JP3981331B2 - 有機エレクトロルミネッセンス素子 - Google Patents
有機エレクトロルミネッセンス素子 Download PDFInfo
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- JP3981331B2 JP3981331B2 JP2002592428A JP2002592428A JP3981331B2 JP 3981331 B2 JP3981331 B2 JP 3981331B2 JP 2002592428 A JP2002592428 A JP 2002592428A JP 2002592428 A JP2002592428 A JP 2002592428A JP 3981331 B2 JP3981331 B2 JP 3981331B2
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- organic
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- 238000005401 electroluminescence Methods 0.000 title claims abstract description 44
- 239000000463 material Substances 0.000 claims abstract description 33
- 150000001412 amines Chemical class 0.000 claims abstract description 29
- 125000002524 organometallic group Chemical group 0.000 claims abstract description 14
- 229910001385 heavy metal Inorganic materials 0.000 claims abstract description 12
- 230000005525 hole transport Effects 0.000 claims description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 239000003446 ligand Substances 0.000 claims description 11
- 229920006389 polyphenyl polymer Polymers 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000000732 arylene group Chemical group 0.000 claims description 5
- 229920003026 Acene Polymers 0.000 claims description 4
- 150000004982 aromatic amines Chemical class 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000005647 linker group Chemical group 0.000 claims description 4
- 150000004696 coordination complex Chemical class 0.000 claims description 3
- 229910052741 iridium Inorganic materials 0.000 claims description 3
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical group C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 claims description 2
- 125000006267 biphenyl group Chemical group 0.000 claims description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 2
- 125000004986 diarylamino group Chemical group 0.000 claims description 2
- 229910052750 molybdenum Inorganic materials 0.000 claims description 2
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- 229910052697 platinum Inorganic materials 0.000 claims description 2
- 229910052702 rhenium Inorganic materials 0.000 claims description 2
- 229910052703 rhodium Inorganic materials 0.000 claims description 2
- 229910052707 ruthenium Inorganic materials 0.000 claims description 2
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical group NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 11
- 230000005611 electricity Effects 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 65
- 239000010408 film Substances 0.000 description 13
- 238000002347 injection Methods 0.000 description 13
- 239000007924 injection Substances 0.000 description 13
- -1 aromatic tertiary amine Chemical class 0.000 description 11
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 238000000034 method Methods 0.000 description 6
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 6
- 239000002356 single layer Substances 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- KBZQJAMUYAMVEK-UHFFFAOYSA-N CC(CC1)CCC1C1CCCCC1 Chemical compound CC(CC1)CCC1C1CCCCC1 KBZQJAMUYAMVEK-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 230000004888 barrier function Effects 0.000 description 3
- 238000005266 casting Methods 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 239000002019 doping agent Substances 0.000 description 3
- 230000005281 excited state Effects 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 238000004528 spin coating Methods 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- 238000001771 vacuum deposition Methods 0.000 description 3
- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical group C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 229940125904 compound 1 Drugs 0.000 description 2
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 150000004866 oxadiazoles Chemical class 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 229910052761 rare earth metal Inorganic materials 0.000 description 2
- 238000004544 sputter deposition Methods 0.000 description 2
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 2
- 238000002834 transmittance Methods 0.000 description 2
- 238000007740 vapor deposition Methods 0.000 description 2
- NGQSLSMAEVWNPU-YTEMWHBBSA-N 1,2-bis[(e)-2-phenylethenyl]benzene Chemical class C=1C=CC=CC=1/C=C/C1=CC=CC=C1\C=C\C1=CC=CC=C1 NGQSLSMAEVWNPU-YTEMWHBBSA-N 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- 150000000183 1,3-benzoxazoles Chemical class 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
- 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 1
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 1
- NZGXEUWGGSDALJ-UHFFFAOYSA-N C1=CC=CC=C1C1=NC=CC=C1[Ir](C=1C(=NC=CC=1)C=1C=CC=CC=1)C1=CC=CN=C1C1=CC=CC=C1 Chemical compound C1=CC=CC=C1C1=NC=CC=C1[Ir](C=1C(=NC=CC=1)C=1C=CC=CC=1)C1=CC=CN=C1C1=CC=CC=C1 NZGXEUWGGSDALJ-UHFFFAOYSA-N 0.000 description 1
- 0 CC1C*CC1 Chemical compound CC1C*CC1 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 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
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical group [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 229910020923 Sn-O Inorganic materials 0.000 description 1
- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 239000010405 anode material Substances 0.000 description 1
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-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
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 150000001716 carbazoles Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000010549 co-Evaporation Methods 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 125000005594 diketone group Chemical group 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- 230000005283 ground state Effects 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
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 150000004989 p-phenylenediamines Chemical class 0.000 description 1
- 125000002080 perylenyl group Chemical class C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 150000005041 phenanthrolines Chemical class 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920001230 polyarylate Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 150000003252 quinoxalines Chemical class 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000006836 terphenylene group Chemical group 0.000 description 1
- 239000012780 transparent material Substances 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
- 150000003918 triazines Chemical class 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
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- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/16—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing only one pyridine ring
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
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- 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
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
