current density of, light emission of 以上 or more of the initial luminance was maintained for 3,000 hours or more.
[0083]
Example 41
TPD was deposited on the washed glass plate with ITO electrodes to form a hole injection layer having a thickness of 50 nm, and then Alq3 was deposited to obtain a light emitting layer having a thickness of 20 nm. The compound (28) was vapor-deposited to form an electron injection layer having a thickness of 60 nm, and an electrode having a thickness of 100 nm was formed thereon using an alloy in which magnesium and silver were mixed at a ratio of 10: 1 to obtain an organic EL device. The hole injection layer and the light emitting layer are 10 -6 Vapor deposition was performed in a Torr vacuum at a substrate temperature of room temperature. This device emits light at a luminance of 100 cd / m at a DC voltage of 5 V. 2 , Maximum emission luminance 6000 cd / m 2 Light emission with a luminous efficiency of 0.9 lm / W at 5 V was obtained. Next, 3 mA / cm 2 As a result of a life test in which the device was continuously lit at a current density of, light emission of 以上 or more of the initial luminance was maintained for 3,000 hours or more.
[0084]
Example 42
TPD was vacuum-deposited on the washed glass plate with ITO electrodes to obtain a 20-nm-thick hole injection layer. Next, N, N '-(4-methylphenyl) -N, N'-(4-n-butylphenyl) -phenanthrene-9,10-diamine and compound (1) were added at a weight ratio of 100: 1. A light emitting layer having a thickness of 40 nm was formed by vapor deposition, and Alq3 was vapor deposited to obtain an electron injection layer having a thickness of 10 nm. An electrode having a thickness of 100 nm was formed thereon using an alloy in which magnesium and silver were mixed at a ratio of 10: 1 to obtain an organic EL device. The hole injection layer and the light emitting layer are 10 -6 Vapor deposition was performed in a Torr vacuum at a substrate temperature of room temperature. This device has a luminance of 150 cd / m at a DC voltage of 5 V. 2 , Maximum emission luminance 14000 cd / m 2 A yellow luminescence with a luminous efficiency of 2.8 lm / W at 5 V was obtained. Next, 3 mA / cm 2 As a result of a life test in which the device was continuously lit at a current density of, light emission of １ ／ or more of the initial luminance was maintained for 10000 hours or more.
[0085]
Example 43
Place 4 on the cleaned glass plate with ITO electrode. , 4 ' , 4 "-Tris [N- (3-methylphenyl) -N-phenylamino] triphenylamine was vacuum-deposited to obtain a hole injection layer having a thickness of 40 nm. Then, 4,4'-bis [N -(1-Naphthyl) -N-phenylamino] biphenyl (α-NPD) was vacuum-deposited to obtain a 10-nm-thick second hole-injection layer, and the compound (1) was further vacuum-deposited. A light emitting layer having a thickness of 30 nm was formed, and a bis (2-methyl-8-hydroxyquinolinato) (1-phenolate) gallium complex was further vacuum-deposited to form a 30 nm-thick electron injection layer. An electrode having a thickness of 150 nm was formed using an alloy in which aluminum and lithium were mixed at a ratio of 25: 1 to obtain an organic EL device. -6 Vapor deposition was performed in a Torr vacuum at a substrate temperature of room temperature. This device has an emission luminance of 210 (cd / m) at a DC voltage of 5 V. 2 ), Maximum emission luminance 29000 (cd / m 2 ), And orange light emission with a luminous efficiency of 2.8 (lm / W) was obtained.
[0086]
Examples 44 to 90
An organic EL device was manufactured in the same manner as in Example 1 except that the compounds shown in Table 4 were used in the light emitting layer instead of the compound (1). This device exhibited the emission characteristics shown in Table 4.
[0087]
[Table 4]
Example 91
Compound (3), Alq3, TPD, and polycarbonate resin (PC-A) were dissolved in tetrahydrofuran at a weight ratio of 3: 2: 3: 8 on a washed glass plate with an ITO electrode, and the film thickness was 100 nm by spin coating. Was obtained. An electrode having a thickness of 150 nm was formed thereon using an alloy in which magnesium and silver were mixed at a ratio of 10: 1 to obtain an organic EL device. This device emits light at a luminance of 12 cd / m at a DC voltage of 5 V. 2 , Maximum light emission luminance 3100 cd / m 2 Light emission with a luminous efficiency of 0.5 lm / W at 5 V was obtained. Next, 3 mA / cm 2 As a result of a life test in which the device was continuously lit at a current density of, light emission of 以上 or more of the initial luminance was maintained for 3,000 hours or more.
