JP3911775B2 - 有機el素子の製造方法 - Google Patents
有機el素子の製造方法 Download PDFInfo
- Publication number
- JP3911775B2 JP3911775B2 JP20469797A JP20469797A JP3911775B2 JP 3911775 B2 JP3911775 B2 JP 3911775B2 JP 20469797 A JP20469797 A JP 20469797A JP 20469797 A JP20469797 A JP 20469797A JP 3911775 B2 JP3911775 B2 JP 3911775B2
- Authority
- JP
- Japan
- Prior art keywords
- organic
- composition
- producing
- light emitting
- emitting layer
- 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.)
- Expired - Lifetime
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 32
- 239000000203 mixture Substances 0.000 claims description 151
- 239000002243 precursor Substances 0.000 claims description 43
- 239000000463 material Substances 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 20
- 150000002894 organic compounds Chemical class 0.000 claims description 19
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical group [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 claims description 13
- KLCLIOISYBHYDZ-UHFFFAOYSA-N 1,4,4-triphenylbuta-1,3-dienylbenzene Chemical group C=1C=CC=CC=1C(C=1C=CC=CC=1)=CC=C(C=1C=CC=CC=1)C1=CC=CC=C1 KLCLIOISYBHYDZ-UHFFFAOYSA-N 0.000 claims description 11
- 239000007787 solid Substances 0.000 claims description 10
- 239000002798 polar solvent Substances 0.000 claims description 9
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical group N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 claims description 8
- 238000010438 heat treatment Methods 0.000 claims description 8
- 239000000080 wetting agent Substances 0.000 claims description 8
- 229920000642 polymer Polymers 0.000 claims description 7
- -1 polyparaphenylene vinylene Polymers 0.000 claims description 7
- ZMLPKJYZRQZLDA-UHFFFAOYSA-N 1-(2-phenylethenyl)-4-[4-(2-phenylethenyl)phenyl]benzene Chemical group C=1C=CC=CC=1C=CC(C=C1)=CC=C1C(C=C1)=CC=C1C=CC1=CC=CC=C1 ZMLPKJYZRQZLDA-UHFFFAOYSA-N 0.000 claims description 6
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N benzo-alpha-pyrone Natural products C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 claims description 5
- 239000011347 resin Substances 0.000 claims description 5
- 229920005989 resin Polymers 0.000 claims description 5
- 239000000049 pigment Substances 0.000 claims description 4
- 229960000956 coumarin Drugs 0.000 claims description 3
- 235000001671 coumarin Nutrition 0.000 claims description 3
- CFNMUZCFSDMZPQ-GHXNOFRVSA-N 7-[(z)-3-methyl-4-(4-methyl-5-oxo-2h-furan-2-yl)but-2-enoxy]chromen-2-one Chemical compound C=1C=C2C=CC(=O)OC2=CC=1OC/C=C(/C)CC1OC(=O)C(C)=C1 CFNMUZCFSDMZPQ-GHXNOFRVSA-N 0.000 claims description 2
- 125000000332 coumarinyl group Chemical group O1C(=O)C(=CC2=CC=CC=C12)* 0.000 claims 1
- 239000010410 layer Substances 0.000 description 63
- 239000007850 fluorescent dye Substances 0.000 description 45
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 21
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- 239000000975 dye Substances 0.000 description 14
- 238000007641 inkjet printing Methods 0.000 description 13
- 239000010409 thin film Substances 0.000 description 13
- 238000005452 bending Methods 0.000 description 12
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 12
- 229920000547 conjugated polymer Polymers 0.000 description 10
- 238000000059 patterning Methods 0.000 description 10
- 239000007788 liquid Substances 0.000 description 9
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- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 8
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 108010043121 Green Fluorescent Proteins Proteins 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- VBVAVBCYMYWNOU-UHFFFAOYSA-N coumarin 6 Chemical compound C1=CC=C2SC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 VBVAVBCYMYWNOU-UHFFFAOYSA-N 0.000 description 3
