GB2439887A - Organic electroluminescent device - Google Patents
Organic electroluminescent device Download PDFInfo
- Publication number
- GB2439887A GB2439887A GB0721118A GB0721118A GB2439887A GB 2439887 A GB2439887 A GB 2439887A GB 0721118 A GB0721118 A GB 0721118A GB 0721118 A GB0721118 A GB 0721118A GB 2439887 A GB2439887 A GB 2439887A
- Authority
- GB
- United Kingdom
- Prior art keywords
- layer
- organic
- cathode
- metal
- electroluminescence device
- 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.)
- Granted
Links
- 229910052751 metal Inorganic materials 0.000 claims abstract description 60
- 239000002184 metal Substances 0.000 claims abstract description 60
- 150000002894 organic compounds Chemical class 0.000 claims abstract description 37
- 150000004945 aromatic hydrocarbons Chemical group 0.000 claims abstract description 20
- 150000002739 metals Chemical class 0.000 claims abstract description 13
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 10
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract description 9
- 150000001342 alkaline earth metals Chemical class 0.000 claims abstract description 9
- 239000010410 layer Substances 0.000 claims description 143
- 238000005401 electroluminescence Methods 0.000 claims description 24
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 claims description 24
- 229910052738 indium Inorganic materials 0.000 claims description 22
- 125000005842 heteroatom Chemical group 0.000 claims description 15
- 125000000962 organic group Chemical group 0.000 claims description 13
- 238000010521 absorption reaction Methods 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 10
- 239000010409 thin film Substances 0.000 claims description 5
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 4
- 229910052782 aluminium Inorganic materials 0.000 claims description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 4
- 229910052791 calcium Inorganic materials 0.000 claims description 4
- 239000011575 calcium Substances 0.000 claims description 4
- 239000011159 matrix material Substances 0.000 claims description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 3
- 229910052788 barium Inorganic materials 0.000 claims description 3
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 claims description 3
- 239000004973 liquid crystal related substance Substances 0.000 claims description 3
- 229910052749 magnesium Inorganic materials 0.000 claims description 3
- 239000011777 magnesium Substances 0.000 claims description 3
- 229910052712 strontium Inorganic materials 0.000 claims description 3
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 claims description 3
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 claims description 2
- 229910052733 gallium Inorganic materials 0.000 claims description 2
- 229910052716 thallium Inorganic materials 0.000 claims description 2
- BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 238000000034 method Methods 0.000 description 81
- 239000010408 film Substances 0.000 description 37
- 238000007740 vapor deposition Methods 0.000 description 28
- 239000000243 solution Substances 0.000 description 24
- -1 naphtha].ene ring Chemical group 0.000 description 22
- YTVNOVQHSGMMOV-UHFFFAOYSA-N naphthalenetetracarboxylic dianhydride Chemical compound C1=CC(C(=O)OC2=O)=C3C2=CC=C2C(=O)OC(=O)C1=C32 YTVNOVQHSGMMOV-UHFFFAOYSA-N 0.000 description 21
- 239000000463 material Substances 0.000 description 19
- 238000005259 measurement Methods 0.000 description 17
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 230000015572 biosynthetic process Effects 0.000 description 14
- STTGYIUESPWXOW-UHFFFAOYSA-N 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline Chemical compound C=12C=CC3=C(C=4C=CC=CC=4)C=C(C)N=C3C2=NC(C)=CC=1C1=CC=CC=C1 STTGYIUESPWXOW-UHFFFAOYSA-N 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- 239000000758 substrate Substances 0.000 description 13
- 229920005596 polymer binder Polymers 0.000 description 12
- 239000002491 polymer binding agent Substances 0.000 description 12
- 125000004429 atom Chemical group 0.000 description 11
- 230000000052 comparative effect Effects 0.000 description 11
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 11
- 229910052737 gold Inorganic materials 0.000 description 11
- 239000010931 gold Substances 0.000 description 11
- 238000004519 manufacturing process Methods 0.000 description 11
- 229920000642 polymer Polymers 0.000 description 11
- 238000004062 sedimentation Methods 0.000 description 11
- 238000000862 absorption spectrum Methods 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 10
- 238000005755 formation reaction Methods 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 239000012298 atmosphere Substances 0.000 description 9
- 238000001362 electron spin resonance spectrum Methods 0.000 description 9
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 8
- 238000002347 injection Methods 0.000 description 8
- 239000007924 injection Substances 0.000 description 8
- 229910045601 alloy Inorganic materials 0.000 description 7
- 239000000956 alloy Substances 0.000 description 7
- 239000011521 glass Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 238000000151 deposition Methods 0.000 description 5
- 238000010030 laminating Methods 0.000 description 5
- 238000003475 lamination Methods 0.000 description 5
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 5
- 229920001296 polysiloxane Polymers 0.000 description 5
- 239000011241 protective layer Substances 0.000 description 5
- 238000004544 sputter deposition Methods 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 239000004793 Polystyrene Substances 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 150000001340 alkali metals Chemical class 0.000 description 4
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 4
- 230000000903 blocking effect Effects 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- 229930192419 itoside Natural products 0.000 description 4
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 4
- 229920000767 polyaniline Polymers 0.000 description 4
- 229920002223 polystyrene Polymers 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 239000011787 zinc oxide Substances 0.000 description 4
- YMMGRPLNZPTZBS-UHFFFAOYSA-N 2,3-dihydrothieno[2,3-b][1,4]dioxine Chemical compound O1CCOC2=C1C=CS2 YMMGRPLNZPTZBS-UHFFFAOYSA-N 0.000 description 3
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 3
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 3
- 238000005266 casting Methods 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000003759 ester based solvent Substances 0.000 description 3
- 239000004210 ether based solvent Substances 0.000 description 3
- 239000003574 free electron Substances 0.000 description 3
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 3
- 238000007641 inkjet printing Methods 0.000 description 3
- 239000005453 ketone based solvent Substances 0.000 description 3
- 229910044991 metal oxide Inorganic materials 0.000 description 3
- 150000004706 metal oxides Chemical class 0.000 description 3
- 238000007645 offset printing Methods 0.000 description 3
- 229910052697 platinum Inorganic materials 0.000 description 3
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 3
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 3
- 229920000548 poly(silane) polymer Polymers 0.000 description 3
- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 description 3
- 229920000058 polyacrylate Polymers 0.000 description 3
- 239000004417 polycarbonate Substances 0.000 description 3
- 229920000515 polycarbonate Polymers 0.000 description 3
- 239000004926 polymethyl methacrylate Substances 0.000 description 3
- 229940005642 polystyrene sulfonic acid Drugs 0.000 description 3
- 229920000123 polythiophene Polymers 0.000 description 3
- 229920000915 polyvinyl chloride Polymers 0.000 description 3
- 239000004800 polyvinyl chloride Substances 0.000 description 3
- 238000007639 printing Methods 0.000 description 3
- 238000007650 screen-printing Methods 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 229910052718 tin Inorganic materials 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- 229910052725 zinc Inorganic materials 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 230000008033 biological extinction Effects 0.000 description 2
- 229910052792 caesium Inorganic materials 0.000 description 2
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 2
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical class C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 2
- 238000010894 electron beam technology Methods 0.000 description 2
- 229910002804 graphite Inorganic materials 0.000 description 2
- 239000010439 graphite Substances 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 238000003780 insertion Methods 0.000 description 2
- 230000037431 insertion Effects 0.000 description 2
- 238000007733 ion plating Methods 0.000 description 2
