JP4285741B2 - 有機電界発光素子およびその作製方法 - Google Patents
有機電界発光素子およびその作製方法 Download PDFInfo
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- JP4285741B2 JP4285741B2 JP2003364219A JP2003364219A JP4285741B2 JP 4285741 B2 JP4285741 B2 JP 4285741B2 JP 2003364219 A JP2003364219 A JP 2003364219A JP 2003364219 A JP2003364219 A JP 2003364219A JP 4285741 B2 JP4285741 B2 JP 4285741B2
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- 238000004519 manufacturing process Methods 0.000 title claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 57
- 229920000553 poly(phenylenevinylene) Polymers 0.000 claims description 39
- 239000000975 dye Substances 0.000 claims description 32
- 239000010410 layer Substances 0.000 claims description 30
- 239000000126 substance Substances 0.000 claims description 30
- 229920000620 organic polymer Polymers 0.000 claims description 24
- -1 poly (p-phenylene vinylene) Polymers 0.000 claims description 21
- 230000032258 transport Effects 0.000 claims description 20
- 238000010438 heat treatment Methods 0.000 claims description 9
- 230000005525 hole transport Effects 0.000 claims description 9
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 8
- 229920000123 polythiophene Polymers 0.000 claims description 8
- 239000002346 layers by function Substances 0.000 claims description 5
- 229910052693 Europium Inorganic materials 0.000 claims description 4
- 229920000265 Polyparaphenylene Polymers 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
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 claims description 4
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 claims description 4
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 claims description 3
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 3
- XZCJVWCMJYNSQO-UHFFFAOYSA-N butyl pbd Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=NN=C(C=2C=CC(=CC=2)C=2C=CC=CC=2)O1 XZCJVWCMJYNSQO-UHFFFAOYSA-N 0.000 claims description 3
- 239000000463 material Substances 0.000 claims description 3
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 3
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 claims description 3
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 claims description 3
- SLLFVLKNXABYGI-UHFFFAOYSA-N 1,2,3-benzoxadiazole Chemical group C1=CC=C2ON=NC2=C1 SLLFVLKNXABYGI-UHFFFAOYSA-N 0.000 claims description 2
- POXIZPBFFUKMEQ-UHFFFAOYSA-N 2-cyanoethenylideneazanide Chemical group [N-]=C=[C+]C#N POXIZPBFFUKMEQ-UHFFFAOYSA-N 0.000 claims description 2
- KLKLRQGPTGBOAU-UHFFFAOYSA-N N#CC1=CC=CNN=C1C#N Chemical compound N#CC1=CC=CNN=C1C#N KLKLRQGPTGBOAU-UHFFFAOYSA-N 0.000 claims description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
- BYVQWWJWFUMPMC-UHFFFAOYSA-N acetonitrile;n,n-diphenylaniline Chemical compound CC#N.C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 BYVQWWJWFUMPMC-UHFFFAOYSA-N 0.000 claims description 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 2
- 229910052790 beryllium Inorganic materials 0.000 claims description 2
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 2
- 229960000956 coumarin Drugs 0.000 claims description 2
- 235000001671 coumarin Nutrition 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 2
- RGLYKWWBQGJZGM-ISLYRVAYSA-N diethylstilbestrol Chemical group C=1C=C(O)C=CC=1C(/CC)=C(\CC)C1=CC=C(O)C=C1 RGLYKWWBQGJZGM-ISLYRVAYSA-N 0.000 claims description 2
- 238000005401 electroluminescence Methods 0.000 claims description 2
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 claims description 2
- VHBFFQKBGNRLFZ-UHFFFAOYSA-N flavone Chemical group O1C2=CC=CC=C2C(=O)C=C1C1=CC=CC=C1 VHBFFQKBGNRLFZ-UHFFFAOYSA-N 0.000 claims description 2