- 238000001723 curing Methods 0.000 description 3
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- 238000001771 vacuum deposition Methods 0.000 description 3
- 238000007740 vapor deposition Methods 0.000 description 3
- 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 2
- YWKSINPSASCIMZ-UHFFFAOYSA-N 4,5-dimethyl-4,5-dihydro-1h-imidazole Chemical compound CC1NC=NC1C YWKSINPSASCIMZ-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
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- 230000031700 light absorption Effects 0.000 description 2
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- DZNJMLVCIZGWSC-UHFFFAOYSA-N 3',6'-bis(diethylamino)spiro[2-benzofuran-3,9'-xanthene]-1-one Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC=C(N(CC)CC)C=C1OC1=CC(N(CC)CC)=CC=C21 DZNJMLVCIZGWSC-UHFFFAOYSA-N 0.000 description 1
- RIUSGHALMCFISX-UHFFFAOYSA-N 7-(dimethylamino)-2,3-dihydro-1h-cyclopenta[c]chromen-4-one Chemical compound O=C1OC2=CC(N(C)C)=CC=C2C2=C1CCC2 RIUSGHALMCFISX-UHFFFAOYSA-N 0.000 description 1
- GZEYLLPOQRZUDF-UHFFFAOYSA-N 7-(dimethylamino)-4-methylchromen-2-one Chemical compound CC1=CC(=O)OC2=CC(N(C)C)=CC=C21 GZEYLLPOQRZUDF-UHFFFAOYSA-N 0.000 description 1
- 229910017073 AlLi Inorganic materials 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229920000109 alkoxy-substituted poly(p-phenylene vinylene) Polymers 0.000 description 1
- 230000003712 anti-aging effect Effects 0.000 description 1
- 230000002421 anti-septic effect Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
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- VYXSBFYARXAAKO-WTKGSRSZSA-N chembl402140 Chemical compound Cl.C1=2C=C(C)C(NCC)=CC=2OC2=C\C(=N/CC)C(C)=CC2=C1C1=CC=CC=C1C(=O)OCC VYXSBFYARXAAKO-WTKGSRSZSA-N 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
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- 229920001940 conductive polymer Polymers 0.000 description 1
- GLNDAGDHSLMOKX-UHFFFAOYSA-N coumarin 120 Chemical compound C1=C(N)C=CC2=C1OC(=O)C=C2C GLNDAGDHSLMOKX-UHFFFAOYSA-N 0.000 description 1
- KDTAEYOYAZPLIC-UHFFFAOYSA-N coumarin 152 Chemical compound FC(F)(F)C1=CC(=O)OC2=CC(N(C)C)=CC=C21 KDTAEYOYAZPLIC-UHFFFAOYSA-N 0.000 description 1
- VSSSHNJONFTXHS-UHFFFAOYSA-N coumarin 153 Chemical compound C12=C3CCCN2CCCC1=CC1=C3OC(=O)C=C1C(F)(F)F VSSSHNJONFTXHS-UHFFFAOYSA-N 0.000 description 1
- JBPCDMSEJVCNGV-UHFFFAOYSA-N coumarin 334 Chemical compound C1CCC2=C(OC(C(C(=O)C)=C3)=O)C3=CC3=C2N1CCC3 JBPCDMSEJVCNGV-UHFFFAOYSA-N 0.000 description 1
- LGDDFMCJIHJNMK-UHFFFAOYSA-N coumarin 337 Chemical compound C12=C3CCCN2CCCC1=CC1=C3OC(=O)C(C#N)=C1 LGDDFMCJIHJNMK-UHFFFAOYSA-N 0.000 description 1
- KCDCNGXPPGQERR-UHFFFAOYSA-N coumarin 343 Chemical compound C1CCC2=C(OC(C(C(=O)O)=C3)=O)C3=CC3=C2N1CCC3 KCDCNGXPPGQERR-UHFFFAOYSA-N 0.000 description 1
- AFYCEAFSNDLKSX-UHFFFAOYSA-N coumarin 460 Chemical compound CC1=CC(=O)OC2=CC(N(CC)CC)=CC=C21 AFYCEAFSNDLKSX-UHFFFAOYSA-N 0.000 description 1
- VMJKUPWQKZFFCX-UHFFFAOYSA-N coumarin 504 Chemical compound C1CCC2=C(OC(C(C(=O)OCC)=C3)=O)C3=CC3=C2N1CCC3 VMJKUPWQKZFFCX-UHFFFAOYSA-N 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
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- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 238000000295 emission spectrum Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 238000013007 heat curing Methods 0.000 description 1
- 229910001867 inorganic solvent Inorganic materials 0.000 description 1
- 239000003049 inorganic solvent Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- AHLBNYSZXLDEJQ-FWEHEUNISA-N orlistat Chemical compound CCCCCCCCCCC[C@H](OC(=O)[C@H](CC(C)C)NC=O)C[C@@H]1OC(=O)[C@H]1CCCCCC AHLBNYSZXLDEJQ-FWEHEUNISA-N 0.000 description 1