- BSIHWSXXPBAGTC-UHFFFAOYSA-N isoviolanthrone Chemical compound C12=CC=CC=C2C(=O)C2=CC=C3C(C4=C56)=CC=C5C5=CC=CC=C5C(=O)C6=CC=C4C4=C3C2=C1C=C4 BSIHWSXXPBAGTC-UHFFFAOYSA-N 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 2
- 229910001512 metal fluoride Inorganic materials 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- 150000004866 oxadiazoles Chemical class 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 230000035699 permeability Effects 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
- CLYVDMAATCIVBF-UHFFFAOYSA-N pigment red 224 Chemical compound C=12C3=CC=C(C(OC4=O)=O)C2=C4C=CC=1C1=CC=C2C(=O)OC(=O)C4=CC=C3C1=C42 CLYVDMAATCIVBF-UHFFFAOYSA-N 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 230000001681 protective effect Effects 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
- 239000002994 raw material Substances 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- IATRAKWUXMZMIY-UHFFFAOYSA-N strontium oxide Chemical compound [O-2].[Sr+2] IATRAKWUXMZMIY-UHFFFAOYSA-N 0.000 description 2
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 2
- 229910001887 tin oxide Inorganic materials 0.000 description 2
- UWRZIZXBOLBCON-VOTSOKGWSA-N (e)-2-phenylethenamine Chemical class N\C=C\C1=CC=CC=C1 UWRZIZXBOLBCON-VOTSOKGWSA-N 0.000 description 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical class C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- VFBJMPNFKOMEEW-UHFFFAOYSA-N 2,3-diphenylbut-2-enedinitrile Chemical group C=1C=CC=CC=1C(C#N)=C(C#N)C1=CC=CC=C1 VFBJMPNFKOMEEW-UHFFFAOYSA-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
- LGLDSEPDYUTBNZ-UHFFFAOYSA-N 3-phenylbuta-1,3-dien-2-ylbenzene Chemical class C=1C=CC=CC=1C(=C)C(=C)C1=CC=CC=C1 LGLDSEPDYUTBNZ-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
- ZYASLTYCYTYKFC-UHFFFAOYSA-N 9-methylidenefluorene Chemical class C1=CC=C2C(=C)C3=CC=CC=C3C2=C1 ZYASLTYCYTYKFC-UHFFFAOYSA-N 0.000 description 1
- 229910001316 Ag alloy Inorganic materials 0.000 description 1
- 229910000838 Al alloy Inorganic materials 0.000 description 1
- 229910052684 Cerium Inorganic materials 0.000 description 1
- 238000004435 EPR spectroscopy Methods 0.000 description 1
- 229910052693 Europium Inorganic materials 0.000 description 1
- 229910000846 In alloy Inorganic materials 0.000 description 1
- 229910000861 Mg alloy Inorganic materials 0.000 description 1
- 229930192627 Naphthoquinone Natural products 0.000 description 1
- 229920002319 Poly(methyl acrylate) Polymers 0.000 description 1
- 229920000292 Polyquinoline Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical class N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 1
- 229910052772 Samarium Inorganic materials 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 229910052771 Terbium Inorganic materials 0.000 description 1
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-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
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical group C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- JFBZPFYRPYOZCQ-UHFFFAOYSA-N [Li].[Al] Chemical compound [Li].[Al] JFBZPFYRPYOZCQ-UHFFFAOYSA-N 0.000 description 1
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000005577 anthracene group Chemical group 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- RJGDLRCDCYRQOQ-UHFFFAOYSA-N anthrone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3CC2=C1 RJGDLRCDCYRQOQ-UHFFFAOYSA-N 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- XJHABGPPCLHLLV-UHFFFAOYSA-N benzo[de]isoquinoline-1,3-dione Chemical class C1=CC(C(=O)NC2=O)=C3C2=CC=CC3=C1 XJHABGPPCLHLLV-UHFFFAOYSA-N 0.000 description 1
- 229910052790 beryllium Inorganic materials 0.000 description 1
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 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
- 239000003086 colorant Substances 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 150000001893 coumarin derivatives Chemical class 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- 150000008376 fluorenones Chemical class 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 150000002471 indium Chemical class 0.000 description 1
- LHJOPRPDWDXEIY-UHFFFAOYSA-N indium lithium Chemical compound [Li].[In] LHJOPRPDWDXEIY-UHFFFAOYSA-N 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- YZASAXHKAQYPEH-UHFFFAOYSA-N indium silver Chemical compound [Ag].[In] YZASAXHKAQYPEH-UHFFFAOYSA-N 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
- 239000011261 inert gas Substances 0.000 description 1
- 239000011810 insulating material Substances 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- 238000000608 laser ablation Methods 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- GCICAPWZNUIIDV-UHFFFAOYSA-N lithium magnesium Chemical compound [Li].[Mg] GCICAPWZNUIIDV-UHFFFAOYSA-N 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
- 229920003240 metallophthalocyanine polymer Polymers 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- AODWRBPUCXIRKB-UHFFFAOYSA-N naphthalene perylene Chemical group C1=CC=CC2=CC=CC=C21.C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 AODWRBPUCXIRKB-UHFFFAOYSA-N 0.000 description 1
- 150000002791 naphthoquinones Chemical class 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 150000007978 oxazole derivatives Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 125000005582 pentacene group Chemical group 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000000016 photochemical curing Methods 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- INAAIJLSXJJHOZ-UHFFFAOYSA-N pibenzimol Chemical compound C1CN(C)CCN1C1=CC=C(N=C(N2)C=3C=C4NC(=NC4=CC=3)C=3C=CC(O)=CC=3)C2=C1 INAAIJLSXJJHOZ-UHFFFAOYSA-N 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 229920000412 polyarylene Polymers 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 229920006389 polyphenyl polymer Polymers 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 150000005255 pyrrolopyridines Chemical class 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical class C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
- 229910052706 scandium Inorganic materials 0.000 description 1
- SIXSYDAISGFNSX-UHFFFAOYSA-N scandium atom Chemical compound [Sc] SIXSYDAISGFNSX-UHFFFAOYSA-N 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- GZCRRIHWUXGPOV-UHFFFAOYSA-N terbium atom Chemical compound [Tb] GZCRRIHWUXGPOV-UHFFFAOYSA-N 0.000 description 1
- 125000005579 tetracene group Chemical group 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- QKTRRACPJVYJNU-UHFFFAOYSA-N thiadiazolo[5,4-b]pyridine Chemical class C1=CN=C2SN=NC2=C1 QKTRRACPJVYJNU-UHFFFAOYSA-N 0.000 description 1
- NZFNXWQNBYZDAQ-UHFFFAOYSA-N thioridazine hydrochloride Chemical class Cl.C12=CC(SC)=CC=C2SC2=CC=CC=C2N1CCC1CCCCN1C NZFNXWQNBYZDAQ-UHFFFAOYSA-N 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 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
Classifications
-
- 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
-
- H01L51/5088—
-
- H01L51/5092—
-
- 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]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
- H10K50/157—Hole transporting layers between the light-emitting layer and the cathode
-
- 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]
- H10K50/14—Carrier transporting layers
- H10K50/16—Electron transporting layers
- H10K50/167—Electron transporting layers between the light-emitting layer and the anode
-
- 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
- H10K50/171—Electron injection layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
- H10K71/30—Doping active layers, e.g. electron transporting layers
-
- 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
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
- H10K85/113—Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
- H10K85/1135—Polyethylene dioxythiophene [PEDOT]; Derivatives thereof
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/621—Aromatic anhydride or imide compounds, e.g. perylene tetra-carboxylic dianhydride or perylene tetracarboxylic di-imide
-
- H01L27/3241—
-
- H01L27/3293—
-
- H01L51/0062—
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
- H10K59/10—OLED displays
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
- H10K59/10—OLED displays
- H10K59/18—Tiled displays
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
Landscapes
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Engineering & Computer Science (AREA)
- Chemical & Material Sciences (AREA)
- Materials Engineering (AREA)
- Manufacturing & Machinery (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
Disclosed is an organic electroluminescent device having a light-emitting layer between an anode and a cathode. This organic electroluminescent device is characterized in that a layer (L) is arranged between the cathode and the light-emitting layer in contact with the cathode, and the layer (L) contains an organic compound (A) having an aromatic hydrocarbon ring or heterocyclic ring and a carbonyl group, and one or more metals (B) selected from alkaline earth metals and group III metals.