- HVQAJTFOCKOKIN-UHFFFAOYSA-N flavonol Chemical group O1C2=CC=CC=C2C(=O)C(O)=C1C1=CC=CC=C1 HVQAJTFOCKOKIN-UHFFFAOYSA-N 0.000 claims description 2
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- 239000003446 ligand Substances 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000005493 quinolyl group Chemical group 0.000 claims description 2
- 125000004151 quinonyl group Chemical group 0.000 claims description 2
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 claims description 2
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 claims description 2
- 229910052725 zinc Inorganic materials 0.000 claims description 2
- 239000011701 zinc Substances 0.000 claims description 2
- 229910052691 Erbium Inorganic materials 0.000 claims 1
- ZCNCOFBVUYXSGY-UHFFFAOYSA-N anthracene 2H-pyran Chemical compound O1CC=CC=C1.C1=CC=CC2=CC3=CC=CC=C3C=C12 ZCNCOFBVUYXSGY-UHFFFAOYSA-N 0.000 claims 1
- UYAHIZSMUZPPFV-UHFFFAOYSA-N erbium Chemical compound [Er] UYAHIZSMUZPPFV-UHFFFAOYSA-N 0.000 claims 1
- 125000005504 styryl group Chemical group 0.000 claims 1
- 125000001425 triazolyl group Chemical group 0.000 claims 1
- 239000011521 glass Substances 0.000 description 38
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- 229920005989 resin Polymers 0.000 description 34
- 239000010409 thin film Substances 0.000 description 32
- 150000002894 organic compounds Chemical class 0.000 description 19
- 238000002360 preparation method Methods 0.000 description 16
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- 238000000859 sublimation Methods 0.000 description 10
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- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 238000002347 injection Methods 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 238000009834 vaporization Methods 0.000 description 5
- 230000008016 vaporization Effects 0.000 description 5
- 239000010408 film Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- YVBBRRALBYAZBM-UHFFFAOYSA-N perfluorooctane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F YVBBRRALBYAZBM-UHFFFAOYSA-N 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
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- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 239000003708 ampul Substances 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
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 2
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- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- KYGSXEYUWRFVNY-UHFFFAOYSA-N 2-pyran-2-ylidenepropanedinitrile Chemical compound N#CC(C#N)=C1OC=CC=C1 KYGSXEYUWRFVNY-UHFFFAOYSA-N 0.000 description 1
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 description 1
- GOLORTLGFDVFDW-UHFFFAOYSA-N 3-(1h-benzimidazol-2-yl)-7-(diethylamino)chromen-2-one Chemical compound C1=CC=C2NC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 GOLORTLGFDVFDW-UHFFFAOYSA-N 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- 150000000917 Erbium Chemical class 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
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- 238000002474 experimental method Methods 0.000 description 1
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- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- 239000012212 insulator Substances 0.000 description 1
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- 230000003287 optical effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
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- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
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- 150000003852 triazoles Chemical group 0.000 description 1
