JP2008511598A - エレクトロルミネセンス物質およびデバイス - Google Patents
エレクトロルミネセンス物質およびデバイス Download PDFInfo
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- JP2008511598A JP2008511598A JP2007528980A JP2007528980A JP2008511598A JP 2008511598 A JP2008511598 A JP 2008511598A JP 2007528980 A JP2007528980 A JP 2007528980A JP 2007528980 A JP2007528980 A JP 2007528980A JP 2008511598 A JP2008511598 A JP 2008511598A
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- JP
- Japan
- Prior art keywords
- quinolate
- zirconium
- electroluminescent
- electroluminescent device
- substituted
- 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.)
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- 239000000463 material Substances 0.000 title claims description 68
- -1 zirconium 2-methyl-8-hydroxyquinolate Chemical compound 0.000 claims abstract description 69
- 238000000034 method Methods 0.000 claims abstract description 17
- NBYLBWHHTUWMER-UHFFFAOYSA-N 2-Methylquinolin-8-ol Chemical compound C1=CC=C(O)C2=NC(C)=CC=C21 NBYLBWHHTUWMER-UHFFFAOYSA-N 0.000 claims abstract description 9
- 150000003839 salts Chemical class 0.000 claims abstract description 7
- 125000005594 diketone group Chemical group 0.000 claims abstract description 5
- 150000003754 zirconium Chemical class 0.000 claims abstract description 5
- 125000003118 aryl group Chemical group 0.000 claims description 17
- 230000005525 hole transport Effects 0.000 claims description 15
- 229920000767 polyaniline Polymers 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 14
- 239000002019 doping agent Substances 0.000 claims description 14
- JTVKNDSPAQUVHT-UHFFFAOYSA-N methyl quinoline-2-carboxylate zirconium Chemical class N1=C(C=CC2=CC=CC=C12)C(=O)OC.[Zr] JTVKNDSPAQUVHT-UHFFFAOYSA-N 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 229910052751 metal Inorganic materials 0.000 claims description 11
- 239000002184 metal Substances 0.000 claims description 11
- 230000009467 reduction Effects 0.000 claims description 11
- YXLXNENXOJSQEI-UHFFFAOYSA-L Oxine-copper Chemical compound [Cu+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 YXLXNENXOJSQEI-UHFFFAOYSA-L 0.000 claims description 10
- 125000000623 heterocyclic group Chemical group 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 229920001577 copolymer Polymers 0.000 claims description 9
- 239000011521 glass Substances 0.000 claims description 9
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 claims description 8
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 8
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N benzo-alpha-pyrone Natural products C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 claims description 8
- 229920000547 conjugated polymer Polymers 0.000 claims description 8
- 229920000553 poly(phenylenevinylene) Polymers 0.000 claims description 8
- 125000003277 amino group Chemical group 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 125000003367 polycyclic group Chemical group 0.000 claims description 7
- 235000001671 coumarin Nutrition 0.000 claims description 6
- 229920000123 polythiophene Polymers 0.000 claims description 6
- VNZZUWADVGKWCN-UHFFFAOYSA-J quinoline-2-carboxylate zirconium(4+) Chemical compound [Zr+4].C1=CC=CC2=NC(C(=O)[O-])=CC=C21.C1=CC=CC2=NC(C(=O)[O-])=CC=C21.C1=CC=CC2=NC(C(=O)[O-])=CC=C21.C1=CC=CC2=NC(C(=O)[O-])=CC=C21 VNZZUWADVGKWCN-UHFFFAOYSA-J 0.000 claims description 6
- 238000010521 absorption reaction Methods 0.000 claims description 5
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical group CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 claims description 5