Description
<p>ORGANIC ELECTROLUMINESCENCE DEVICE</p>
<p>Technical Field</p>
<p>The present invention relates to an organic electroluminescence device (hereinafter, referred to as organic EL device in some cases).</p>
<p>Background Art</p>
<p>An organic EL device is an EL device using an organic material as a light emitting material, and has a light emitting layer between an anode and a cathode as a basic structure.</p>
<p>For improvement of its performance, there is disclosed, for example, an organic EL device having a layer containing an organic compound, alkali metal and the like between the above-described cathode and light emitting layer so as to contact the cathode (Japanese Patent Application Laid-Open (JP-A) No. 10-270171).</p>
<p>The above-described known device, however, is not sufficient in electron injectability, durability and the like yet for practical application.</p>
<p>DISCLOSURE OF THE INVENTION</p>
<p>The present invention has an object of providing an organic EL device excellent in electron injectability, durability and the like. * 2</p>
<p>The present invention provides an organic electroluminescence device having a light emitting layer between an anode and a cathode wherein the device has a layer CL) between said cathode and said light emitting layer so as to contact the cathode, and the layer (L) comprises an organic compound (A) containing an aromatic hydrocarbon ring or hetero ring and a carbony). group and a metal (B) selected from alkaline earth metals and group III metals.</p>
<p>Further, the present invention provides an organic electroluminescence device having a light emitting layer between an anode and a cathode wherein the device has a layer (L) between said cathode and said light emitting layer so as to contact the cathode, and the layer (L) is obtained by using an organic compound (A) containing an aromatic hydrocarbon ring or hetero ring and a carbonyl group and a metal (B) selected from alkaline earth metals and group III metals.</p>
<p>BRIEF EXPLANATION OF DRAWINGS</p>
<p>Fig. 1 is a schematic view showing a cross-section of a lamination structure examples of an organic electroluminescence device of the present invention.</p>
<p>Fig. 2 is -a graph showing current density-voltage properties of an organic electroluminescence device of the present invention and a comparative example.</p>
<p>Pig. 3 is a graph showing luminance-voltage properties S 3 of an organic electroluminescence device of the present invention and a comparative example.</p>
<p>Fig. 4 is a graph showing current density-time properties of an organic electroluminescence device of the present invention and a comparative example.</p>
<p>Fig. 5 is a graph showing absorption spectra of a mixture Contained in a layer (L) used in an organic electroluminescence device of the present invention and a comparative example.</p>
<p>Fig. 6 is a graph showing an ESR spectrum of a mixture contained in a layer CL) used in an organic electroluminescence device of the present invention.</p>
<p>Fig. 7 is a graph showing an absorption spectrum of a</p>
<p>comparative example.</p>
<p>Fig. 8 is a graph showing an ESR spectrum of a comparative</p>
<p>example.</p>
<p>BEST MODES FOR CARRYING OUT THE INVENTION</p>
<p>The organic EL device of the present invention is an organic electroluminescence device having a light emitting layer between an anode and a cathode in which the device has a layer CL) between the above-described cathode and the above-described light emitting layer so as to contact the cathode. That is, the device of the present invention has a lamination structure represented by cathode/layer (L)/light emitting layer/anode. It is necessary that the cathode and the * . 4 layer (L) are in contact. Between the layer CL) and the light emitting layer, and between the light emitting layer and the anode, other layers may be present.</p>
<p>The cathode, layer (L), light emitting layer and anode will be illustrated in turn below.</p>
<p>The material of the cathode in the organic EL device of the present invention includes inorganic semiconductors such as metals, graphite or graphite interlaminar compounds, ZnO (zinc oxide) and the like, electrically conductive transparent electrodes such as ITO (indium.tin.oxjde) IZO (ifldiuifl*zinc.Qxjde) and the like, metal oxides such as strontium oxide, barium oxide, and the like.</p>
<p>Examples of the metal include alkali metals such as lithium, sodium, potassium, rubidium, cesium and the like; alkaline earth metals such as beryllium, magnesium, calcium, strontium, barium and the like; transition metals such as gold, silver, platinum, copper, manganese, titanium, cobalt, nickel, tungsten and the like; tin, aluminum, scandium, vanadium, zinc, yttrium, indium, cerium, samarium, europium, terbium, ytterbium; and alloys composed of two or more metals of them, and the like.</p>
<p>Examples of the alloy.incjud a alloy, alloy, magnes1um_alj alloy, indium-silver alloy, lithium-aluminum alloy, lithium-magnesium alloy, lithium-indium alloy, calcjum-alunijnum alloy and the like.</p>
<p>The cathode may have a lamination structure composed of two or more layers. For example, cathodes obtained by laminating a metal, alloy and the like on a layer made of a metal fluoride such as lithium fluoride, cesium fluoride and the like or a conductive polymer, or a layer having an average film thickness of 5 run or less made of an organic insulating material and the like, and cathodes obtained by laminating aluminum on a calcium layer, and the like, are mentioned.</p>
<p>The organic EL device of the present invention has a layer (L) between a cathode and a light emitting layer so as to contact the cathode. The film thickness of the layer (L) is usually about 0.1 urn to 500 urn, preferably 1 run to 100 nun, more preferably nun to 20 nun.</p>
<p>The layer (L) contains an organic compound (A) and a metal (B) selected from alkaline earth metals and group III metals, or is obtained by using an organic compound (A) containing an aromatic hydrocarbon ring or hetero ring and a carbonyl group and a metal (B) selected from alkaline earth metals and group III metals. Two or more layers (L) may be laminated.</p>
<p>Examples of the alkaline earth metal in the metal (B) used in the layer (L) include magnesium, calcium, strontium and barium, and the group III metal includes aluminum, gallium, indium and thallium, and from the standpoint of durability, preferable are group III metals, and more preferable is indium. * S 6</p>
<p>The organic compound (A) used in the layer (L) is an organic compound containing an aromatic hydrocarbon ring or hetero ring and a carbonyl group.</p>
<p>Here, the aromatic hydrocarbon ring includes a benzene ring, naphtha].ene ring, anthracene ring, tetracene ring, pentacene ring, pyrene, phenanthrene and the like, and the hetero ring includes a pyridine ring, bipyrjdjne ring, phenanthroline ring, quinoline ring, isoquino].jne ring.</p>
<p>thiophene ring, furan ring, pyrroj.e ring and the like. The aromatic hydrocarbon ring and hetero ring may have a subs tituent such as alkyl groups, alkoxy groups, alkylthjo groups and the like.</p>
<p>As the organic compound (A), the following formulae (1), (2), (3) and (4) are preferable.</p>
<p>Ar1 (1) (wherein, Ar1 represents an organic group containing an aromatic hydrocarbon ring or hetero ring. X represents 0 or NH. n represents an integer of 1 or more and 4 or less. When there are a plurality of Xe, they may be the same or different.) * . Ar2 Ar3) o Irn (2) (wherein, Ar2 and Ar3 represent each independently an organic group containing an aromatic hydrocarbon ring or hetero ring.</p>
<p>m represents an integer of 1 or more and 4 or less. When there are a plurality of Ar3s, they may be the same or different.) Ar2 is a 2m-valent organic group, and Ar3 is a di-valent organic group.</p>
<p>Ar4"'"Ar5) (wherein, Ar4 and Ar5 represent each independently an organic group containing an aromatic hydrocarbon ring or hetero ring.</p>
<p>1 represents an integer of 1 or more and 4 or less. Ar5s may be the same or different.) Ar4 is a 2l-valent organic group, and Ar5 is a di-valent organic group. /1'9</p>
<p>Ar8ZN) k (4) (wherein, Ar6 and Ar7 represent each independently an organic * . group containing an aromatic hydrocarbon ring or hetero ring.</p>
<p>k represents an integer of 1 or more and 4 or less. When there are a plurality of Ar7s, they may be the same or different.).</p>
<p>Ar6 is a 2k-valent organic group, and Ar7 is a di-valent organic group.</p>
<p>As the compound of the formula (1), NTCDA (Naphthalene-1,8:4, 5-tetracarboxylic dianhydride), PTCDA (Perylene-3, 4,9. 1Otetracarboxylic dianhydride), NTCDI (3,4,7,8 -naphthalenetetracarboxyljc_djjjd) and the like are mentioned. o 0 o 0</p>
<p>0 0 NTCDA 118118110 P T C D A o 0</p>
<p>HN</p>
<p>0 0 NTCDI As the compound of the formula (2), PQ4 (5.7.l214-Pentacentetrone) and the like are mentioned. * . cxxc</p>