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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
- 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
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/10—Apparatus or processes specially adapted to the manufacture of electroluminescent light sources
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- 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
- 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
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- 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
- H10K71/50—Forming devices by joining two substrates together, e.g. lamination techniques
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- 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
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- 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
- H10K71/40—Thermal treatment, e.g. annealing in the presence of a solvent vapour
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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
- H10K85/10—Organic polymers or oligomers
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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
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
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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
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
- H10K85/114—Poly-phenylenevinylene; Derivatives thereof
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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
- H10K85/60—Organic compounds having low molecular weight
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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
- H10K85/60—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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- 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
- H10K85/656—Aromatic compounds comprising a hetero atom comprising two or more different heteroatoms per ring
- H10K85/6565—Oxadiazole compounds
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- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
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- Organic Chemistry (AREA)
- Electroluminescent Light Sources (AREA)
- Luminescent Compositions (AREA)
Description
図2に示すように1端を閉じたガラス管10(例えば外径15mm、内径12mm)内に蒸気圧を有する有機化合物20として例えば電子輸送性化合物として2−(4−ビフェニル)−5−(4−tert−ブチルフェニル)−1,3,4−オキサジアゾール(PBD)100mgを端部に設置した。次に、ITO電極付きガラス基板上に製膜したPPVからなる樹脂薄膜30(厚さ:1mm、横:8mm、長さ:40mm)を、管の中心部に設置した。次いで、このガラス管10の開放端を真空排気装置50に接続して真空排気を行った。その後、図3に示すように真空排気装置50に接続されたガラス管10の開放端に近い部分をガラス管封管用のバーナー60にて溶融封管して、図4に示すように、前記有機化合物20および樹脂薄膜30をガラス封管11に密閉した。密閉の後、ガラス封管11を図5に示すように恒温槽70の内部に置き、恒温槽70に1時間、内部温度120℃で維持し、その後室温まで1時間を要し徐冷した。徐冷後、ガラス管11を切断して有機化合物20が浸透・分散した樹脂薄膜30を取り出した。その後銀マグネシウムを共蒸着して負極を積層して電界発光素子を作製した。この電界発光素子は黄緑色の発光色を示し、14Vで最大輝度、3000cd/m2に達した。外部量子効率は3.2lm/wであった。
実施例1において2−(4−ビフェニル)−5−(4−tert−ブチルフェニル)−1,3,4−オキサジアゾール(PBD)の効果を確認するため、ITO電極付きガラス基板上に製膜したPPVからなる樹脂薄膜31(厚さ:1mm、横:8mm、長さ:40mm)を加熱処理する比較実験を以下のように行った。すなわち、図6に示したように、一端を閉じたガラス管12(例えば外径15mm、内径12mm、長さ200mm)内にITO電極付きガラス基板上に製膜したPPVからなる樹脂薄膜31のみを設置した。このガラス管12の開放端を真空排気装置51に接続して真空排気を行った。その後、図7に示すように、真空排気装置51に接続されたガラス管12の開放端に近い部分をガラス管封管用のバーナー61にて溶融封管して、前記樹脂薄膜をガラス封管12に密閉した。密封したガラス封管12を恒温槽71の内部に置き、恒温槽71の内部温度を120℃で24時間維持し、その後室温まで徐冷した。徐冷後、ガラス管12を切断して、加熱処理したITO電極付きガラス基板上に製膜したPPVからなる樹脂薄膜31を取り出した。その後銀マグネシウムを共蒸着して負極を積層して電界発光素子を作製した。この電界発光素子は黄緑色の発光色を示し、14Vで最大輝度、20cd/m2に達した。外部量子効率は0.7lm/wであった。
PBDの代わりにパーフルオロオクタンを用いた他は、実施例1の場合と全く同様にITO電極付きガラス基板上に製膜したPPVからなる樹脂薄膜を封管、加熱および徐冷して処理した後、得られたPPVからなる樹脂薄膜の紫外・可視・赤外吸収スペクトルを測定した結果、パーフルオロオクタンに帰属される吸収は確認できなかった。これらの結果等からパーフルオクタンはPPVからなる樹脂薄膜に親和性がなく、そのため樹脂薄膜のプレートに浸透・分散が起こらないことが判明した。