- IUFDZNVMARBLOJ-UHFFFAOYSA-K aluminum;quinoline-2-carboxylate Chemical group [Al+3].C1=CC=CC2=NC(C(=O)[O-])=CC=C21.C1=CC=CC2=NC(C(=O)[O-])=CC=C21.C1=CC=CC2=NC(C(=O)[O-])=CC=C21 IUFDZNVMARBLOJ-UHFFFAOYSA-K 0.000 claims description 5
- 238000005401 electroluminescence Methods 0.000 claims description 5
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 claims description 5
- 238000004020 luminiscence type Methods 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- VMGGGNJWSPKQAK-UHFFFAOYSA-N 1-ethynyl-4-(2-methoxypentoxy)benzene Chemical group CCCC(OC)COC1=CC=C(C#C)C=C1 VMGGGNJWSPKQAK-UHFFFAOYSA-N 0.000 claims description 4
- MLPVBIWIRCKMJV-UHFFFAOYSA-N 2-ethylaniline Chemical compound CCC1=CC=CC=C1N MLPVBIWIRCKMJV-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- IVBFNUANRGFDDJ-UHFFFAOYSA-I N1=C(C=CC2=CC=CC=C12)C(=O)[O-].[V+5].N1=C(C=CC2=CC=CC=C12)C(=O)[O-].N1=C(C=CC2=CC=CC=C12)C(=O)[O-].N1=C(C=CC2=CC=CC=C12)C(=O)[O-].N1=C(C=CC2=CC=CC=C12)C(=O)[O-] Chemical compound N1=C(C=CC2=CC=CC=C12)C(=O)[O-].[V+5].N1=C(C=CC2=CC=CC=C12)C(=O)[O-].N1=C(C=CC2=CC=CC=C12)C(=O)[O-].N1=C(C=CC2=CC=CC=C12)C(=O)[O-].N1=C(C=CC2=CC=CC=C12)C(=O)[O-] IVBFNUANRGFDDJ-UHFFFAOYSA-I 0.000 claims description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical group [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 4
- KSUFELKEKRWQPH-UHFFFAOYSA-J hafnium(4+) quinoline-2-carboxylate Chemical compound [Hf+4].C1=CC=CC2=NC(C(=O)[O-])=CC=C21.C1=CC=CC2=NC(C(=O)[O-])=CC=C21.C1=CC=CC2=NC(C(=O)[O-])=CC=C21.C1=CC=CC2=NC(C(=O)[O-])=CC=C21 KSUFELKEKRWQPH-UHFFFAOYSA-J 0.000 claims description 4
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 claims description 4
- 239000004793 Polystyrene Substances 0.000 claims description 3
- 229910045601 alloy Inorganic materials 0.000 claims description 3
- 239000000956 alloy Substances 0.000 claims description 3
- 229910052782 aluminium Inorganic materials 0.000 claims description 3
- 150000001450 anions Chemical class 0.000 claims description 3
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Natural products C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 3
- 125000004104 aryloxy group Chemical group 0.000 claims description 3
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 claims description 3
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 claims description 3
- 229920000548 poly(silane) polymer Polymers 0.000 claims description 3
- 229920002223 polystyrene Polymers 0.000 claims description 3
- YRFKHKBUMKFMAU-UHFFFAOYSA-N 1,2-diphenylacridine Chemical group C1=CC=CC=C1C1=CC=C(N=C2C(C=CC=C2)=C2)C2=C1C1=CC=CC=C1 YRFKHKBUMKFMAU-UHFFFAOYSA-N 0.000 claims description 2
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 claims description 2
- ZAJAQTYSTDTMCU-UHFFFAOYSA-N 3-aminobenzenesulfonic acid Chemical compound NC1=CC=CC(S(O)(=O)=O)=C1 ZAJAQTYSTDTMCU-UHFFFAOYSA-N 0.000 claims description 2
- OGGKVJMNFFSDEV-UHFFFAOYSA-N 3-methyl-n-[4-[4-(n-(3-methylphenyl)anilino)phenyl]phenyl]-n-phenylaniline Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 OGGKVJMNFFSDEV-UHFFFAOYSA-N 0.000 claims description 2
- 229910001316 Ag alloy Inorganic materials 0.000 claims description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 2
- 229910000861 Mg alloy Inorganic materials 0.000 claims description 2
- NQWLQIOFXNJKBW-UHFFFAOYSA-I N1=C(C=CC2=CC=CC=C12)C(=O)[O-].[Nb+5].N1=C(C=CC2=CC=CC=C12)C(=O)[O-].N1=C(C=CC2=CC=CC=C12)C(=O)[O-].N1=C(C=CC2=CC=CC=C12)C(=O)[O-].N1=C(C=CC2=CC=CC=C12)C(=O)[O-] Chemical compound N1=C(C=CC2=CC=CC=C12)C(=O)[O-].[Nb+5].N1=C(C=CC2=CC=CC=C12)C(=O)[O-].N1=C(C=CC2=CC=CC=C12)C(=O)[O-].N1=C(C=CC2=CC=CC=C12)C(=O)[O-].N1=C(C=CC2=CC=CC=C12)C(=O)[O-] NQWLQIOFXNJKBW-UHFFFAOYSA-I 0.000 claims description 2
- 229920000265 Polyparaphenylene Polymers 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 150000004703 alkoxides Chemical class 0.000 claims description 2