<p>As the compound of the formula (3), isoviolanthrone (9.l8-dihydrobenzoErst]phenanthro[lo,l,2..cde]pefltaphefle...9,1 8-dione) and the like are mentioned. c0.</p>
<p>0 Isoviolanthrone As the compound of the formula (4), PTCBI (3, 4,9, 1O-perylenetetracarboxylic bis-benzimidazole) and the like are mentioned.</p>
<p>iiii8i P T C B I Of them, compounds of the formula (1) are preferable, tetracarboxylic anhydride and tetracarboxylic imide are more preferable, NTCDA, PTCDA and NTCDI are further preferable.</p>
<p>The number of carbonyl groups in the organic compound (A) is]. or more, and preferably in the range of]. to 8.</p>
<p>The organic compounds (A) and the metals (B) may be used each in combination of two or more.</p>
<p>The total weight of the organic compound (A) arid the metal (B) in the layer (L) is usually 50 wt% or more, preferably 80 * S I0 wt% or more, more preferably 90 wt% or more based on the total weight of the layer (L).</p>
<p>The number of metal atoms in the metal (B) per carbonyl group in the organic compound (A) is preferably about 0.025 to 25, more preferably 0.06 to 2.25, further preferably 0.16 to 0.38.</p>
<p>From the standpoint of lowering of driving voltage, the electric conductivity of a mixture obtained from the organic compound (A) and the metal (B) is preferably 106 S/cm or more, more preferably S/cm or more, further preferably 102 S/cm or more.</p>
<p>In a mixture used for measurement of electric conductivity, the number ratio of metal atoms in the metal (B) per carbonyl group in the organic compound (A) in the mixture is set equal to the number ratio in the layer (L).</p>
<p>Prom the standpoint of electron injectability, the absorption peak wavelength of a thin film composed of the organic compound (A) and the metal (B) is larger preferably by rim or more, more preferably by 10 rim or more, further preferably by 30 rim or more than the absorption peak wavelength of a thin film composed of the organic compound (A).</p>
<p>As the absorption peak of the organic compound (A), when the organic compound (A) is composed of two or more compounds, the absorption peak of an organic compound having the largest number of molecules in the organic compound (A) (showing the * . maximum mol ratio in the organic compound (A)) is used. In a mixture used for measurement of absorption peak wavelength, the number ratio of metal atoms in the metal (B) per carbony]. group in the organic compound (A) in the mixture is set equal to the number ratio in the layer (L).</p>
<p>The light emitting layer in the organic EL device of the present invention usually contains an organic light emitter.</p>
<p>As the organic light emitter, organic fluorescent molecules and polymer fluorescent substances usually used in organic EL devices can be used.</p>
<p>Exemplified as the organic fluorescent molecule are, for example, benzooxazo].e I benzoimidazole derivatives, benzothiazole derivatives, styrylbenzene derivatives, polyphenyl, diphenylbutadiene derivatives, tetrapheny].butadiene I naphthalimide derivatives, coumarin derivatives, perylene derivatives, perynone derivatives, oxadiazole derivatives, aldazine derivatives, pyralydine I cyclopentadiene derivatives, bisstyrylanthracene derivatives, quinacridone derivatives, pyrrolopyridine derivatives, thiadiazolopyridine derivatives, cyclopentadiene derivatives, styry].amine derivatives, aromatic dimethylidyne compounds, metal complexes and rare earth complexes of 8-quinolinol derivatives, various metal * complexes typified by Ir and Pt complexes. More specifically, compounds disclosed in JP-ANos. 63-70257, 63-175860, 2-135359, * . 2-135361, 2-209988, 3-37992 and 3-152184 are suitably used.</p>
<p>As the polymer fluorescent substance, preferably used are polymer fluorescent substances having a molecule structure in which a t electron system is deloca].ized along the molecule chain, showing fluorescence in solid state, and having a polystyrene-reduced number average molecular weight of lx iO to ixi such as polyarylene, polyarylenevinylene and the like are preferably used. Specifically. materials described in JP-A Nos. 3-244630, 5-202355. 6-73374, 7-278276, 9-45478, WO 99/20675, WO 99/48160, WO 99/13692, WO 00/55927, WO 97/05184.</p>
<p>WO 98/06773, WO 99/ 54385, WO 99/54943, WO 00/0665, WO 00/46321, W098/27136, W099/24526, W000/22026, WO 00/22027, W000/35987, WO 01/34722, GB 2340304A, 11P-A Nos. 10-324870, 11-176576, 2000-34476. 2000-136379, 2000-104057, 2000-154334, 2000-169839 and the like are exemplified.</p>
<p>The optimum value of the film thickness of a light emitting layer varies depending on the material to be used, and may be advantageously selected so as to give suitable driving voltage and light emission efficiency, and at least thickness not causing generation of pin holes is necessary, and too large thickness is undesirable since then the driving voltage of a device increases. Accordingly, the thickness of the light emitting layer is for example 1 rim to 1 pm, preferably 2 rim to 500 rim, further preferably 5 rim to 200 rim.</p>
<p>In the present invention, it is preferable that at least * . one of an anode and a cathode is transparent or semi-transparent.</p>
<p>It is preferable that an anode is transparent or semi-transparent. As the material of the anode, electrically conductive metal oxide films, semi-transparent metal thin films and the like are used. Specifically, films (NESA and the like) manufactured by using indium oxide, zinc oxide, tin oxide, and composite thereof: indium* tin* oxide (ITO), indium. zinc* oxide and the like, and gold, platinum, silver, copper and the like, are used, and preferable are ITO, indium. zinc oxide and tin oxide. As the anode, organic transparent conductive films made of polyaniline or its derivatives, po].ythiophene or its derivatives and the like may be used.</p>
<p>The film thickness of the anode can be appropriately selected taking light permeability and electric conductivity into consideration, and is for example 10 nm to 10 pm, preferably run to 1 pm, further preferably 50 nm to 500 run.</p>
<p>The organic EL device of the present invention may further have layers such as a hole transporting layer, electron transporting layer and the like, in addition to the light emitting layer, anode, cathode and layer (L). For example, structures as described below are mentioned specifically.</p>
<p>a) anode/hole transporting layer/light emitting layer/electron transporting layer/layer (L) /cathode b) anode/hole transporting layer/light emitting layer/layer (L) /cathode c) anode/light emitting layer/layer (L)/cathode Here, the hole transporting layer is a layer having a function of transporting holes, and the electron transporting layer is a layer having a function of transporting electrons.</p>
<p>The hole transporting layer and electron transporting layer are called collectively a charge transporting layer. Among charge transporting layers, those having a function of improving charge injection efficiency from an electrode is in general called particularly a charge injection layer (hole injection layer, electron injection layer). Among charge transporting layers, that existing between an anode and a light emitting layer and having a function of blocking electrons injected from a cathode is in general called particularly an electron blocking layer, and that existing between a cathode and a light emitting layer and having a function of blocking holes injected from an anode is in general called particularly a hole blocking layer, in some cases. Particularly, among charge injection layers, that having a function of decreasing lowering of the light emission intensity of a light emitting layer caused by laminating an electron transporting layer, hole transporting layer, layer (L) or electrode is in general called an extinction preventing layer in some cases.</p>
<p>In the present invention, each two or more layers of the light emitting layer, anode, cathode, hole transporting layer * . and electron transporting layer may be independently used.</p>
<p>When two or more layers of respective layers are used, they can be appropriately used in view of light emission efficiency and device life without particularly restricting a position of use of a second layer.</p>
<p>When the organic EL device of the present invention has a hole transporting layer, preferably used as the hole transporting material used for the hole transporting layer are aromatic amine compounds such as N,N-diphenyl-N,N-bis(3-methylphenyl)-1, l-biphenyl-4, 4-diaxn.i.</p>
<p>ne (TPD) and the like, hydrazone compounds, metallophthalocyanines, porphyrins, styrylamine compounds, polyvinyl carbazole, polysilane (Appl, Phys. Lett. 59, 2760 (1991)), suspension of poly( 3 * 4) ethylenedioxythiophene/polystyrenesulfonic acid (manufactured by Bayer, Bytron PTP Al 4083), and the like.</p>
<p>Specifically, exemplified as the hole transporting material are those described in JP-A Nos. 63-70257, 63-175860, 2-135359, 2-135361, 2-209988. 2-311591, 3-37992, 3-152184, 11-35687, 11-217392 and 2000-80167, and the like.</p>