- 239000003002 pH adjusting agent Substances 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
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
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- DJWWHVKRLDNDJK-UHFFFAOYSA-N rhodamine 640 perchlorate Chemical compound [O-]Cl(=O)(=O)=O.OC(=O)C1=CC=CC=C1C(C1=CC=2CCCN3CCCC(C=23)=C1O1)=C2C1=C(CCC1)C3=[N+]1CCCC3=C2 DJWWHVKRLDNDJK-UHFFFAOYSA-N 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
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- 230000000087 stabilizing effect Effects 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium group Chemical group [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 150000003462 sulfoxides Chemical class 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
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
Images
Classifications
-
- 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
- H10K59/30—Devices specially adapted for multicolour light emission
- H10K59/35—Devices specially adapted for multicolour light emission comprising red-green-blue [RGB] subpixels
-
- 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
- H10K71/10—Deposition of organic active material
- H10K71/12—Deposition of organic active material using liquid deposition, e.g. spin coating
- H10K71/13—Deposition of organic active material using liquid deposition, e.g. spin coating using printing techniques, e.g. ink-jet printing or screen printing
- H10K71/135—Deposition of organic active material using liquid deposition, e.g. spin coating using printing techniques, e.g. ink-jet printing or screen printing using ink-jet printing
Landscapes
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Ink Jet (AREA)
- Electroluminescent Light Sources (AREA)
- Luminescent Compositions (AREA)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP20469797A JP3911775B2 (ja) | 1997-07-30 | 1997-07-30 | 有機el素子の製造方法 |
| US09/111,482 US6843937B1 (en) | 1997-07-16 | 1998-07-08 | Composition for an organic EL element and method of manufacturing the organic EL element |
| EP98113051A EP0892028B1 (en) | 1997-07-16 | 1998-07-14 | Composition for an organic EL element and method of manufacturing the organic EL element |
| DE69838402T DE69838402T2 (de) | 1997-07-16 | 1998-07-14 | Zusammensetzung für eine organische LED |
| DE69821554T DE69821554T2 (de) | 1997-07-16 | 1998-07-14 | Zusammensetzung für organisches elektrolumineszentes Element und Verfahren zur Herstellung eines organischen elektrolumineszenten Elements |
| EP03025785A EP1394236B1 (en) | 1997-07-16 | 1998-07-14 | Composition for an organic EL element |
| CNB981172636A CN1244002C (zh) | 1997-07-16 | 1998-07-16 | 一种用于有机电致发光元件的组合物和制造这种元件的方法 |
| TW087111559A TW417031B (en) | 1997-07-16 | 1998-07-16 | Composition for an organic EL element and method of manufacturing the organic EL element |
| US10/946,101 US20050058770A1 (en) | 1997-07-16 | 2004-09-22 | Composition for an organic el element and method of manufacturing the organic EL element |
| KR1020050020984A KR100554338B1 (ko) | 1997-07-16 | 2005-03-14 | 유기 이엘 소자 제조방법 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP20469797A JP3911775B2 (ja) | 1997-07-30 | 1997-07-30 | 有機el素子の製造方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JPH1154270A JPH1154270A (ja) | 1999-02-26 |
| JPH1154270A5 JPH1154270A5 (enExample) | 2004-10-21 |
| JP3911775B2 true JP3911775B2 (ja) | 2007-05-09 |
Family
ID=16494826
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP20469797A Expired - Lifetime JP3911775B2 (ja) | 1997-07-16 | 1997-07-30 | 有機el素子の製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3911775B2 (enExample) |
