JPH061973A - Organic electroluminescent element - Google Patents
Organic electroluminescent elementInfo
- Publication number
- JPH061973A JPH061973A JP4159575A JP15957592A JPH061973A JP H061973 A JPH061973 A JP H061973A JP 4159575 A JP4159575 A JP 4159575A JP 15957592 A JP15957592 A JP 15957592A JP H061973 A JPH061973 A JP H061973A
- Authority
- JP
- Japan
- Prior art keywords
- layer
- compound
- compounds
- injection layer
- derivatives
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 150000002894 organic compounds Chemical class 0.000 claims abstract description 9
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 125000003118 aryl group Chemical group 0.000 claims abstract description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 3
- 239000000126 substance Substances 0.000 claims description 21
- 238000005401 electroluminescence Methods 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 238000002347 injection Methods 0.000 abstract description 28
- 239000007924 injection Substances 0.000 abstract description 28
- 150000001875 compounds Chemical class 0.000 abstract description 23
- 239000000758 substrate Substances 0.000 abstract description 12
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- -1 methoxy, ethoxy Chemical group 0.000 description 25
- 229910052751 metal Inorganic materials 0.000 description 12
- 239000010408 film Substances 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 239000002184 metal Substances 0.000 description 8
- 238000005406 washing Methods 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 229910045601 alloy Inorganic materials 0.000 description 4
- 239000000956 alloy Substances 0.000 description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 4
- 150000002739 metals Chemical class 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000004793 Polystyrene Substances 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
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 3
- 238000005266 casting Methods 0.000 description 3
- 150000004866 oxadiazoles Chemical class 0.000 description 3
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 3
- 238000004528 spin coating Methods 0.000 description 3
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 3
- 229910052721 tungsten Inorganic materials 0.000 description 3
- 239000010937 tungsten Substances 0.000 description 3
- 238000007740 vapor deposition Methods 0.000 description 3
- UWRZIZXBOLBCON-VOTSOKGWSA-N (e)-2-phenylethenamine Chemical class N\C=C\C1=CC=CC=C1 UWRZIZXBOLBCON-VOTSOKGWSA-N 0.000 description 2
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 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
- 230000000052 comparative effect Effects 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 229940083761 high-ceiling diuretics pyrazolone derivative Drugs 0.000 description 2
- 238000007602 hot air drying Methods 0.000 description 2
- 150000007857 hydrazones Chemical class 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229910052750 molybdenum Inorganic materials 0.000 description 2
- 239000011733 molybdenum Substances 0.000 description 2
- DGBWPZSGHAXYGK-UHFFFAOYSA-N perinone Chemical class C12=NC3=CC=CC=C3N2C(=O)C2=CC=C3C4=C2C1=CC=C4C(=O)N1C2=CC=CC=C2N=C13 DGBWPZSGHAXYGK-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
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 2
- 150000003219 pyrazolines Chemical class 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- 239000011135 tin Substances 0.000 description 2
- 229910052718 tin Inorganic materials 0.000 description 2
- 238000002834 transmittance Methods 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N vinyl-ethylene Natural products C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- BIXMBBKKPTYJEK-UHFFFAOYSA-N 1,3-benzoxazin-2-one Chemical class C1=CC=C2OC(=O)N=CC2=C1 BIXMBBKKPTYJEK-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
- MVWPVABZQQJTPL-UHFFFAOYSA-N 2,3-diphenylcyclohexa-2,5-diene-1,4-dione Chemical class O=C1C=CC(=O)C(C=2C=CC=CC=2)=C1C1=CC=CC=C1 MVWPVABZQQJTPL-UHFFFAOYSA-N 0.000 description 1
- KYGSXEYUWRFVNY-UHFFFAOYSA-N 2-pyran-2-ylidenepropanedinitrile Chemical class N#CC(C#N)=C1OC=CC=C1 KYGSXEYUWRFVNY-UHFFFAOYSA-N 0.000 description 1
- CMSGUKVDXXTJDQ-UHFFFAOYSA-N 4-(2-naphthalen-1-ylethylamino)-4-oxobutanoic acid Chemical compound C1=CC=C2C(CCNC(=O)CCC(=O)O)=CC=CC2=C1 CMSGUKVDXXTJDQ-UHFFFAOYSA-N 0.000 description 1
- DDTHMESPCBONDT-UHFFFAOYSA-N 4-(4-oxocyclohexa-2,5-dien-1-ylidene)cyclohexa-2,5-dien-1-one Chemical class C1=CC(=O)C=CC1=C1C=CC(=O)C=C1 DDTHMESPCBONDT-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 1
- ZYASLTYCYTYKFC-UHFFFAOYSA-N 9-methylidenefluorene Chemical class C1=CC=C2C(=C)C3=CC=CC=C3C2=C1 ZYASLTYCYTYKFC-UHFFFAOYSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical class N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 229910052688 Gadolinium Inorganic materials 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 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
- XBDYBAVJXHJMNQ-UHFFFAOYSA-N Tetrahydroanthracene Natural products C1=CC=C2C=C(CCCC3)C3=CC2=C1 XBDYBAVJXHJMNQ-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 229910052769 Ytterbium Inorganic materials 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 150000001454 anthracenes Chemical class 0.000 description 1
- 150000008425 anthrones Chemical class 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- DZBUGLKDJFMEHC-UHFFFAOYSA-N benzoquinolinylidene Natural products C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 150000001846 chrysenes Chemical class 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 1
- 125000000332 coumarinyl group Chemical class O1C(=O)C(=CC2=CC=CC=C12)* 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 1
- 150000002219 fluoranthenes Chemical class 0.000 description 1
- 150000002220 fluorenes Chemical class 0.000 description 1
- 150000008376 fluorenones Chemical class 0.000 description 1
- 239000007850 fluorescent dye Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- VPUGDVKSAQVFFS-UHFFFAOYSA-N hexabenzobenzene Natural products 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 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- DCZNSJVFOQPSRV-UHFFFAOYSA-N n,n-diphenyl-4-[4-(n-phenylanilino)phenyl]aniline Chemical class C1=CC=CC=C1N(C=1C=CC(=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 DCZNSJVFOQPSRV-UHFFFAOYSA-N 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000007978 oxazole derivatives Chemical class 0.000 description 1
- 150000002916 oxazoles Chemical class 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 150000004986 phenylenediamines Chemical class 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 150000003220 pyrenes Chemical class 0.000 description 1
- RQGPLDBZHMVWCH-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole Chemical class C1=NC2=CC=NC2=C1 RQGPLDBZHMVWCH-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 150000002910 rare earth metals Chemical group 0.000 description 1
- 230000027756 respiratory electron transport chain Effects 0.000 description 1
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical class [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- 150000005075 thioxanthenes Chemical class 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 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 1
- 150000004961 triphenylmethanes Chemical class 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/17—Carrier injection layers
Abstract
Description
【0001】[0001]
【産業上の利用分野】本発明は有機エレクトロルミネッ
センス素子に関し、特に平面光源及びフラットディスプ
レイなどに用いられる有機エレクトロルミネッセンス素
子に関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an organic electroluminescence device, and more particularly to an organic electroluminescence device used for flat light sources and flat displays.