- 125000003368 amide group Chemical group 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- YUENFNPLGJCNRB-UHFFFAOYSA-N anthracen-1-amine Chemical compound C1=CC=C2C=C3C(N)=CC=CC3=CC2=C1 YUENFNPLGJCNRB-UHFFFAOYSA-N 0.000 claims description 2
- BIOPPFDHKHWJIA-UHFFFAOYSA-N anthracene-9,10-dinitrile Chemical compound C1=CC=C2C(C#N)=C(C=CC=C3)C3=C(C#N)C2=C1 BIOPPFDHKHWJIA-UHFFFAOYSA-N 0.000 claims description 2
- 239000011575 calcium Substances 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- IMKMFBIYHXBKRX-UHFFFAOYSA-M lithium;quinoline-2-carboxylate Chemical compound [Li+].C1=CC=CC2=NC(C(=O)[O-])=CC=C21 IMKMFBIYHXBKRX-UHFFFAOYSA-M 0.000 claims description 2
- VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 229920002098 polyfluorene Polymers 0.000 claims description 2
- ZWFYQDWEWDSNDW-UHFFFAOYSA-J quinoline-2-carboxylate titanium(4+) Chemical compound [Ti+4].C1=CC=CC2=NC(C(=O)[O-])=CC=C21.C1=CC=CC2=NC(C(=O)[O-])=CC=C21.C1=CC=CC2=NC(C(=O)[O-])=CC=C21.C1=CC=CC2=NC(C(=O)[O-])=CC=C21 ZWFYQDWEWDSNDW-UHFFFAOYSA-J 0.000 claims description 2
- 239000004332 silver Substances 0.000 claims description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims 1
- 241001553014 Myrsine salicina Species 0.000 claims 1
- WVAHKIQKDXQWAR-UHFFFAOYSA-N anthracene-1-carbonitrile Chemical compound C1=CC=C2C=C3C(C#N)=CC=CC3=CC2=C1 WVAHKIQKDXQWAR-UHFFFAOYSA-N 0.000 claims 1
- 150000004982 aromatic amines Chemical class 0.000 claims 1
- 229910052791 calcium Inorganic materials 0.000 claims 1
- 125000000332 coumarinyl group Chemical class O1C(=O)C(=CC2=CC=CC=C12)* 0.000 claims 1
- NZZIMKJIVMHWJC-UHFFFAOYSA-N dibenzoylmethane Chemical group C=1C=CC=CC=1C(=O)CC(=O)C1=CC=CC=C1 NZZIMKJIVMHWJC-UHFFFAOYSA-N 0.000 claims 1
- 229910052744 lithium Inorganic materials 0.000 claims 1
- 229910052749 magnesium Inorganic materials 0.000 claims 1
- 239000011777 magnesium Substances 0.000 claims 1
- 150000002979 perylenes Chemical class 0.000 claims 1
- 229920006254 polymer film Polymers 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 6
- 229920000642 polymer Polymers 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 239000000126 substance Substances 0.000 description 8
- 239000000975 dye Substances 0.000 description 7
- 150000002431 hydrogen Chemical class 0.000 description 7
- 239000007850 fluorescent dye Substances 0.000 description 6
- 0 C*(C)c1*(*(*)Oc2ccc3)c2c3cc1 Chemical compound C*(C)c1*(*(*)Oc2ccc3)c2c3cc1 0.000 description 5
- 230000008878 coupling Effects 0.000 description 5
- 238000010168 coupling process Methods 0.000 description 5
- 238000005859 coupling reaction Methods 0.000 description 5
- 229910052757 nitrogen Chemical group 0.000 description 5
- 230000003595 spectral effect Effects 0.000 description 5
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 229920001940 conductive polymer Polymers 0.000 description 3
- 150000004775 coumarins Chemical class 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical group FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 230000005588 protonation Effects 0.000 description 3
- 229910052761 rare earth metal Inorganic materials 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 125000001544 thienyl group Chemical group 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- HIYWOHBEPVGIQN-UHFFFAOYSA-N 1h-benzo[g]indole Chemical compound C1=CC=CC2=C(NC=C3)C3=CC=C21 HIYWOHBEPVGIQN-UHFFFAOYSA-N 0.000 description 2
- 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
- HSHNITRMYYLLCV-UHFFFAOYSA-N 4-methylumbelliferone Chemical compound C1=C(O)C=CC2=C1OC(=O)C=C2C HSHNITRMYYLLCV-UHFFFAOYSA-N 0.000 description 2
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 2