Families Citing this family (63)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1310930A (zh) | 1999-03-29 | 2001-08-29 | 精工爱普生株式会社 | 组合物及膜的制造方法以及功能元件及其制造方法 |
| JP2001076872A (ja) * | 1999-06-28 | 2001-03-23 | Semiconductor Energy Lab Co Ltd | 電気光学装置の作製方法 |
| JP4877675B2 (ja) * | 1999-06-28 | 2012-02-15 | 株式会社半導体エネルギー研究所 | 電気光学装置の作製方法 |
| TW512543B (en) | 1999-06-28 | 2002-12-01 | Semiconductor Energy Lab | Method of manufacturing an electro-optical device |
| JP4226159B2 (ja) | 1999-08-06 | 2009-02-18 | シャープ株式会社 | 有機ledディスプレイの製造方法 |
| TW468283B (en) | 1999-10-12 | 2001-12-11 | Semiconductor Energy Lab | EL display device and a method of manufacturing the same |
| TW471011B (en) | 1999-10-13 | 2002-01-01 | Semiconductor Energy Lab | Thin film forming apparatus |
| JP2004014529A (ja) * | 1999-12-08 | 2004-01-15 | Nec Corp | 有機el素子 |
| US6633121B2 (en) | 2000-01-31 | 2003-10-14 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence display device and method of manufacturing same |
| TW495808B (en) | 2000-02-04 | 2002-07-21 | Semiconductor Energy Lab | Thin film formation apparatus and method of manufacturing self-light-emitting device using thin film formation apparatus |
| TW495809B (en) | 2000-02-28 | 2002-07-21 | Semiconductor Energy Lab | Thin film forming device, thin film forming method, and self-light emitting device |
| TW495812B (en) | 2000-03-06 | 2002-07-21 | Semiconductor Energy Lab | Thin film forming device, method of forming a thin film, and self-light-emitting device |
| TWI226205B (en) | 2000-03-27 | 2005-01-01 | Semiconductor Energy Lab | Self-light emitting device and method of manufacturing the same |
| TW490997B (en) | 2000-03-31 | 2002-06-11 | Seiko Epson Corp | Method of manufacturing organic EL element, and organic EL element |
| JP2001341296A (ja) | 2000-03-31 | 2001-12-11 | Seiko Epson Corp | インクジェット法による薄膜形成方法、インクジェット装置、有機el素子の製造方法、有機el素子 |
| WO2001074121A1 (en) | 2000-03-31 | 2001-10-04 | Seiko Epson Corporation | Organic el device and method of manufacture thereof |
| JP4860052B2 (ja) * | 2000-05-12 | 2012-01-25 | 株式会社半導体エネルギー研究所 | 発光装置 |
| SG125891A1 (en) | 2000-09-08 | 2006-10-30 | Semiconductor Energy Lab | Light emitting device, method of manufacturing thesame, and thin film forming apparatus |
| JP4390028B2 (ja) | 2000-10-04 | 2009-12-24 | 日産化学工業株式会社 | ポジ型感光性ポリイミド樹脂組成物 |
| JP2002221616A (ja) | 2000-11-21 | 2002-08-09 | Seiko Epson Corp | カラーフィルタの製造方法及び製造装置、液晶装置の製造方法及び製造装置、el装置の製造方法及び製造装置、インクジェットヘッドの制御装置、材料の吐出方法及び材料の吐出装置、並びに電子機器 |
| JP3491155B2 (ja) * | 2000-11-21 | 2004-01-26 | セイコーエプソン株式会社 | 材料の吐出方法、及び吐出装置、カラーフィルタの製造方法及び製造装置、液晶装置の製造方法及び製造装置、el装置の製造方法及び製造装置 |
| JP3628997B2 (ja) | 2000-11-27 | 2005-03-16 | セイコーエプソン株式会社 | 有機エレクトロルミネッセンス装置の製造方法 |
| JP4021177B2 (ja) | 2000-11-28 | 2007-12-12 | セイコーエプソン株式会社 | 有機エレクトロルミネッセンス装置の製造方法および有機エレクトロルミネッセンス装置並びに電子機器 |
| JP3876684B2 (ja) | 2000-12-21 | 2007-02-07 | セイコーエプソン株式会社 | カラーフィルタの製造方法、カラーフィルタの製造装置、液晶装置の製造方法、液晶装置の製造装置、el装置の製造方法、el装置の製造装置、材料の吐出方法、ヘッドの制御装置、電子機器 |
| JP3953776B2 (ja) | 2001-01-15 | 2007-08-08 | セイコーエプソン株式会社 | 材料の吐出装置、及び吐出方法、カラーフィルタの製造装置及び製造方法、液晶装置の製造装置及び製造方法、el装置の製造装置及び製造方法 |
| US6787063B2 (en) | 2001-03-12 | 2004-09-07 | Seiko Epson Corporation | Compositions, methods for producing films, functional elements, methods for producing functional elements, methods for producing electro-optical devices and methods for producing electronic apparatus |
| JP4683772B2 (ja) | 2001-06-15 | 2011-05-18 | 株式会社半導体エネルギー研究所 | 発光装置の作製方法 |
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| JP2003022892A (ja) | 2001-07-06 | 2003-01-24 | Semiconductor Energy Lab Co Ltd | 発光装置の製造方法 |
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