図2に示すように1端を閉じたガラス管10(例えば外径15mm、内径12mm)内に蒸気圧を有する有機化合物20として例えば朱色蛍光色素として4−(ジシアノメチル)−2−メチル−6−(4−ジメチルアミノスチリル)−4−H−ピラン (DCM)100mgを端部に設置した。次に、ITO電極付きガラス基板上に製膜したPPVからなる樹脂薄膜PPV30(厚さ:1mm、横:8mm、長さ:40mm)を、管の中心部に設置した。次いで、このガラス管10の開放端を真空排気装置50に接続して真空排気を行った。その後、図3に示すように真空排気装置50に接続されたガラス管10の開放端に近い部分をガラス管封管用のバーナー60にて溶融封管して、図4に示すように、前記有機化合物20および樹脂薄膜30をガラス封管11に密閉した。密閉の後、ガラス封管11を図5に示すように恒温槽70の内部に置き、恒温槽70を内部温度120℃で1時間維持し、その後室温まで1時間を要し徐冷した。徐冷後、ガラス管11を切断して有機化合物20が浸透・分散したPPVを取り出した。その後銀マグネシウムを共蒸着して負極を積層して電界発光素子を作製した。この電界発光素子は朱色の発光色であり、14Vで最大輝度、2000cd/m2に達した。外部量子効率は4.1lm/wであった。
図9は、本実施例で用いられる電界発光素子の作製装置の概略構成を示す断面図である。ITO付きガラス基板上にPEDOT−PSSを製膜し、その上にポリ(p−キシレンチオフェニウムクロライド)水溶液を塗布後焼成してPPVを形成した樹脂薄膜300を用い、一方、PBTを設置した昇華源240(例えば厚さ5mm、横10mm、縦400mm)を作製した。ITO付きPEDOT−PSS/PPVからなる樹脂薄膜300は、密閉式容器110に設置され、昇華源240は別の密閉式容器120に設置されている。二つの密閉式容器110,120は配管とバルブ195によって接続されている。ITO付きPEDOT−PSS/PPVからなる樹脂薄膜300が設置されている密閉式容器110の外壁は、ステンレスまたはアルミニウムからなり、樹脂薄膜300の出し入れのために上下分割可能な構造(図示せず)とする。
Claims (6)
- π共役有機高分子化合物を含有する有機電界発光素子の製造方法において、前記π共役有機高分子化合物を加温する工程と、加温された前記π共役有機高分子化合物に、色素および電荷輸送性物質からなる群から選択される少なくとも1種の化合物の気体分子を接触・浸透させる工程と、を有し、
前記π共役有機高分子化合物が、無置換のポリ(p−フェニレンビニレン)、無置換のポリチオフェン、無置換のポリチオフェンビニレン、ポリ(p−フェニレン)、無置換のポリ(p−フェニルアセチレン)からなる群から選ばれる少なくとも1種であり、
前記色素が、発光色素であって、
前記発光色素は、クマリン系色素、キナクリドン系色素、ジシアノメチレン系色素、ジシアノジアゼピン系色素、ベンゾチアゾール系色素、ペリレン系色素、アセトニトリル−トリフェニルアミン系色素、含Eu原子錯体系色素、アザベンゾアントラセン−ピラン系色素からなる群から選ばれる少なくとも1種の色素であり、
前記電荷輸送化合物が、正(+)の電荷を輸送するホール輸送性物質、負(−)の電荷を輸送する電子輸送性物質、および発光能を有する電子輸送性化合物からなる群から選択される少なくとも1種の化合物であって、
前記ホール輸送性物質は、カルバゾール環、チオフェン環、トリフェニルアミン、トリフェニルメタン、ジスチルベン構造を有する低分子化合物、および、それら低分子化合物をジアゾ、トリアゾ基で結合した化合物からなる群から選択される少なくとも1種のホール輸送性物質であり、
前記電子輸送性物質は、オキサジアゾール環、トリアゾール環、キノン環、イミダゾール環、フラボン環、チアゾール環、ベンズイミダゾール環、キノリン環、キノザリン環、ピラジン環を有する化合物、およびそれらの化合物にニトロ基、シアノ基が導入されている化合物からなる群から選択される少なくとも1種の電子輸送性物質であり、
前記発光能を有する電子輸送性化合物は、ベンゾオキサジアゾール環、キノリール環、ベンゾキノリール環、ベンゾチアゾール環、ヒドキシフラボン環を配位子にもつ、アルミニウム、亜鉛、ベリリウム、ユーロピウム、エルビウム錯体からなる群から選択される少なくとも1種であることを特徴とする有機電界発光素子の製造方法。 - 請求項1に記載の有機電界発光素子の製造方法において、
有機電界発光素子は、前記ドープされたπ共役有機高分子化合物を含む発光層を有することを特徴とする有機電界発光素子の製造方法。 - 請求項1に記載の有機電界発光素子の製造方法において、
有機電界発光素子は、前記ドープされたπ共役有機高分子化合物を含む電荷輸送層を有することを特徴とする有機電界発光素子の製造方法。 - 請求項1に記載の有機電界発光素子の製造方法において、
有機電界発光素子は、前記ドープされたπ共役有機高分子化合物を含む発光層および電荷輸送層を有することを特徴とする有機電界発光素子の製造方法。 - π共役有機高分子化合物として無置換のポリ(p−フェニレンビニレン)を含有する有機電界発光素子において、前記π共役有機高分子化合物の無置換のポリ(p−フェニレンビニレン)に、電荷輸送性物質として2−(4−ビフェニル)−5−(4−tert−ブチルフェニル)−1,3,4−オキサジアゾールまたは色素として4−(ジシアノメチル)−2−メチル−6−(4−ジメチルアミノスチリル)−4−H−ピランを含有することにより形成される機能層を有することを特徴とする有機電界発光素子。
- 請求項5に記載の有機電界発光素子において、
前記機能層は、発光層または電荷輸送層であることを特徴とする有機電界発光素子。
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JP2003364219A JP4285741B2 (ja) | 2003-10-24 | 2003-10-24 | 有機電界発光素子およびその作製方法 |
PCT/JP2004/015564 WO2005041320A1 (en) | 2003-10-24 | 2004-10-14 | Organic electroluminescent element and manufacturing method thereof |
US10/572,643 US20070072000A1 (en) | 2003-10-24 | 2004-10-14 | Organic electroluminescent element and manufacturing method thereof |
CN200480031408XA CN1871720B (zh) | 2003-10-24 | 2004-10-14 | 有机电致发光元件及其生产方法 |
GB0605822A GB2422486B (en) | 2003-10-24 | 2004-10-14 | Method of manufacturing an organic electroluminescent element |
KR1020067007138A KR101056758B1 (ko) | 2003-10-24 | 2004-10-14 | 유기 전계 발광 소자 및 그 제조 방법 |
TW093132142A TWI390750B (zh) | 2003-10-24 | 2004-10-22 | 有機電致發光元件之製作方法 |
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KR102304990B1 (ko) | 2015-01-20 | 2021-09-28 | 삼성디스플레이 주식회사 | 터치 스크린 패널, 디스플레이 장치 및 그 제조 방법 |
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GB0605822D0 (en) | 2006-05-03 |
WO2005041320A1 (en) | 2005-05-06 |
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GB2422486A (en) | 2006-07-26 |
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