【0002】[0002]
【従来の技術】有機エレクトロルミネッセンス素子は、
有機発光層および該層をはさんだ一対の対向電極から構
成されており、その発光は一方の電極から注入された電
子、もう一方の電極から注入された正孔により、発光層
内で再結合がおこり発光体がより高いエネルギー準位に
励起され、励起された発光体が元の基底状態にもどる際
にエネルギーを光として放出することにより発生する。
このようなキャリア注入型エレクトロルミネッセンス素
子は、発光層として有機化合物薄膜を用いるようになっ
てから発光強度の強いものが得られるようになってき
た。例えば、米国特許3,530,325号には発光体として単
結晶アントラセン等を用いたもの、特開昭59-194393号
には正孔注入層と有機発光体層を組合せたもの、特開昭
63-295695号には正孔注入輸送層と有機電子注入輸送層
を組合せたものおよびJpn.Journal of Applied Physic
s,vo127,No2,P269〜271には正孔移動層と発光層と電子
移動層を組合せたものなどが開示されており、これらに
よりこれまで発光強度は改良されてきた。2. Description of the Related Art Organic electroluminescent devices are
It is composed of an organic light-emitting layer and a pair of counter electrodes sandwiching the layer, and its light emission is recombined in the light-emitting layer by electrons injected from one electrode and holes injected from the other electrode. It occurs when the luminescent material is excited to a higher energy level and emits energy as light when the excited luminescent material returns to the original ground state.
In such a carrier injection type electroluminescence device, since an organic compound thin film is used as a light emitting layer, a device having high emission intensity has been obtained. For example, U.S. Pat. No. 3,530,325 uses a single crystal anthracene or the like as a light emitter, and JP-A-59-194393 discloses a combination of a hole injection layer and an organic light-emitting layer.
63-295695 is a combination of a hole injecting and transporting layer and an organic electron injecting and transporting layer and Jpn. Journal of Applied Physic
s, vo127, No2, P269-271 discloses a combination of a hole transfer layer, a light emitting layer and an electron transfer layer, and these have improved the emission intensity.
【0003】しかしながら上述した構成の従来の有機エ
レクトロルミネッセンス素子においては、発光強度は改
良されてきてはいるが、耐久性に問題があり、まだ実用
レベルの発光強度及び耐久性に達していなかった。従っ
て、より発光の強度が強くかつ高耐久性のエレクトロル
ミネッセンス素子の開発が望まれていた。However, in the conventional organic electroluminescence device having the above-mentioned structure, although the emission intensity has been improved, there is a problem in durability, and the emission intensity and durability of a practical level have not yet been reached. Therefore, it has been desired to develop an electroluminescence device having higher emission intensity and higher durability.
【0004】[0004]
【発明の目的】本発明は上記の実情を鑑みてなされたも
ので、その目的は、より発光強度が強くかつ高耐久性の
実用レベルのエレクトロルミネッセンス素子を提供する
ことにある。SUMMARY OF THE INVENTION The present invention has been made in view of the above circumstances, and an object of the invention is to provide a practical-level electroluminescence element having higher emission intensity and higher durability.
【0005】[0005]
【問題点を解決する手段】本発明者らは上記の目的を達
成するため鋭意努力の研究を重ねた結果、一対の対向電
極とこれらによって挟持された一層または複数層の有機
化合物層から構成されているエレクトロルミネッセンス
素子において、前記「化1」に示した構成要素を規定し
た一般式〔1〕で表される有機化合物を含有する層を、
少なくとも一層以上設け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により達成されることを見出し
た。DISCLOSURE OF THE INVENTION As a result of intensive research to achieve the above object, the present inventors have made up of a pair of counter electrodes and one or a plurality of organic compound layers sandwiched by these electrodes. In the electroluminescent element, the layer containing the organic compound represented by the general formula [1] which defines the constituent elements shown in the above "Chemical formula 1",
It has been found that this can be achieved by an organic electroluminescence device characterized in that at least one layer is provided.
【0006】一般式〔1〕において、Ar1,Ar2のアル
キル基としては、メチル、エチル、プロピル、ブチルが
挙げられ、アラルキル基としては、ベンジルが挙げら
れ、アリール基としては、フェニル、ナフチルが挙げら
れる。In the general formula [1], the alkyl groups of Ar 1 and Ar 2 include methyl, ethyl, propyl and butyl, the aralkyl group includes benzyl, and the aryl groups include phenyl and naphthyl. Is mentioned.
【0007】Rのアルキル基としては、メチル、エチ
ル、プロピル、ブチルが挙げられ、アルコキシ基として
は、メトキシ、エトキシ、プロポキシが挙げられ、ハロ
ゲン原子としては、弗素原子、塩素原子、臭素原子、沃
素原子が挙げられる。Examples of the alkyl group of R include methyl, ethyl, propyl and butyl, examples of the alkoxy group include methoxy, ethoxy and propoxy, and examples of the halogen atom include fluorine atom, chlorine atom, bromine atom and iodine. Atoms.