- H10K85/324—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising aluminium, e.g. Alq3
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
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- 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
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- 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
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/18—Metal complexes
- C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2102/00—Constructional details relating to the organic devices covered by this subclass
- H10K2102/10—Transparent electrodes, e.g. using graphene
- H10K2102/101—Transparent electrodes, e.g. using graphene comprising transparent conductive oxides [TCO]
- H10K2102/103—Transparent electrodes, e.g. using graphene comprising transparent conductive oxides [TCO] comprising indium oxides, e.g. ITO
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/344—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising ruthenium
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Organic Chemistry (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Optics & Photonics (AREA)
- Inorganic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Electroluminescent Light Sources (AREA)
Description
従来の有機EL素子の構成としては、様々なものが知られているが、例えば、特許文献1には、ITO(インジウムチンオキシド)/正孔輸送層/発光層/陰極の素子構成の有機EL素子において、正孔輸送層の材料として、芳香族第三級アミンを用いることが開示されており、この素手構成により、20V以下の印加電圧で数百cd/m2 の高輝度が可能となった。さらに、燐光性発光ドーパントであるイリジウム錯体を発光層にドーパントとして用いることにより、輝度数百cd/m2 以下では、発光効率が約40ルーメン/W以上であることが報告されている(非特許文献1) 。
また、有機EL素子をフラットパネルディスプレイなどへ応用する場合、発光効率を改善し、低消費電力化することが求められているが、上記素子構成では、発光輝度向上とともに、発光効率が著しく低下するという欠点を有しており、そのためフラットパネルディスプレイの消費電力が低下しないという問題がある。特に、パッシブ駆動の場合、実用上、瞬間的に数千cd/m2 以上の輝度が必要となるため、高輝度域での発光効率を向上させることが重要であった。しかしながら、現状用いられている正孔輸送材料では、高輝度域において3重項の失活過程が支配的となるため、発光効率の減少は、改善できていなかった。
一般式(I)
前記一般式(I)で表されるアミン誘導体が、ポリアセン系縮合芳香族構造を含まないアリールアミン誘導体又はポリアリールアミン誘導体からなることが好ましい。
この正孔輸送層は、前記アミン誘導体のみからなる単層構造でもよいし、前記アミン化合物と、公知の正孔輸送層材料からなる層との複層構造であってもよい。また、前記アミン誘導体と公知の正孔輸送層材料との混合物からなる層を含む単層構造又は複層構造であってもよい。
前記アミン誘導体を含む正孔輸送層は、前記アミン誘導体と、必要に応じて他の有機発光材料とを用い、真空蒸着法、キャスト法、塗布法、スピンコート法などにより形成することができる。
重金属を含有する有機金属錯体は、特に限定されないが、発光性ドーパントとして機能することが好ましい。重金属としては、例えば、Ir、Pt、Pd、Ru、Rh、Mo又はReが挙げられる。また、有機金属錯体の配位子としては、C,Nが金属に配位又は結合する配位子(CN配位子)があり、例えば、
さらに、前記有機金属錯体からなる発光材料は、燐光性の発光材料である。
また、有機発光層の主材料の3重項準位エネルギーは、重金属を含有する有機金属錯体の3重項準位エネルギーよりも大きいことが好ましい。このような関係により、発光層の主材料のエネルギーが効率よく有機金属錯体へ移動し、発光効率がより向上するためである。
本発明の有機EL素子は、基板により支持されることが好ましい。基板の材料については、特に制限はなく、公知の有機EL素子に慣用されているもの、例えば、ガラス、透明プラスチック又は石英などからなるもを用いることができる。 陽極の材料としては、仕事関数が4eV以上と大きい金属、合金、電気伝導性化合物又はこれらの混合物が好ましく用いられる。具体例としては、Au等の金属、CuI、ITO、SnO2 又はZnO等の誘電性透明材料が挙げられる。陽極は、例えば蒸着法やスパッタリング法などの方法で、前記材料の薄膜を形成することにより作製することができる。有機発光層からの発光を陽極より取り出す場合、陽極の透過率は10%より大きいことが好ましい。また、陽極のシート抵抗は、数百Ω/□以下が好ましい。陽極の膜厚は材料にもよるが、通常10nm〜1μm、好ましくは10〜200nmの範囲で選択される。
なお、有機発光層からの発光を効率よく取り出すために、前記陽極及び陰極の少なくとも一方は透明又は半透明物質により形成することが好ましい。
参考例1
25mm×75mm×1.1mm厚のITO(In−Sn−O)透明電極付きガラス基板(ジオマティック社製) をイソプロピルアルコール中で5分間超音波洗浄を行なった後、UVオゾン洗浄を30分問行なった。洗浄後の透明電極ライン付きガラス基板を真空蒸着装置の基板ホルダーに装着し、酸素−アルゴンの混合雰囲気下、プラズマ洗浄を行った。次に、透明電極ラインが形成されている側の面上に、前記透明電極を覆うようにして膜厚50nmの下記化合物1を成膜した。この化合物1膜は正孔輸送層として機能する。この膜上に、4,4’−N,N’−ジカルバゾール−ビフェニル(CBP)とトリス−(2−フェニルピリジル)イリジウム(Ir(Ppy))を組成比8重量%に制御して、二元蒸着して成膜した。この膜は、発光層として機能する。次に、この発光層上に、膜厚10nmの2,9−ジメチル−4,7−ジフェニル−1,10−フェナントロリン(BCP)及び膜厚40nmのトリス(8−キノリノール) アルミニウム膜(Alq膜) を積層し、成膜した。BCP膜は正孔障壁層として、Alq膜は、電子注入層として機能する。その後、アルカリ金属であるLi(Li源:サエスゲッター社製) とAlqを二元蒸着させ、電子注入層(陰極) としてAlq:Li膜を形成した。このAlq:Li膜上に金属Alを蒸着させ金属陰極を形成し有機EL素子を製造した。
得られた有機EL素子について、電圧、電流を変えて、発光輝度を測定し、発光輝度10000cd/m2 時の発光効率(=(輝度)/(電流密度))を算出したところ35cd/Aであった。