<p>The optimum value of the film thickness of a hole transporting layer varies depending on the material to be used, and may be advantageously selected so as to give suitable driving voltage and light emission efficiency, and at least thickness not causing generation of pin holes is necessary, and * . too large thickness is undesirable since then the driving voltage of a device increases. Accordingly, the thickness of the hole transporting layer is for example 1 nm to 1 mn, preferably 2 nm to 500 nm, further preferably 5 nm to 200 nm.</p>
<p>When the organic EL device of the present invention has an electron transporting layer, exemplified as the electron * transporting material used for the electron transporting layer are triazole derivatives, oxazole derivatives, oxadiazole derivatives, fluorenone derivatives, anthraquinodimethane derivatives, anthrone I diphenylquinone derivatives, thiopyrane dioxide derivatives, carbodiimide derivatives, fluorenylidenemethane derivatives, d.tstyrylpyrazine derivatives; beterocyclic tetracarboxylic anhydrides such as naphthaleneperylene and the like; phthalocyanine derivatives, metal complexes of 8-quinolino].</p>
<p>derivatives, various metal complexes typified by metal complexes containing metallophthalocyanjne, benzooxazole and benzothiazole as a ligand, benzoquinone or its derivatives, naphthoquinone or its derivatives, anthraquinone or its derivatives, diphenyldicyanoethylene or its derivatives, diphenoquinone derivatives, polyquinoline or its derivatives, polyquinoxaline or its derivatives, polyfluorene or its derivatives, bathocuprolne or its derivatives, and the like.</p>
<p>Specifically, those described in JP-A Nos. 63-70257, 63-175860, 2-135359, 2-135361, 2-209988, 3-37992and3-152184, * S and the like are exemplified.</p>
<p>The optimum value of the film thickness of an electron transporting layer varies depending on the material to be used, and may be advantageously selected so as to give suitable driving voltage and light emission efficiency, and at least thickness not causing generation of pin holes is necessary, and too large thickness is undesirable since then the driving voltage of a device increases. Accordingly, the thickness of the electron transporting layer is for example 1 run to 1 pm, preferably 2 run to 500 nm, further preferably 5 run to 200 run.</p>
<p>The organic EL device of the present invention may have a protective layer outside of an anode or cathode. For use of the organic EL device stably for a long period of time, it is preferable to fit a protective layer and/or protective cover for protecting the device from the outside. When a protective layer is present at the side of a cathode, a protective layer is fitted, after manufacturing of a cathode, from the side of the cathode so as to be sandwiched with a substrate on which the device is laminated-As the material of the protective layer, polymer compounds, metal oxides, metal fluorides, metal borides and the like can be used. As the protective cover, there can be used glass plates, plastic plates having a surface on which a water permeability coefficient- lowering treatment has been performed. and the like. A method for pasting the cover to a device substrate with a thermosetting resin or photo-curing resin to attain sealing is suitably used. When a space is maintained using a spacer, it is easy to prevent flawing of a device. When an inert gas such as nitrogen and argon is enclosed in this space, oxidation of a cathode can be prevented, further.</p>
<p>by placing a desiccant agent such as barium oxide and the like in this space, it becomes easy to suppress imparting damage to a device by moisture adsorbed in a production process. Also, by forming a lamination film composed of at least a pair of organic layer/inorganic layer on an organic EL device, a film protecting the organic EL device can be formed. It is preferable to adopt any one or more strategies of them.</p>
<p>Next, a method for producing the organic EL device of the present invention will be illustrated.</p>
<p>The device of the present invention has, as described above, a lamination structure represented by cathode/layer (L)/light emitting layer/anode and may have other layer between the layer (L) and the light emitting layer, and between the light emitting layer and the anode.</p>
<p>Hereinafter, methods for producing a hole transporting layer and an electron transporting layer among a cathode, layer (L), light emitting layer, anode and, layers to be used if necessary, will be illustrated in turn.</p>
<p>In the present invention, the method for manufacturing * . a cathode is not particularly restricted, and for example, a cathode is formed by a vacuum vapor deposition method, sputtering method, electron beam method and the like with a metal.</p>
<p>As the method for forming a layer (L), a vacuum vapor deposition method Is preferably used. As the vacuum vapor deposition, methods of co-vapor depositing a metal (B), an organic compound (A) and the like are mentioned. Specifically, raw materials such as a metal (B), an organic compound (A) and the like are filled in a crucible, boat and the like and the raw materials are heated by resistive heating to evaporate. In this operation, by monitoring and controlling the sedimentation speed of a metal (B) and an organic compound (A). co-vapor deposition at any ratio Is made possible, and any formulation ratio and film thickness can be obtained.</p>
<p>As the vacuum vapor deposition, there is also mentioned a method of laminating an organic compound (A) before vapor-depositing a metal (B), in addition to the co-vapor deposition. By this, a metal can be diffused In an organic compound thereby forming a layer. Further, in this case, the method for laminating an organic compound (A) is not limited to a vacuum vapor deposition method, and there are methods in which an organic compound (A) is dissolved or dispersed in a solvent to prepare a solution which is applied (on a substrate).</p>
<p>The application method include, but not particularly limited * S to, a drop cast method, spin coat method, inkjet method and the like. For vapor deposition of a metal (B). there are a sputtering method, electron beam method, ion plating method, laser ablation method and the like.</p>
<p>As the method for forming a light emitting layer of the organic electroluminescence device of the present invention, there are exemplified a vacuum vapor deposition method when the organic light emitter is an organic fluorescent molecule, and a method of application from solution when the organic light emitter is a polymer fluorescent substance. In the case of application from solution, though a solution of a light emitter may be used, a mixed solution with a polymer binder may also be used.</p>
<p>The solvent to be used for film formation from solution is not particularly restricted providing it dissolves a light emitter. Exemplified as the solvent are chlorine-based solvents such as chloroform, methylene chloride, dichioroethane and the like; ether solvents such as tetrahydrofuran and the like; aromatic hydrocarbon solvents such as toluene, xylene and the like; ketone solvents such as acetone, methyl ethyl ketone and the like; and ester solvents such as ethyl acetate, butyl acetate, ethylcellosolve acetate and the like.</p>
<p>As the method for film formation from solution, application methods can be used such as a spin coat method, * S casting method, microgravure coat method, gravure coat method.</p>
<p>bar coat method, roll coat method, wire bar coat method, dip coat method, spray coat method, screen printing method, flexographic printing method, offset printing method, inkjet printing method and the like from solution.</p>
<p>As the polymer binder to be mixed, those not extremely disturbing light emitability are preferable, and those showing no intense absorption for visible light are suitably used. As the polymer binder, exemplified are polycarbonate, polyacrylate, polymethy]. acrylate, polymethyl methacrylate.</p>
<p>polystyrene, polyvinyl chloride, polysiloxane and the like.</p>
<p>Further, as the polymer binder, polymer hole transporting materials such as polyvinyl carbazole or its derivatives.</p>
<p>polysilane or its derivatives, polysiloxane derivatives having an aromatic amine compound group at the side chain or main chain.</p>
<p>polyaniline or its derivatives, polythiophene or its derivatives, poly(p-phenylenevinylene) or its derivatives, poly(2,5-thienylenevinylene) or its derivatives, and the like may be used.</p>
<p>As the method for manufacturing an anode, a vacuum vapor deposition method, sputtering method, ion plating method, plating method and the like are mentioned.</p>
<p>When the organic EL device of the present invention has a hole transporting layer, a method for forming the layer will be described below. In the case of use of a hole transporting * S material of low molecular weight, film formations by vacuum vapor deposition, application from solution, and the like are mentioned. In the case of application from solution, though a solution of a hole transporting material may be used, also a mixed solution with a polymer binder may be used.</p>