【0008】次に、一般式〔1〕で表される具体例を示
す。Next, a specific example represented by the general formula [1] will be shown.
【0009】[0009]
【化2】 [Chemical 2]
【0010】[0010]
【化3】 [Chemical 3]
【0011】[0011]
【化4】 [Chemical 4]
【0012】[0012]
【化5】 [Chemical 5]
【0013】[0013]
【化6】 [Chemical 6]
【0014】[0014]
【化7】 [Chemical 7]
【0015】[0015]
【化8】 [Chemical 8]
【0016】[0016]
【化9】 [Chemical 9]
【0017】[0017]
【化10】 [Chemical 10]
【0018】[0018]
【化11】 [Chemical 11]
【0019】[0019]
【化12】 [Chemical 12]
【0020】[0020]
【化13】 [Chemical 13]
【0021】[0021]
【化14】 [Chemical 14]
【0022】[0022]
【化15】 [Chemical 15]
【0023】本発明の有機薄膜エレクトロルミネッセン
ス素子の構成には各種態様があるが、基本的には複数の
有機化合物層および該層を挟んだ一対の対向電極から構
成されており、具体的には、基板/陽極/正孔注入層
/発光層/陰極(図1(1))、基板/陽極/発光層
/電子注入層/陰極(図1(2))、基板/陽極/正
孔注入層/発光層/電子注入層/陰極(図1(3))な
どが挙げられるが、本発明は必ずしもこの構成に限定さ
れるものではなく、それぞれにおいて発光層,正孔注入
層,電子注入層を複数層設けたり、またそれぞれにおい
て正孔注入層/発光層,発光層/電子注入層,正孔注入
層/発光層/電子注入層を繰返し積層した構成にした
り、発光層と電子注入層との間に電子注入材と発光材と
の混合層、正孔注入層と発光層との間に正孔注入材と発
光材との混合層を設けたりまたそれぞれにおいて他の層
を設けてもさしつかえない。The organic thin film electroluminescent element of the present invention has various configurations, but basically, it is composed of a plurality of organic compound layers and a pair of counter electrodes sandwiching the layers, and specifically, , Substrate / anode / hole injection layer / emission layer / cathode (FIG. 1 (1)), substrate / anode / emission layer / electron injection layer / cathode (FIG. 1 (2)), substrate / anode / hole injection layer / Emission layer / electron injection layer / cathode (FIG. 1 (3)) and the like, but the present invention is not necessarily limited to this configuration, and a light emission layer, a hole injection layer, and an electron injection layer are respectively provided. A plurality of layers may be provided, or a hole injection layer / a light emitting layer, a light emitting layer / an electron injection layer, and a hole injection layer / a light emitting layer / an electron injection layer may be repeatedly laminated in each layer, or a light emitting layer and an electron injection layer may be formed. Between the mixed layer of electron injection material and light emitting material, hole injection layer and emission layer No problem be provided other layers in the mixed layer is provided or also each of the hole injecting material and a light emitting material between the layers.
【0024】本発明の化合物(一般式〔1〕)は正孔注
入層もしくは発光層に用いられる。The compound of the present invention (general formula [1]) is used in the hole injection layer or the light emitting layer.
【0025】発光層は蒸着法,スピンコート法,キャス
ト法などにより形成しその膜厚は10〜1000nmが好まし
く、より好ましくは20〜150nmである。正孔注入層は蒸
着法,スピンコート法,キャスト法などにより形成しそ
の膜厚は10〜1000nmが好ましく、より好ましくは40〜20
0nmである。電子注入層は蒸着法,スピンコート法,キ
ャスト法などにより形成しその膜厚は10〜1000nmが好ま
しく、より好ましくは30〜200nmである。The light emitting layer is formed by a vapor deposition method, a spin coating method, a casting method or the like, and its film thickness is preferably 10 to 1000 nm, more preferably 20 to 150 nm. The hole injection layer is formed by a vapor deposition method, a spin coating method, a casting method or the like, and its film thickness is preferably 10 to 1000 nm, more preferably 40 to 20 nm.
It is 0 nm. The electron injection layer is formed by a vapor deposition method, a spin coating method, a casting method or the like, and its film thickness is preferably 10 to 1000 nm, more preferably 30 to 200 nm.
【0026】基板1は、ソーダガラス,無蛍光ガラス,
燐酸系ガラス,硼酸系ガラスなどのガラス板、石英、ア
クリル系樹脂,スチレン系樹脂,ポリカーボネート系樹
脂,エポキシ系樹脂,ポリエチレン,ポリエステル,シ
リコーン系樹脂などのプラスチック板およびプラスチッ
クフィルム、アルミナなどの金属板および金属ホイルな
どが用いられる。The substrate 1 is made of soda glass, non-fluorescent glass,
Phosphate-based glass, boric acid-based glass, etc., quartz, acrylic resin, styrene-based resin, polycarbonate-based resin, epoxy-based resin, polyethylene, polyester, silicone-based resin, etc. plastic plate and plastic film, metal plate such as alumina And a metal foil or the like is used.
【0027】陽極2は4eVより大きい仕事関数を持つ
ものが好ましく、炭素、アルミニウム、バナジウム、
鉄、コバルト、ニッケル、クロム、銅、亜鉛、タングス
テン、銀、錫、白金、金などの金属およびこれらの合
金、酸化亜鉛、酸化インジウム、ITO,NESA等の
酸化錫もしくは酸化錫インジウム系等の複合化合物、沃
化銅などの化合物、ZnO:Al、SnO2:Sbなど
の酸化物と金属の混合物、更にはポリ(3-メチルチオフ
ェン) 、ポリピロール、ポリアニリンなどの導電性ポリ
マーなどが用いられる。膜厚は10〜1000nmが好ましく、
より好ましくは10〜200nmである。The anode 2 preferably has a work function larger than 4 eV, such as carbon, aluminum, vanadium,
Metals such as iron, cobalt, nickel, chromium, copper, zinc, tungsten, silver, tin, platinum and gold and alloys thereof, tin oxide such as zinc oxide, indium oxide, ITO and NESA or indium tin oxide-based composites Compounds, compounds such as copper iodide, mixtures of oxides and metals such as ZnO: Al, SnO 2 : Sb, and conductive polymers such as poly (3-methylthiophene), polypyrrole, and polyaniline are used. The film thickness is preferably 10 to 1000 nm,
More preferably, it is 10 to 200 nm.