参考例1において、化合物1の代わりに、一般式(I)で表される下記化合物2を使用した以外は同様にして有機EL素子を作製した。
得られた有機EL素子について、電圧、電流を変えて、発光輝度を測定し、発光輝度10000cd/m2 時の発光効率(=(輝度)/(電流密度))を算出したところ37cd/Aであった。
参考例1において、化合物1の代わりに、一般式(I)で表される下記化合物3を使用した以外は同様にして有機EL素子を作製した。
得られた有機EL素子について、電圧、電流を変えて、発光輝度を測定し、発光輝度10000cd/m2 時の発光効率(=(輝度)/(電流密度))を算出したところ50cd/Aであった。
参考例1において、化合物1の代わりに、一般式(I)で表される下記化合物4を使用した以外は同様にして有機EL素子を作製した。
得られた有機EL素子について、電圧、電流を変えて、発光輝度を測定し、発光輝度10000cd/m2 時の発光効率(=(輝度)/(電流密度))を算出したところ40cd/Aであった。
参考例1において、化合物1の代わりに、下記化合物5を使用した以外は同様にして有機EL素子を作製した。
得られた有機EL素子について、電圧、電流を変えて、発光輝度を測定し、発光輝度10000cd/m2 時の発光効率(=(輝度)/(電流密度))を算出したところ25cd/Aであった。
参考例1において、化合物1の代わりに、一般式(I)で表される下記化合物6を使用した以外は同様にして有機EL素子を作製した。
得られた有機EL素子について、電圧、電流を変えて、発光輝度を測定し、発光輝度10000cd/m2 時の発光効率(=(輝度)/(電流密度))を算出したところ40cd/Aであった。
参考例1において、化合物1の代わりに、下記化合物NPDを使用した以外は同様にして有機EL素子を作製した。
得られた有機EL素子について、電圧、電流を変えて、発光輝度を測定し、発光輝度10000cd/m2 時の発光効率(=(輝度)/(電流密度))を算出したところ20cd/Aと、実施例1〜4に比べ発光効率が劣るものであった。
Claims (11)
- 一対の電極間に発光層または発光層を含む複数層の有機媒体を形成してなり、該有機媒体内に重金属を含有する有機金属錯体からなる燐光性の発光材料を含有する有機エレクトロルミネッセンス素子において、該有機媒体内に下記一般式(I)で表されるアミン誘導体を含有することを特徴とする有機エレクトロルミネッセンス素子。
一般式(I)
- 前記一般式(I)で表されるアミン誘導体において、Ar1 、Ar2 、Ar3 及びAr4 のうち、少なくとも2つは置換もしくは無置換のフェニル基が2〜4個連結した構造を有することを特徴とする請求項1に記載の有機エレクトロルミネッセンス素子。
- 前記一般式(I)で表されるアミン誘導体において、Ar1 、Ar2 、Ar3 及びAr4 のうち、少なくとも2つは置換もしくは無置換のビフェニル基を有することを特徴とする請求項1に記載の有機エレクトロルミネッセンス素子。
- 前記アミン誘導体が、ポリアセン系縮合芳香族構造を含まないアリールアミン誘導体又はポリアリールアミン誘導体からなることを特徴とする請求項1〜5のいずれかに有機エレクトロルミネッセンス素子。
- 前記一般式(I)、(II)又は(III) で表されるアミン誘導体を正孔輸送材料として用いることを特徴とする請求項1〜6のいずれかに記載の有機エレクトロルミネッセンス素子。
- 前記発光層を形成する主材料の3重項準位エネルギーが、重金属を含有する有機金属錯体の3重項準位エネルギーよりも大きいことを特徴とする請求項1〜6のいずれかに記載の有機エレクトロルミネッセンス素子。
- 前記重金属が、Ir、Pt、Pd、Ru、Rh、Mo及びReの中から選ばれる少なくとも一種類であることを特徴とする請求項1〜6のいずれかに記載の有機エレクトロルミネッセンス素子。
- 前記有機金属錯体が、重金属に前記配位子が2〜4個配位したものであることを特徴とする請求項10に記載の有機エレクトロルミネッセンス素子。
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JP2001155290 | 2001-05-24 | ||
JP2001155290 | 2001-05-24 | ||
PCT/JP2002/004485 WO2002094965A1 (fr) | 2001-05-24 | 2002-05-08 | Élément électroluminescent organique |
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JP2003109768A (ja) * | 2001-07-25 | 2003-04-11 | Toray Ind Inc | 発光素子 |
JP3919583B2 (ja) | 2002-04-12 | 2007-05-30 | キヤノン株式会社 | 有機発光素子 |
US7452257B2 (en) * | 2002-12-27 | 2008-11-18 | Semiconductor Energy Laboratory Co., Ltd. | Method of manufacturing a display device |
KR100696470B1 (ko) * | 2004-06-15 | 2007-03-19 | 삼성에스디아이 주식회사 | 유기 전계 발광 소자 |
KR100751316B1 (ko) * | 2004-06-25 | 2007-08-22 | 삼성에스디아이 주식회사 | 유기 전계 발광 소자 |
JPWO2007116750A1 (ja) * | 2006-03-30 | 2009-08-20 | 出光興産株式会社 | 有機エレクトロルミネッセンス素子用材料、及びこれを用いた有機エレクトロルミネッセンス素子 |
EP2097938B1 (en) * | 2006-12-28 | 2019-07-17 | Universal Display Corporation | Long lifetime phosphorescent organic light emitting device (oled) structures |
WO2009008277A1 (ja) * | 2007-07-11 | 2009-01-15 | Idemitsu Kosan Co., Ltd. | 有機エレクトロルミネッセンス素子用材料及び有機エレクトロルミネッセンス素子 |
US8040053B2 (en) * | 2008-02-09 | 2011-10-18 | Universal Display Corporation | Organic light emitting device architecture for reducing the number of organic materials |
EP2329544B1 (en) * | 2008-09-04 | 2017-05-17 | Universal Display Corporation | White phosphorescent organic light emitting devices |
JP2010073598A (ja) * | 2008-09-22 | 2010-04-02 | Mitsubishi Chemicals Corp | 有機薄膜パターニング用基板、有機電界発光素子、有機el表示装置および有機el照明 |
US8288187B2 (en) | 2010-01-20 | 2012-10-16 | Universal Display Corporation | Electroluminescent devices for lighting applications |
US9349964B2 (en) * | 2010-12-24 | 2016-05-24 | Lg Chem, Ltd. | Organic light emitting diode and manufacturing method thereof |