<p>The solvent to be used for film formation from solution is not particularly restricted providing it dissolves a hole transporting material. Exemplified as the solvent are chlorine-based solvents such as chloroform, methylene chloride, dichioroetbane and the like; ether solvents such as tetrahydrofuran and the like; aromatic hydrocarbon solvents such as toluene, xylene and the like; ketone solvents such as acetone, methyl ethyl ketone and the like; and ester solvents such as ethyl acetate, butyl acetate, ethylcellosolve acetate and the like.</p>
<p>As the method for film formation from solution, application methods canbe used such as a spin coat method, casting method, microgravure coat method, gravure coat method, bar coat method, roll coat method, wire bar coat method, dip coat method, spray coat method, screen printing method, flexographic printing method, offset printing method, inkjet printing method and the like from solution.</p>
<p>As the polymer binder to be mixed, those not extremely disturbing charge transportation are preferable, and those showing no intense absorption for visible light are suitably * . used. As the polymer binder, exemplified are polycarbonate, polyacrylate, polymethy]. acrylate, polymethyl methacrylate, polystyrene, polyvinyl chloride, polysiloxane and the like.</p>
<p>Further, as the polymer binder, polymer hole transporting materials such as polyvinyl carbazole or its derivatives, polysilane or its derivatives, polysiloxane derivatives having an aromatic amine compound group at the side chain or main chain, polyaniline or its derivatives, polythiophene or its derivatives, poly(p-phenylenevinylene) or its derivatives, poly(2,5-thienyleneviny].ene) or its derivatives, and the like may be used.</p>
<p>When the organic EL device of the present invention has an electron transporting layer, the method for forming an electron transporting layer is not particularly restricted, and in the case of an electron transporting material of low molecular weight, exemplified are a vacuum vapor deposition method from powder and a method of film formation from solution or melted state, and in the case of an electron transporting material of high molecular weight, exemplified is a method of film formation from solution or melted state, respectively. In film formation from solution or melted state, a polymer binder may be used together.</p>
<p>The solvent to be used for film formation from solution is not particularly restricted providing It dissolves an electron transporting material and/or a polymer binder. * S</p>
<p>Exemplified as the solvent are chlorine-based solvents such as chloroform, methylene chloride, dichioroethane and the like; ether solvents such as tetrahydrofuran and the like; aromatic hydrocarbon solvents such as toluene, xylene and the like; ketone solvents such as acetone, methyl ethyl ketone and the like; and ester solvents such as ethyl acetate, butyl acetate, ethylcellosolve acetate and the like.</p>
<p>As the method for film formation from solution or melted state, application methods can be used such as a spin coat method, casting method, microgravure coat method, gravure coat method, bar coat method, roll coat method, wire bar coat method, dip coat method, spray coat method, screen printing method, flexographic printing method, offset printing method, inkjet printing method and the like.</p>
<p>As the polymer binder to be mixed, those not extremely disturbing charge transportation are preferable, and those showing no intense absorption for visible light are suitably used. As the polymer binder, exemplified are poly(N-vinylcarbazole), polyaniline or its derivatives, polythiophene or its derivatives. poly(p-phenylenevinylene) or its derivatives, poly(2,5-thienylenevinylene) or its derivatives, polycarbonate, polyacrylate, polymethyl acrylate, polymethyl methacrylate, polystyrene, polyvinyl chloride, polysiloxane and the like.</p>
<p>For obtaining the organic EL device of the present * . invention, a cathode, layer (L), (if necessary, electron transporting layer and the like), light emitting layer, (if necessary, electron transporting layer and the like) and anode may be produced in this order, or may be produced in the reverse order.</p>
<p>In forming the organic EL device of the present invention, a substrate is usually used, and advantageous as the substrate are those which do not change In forming an electrode and forming a layer of an organic substance, and exemplified are glass, plastic, polymer film, silicon substrate and the like. In the case of an opaque substrate, It Is preferable that the opposite electrode is transparent or semi-transparent.</p>
<p>Next, examples will be provided to illustrate the present invention further in detail, but the present Invention Is no limited to these examples.</p>
<p>Synthesis Example 1</p>
<p><Synthesis of polymer> Poly(9,9-dloctylfluorene) (PFO) was synthesized by a method described In WO 00/53656. This PFO had a number average molecular weight of 4.8 x l0.</p>
<p>Poly(2,7-(9,9-dioctylfluorene)-alt-(1,4-phenylene-( (4-sec butylphenyl)iinino) -1, 4-phenylene)) (TFB) was synthesized by a method described in WO 00/55927. This TFB had a number average molecular weight of 1.8 x i .</p>
<p>Example 1</p>
<p>The polymers PFO and TFB in Synthesis Example 1 were dissolved in toluene to prepare an application solution (The concentrations of PFO and TFB in the application solution were each 1.5 wt%).</p>
<p>On a glass substrate carrying an ITO film of a thickness of 150 urn formed by a sputtering method, a suspension of po].y( 3,4) ethylenedioxythiophene/polystyrenesulfonic acid (manufactured by Bayer, Bytron P TP Al 4083) was spin-coated to form a film of a thickness of 60 nm, and dried on a hot plate at 200 C for 10 minutes. Thereon, the above-described application solution was spin-coated to form a light emitting layer having a thickness of 200 nm. As the layer (L) (electron injection layer), NTCDA and indium were co-vapor-deposited at sedimentation speeds of 0.4 nm/s and 0.02 nm/s. respectively.</p>
<p>so as to give a film thickness of 10 urn together, further, gold was vapor-deposited as a cathode of a thickness of 20 urn, manufacturing an organic EL device. The degree of vacuum in vapor deposition was 1.0 x 10 Torr or less in all cases. The proportion of an indium atom per mole of this NTCDA was one (0.25 indium atoms per carbony]. group) (Fig. 1).</p>
<p>The device was removed from the vapor deposition apparatus, and immediately, a current-voltage property was measured -On the resultant device, a minus electrode was disposed at the ITO side and a plus electrode was disposed at the gold * . side, and a current density of 120 mA/cm2 was shown when the voltage was -10 V (Fig. 2).</p>
<p>Example 2</p>
<p>The polymers PFO and TFB in Synthesis Example 1 were dissolved in toluene to prepare an application solution (The concentrations of PFO and TFB in the application solution were each 1.5 wt%).</p>
<p>On a glass substrate carrying an ITO film of a thickness of 150 nm formed by a sputtering method, a suspension of poly( 3,4) ethylenedioxythiophene/polystyrenesulfonic acid (manufactured by Bayer, Bytron P TP Al 4083) was spin-coated to form a film of a thickness of 60 rim, and dried on a hot plate at 200 C for 10 minutes. Thereon, the above-described application solution was spin-coated to form a light emitting layer having a thickness of 200 mu. Thereon, bathocuproine (BCP) was vapor-deposited at a sedimentation speed of 0.45 nm/s as an electron transporting layer (extinction preventing layer) with a thickness of 40 rim. Further, as the layer (L), NTCDA and indium were co-vapor-deposited at sedimentation speeds of 0.4 nm/s and 0.02 nm/s. respectively, so as to give a film thickness of 10 rim together. Further, gold was vapor-deposited as a cathode of a thickness of 20 rim, manufacturing an organic EL device. The degree of vacuum in vapor deposition was 1.0 x io Torr or less in all cases. The proportion of an indium atom per mole of this NTCDA was one (0.25 indium atoms per * . carbonyl group).</p>
<p>The device was removed from the vapor deposition apparatus, and immediately, a current-voltage property was measured.</p>
<p>On the resultant device, a plus electrode was disposed at the ITO side and a minus electrode was disposed at the gold side, and a luminance of 130 cm/rn2 was shown when the voltage was 28 V (Fig. 3).</p>
<p>For evaluating stability of electric conductivity, change by time of current density in atmosphere was measured.</p>
<p>The ratio of the initial current value to the current value after hours was 9.0 (Fig. 4).</p>
<p>Comparative Example 1 The same device as in Example 1 excepting no vapor deposition of a layer (L) was manufactured.</p>