【0028】陰極3は4eVより小さい仕事関数を持つ
ものが好ましく、マグネシウム、カルシウム、ナトリウ
ム、カリウム、チタニウム、インジウム、イットリウ
ム、リチウム、ガドリニウム、イッテルビウム、ルテニ
ウム、マンガン、アルミニウム、銀、錫、鉛などの金属
及びこれらの合金、アルミニウム/酸化アルミニウム複
合体などが用いられる。膜厚は10〜1000nmが好ましく、
より好ましくは10〜900nmである。The cathode 3 preferably has a work function of less than 4 eV, such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, ytterbium, ruthenium, manganese, aluminum, silver, tin and lead. Metals and alloys thereof, aluminum / aluminum oxide composites and the like are used. The film thickness is preferably 10 to 1000 nm,
More preferably, it is 10 to 900 nm.
【0029】電極より光を取り出す場合は、陽極2、陰
極3のうち少なくともどちらか一方は、透過率10%以上
の透明又は半透明であり、陽極2のみが透過率10%以上
の透明又は半透明である場合は基板1も透明又は半透明
であることが好ましい。When light is extracted from the electrode, at least one of the anode 2 and the cathode 3 is transparent or semitransparent with a transmittance of 10% or more, and only the anode 2 is transparent or semitransparent with a transmittance of 10% or more. When it is transparent, the substrate 1 is also preferably transparent or semi-transparent.
【0030】発光層4に用いられる発光物質の具体例と
しては、前記一般式により表される有機化合物以外にオ
キシノイド化合物(特開昭63-295695号,特開平2-15595
号,同2-66873号などに記載のもの)、ペリレン化合物
(「Soluble Perylene Fluorescent Dyes with Photost
ability,vol.115,P2927(1982)」,「Jpn.Journal of Ap
plied Physics,vol.27,No2,L269(1988)」,「Bull.Che
m.Soc.Jpn.vol.25,L411(1952)」,欧州特許553,353A1
号,特開昭55-36849号,同57-51781号,特開平2-66873
号,同2-196885号,同2-288188号,同3-791号などに記
載のもの)、クマリン化合物(特開昭57-51781号,特開
平2-66873号,同3-792などに記載のもの)、アザクマリ
ン化合物(特開平3-792号などに記載のもの)、オキサ
ゾール化合物(米国特許3,257,203号,特開平3-193763
号,同3-162482号,同2-220396号などに記載のもの)、
オキサジアゾール化合物(米国特許3,189,447号,特開
平2-216791号などに記載のもの)、ペリノン化合物(特
開平2-88689号,同2-289676号などに記載のもの)、ピ
ロロピロール化合物(特開平2-296891号などに記載のも
の)、ナフタレン化合物(特開昭57-51781号,特開平2-2
55789号,同3-162485号などに記載のもの)、アントラ
セン化合物(特開昭56-46234号,同57-51781号,特開平
2-66873号,同3-162485号などに記載のもの)、フルオ
レン化合物(特開昭54-110837号,特開平3-162485号な
どに記載のもの)、フルオランテン化合物(特開平3-16
2485号などに記載のもの)、テトラセン化合物(特開平
3-162485号などに記載のもの)、ピレン化合物(特開昭
57-51781号,特開平3-162485号,同3-502333号などに記
載のもの)、コロネン化合物(特開平3-162485号などに
記載のもの)、キノロン化合物及びアザキノロン化合物
(特開平3-162483号などに記載のもの)、ピラゾリン誘
導体及びピラゾロン誘導体(米国特許3,180,729号,同
4,278,746号,特開昭55-88064号,同55-88065号,同49-
105537号,同55-51086号,同56-80051号,同56-88141
号,同57-45545号,同54-112637号,同55-74546号,特
開平2-220394号,同3-162486号などに記載のもの)、ロ
ーダミン化合物(特開平2-66873号,同3-188189号など
に記載のもの)、クリセン化合物(特開昭57-51781号,
特開平3-502333号などに記載のもの)、フェナントレン
化合物(特開昭57-51781号などに記載のもの)、シクロ
ペンタジエン化合物(特開平2-289675号などに記載のも
の)、スチルベン化合物(米国特許4,356,429号,特開
昭57-51781号,同61-210363号,同61-228451号,同61-1
4642号,同61-72255号,同62-47646号,同62-36674号,
同62-10652号,同62-30255号,同60-934454号,同60-94
462号,同60-174749号,同60-175052号,同63-149652
号,特開平1-173034号,同1-200262号,同1-245087号な
どに記載のもの)、ジフェニルキノン化合物(「Polyme
r Preprints,Japan,vol.37,p681(1988)」,特開平3-152
184号などに記載のもの)、スチリル化合物(特開平1-2
45087号,同2-209988号,同2-222484号,同2-247278号
などに記載のもの)、ブタジエン化合物(米国特許4,35
6,429号,特開昭57-51781号などに記載のもの)、ジシ
アノメチレンピラン化合物(特開平2-66873号,同3-162
481号などに記載のもの)、ジシアノメチレンチオピラ
ン化合物(特開平2-66873号,同3-162481号などに記載
のもの)、フルオレセイン化合物(特開平2-66873号な
どに記載のもの)、ピリリウム化合物(特開平2-66873
号などに記載のもの)、チアピリリウム化合物(特開平
2-66873号などに記載のもの)、セレナピリリウム化合
物(特開平2-66873号などに記載のもの)、テルロピリ
リウム化合物(特開平2-66873号などに記載のもの)、
芳香族アルダジエン化合物(特開平2-220393号などに記
載のもの)、オリゴフェニレン化合物(特開平3-162484
号などに記載のもの)、チオキサンテン化合物(特開平
3-177486号などに記載のもの)、アンスラセン化合物
(特開平3-178942号などに記載のもの)、シアニン化合
物(特開平2-66873号などに記載のもの)、アクリジン
化合物(特開昭57-51781号などに記載のもの)、8-ヒド
ロキシキノリン化合物の金属鎖体(特開平2-8287号,同
2-8290号などに記載のもの)、2,2′-ビピリジン化合物
の金属鎖体(特開平2-8288号,同2-8289号などに記載の
もの)、シッフ塩とIII族金属との鎖体(特開平1-29749
0号などに記載のもの)、オキシン金属鎖体(特開平3-1
76993号などに記載のもの)、希土類鎖体(特開平1-256
584号,同1-282291号などに記載のもの)などの蛍光物
質を使用することができる。Specific examples of the light-emitting substance used in the light-emitting layer 4 include oxinoid compounds (JP-A-63-295695 and JP-A-2-15595) in addition to the organic compound represented by the above general formula.