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US4720432A (en) | 1987-02-11 | 1988-01-19 | Eastman Kodak Company | Electroluminescent device with organic luminescent medium |
US5837166A (en) † | 1993-09-29 | 1998-11-17 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device and arylenediamine derivative |
DE69412567T2 (de) * | 1993-11-01 | 1999-02-04 | Hodogaya Chemical Co., Ltd., Tokio/Tokyo | Aminverbindung und sie enthaltende Elektrolumineszenzvorrichtung |
EP0666298A3 (en) * | 1994-02-08 | 1995-11-15 | Tdk Corp | Organic electroluminescent element and compound used therein. |
US5707745A (en) * | 1994-12-13 | 1998-01-13 | The Trustees Of Princeton University | Multicolor organic light emitting devices |
JP3168897B2 (ja) * | 1996-01-12 | 2001-05-21 | 出光興産株式会社 | ナフチル基を有するジアミン誘導体及び該誘導体を用いた有機エレクトロルミネッセンス素子 |
JP3650218B2 (ja) * | 1996-05-10 | 2005-05-18 | ケミプロ化成株式会社 | 高分子量芳香族アミン化合物およびそれよりなるホール輸送性材料 |
WO1998000474A1 (fr) * | 1996-06-28 | 1998-01-08 | Chisso Corporation | Materiau emetteur de lumiere rouge et composant electroluminescent organique fabrique a l'aide de ce materiau |
JP3764218B2 (ja) * | 1996-10-01 | 2006-04-05 | 出光興産株式会社 | 有機電界発光素子 |
JP3654909B2 (ja) * | 1996-12-28 | 2005-06-02 | Tdk株式会社 | 有機el素子 |
JPH11144773A (ja) * | 1997-09-05 | 1999-05-28 | Fuji Photo Film Co Ltd | 光電変換素子および光再生型光電気化学電池 |
JP3757583B2 (ja) * | 1997-11-17 | 2006-03-22 | 三菱化学株式会社 | 有機電界発光素子 |
CN1252034C (zh) * | 1999-09-30 | 2006-04-19 | 出光兴产株式会社 | 胺化合物和使用该化合物的有机电致发光元件 |
JP3938263B2 (ja) * | 1999-11-09 | 2007-06-27 | 独立行政法人科学技術振興機構 | 金属錯体の製造方法 |
DE60045110D1 (de) * | 1999-12-01 | 2010-11-25 | Univ Princeton | Erungsmittel in organischen led's |
JP2001313178A (ja) * | 2000-04-28 | 2001-11-09 | Pioneer Electronic Corp | 有機エレクトロルミネッセンス素子 |
US6645645B1 (en) * | 2000-05-30 | 2003-11-11 | The Trustees Of Princeton University | Phosphorescent organic light emitting devices |
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- 2002-05-08 WO PCT/JP2002/004485 patent/WO2002094965A1/ja active Application Filing
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- 2002-05-08 DE DE20221915U patent/DE20221915U1/de not_active Expired - Lifetime
- 2002-05-08 US US10/477,752 patent/US20040131882A1/en not_active Abandoned
- 2002-05-08 EP EP02724727.9A patent/EP1391495B2/en not_active Expired - Lifetime
- 2002-05-08 KR KR1020087023669A patent/KR101000355B1/ko active IP Right Review Request
- 2002-05-08 DE DE60229934T patent/DE60229934D1/de not_active Expired - Lifetime
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- 2002-05-08 JP JP2002592428A patent/JP3981331B2/ja not_active Expired - Lifetime
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Also Published As
Publication number | Publication date |
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EP1391495B2 (en) | 2021-07-21 |
KR20080100278A (ko) | 2008-11-14 |
WO2002094965A1 (fr) | 2002-11-28 |
US20120168740A1 (en) | 2012-07-05 |
KR101000355B1 (ko) | 2010-12-13 |
US20060141288A1 (en) | 2006-06-29 |
CN1531581A (zh) | 2004-09-22 |
EP1391495A4 (en) | 2007-04-25 |
EP1391495B1 (en) | 2008-11-19 |
JPWO2002094965A1 (ja) | 2004-09-09 |
US20100109001A1 (en) | 2010-05-06 |
TWI290804B (en) | 2007-12-01 |
US20040131882A1 (en) | 2004-07-08 |
DE20221915U1 (de) | 2009-06-04 |
EP1391495A1 (en) | 2004-02-25 |
KR20040012860A (ko) | 2004-02-11 |
DE60229934D1 (de) | 2009-01-02 |
ATE414754T1 (de) | 2008-12-15 |
CN100377382C (zh) | 2008-03-26 |
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