<p>On the resultant device, a minus electrode was disposed at the ITO side and a plus electrode was disposed at the gold side, and a current density of 0.4 mA/cm2 was shown when the voltage was -10 V. Apparently, the current density falls and electrons are not injected, as compared with the case of insertion of an electron injection layer (Fig. 2).</p>
<p>Comparative Example 2 The same device as in Example 2 excepting no vapor deposition of a layer CL) was manufactured.</p>
<p>On the resultant device, a plus electrode was disposed * . at the ITO side and a minus electrode was disposed at the gold side, and a luminance of 1 cd/rn2 was shown when the voltage was 28 V. Apparently, the luminance falls and electrons are not injected efficiently, as compared with the case of insertion of an electron injection layer (Fig. 3).</p>
<p>Comparative Example 3 [n the device of Example 2, BCP and cesium were co-vapor-deposited at sedimentation speeds of 0.4 nm/s and 0.1 nm/s, respectively, so as to give a film thickness of 10 nm together instead of a co-vapor deposition layer of NTCDA and indium contacting the cathode. For evaluating stability of electric conductivity, change by time of current density in atmosphere was measured. The ratio of the initial current value to the current value after 10 hours was 40000. Because of significant change as compared with Example 2, this device is judged to be instable under atmosphere (Fig. 4).</p>
<p>Example 3</p>
<p>(Manufacturing of sample for measuring absorption spectrum, ESR spectrum) A washed glass substrate was set on a vacuum vapor deposition machine, and as the layer (L), NTCDA and indium were co-vapor-deposited at sedimentation speeds of 0.4 nm/s and 0.02 nm/s, respectively, so as to give a film thickness of 200 run together. The proportion of an indium atom per mole of this NTCDA molecule was one (0.25 indium atoms per carbony]. group). * 30</p>
<p>On the other hand, a sample was also manufactured by vapor-depositing NTCDA at a sedimentation speed of 0.4 nm/s so as to give a film thickness of 200 nm without vapor deposition of a metal. The degree of vacuum was 1.0 x 1o Torr or less in all cases.</p>
<p>(Measurement of absorption spectrum) The absorption spectrum was measured by an ultraviolet-visible absorption spectrum measuring apparatus.</p>
<p>The measurement was performed in atmosphere at room temperature.</p>
<p>The absorption spectrum peak of a sample obtained by co-vapor deposition of NTCDA/indjum shifts by about 70 run toward longer wavelength side as compared with the case using only NTCDA (Fig. 5).</p>
<p>(Measurement of ESR spectrum) For verifying stability and the presence of free electrons, the ESR spectrum of a sample obtained by co-vapor deposition of NTCDA/indium in an electron spin resonance absorption (ESR) measurement apparatus was measured. Clear ESR spectrum in atmosphere teaches stability in atmosphere, indicating excellent durability. It is understood that free electrons contributing to electron conduction are generated in the layer (Fig. 6).</p>
<p>Comparative Example 4 (Manufacturing of sample for measuring absorption spectrum, ESR spectrum) * . A washed glass substrate was set on a vacuum vapor deposition machine, and BCP and indium were co-vapor-deposited at sedimentation speeds of 0.45 nm/s and 0.02 nm/s. respectively, so as to give a film thickness of 200 mu together. The proportion of an indium atom per mole of this BCP molecule was one. On the other hand, a sample was also manufactured by vapor-depositing BCP at a sedimentation speed of 0.45 nm/s so as to give a film thickness of 200 nm without vapor deposition of a metal. The degree of vacuum was 1.0 x 1o Torr or less in all cases.</p>
<p>(Measurement of absorption spectrum) The measurement environments are the same as in Example 3.</p>
<p>The absorption spectrum peak of a sample obtained by co-vapor deposition of BCP/indium shifts by 10 mu or more toward shorter wavelength side as compared with the case using only BCP (Fig. 7).</p>
<p>(Measurement of ESR spectrum) In measurement of ESR, no clear ESR spectrum shown in atmosphere teaches that the sample of Comparative Example 4 is instable in atmosphere. It is understood that free electrons contributing to electron conduction are not generated in the layer (Fig. 8).</p>
<p>Example 3</p>
<p>(Measurement of electric conductivity) * . (Manufacturing of sample for measurement) A washed glass substrate was set on a vacuum vapor deposition machine, and as the layer (L), NTCDA and metal atom were co-vapor-deposited at sedimentation speeds of 0.4 nm/s and 0.02 nm/s, respectively, so as to give a film thickness of 200 nm together. The proportion of a metal atom per mole of this NPCDA molecule was one (0.25 metal atoms per carbonyl group).</p>
<p>Further, a gold electrode was vapor-deposited as a parallel electrode with an interval of 100 pm using a vapor deposition mask.</p>
<p>On the other hand, BCP and metal atom were co-vapor-deposited at sedimentation speeds of 0.45 nm/s and 0.02 nm/s. respectively, so as to give a film thickness of 200 nm together. Further, a gold electrode was vapor-deposited.</p>
<p>The degree of vacuum was 1.0 x Torr or less in all cases.</p>
<p>(Manufacturing of sample for measurement) The electric conduction of a co-deposition film obtained by doping a metal atom into NTCDA or BCP was measured by measuring the current quantity when voltage was applied between gold electrodes For measurement, an electro meter was used. The measurement was performed in vacuum at room temperature.</p>
<p>(Measurement results) The results of measurement of the electric conductivity of the film obtained by doping a metal atom into NTCDA or BCP are shown in Table 1. The doping amount of metals is a * S proportion of one each metal atom per NTCDA or BCP molecule.</p>
<p>There is also a case showing improvement in conductivity by 6 digits or more as compared with a case of no doping. When an alkali metal such as lithium, sodium and the like is doped, electric conductivity increases, however, since an alkali metal shows extremely excellent reactivity with water and oxygen, a composition of this metal atom and an organic compound is instable against atmosphere. On the other hand, indium is relatively stable against water and oxygen. When NTCDA and BCP each doped with this indium are compared, NTCDA doped with indium shows an electric conductivity of 9.1 x 102 S/cm which is higher by about 5 digits or more.</p>
<p>Table 1</p>
<p>Doped metal ____________ (S/cm) Non 2.5x1O 5.7x1O In 9.1x1O 2.0x101 Li 6.].x1O 4.2x1O Na 2.9x1O 5.2x1O * K 6.3x1O 9.1x1O Rb 2.Ox1O 1.4x104 Cs 1.2x1O 1.4x104 The organic EL device of the present invention is excellent in durability, electron injectability and the like.</p>
<p>INDUSTRIAL APPLICABILITY</p>
<p>A sheet light source, segment display and dot matrix display can be manufactured using the organic * . electroluminescence device of the present invention. Further, a liquid crystal display can be manufactured using the organic electroluminescence device of the present invention as backlight.</p>
<p>For obtaining light emission in the form of sheet using the organic EL device of the present invention, it is advantageous that an anode and a cathode each in the form of sheet are disposed so as to overlap. For obtaining light emission in the form of pattern, there are a method in which a mask equipped with a window in the form of pattern is disposed on the surface of the above-described sheet light emitting device, a method in which an organic substance layer at no-emitting portions is formed with extremely large thickness to attain substantially no-emission, and a method in which either an anode or a cathode, or both electrode are formed in the form of pattern. By forming a pattern by any of these methods and disposing some electrodes to allow On/OFF independently, a segment type display device which can display numbers, letters, simple marks and the like is obtained.</p>
<p>Further, for obtaining a dot matrix device, it may be advantageous that both an anode and a cathode are formed in the form of stripe and disposed so as to cross. Partial color display and multi color display are made possible by a method of coating a plurality of polymer fluorescent substances of different emission colors divisionally, and a method of using * . a color filter or a fluorescence converting filter. A dot matrix device can be passively driven, and or may be actively driven in combination with TFT and the like. These display devices can be used as a display such as computers, televisions, portable terminals, portable telephones, car navigations, video camera view finders and the like.</p>
<p>Further, the above-described sheet light emitting device is of self-luminous thin type, and can be suitably used as a sheet light source for backlight of a liquid crystal display or a sheet light source for illumination. When a flexible substrate is used, it can also be used as a light source or display in the form of curved surface.</p>