No. 2-66873, etc.), perylene compound (“Soluble Perylene Fluorescent Dyes with Photost
ability, vol.115, P2927 (1982), "Jpn. Journal of Ap
plied Physics, vol.27, No2, L269 (1988) "," Bull.Che
m.Soc.Jpn.vol.25, L411 (1952) ", European Patent 553,353A1
No. 55, No. 55-36849, No. 57-51781, No. 2-66873
Nos. 2-196885, 2-288188, 3-791, etc.) and coumarin compounds (JP-A-57-51781, JP-A-2-66873, 3-792, etc.). Described), azacoumarin compounds (described in JP-A-3-792, etc.), oxazole compounds (US Pat. No. 3,257,203, JP-A-3-93763).
No., No. 3-162482, No. 2-220396, etc.),
Oxadiazole compounds (described in US Pat. No. 3,189,447, JP-A-2-216791, etc.), perinone compounds (described in JP-A-2-88689, JP-A-2-289676, etc.), pyrrolopyrrole compounds (special Those described in Kaihei 2-296891), naphthalene compounds (JP-A-57-51781, JP-A-2-2)
55789, 3-162485, etc.), anthracene compounds (JP-A-56-46234, JP-A-57-51781, JP-A-5-51781)
2-66873, 3-162485, etc.), fluorene compounds (described in JP-A-54-110837, JP-A-3-162485, etc.), fluoranthene compounds (JP-A-3-16)
2485), a tetracene compound (JP
3-162485, etc.), pyrene compounds (JP
57-51781, JP-A-3-162485, JP-A-3-502333, etc.), coronene compound (JP-A-3-162485, etc.), quinolone compound, and azaquinolone compound (JP-A-3-261485). 162483, etc.), pyrazoline derivatives and pyrazolone derivatives (US Pat. No. 3,180,729;
4,278,746, JP-A-55-88064, 55-88065, 49-
105537, 55-51086, 56-80051, 56-88141
No. 57-45545, No. 54-112637, No. 55-74546, those described in JP-A-2-220394, 3-162486, etc.), rhodamine compounds (JP-A-2-66873, JP-A-2-66873, 3-188189 etc.), chrysene compounds (JP-A-57-51781,
JP-A-3-502333, etc.), phenanthrene compound (JP-A-57-51781, etc.), cyclopentadiene compound (JP-A-2-289675, etc.), stilbene compound ( U.S. Pat. No. 4,356,429, JP-A-57-51781, 61-210363, 61-228451, 61-1.
No. 4642, No. 61-72255, No. 62-47646, No. 62-36674,
62-10652, 62-30255, 60-934454, 60-94
No. 462, No. 60-174749, No. 60-175052, No. 63-149652
JP-A Nos. 1-173034, 1-200262, 1-245087, etc.), diphenylquinone compounds ("Polyme
r Preprints, Japan, vol.37, p681 (1988) ", JP-A-3-152
No. 184) and styryl compounds (JP-A 1-2
45087, 2-209988, 2-222484, 2-247278, etc.), butadiene compound (US Pat.
6,429, those described in JP-A-57-51781), dicyanomethylenepyran compounds (JP-A-2-66873, JP-A-3-162)
481), dicyanomethylene thiopyran compound (described in JP-A-2-66873, JP-A-3-162481, etc.), fluorescein compound (described in JP-A-2-66873, etc.), Pyrylium compound (JP-A-2-66873
, Etc.), thiapyrylium compounds (JP
2-66873 etc.), selenapyrylium compound (described in JP-A-2-66873 etc.), telluropyrylium compound (described in JP-A-2-66873 etc.),
Aromatic aldadien compounds (described in JP-A-2-220393, etc.), oligophenylene compounds (JP-A-3-62484)
, Etc.), thioxanthene compounds (JP
3-177486), anthracene compound (described in JP-A-3-178942), cyanine compound (described in JP-A-2-66873), acridine compound (JP-A-57). -51781), metal chain of 8-hydroxyquinoline compound (Japanese Patent Laid-Open No. 2-8287,
2-8290), metal chains of 2,2'-bipyridine compounds (such as those described in JP-A Nos. 2-8288 and 2-8289), Schiff salts and Group III metals Chain (Japanese Patent Laid-Open No. 1-29749
No. 0, etc.), oxine metal chain (Japanese Patent Laid-Open No. 3-1
76993, etc.), rare earth chain (Japanese Patent Laid-Open No. 1-256)
No. 584, No. 1-282291, etc.) can be used.