[0090]
Example 92
Α-NPD was vacuum-deposited on the washed glass plate with ITO electrodes to obtain a hole injection layer having a thickness of 30 nm. Next, a bis (2-methyl-8-hydroxyquinolinato) (1-phenolate) gallium complex as a host material and a compound (1) as a doping material are deposited at a weight ratio of 50: 1, and a film thickness of 30 nm. And a 20 nm-thick electron injection layer of [2- (4-tert-butylphenyl) -5- (biphenyl) -1,3,4-oxadiazole] is obtained by vacuum evaporation. Was. An electrode having a thickness of 150 nm was formed thereon using an alloy in which magnesium and silver were mixed at a ratio of 10: 1 to obtain an organic EL device. The hole injection layer, the light emitting layer, the electron injection layer and the cathode -6 Vapor deposition was performed in a Torr vacuum at a substrate temperature of room temperature. This device emits 330 cd / m light at a DC voltage of 5 V. 2 , Maximum light emission luminance 53000 cd / m 2 A yellow luminescence with a luminous efficiency of 4.3 lm / W at 5 V was obtained. Next, 3 mA / cm 2 As a result of a life test in which the device was continuously lit at a current density of, light emission of １ ／ or more of the initial luminance was maintained for 10000 hours or more.
[0091]
Examples 93 to 103
An organic EL device was manufactured in the same manner as in Example 24 except that the compounds shown in Table 5 were used as the host material and the doping material in the light emitting layer. This device exhibited the emission characteristics shown in Table 5.
[0092]
[Table 5]
The organic EL device of the present invention achieves improvement in luminous efficiency, luminous brightness and long life, and is used together with a luminescent material, a doping material, a hole injection material, an electron injection material, a sensitizer, and a resin. It does not limit the electrode material and the like and the element manufacturing method.
【The invention's effect】
According to the present invention, it is possible to obtain an organic EL device having high luminous efficiency and high luminance in a yellow to red wavelength region and a long life as compared with the related art.
[Brief description of the drawings]
FIG. 1 is an infrared absorption spectrum of compound (1).
Claims (10)
一般式［１］
General formula [1]
一般式［２］
General formula [2]
一般式［３］
General formula [3]
一般式［４］
General formula [4]
一般式［５］
General formula [5]
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| JP4003299B2 (en) * | 1998-07-06 | 2007-11-07 | 三菱化学株式会社 | Organic electroluminescence device |
| KR100868144B1 (en) * | 2000-09-01 | 2008-11-10 | 이데미쓰 고산 가부시키가이샤 | Novel styryl compounds and organic electroluminescent devices |
| KR20010044090A (en) * | 2000-09-06 | 2001-06-05 | 박종욱 | A compound for electrolumines cene display containing carbazol and stilbene, and the high efficiency electroluminescene display using thereof |
| JP4220669B2 (en) | 2000-12-26 | 2009-02-04 | 出光興産株式会社 | Organic electroluminescence device |
| EP1390664A4 (en) * | 2001-03-30 | 2008-01-02 | Univ Arizona | Materials, methods, and uses for photochemical generation of acids and/or radical species |
| JP4356363B2 (en) * | 2002-11-26 | 2009-11-04 | 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 having the same |
| JP3848307B2 (en) | 2003-06-27 | 2006-11-22 | キヤノン株式会社 | Aminoanthryl derivative-substituted compound and organic light-emitting device using the same |
| JP3848306B2 (en) | 2003-06-27 | 2006-11-22 | キヤノン株式会社 | Anthryl derivative-substituted compound and organic light emitting device using the same |
| JP4035482B2 (en) | 2003-06-27 | 2008-01-23 | キヤノン株式会社 | Substituted anthryl derivative and organic light emitting device using the same |
| JP3840235B2 (en) | 2003-06-27 | 2006-11-01 | キヤノン株式会社 | Organic light emitting device |
| CN100335462C (en) * | 2003-09-05 | 2007-09-05 | 清华大学 | Carbazole derivative and its application in electroluminescent device |
| JP4955971B2 (en) | 2004-11-26 | 2012-06-20 | キヤノン株式会社 | Aminoanthryl derivative-substituted pyrene compound and organic light-emitting device |
| JP4599142B2 (en) | 2004-11-26 | 2010-12-15 | キヤノン株式会社 | Organic light emitting device |
| DE102005029574A1 (en) * | 2005-06-25 | 2006-12-28 | Technische Universität Darmstadt | New oligo-tetracene compound, useful as semiconductor in organic field-effect transistors, organic light emitting diodes, sensors and organic solar cells |
| JP4963214B2 (en) * | 2005-11-03 | 2012-06-27 | 株式会社半導体エネルギー研究所 | Stilbene derivative, material for light emitting element, light emitting element, light emitting device and electronic device |
| JP5100146B2 (en) | 2006-02-28 | 2012-12-19 | キヤノン株式会社 | Optical element and optical element manufacturing method |
| JP2007230951A (en) | 2006-03-02 | 2007-09-13 | Canon Inc | Silyl compound, luminescent material and organic electroluminescent element using the same |
| JP2007208289A (en) * | 2007-03-30 | 2007-08-16 | Idemitsu Kosan Co Ltd | Organic electroluminescent device |
| KR100974562B1 (en) * | 2007-12-31 | 2010-08-06 | 다우어드밴스드디스플레이머티리얼 유한회사 | Novel organic electroluminescent compounds and organic electroluminescent device using the same |
| JP2009062377A (en) * | 2008-09-29 | 2009-03-26 | Idemitsu Kosan Co Ltd | Organic electroluminescent element |
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