Claims (1)
- <p>CLAIMS</p><p>1. An organic electroluminescence device having a light emitting layer between an anode and a cathode wherein the device has a layer CL) between said cathode and said light emitting layer so as to contact the cathode, and the layer (L) comprises an organic compound (A) containing an aromatic hydrocarbon ring or hetero ring and a carbony]. group and a metal (B) selected from alkaline earth metals and group III metals.</p><p>2. An organic electroluminescence device having a light emitting layer between an anode and a cathode wherein the device has a layer (L) between said cathode and said light emitting layer so as to contact the cathode, and the layer (L) is obtained by using an organic compound (A) containing an aromatic hydrocarbon ring or hetero ring and a carbonyl group and a metal (B) selected from alkaline earth metals and group III metals.</p><p>3. The organic electroluminescence device according to Claim 1 or 2, wherein a mixture obtained from the organic compound (A) and the metal (B) has an electric conductivity of 106 S/cm or more.</p><p>4. The organic electroluminescence device according to any one of Claims 1 to 3, wherein the absorption peak wavelength of a thin film composed of the organic compound (A) and the metal (B) is larger by 5 nm or more than the absorption peak wavelength of a thin film composed of the organic compound (A). * S</p><p>5. The organic electroluminescence device according to any one of Claims 1 to 4, wherein the metal (B) is selected from magnesium, calcium, strontium, barium, aluminum, gallium, * indium and thallium.</p><p>6. The organic electroluminescence device according to * any one of Claims 1. to 5, wherein the organic compound (A) is selected from the following formulae (1), (2), (3) and (4).</p><p>Ar1 (1) (wherein, Ar1 represents an organic group containing an aromatic hydrocarbon ring or betero ring. X represents 0 or NH. n represents an integer of 1 or more and 4 or less. When there are a plurality of Xs, they may be the same or different.) /0 \ Ar2 ()Ar3) /m (2) (wherein, Ar2 and Ar3 represent each independently an organic group containing an aromatic hydrocarbon ring or hetero ring.</p><p>m represents an integer of 1 or more and 4 or less. When there are a plurality of Ar3s, they may be the same or different.) Ar4Ar5) (wherein, Ar4 arid Ar5 represent each independently an organic group containing an aromatic hydrocarbon ring or hetero ring.</p><p>1 represents an integer of 1 or more and 4 or less. Ar5s may be the same or different.) /19 \ k (4) (wherein, Ar6 and Ar7 represent each independently an organic group containing an aromatic hydrocarbon ring or hetero ring.</p><p>k represents an integer of 1 or more and 4 or less. When there are a plurality of Ar7s, they may be the same or different.).</p><p>7. A sheet light source using the organic electroluminescence device according to any one of Claims 1 to 6.</p><p>8. A segment display using the organic electroluminescence device according to any one of Claims 1 to 6.</p><p>9. A dot matrix display using the organic electroluminescence device according to any one of Claims 1 to 6. * S</p><p>10. A liquid crystal display using the organic electroluminescence device according to any one of Claims 1 to 6 as backlight.</p>
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2005091263A JP2006278419A (en) | 2005-03-28 | 2005-03-28 | Organic electroluminescence element |
PCT/JP2006/306988 WO2006104230A1 (en) | 2005-03-28 | 2006-03-27 | Organic electroluminescent device |
Publications (3)
Publication Number | Publication Date |
---|---|
GB0721118D0 GB0721118D0 (en) | 2007-12-12 |
GB2439887A true GB2439887A (en) | 2008-01-09 |
GB2439887B GB2439887B (en) | 2010-10-27 |
Family
ID=37053484
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB0721118A Expired - Fee Related GB2439887B (en) | 2005-03-28 | 2006-03-27 | Organic electroluminescent device |
Country Status (6)
Country | Link |
---|---|
JP (1) | JP2006278419A (en) |
KR (1) | KR20080003365A (en) |
DE (1) | DE112006000714T5 (en) |
GB (1) | GB2439887B (en) |
TW (1) | TW200643141A (en) |
WO (1) | WO2006104230A1 (en) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP5196764B2 (en) * | 2006-11-17 | 2013-05-15 | キヤノン株式会社 | Organic EL device and manufacturing method thereof |
KR101468592B1 (en) * | 2008-06-25 | 2014-12-05 | 삼성전자주식회사 | Organic photoelectric conversion film, photoelectric conversion device and image sensor |
KR101912675B1 (en) * | 2010-10-04 | 2018-10-29 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | Composite material, light-emitting element, light-emitting device, electronic device, and lighting device |
CN109698281B (en) * | 2019-01-11 | 2022-07-08 | 中国科学院重庆绿色智能技术研究院 | Photovoltaic device containing pyridine polymer |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH10270171A (en) * | 1997-01-27 | 1998-10-09 | Junji Kido | Organic electroluminescent element |
JP2000196140A (en) * | 1998-12-28 | 2000-07-14 | Sharp Corp | Organic electroluminescence element and fabrication thereof |
JP2000306676A (en) * | 1999-04-21 | 2000-11-02 | Chemiprokasei Kaisha Ltd | Organic electroluminescent element |
JP2003292587A (en) * | 2002-04-05 | 2003-10-15 | National Institute Of Advanced Industrial & Technology | Copolymer and electroluminescence element |
-
2005
- 2005-03-28 JP JP2005091263A patent/JP2006278419A/en active Pending
-
2006
- 2006-03-27 GB GB0721118A patent/GB2439887B/en not_active Expired - Fee Related
- 2006-03-27 WO PCT/JP2006/306988 patent/WO2006104230A1/en active Application Filing
- 2006-03-27 TW TW095110497A patent/TW200643141A/en unknown
- 2006-03-27 DE DE112006000714T patent/DE112006000714T5/en not_active Withdrawn
- 2006-03-27 KR KR1020077024557A patent/KR20080003365A/en not_active Application Discontinuation
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH10270171A (en) * | 1997-01-27 | 1998-10-09 | Junji Kido | Organic electroluminescent element |
JP2000196140A (en) * | 1998-12-28 | 2000-07-14 | Sharp Corp | Organic electroluminescence element and fabrication thereof |
JP2000306676A (en) * | 1999-04-21 | 2000-11-02 | Chemiprokasei Kaisha Ltd | Organic electroluminescent element |
JP2003292587A (en) * | 2002-04-05 | 2003-10-15 | National Institute Of Advanced Industrial & Technology | Copolymer and electroluminescence element |
Also Published As
Publication number | Publication date |
---|---|
GB0721118D0 (en) | 2007-12-12 |
WO2006104230A1 (en) | 2006-10-05 |
TW200643141A (en) | 2006-12-16 |
DE112006000714T5 (en) | 2008-02-28 |
GB2439887B (en) | 2010-10-27 |
KR20080003365A (en) | 2008-01-07 |
JP2006278419A (en) | 2006-10-12 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US6597012B2 (en) | Organic electroluminescent device | |
JP3747686B2 (en) | Polymer phosphor and polymer light emitting device using the same | |
EP1074600B1 (en) | Polymeric fluorescent substance and polymer light emitting device | |
KR20100054798A (en) | Organic electroluminescent device containing metal-doped molybdenum oxide layer and method for manufacturing the same | |
JP2000299189A (en) | Light emitting polymer element and display device and surface light source using it | |
JPH07126616A (en) | El device containing polythiophene | |
KR20120093354A (en) | Method for manufacturing organic electroluminescent element, organic electroluminescent element, display device and illuminating device | |
JP4934888B2 (en) | Polymer phosphor and polymer light emitting device using the same | |
JP4724944B2 (en) | Method for producing polymer light emitting device and polymer light emitting device | |
KR20110000733A (en) | Organic electroluminescence element and method for manufacturing the same | |
JP2001003045A (en) | Polymeric phosphor and polymeric luminescent element using same | |
JP4846191B2 (en) | Color conversion film and light emitting device | |
KR20020083494A (en) | Polymeric fluorescent substance and polymer light-emitting device using the same | |
US7230070B2 (en) | Electroactive fluorene copolymers and devices made with such polymers | |
WO2002102925A1 (en) | Polymeric fluorescent material, process for producing the same, and polymeric luminescent element | |
JP2001076880A (en) | Organic exectroluminescent element | |
GB2439887A (en) | Organic electroluminescent device | |
EP1168891B1 (en) | Polymeric fluorescent substance and polymer light-emitting device using the same | |
KR20110053974A (en) | Organic electroluminescent element and method for manufacturing same | |
US20080260970A1 (en) | Organic Electroluminescence Device | |
JP4045691B2 (en) | Polymer light emitting device | |
JP2003034715A (en) | Polymer fluorescent substance and polymeric light emitting element | |
KR20110018375A (en) | Composition and light-emitting element comprising the same | |
JP3927221B2 (en) | EL device using polythiophene | |
JP2002100480A (en) | Organic electroluminescence element |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 20220327 |