【0031】正孔注入層5に用いられる正孔輸送能を有
する正孔注入化合物の具体例としては、トリアゾール誘
導体(米国特許3,112,197号などに記載のもの)、オキ
サジアゾール誘導体(米国特許3,189,447号などに記載
のもの)、イミダゾール誘導体(特公昭37-16096号など
に記載のもの)、ポリアリールアルカン誘導体(米国特
許3,615,402号、同3,820,989号、同3,542,544号、特公
昭45-555号、同51-10983号、特開昭51-93224号、同55-1
7105号、同56-4148号、同55-108667号、同56-36656号、
同55-156953号などに記載のもの)、ピラゾリン誘導体
及びピラゾロン誘導体(米国特許3,180,729、同4,278,7
46号、特開昭55-88064号、同55-88065号、同49-105537
号、同55-51086号、同56-80051号、同56-88141号、同57
-45545号、同54-112637号、同55-74546号などに記載の
もの)、フェニレンジアミン誘導体(米国特許3,615,40
4号、特公昭51-10105号、同46-3712号、同47-25336号、
特開昭54-53435号、同54-110536号、同54-119925号など
に記載のもの)、アリールアミン誘導体(米国特許3,56
7,450号、同3,180,703号、同3,240,597号、同3,658,520
号、同4,232,103、同4,175,961号、同4,012,376号、特
公昭49-35702号、同39-27577号、特開昭55-144250号、
同56-223437号、西ドイツ特許1,110,518号などに記載の
もの)、アミノ置換カルコン誘導体(米国特許3,526,50
1号などに記載のもの)、オキサゾール誘導体(米国特
許3,257,203号などに記載のもの)、スチリルアントラ
セン誘導体(特開昭56-46234号などに記載のもの)、フ
ルオレノン誘導体(特開昭54-110837号などに記載のも
の)、ヒドラゾン誘導体(米国特許3,717,462号、特開
昭54-59143号、同55-52063号、同55-52064号、同55-467
60号、同55-8495号、同57-148749号、特開平3-136059
号、同3-138654号などに記載のもの)、スチルベン誘導
体(特開昭61-210363号、同61-228451号、同61-14642
号、同61-72255号、同62-47646号、同62-36674号、同62
-10652号、同62-30255号、同60-934454号、同60-94462
号、同60-174749号、同60-175052号、同63-149652号、
特開平1-173034号、同1-200262号などに記載のもの)、
ポリフィリン化合物(特開昭63-295695号、特開平2-127
95号などに記載のもの)、芳香族第三級アミン化合物及
びスチリルアミン化合物(米国特許4,127,412号、特開
昭53-27033号、同54-58445号、同54-149634号、同54-64
299号、同55-79450号、同55-144250号、同56-119132
号、同61-295558号、同61-98353号、同63-295695号、特
開平1-274154号、同1-243393号、同3-111485号などに記
載のもの)、ブタジエン化合物(特開平3-111484号など
に記載のもの)、ポリスチレン誘導体(特開平3-95291
号などに記載のもの)、ヒドラゾン誘導体(特開平3-13
7187号などに記載のもの)、トリフェニルメタン誘導
体、テトラフェニルベンジジン誘導体(特開平3-54289
号などに記載のもの)などを使用することができるが、
特に好ましくは、ポリフィリン化合物、芳香族第三級ア
ミン化合物及びスチリルアミン化合物である。Specific examples of the hole injecting compound having a hole transporting ability used in the hole injecting layer 5 include triazole derivatives (described in US Pat. No. 3,112,197) and oxadiazole derivatives (US Pat. No. 3,189,447). Etc.), imidazole derivatives (those described in JP-B-37-16096, etc.), polyarylalkane derivatives (US Pat. Nos. 3,615,402, 3,820,989, 3,542,544, and JP-B-45-555, 51). -10983, JP-A-51-93224, 55-1
No. 7105, No. 56-4148, No. 55-108667, No. 56-36656,
55-156953), pyrazoline derivatives and pyrazolone derivatives (US Pat. Nos. 3,180,729 and 4,278,7).
46, JP-A-55-88064, 55-88065, 49-105537
No. 55, No. 55-51086, No. 56-80051, No. 56-88141, No. 57.
-45545, 54-112637, 55-74546, etc.), phenylenediamine derivatives (US Pat. No. 3,615,40)
No. 4, Japanese Patent Publication No. 51-10105, No. 46-3712, No. 47-25336,
JP-A-54-53435, JP-A-54-110536, JP-A-54-119925, etc.), arylamine derivatives (US Pat.
7,450, 3,180,703, 3,240,597, 3,658,520
No. 4,232,103, 4,175,961, 4,012,376, JP-B-49-35702, 39-27577, JP-A-55-144250,
56-223437, West German Patent 1,110,518, etc.), amino-substituted chalcone derivative (US Patent 3,526,50)
No. 1), oxazole derivatives (U.S. Pat. No. 3,257,203, etc.), styrylanthracene derivatives (such as those described in JP-A-56-46234), fluorenone derivatives (JP-A-54-110837). And the like), hydrazone derivatives (US Pat. No. 3,717,462, JP-A-54-59143, JP-A-55-52063, JP-A-55-52064, and JP-A-55-467).
No. 60, No. 55-8495, No. 57-148749, JP-A-3-136059
Nos. 3-138654, etc.), stilbene derivatives (JP-A-61-210363, 61-228451, 61-14642).
Issue 61-72255, Issue 62-47646, Issue 62-36674, Issue 62
-10652, 62-30255, 60-934454, 60-94462
No. 60, No. 60-174749, No. 60-175052, No. 63-149652,
Japanese Patent Laid-Open No. 1-173034, 1-200262, etc.),
Porphyrin compound (JP-A-63-295695, JP-A-2-127)
95, etc.), aromatic tertiary amine compounds and styrylamine compounds (US Pat. No. 4,127,412, JP-A-53-27033, JP-A-54-58445, JP-A-54-149634, JP-A-54-64).
No. 299, No. 55-79450, No. 55-144250, No. 56-119132
Nos. 61-295558, 61-98353, 63-295695, JP-A 1-274154, 1-243393, 3-111485, etc.), butadiene compounds (JP-A 3-111484, etc.), polystyrene derivatives (JP-A-3-95291)
, Etc.) and hydrazone derivatives (Japanese Patent Laid-Open No. 3-13
No. 7187), triphenylmethane derivative, tetraphenylbenzidine derivative (JP-A-3-54289).
No. etc.) can be used,
Particularly preferred are porphyrin compounds, aromatic tertiary amine compounds and styrylamine compounds.
【0032】電子注入層6に用いられる電子輸送能を有
する電子注入化合物の具体例としては、ニトロ置換フル
オレノン誘導チオピランジオキサイド誘導体、ジフェノ
キノン誘導体(「Polymer Preprints、Japan,vo1.37,No
3,P681,(1988)」,特開平3-152184号などに記載のも
の)、ペリレンテトラカルボキシル誘導体(「Jpn.Jour
nal of Applied Physics,vol.27,No2,L269(1988)」「Bu
l1.Chem.Soc.Jpn.,vol.25,L411(1952)」などに記載のも
の)、アントラキノジメタン誘導体(特開昭57-149259
号、同58-55450号、同61-225151号、同61-133750号、同
63-104061号などに記載のもの)、フレオレニリデンメ
タン誘導体(特開昭60-69657号、同61-143764号、同61-
148159号などに記載のもの)、アントロン誘導体(特開
昭61-225151号、同61-233750号などに記載のもの)、オ
キサジアゾール誘導体(特開平3-79692号などに記載の
もの)、ペリノン誘導体(特開平2-289676号などに記載
のもの)、キノリン錯体誘導体などの化合物を使用する
ことができる。Specific examples of the electron injecting compound having an electron transporting ability used in the electron injecting layer 6 include nitro-substituted fluorenone-derived thiopyrandioxide derivatives and diphenoquinone derivatives ("Polymer Preprints, Japan, vo1.37, No.
3, P681, (1988) ", JP-A-3-152184, etc.), perylene tetracarboxyl derivative (" Jpn. Jour.
nal of Applied Physics, vol.27, No2, L269 (1988), `` Bu
L1.Chem.Soc.Jpn., vol.25, L411 (1952) ", anthraquinodimethane derivative (JP-A-57-149259).
No. 58, No. 58-55450, No. 61-225151, No. 61-133750, No.
63-104061, etc.), fluorenylidene methane derivative (JP-A-60-69657, JP-A-61-143764, JP-A-61-143764)
148159, etc.), anthrone derivatives (such as those described in JP-A-61-225151 and 61-233750), oxadiazole derivatives (such as those described in JP-A-3-79692), Compounds such as a perinone derivative (described in JP-A-2-289676) and a quinoline complex derivative can be used.
【0033】[0033]
【実施例】次に実施例によって本発明を具体的に説明す
る。EXAMPLES The present invention will be described in detail with reference to examples.
【0034】実施例1 陽極としてガラス上にITOを150nm成膜した基板(日
本板硝子株式会社製P110E-H-PS)を所望の形にパ
ターニングを行った後、アルミナ研磨剤にて水とともに
研磨を行った。水洗後、水超音波洗浄10分間2回、アセ
トン超音波洗浄10分間2回、イソプロピルアルコール超
音波洗浄10分間2回行い、さらに90℃にて熱風乾燥を行
った。Example 1 A substrate (P110E-H-PS manufactured by Nippon Sheet Glass Co., Ltd.) on which ITO was deposited to a thickness of 150 nm on a glass as an anode was patterned into a desired shape and then polished with water using an alumina abrasive. went. After washing with water, ultrasonic washing with water for 10 minutes twice, ultrasonic washing with acetone for 10 minutes twice, ultrasonic washing with isopropyl alcohol for 10 minutes twice, and further hot air drying at 90 ° C were performed.
【0035】つぎにこの基板に、前記化合物(2)をタ
ングステンボード(日本バックスメタル株式会社製SF
208)に入れ、8.0×10-7Torrの真空条件下で0.2nm/sec
の成膜速度で真空蒸着し約80nmの正孔注入層を形成し
た。Then, the compound (2) was added to the substrate by using a tungsten board (SF, manufactured by Nippon Bucks Metal Co., Ltd.).
208) and 0.2 nm / sec under a vacuum condition of 8.0 × 10 -7 Torr.
A hole injection layer having a thickness of about 80 nm was formed by vacuum evaporation at a film formation rate of.
【0036】次いで、真空条件を破ることなく8-ヒドロ
キシキノリンアルミニウムをモリブテンボート(日本バ
ックスメタル株式会社製SS-1-9)に入れ、8.0×10
-7Torrの真空条件下で0.2nm/secの成膜速度で約60nmの
発光層を積層蒸着した。Then, 8-hydroxyquinoline aluminum was placed in a molybdenum boat (SS-1-9 manufactured by Nippon Bucks Metal Co., Ltd.) without breaking vacuum conditions, and 8.0 × 10
Under vacuum conditions of -7 Torr, a light emitting layer of about 60 nm was laminated and deposited at a film forming rate of 0.2 nm / sec.
【0037】さらにこの上に真空条件を破ることなくM
g:Ag(10:1原子比合金)を500nm真空蒸着し、陰
極を形成した。On top of this, without breaking vacuum conditions, M
g: Ag (10: 1 atomic ratio alloy) was vacuum-deposited at 500 nm to form a cathode.
【0038】このようにして得られた有機エレクトロル
ミネッセンス素子に外部電源を接続し18V直流電圧を印
加し、その時の最大輝度を測定した。また温度23℃乾燥
窒素ガス雰囲気下で18V直流電圧印加による連続点灯を
行ない、輝度の半減する時間を測定した。An external power supply was connected to the thus obtained organic electroluminescence device, a direct current voltage of 18 V was applied, and the maximum luminance at that time was measured. Further, continuous lighting was carried out by applying a DC voltage of 18 V in a dry nitrogen gas atmosphere at a temperature of 23 ° C., and the time at which the luminance was reduced by half was measured.
【0039】その結果を表1に示す。The results are shown in Table 1.
【0040】実施例2〜7 正孔注入層に用いた化合物に代えて、表1の示したもの
を用いた以外は、実施例1と同様にして有機エレクトロ
ルミネッセンス素子を得た。その特性を表1に示す。Examples 2 to 7 Organic electroluminescent elements were obtained in the same manner as in Example 1 except that the compounds shown in Table 1 were used instead of the compounds used in the hole injection layer. The characteristics are shown in Table 1.
【0041】比較例(1) 正孔注入層に後記「化16」に示す化合物(A−1)を
用いた以外は、実施例1と同様にして様子を作成した。
その結果を表1に示す。Comparative Example (1) A state was prepared in the same manner as in Example 1 except that the compound (A-1) shown in the following "Chemical Formula 16" was used for the hole injection layer.
The results are shown in Table 1.
【0042】[0042]
【表1】 [Table 1]
【0043】実施例8 陽極としてガラス上にITOを150nm成膜した基板(日
本板硝子株式会社製P110E-H-PS)を所望の形にパ
ターニングを行った後、アルミナ研磨剤にて水とともに
研磨を行った。水洗後、水超音波洗浄10分間2回、アセ
トン超音波洗浄10分間2回、イソプロピルアルコール超
音波洗浄10分間2回行い、さらに90℃にて熱風乾燥を行
った。Example 8 A substrate (P110E-H-PS manufactured by Nippon Sheet Glass Co., Ltd.) having a 150 nm ITO film formed on glass as an anode was patterned into a desired shape and then polished with water using an alumina abrasive. went. After washing with water, ultrasonic washing with water for 10 minutes twice, ultrasonic washing with acetone for 10 minutes twice, ultrasonic washing with isopropyl alcohol for 10 minutes twice, and further hot air drying at 90 ° C were performed.
【0044】つぎにこの基板に、前記化合物(1)をタ
ングステンボード(日本バックスメタル株式会社製SF
208)に入れ、8.0×10-7Torrの真空条件下で0.2nm/sec
の成膜速度で真空蒸着し約60nmの発光層を形成した。Then, the compound (1) was added to the substrate by using a tungsten board (SF, manufactured by Nippon Bucks Metal Co., Ltd.).
208) and 0.2 nm / sec under a vacuum condition of 8.0 × 10 -7 Torr.
It was vacuum-deposited at a film forming speed of to form a light emitting layer of about 60 nm.
【0045】次いで、真空条件を破ることなく後記「化
16」に示す化合物(A−2)をモリブテンボート(日
本バックスメタル株式会社製SS-1-9)に入れ、8.0
×10-7Torrの真空条件下で0.2nm/secの成膜速度で約80n
mの電子注入層を積層蒸着した。Next, the compound (A-2) shown below in "Chemical formula 16" was placed in a molybdenum boat (SS-1-9 manufactured by Nippon Bucks Metal Co., Ltd.) without breaking vacuum conditions,
Approximately 80n at a deposition rate of 0.2nm / sec under a vacuum of × 10 -7 Torr
An electron injection layer of m was laminated and vapor deposited.
【0046】さらにこの上に真空条件を破ることなくM
g:Ag(10:1原子比合金)を500nm真空蒸着し、陰
極を形成した。On top of this, M
g: Ag (10: 1 atomic ratio alloy) was vacuum-deposited at 500 nm to form a cathode.
【0047】このようにして得られた有機エレクトロル
ミネッセンス素子に外部電源を接続し18V直流電圧を印
加し、その時の最大輝度を測定した。また温度23℃乾燥
窒素ガス雰囲気下で18V直流電圧印加による連続点灯を
行ない、輝度の半減する時間を測定した。その結果を表
2に示す。An external power supply was connected to the thus obtained organic electroluminescence device, a 18 V DC voltage was applied, and the maximum luminance at that time was measured. Further, continuous lighting was carried out by applying a DC voltage of 18 V in a dry nitrogen gas atmosphere at a temperature of 23 ° C., and the time at which the luminance was reduced by half was measured. The results are shown in Table 2.
【0048】実施例9〜14 発光層に用いた化合物に代えて、表2に示したものを用
いた以外は実施例と同様にして有機エレクトロルミネッ
センス素子を得た。その特性を表2に示す。Examples 9 to 14 Organic electroluminescent devices were obtained in the same manner as in Examples except that the compounds shown in Table 2 were used instead of the compounds used in the light emitting layer. The characteristics are shown in Table 2.
【0049】比較例(2) 発光層に後記「化16」に示す化合物(A−3)を用い
た以外は、実施例8と同様にして素子を作成した。その
結果を表2に示す。Comparative Example (2) A device was prepared in the same manner as in Example 8 except that the compound (A-3) shown in "Chemical Formula 16" below was used in the light emitting layer. The results are shown in Table 2.
【0050】[0050]
【表2】 [Table 2]
【0051】[0051]
【化16】 [Chemical 16]
【0052】[0052]
【発明の効果】本発明に係る特定の有機化合物を用いる
ことにより、発光強度、耐久性において充分に実用に耐
える有機エレクトロルミネッセンス素子が得られる。By using the specific organic compound according to the present invention, it is possible to obtain an organic electroluminescence device which is sufficiently practical for emission intensity and durability.
【図1】(1)〜(3)は本発明の態様例の有機エレク
トロルミネッセンス素子の断面図である。FIG. 1 (1) to (3) are cross-sectional views of an organic electroluminescence element according to an embodiment of the present invention.
1 基板 2 陽極 3 陰極 4 発光層 5 正孔注入層 6 電子注入層 1 substrate 2 anode 3 cathode 4 light emitting layer 5 hole injection layer 6 electron injection layer
Claims (1)
を含有する層を、少くとも一層以上設けたことを特徴と
する有機エレクトロルミネッセンス素子。 【化1】 〔一般式〔1〕中、Ar1,Ar2はアルキル基、アラルキ
ル基、アリール基を表し、Rは水素原子、ハロゲン原
子、アルキル基、アルコキシ基を表す。nは0〜4の整
数である。〕1. An organic electroluminescence device comprising at least one layer containing an organic compound represented by the following general formula [1]. [Chemical 1] [In the general formula [1], Ar 1 and Ar 2 represent an alkyl group, an aralkyl group or an aryl group, and R represents a hydrogen atom, a halogen atom, an alkyl group or an alkoxy group. n is an integer of 0-4. ]
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP4159575A JPH061973A (en) | 1992-06-18 | 1992-06-18 | Organic electroluminescent element |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP4159575A JPH061973A (en) | 1992-06-18 | 1992-06-18 | Organic electroluminescent element |
Publications (1)
Publication Number | Publication Date |
---|---|
JPH061973A true JPH061973A (en) | 1994-01-11 |
Family
ID=15696712
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP4159575A Pending JPH061973A (en) | 1992-06-18 | 1992-06-18 | Organic electroluminescent element |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPH061973A (en) |
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