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
- 125000005577 anthracene group Chemical group 0.000 description 2
- BSDOQSMQCZQLDV-UHFFFAOYSA-N butan-1-olate;zirconium(4+) Chemical compound [Zr+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] BSDOQSMQCZQLDV-UHFFFAOYSA-N 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 229960000956 coumarin Drugs 0.000 description 2
- XHXMPURWMSJENN-UHFFFAOYSA-N coumarin 480 Chemical compound C12=C3CCCN2CCCC1=CC1=C3OC(=O)C=C1C XHXMPURWMSJENN-UHFFFAOYSA-N 0.000 description 2
- 230000005595 deprotonation Effects 0.000 description 2
- 238000010537 deprotonation reaction Methods 0.000 description 2
- 238000006073 displacement reaction Methods 0.000 description 2
- 230000001747 exhibiting effect Effects 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 239000000990 laser dye Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 238000000691 measurement method Methods 0.000 description 2
- 229910001512 metal fluoride Inorganic materials 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 229920000620 organic polymer Polymers 0.000 description 2
- 125000002524 organometallic group Chemical group 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920000058 polyacrylate Polymers 0.000 description 2
- 150000002910 rare earth metals Chemical class 0.000 description 2
- 238000005215 recombination Methods 0.000 description 2
- 230000006798 recombination Effects 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 230000032258 transport Effects 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- 229910052726 zirconium Inorganic materials 0.000 description 2
- QGKMIGUHVLGJBR-UHFFFAOYSA-M (4z)-1-(3-methylbutyl)-4-[[1-(3-methylbutyl)quinolin-1-ium-4-yl]methylidene]quinoline;iodide Chemical compound [I-].C12=CC=CC=C2N(CCC(C)C)C=CC1=CC1=CC=[N+](CCC(C)C)C2=CC=CC=C12 QGKMIGUHVLGJBR-UHFFFAOYSA-M 0.000 description 1
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 description 1
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- AIGNCQCMONAWOL-UHFFFAOYSA-N 1,3-benzoselenazole Chemical compound C1=CC=C2[se]C=NC2=C1 AIGNCQCMONAWOL-UHFFFAOYSA-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
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 1
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- KYGSXEYUWRFVNY-UHFFFAOYSA-N 2-pyran-2-ylidenepropanedinitrile Chemical compound N#CC(C#N)=C1OC=CC=C1 KYGSXEYUWRFVNY-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N 3H-indole Chemical compound C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- DXHWPUIXEDWFKD-UHFFFAOYSA-N 3h-benzo[g]indole Chemical compound C1=CC2=CC=CC=C2C2=C1CC=N2 DXHWPUIXEDWFKD-UHFFFAOYSA-N 0.000 description 1
- GDRVFDDBLLKWRI-UHFFFAOYSA-N 4H-quinolizine Chemical compound C1=CC=CN2CC=CC=C21 GDRVFDDBLLKWRI-UHFFFAOYSA-N 0.000 description 1
- 125000004070 6 membered heterocyclic group Chemical group 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
- QZXAEJGHNXJTSE-UHFFFAOYSA-N 7-(ethylamino)-4,6-dimethylchromen-2-one Chemical compound O1C(=O)C=C(C)C2=C1C=C(NCC)C(C)=C2 QZXAEJGHNXJTSE-UHFFFAOYSA-N 0.000 description 1
- NRZJOTSUPLCYDJ-UHFFFAOYSA-N 7-(ethylamino)-6-methyl-4-(trifluoromethyl)chromen-2-one Chemical compound O1C(=O)C=C(C(F)(F)F)C2=C1C=C(NCC)C(C)=C2 NRZJOTSUPLCYDJ-UHFFFAOYSA-N 0.000 description 1
- IJCLOOKYCQWSJA-UHFFFAOYSA-N 7-amino-3-phenylchromen-2-one Chemical compound O=C1OC2=CC(N)=CC=C2C=C1C1=CC=CC=C1 IJCLOOKYCQWSJA-UHFFFAOYSA-N 0.000 description 1
- JAJIPIAHCFBEPI-UHFFFAOYSA-N 9,10-dioxoanthracene-1-sulfonic acid Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2S(=O)(=O)O JAJIPIAHCFBEPI-UHFFFAOYSA-N 0.000 description 1
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 1
- 229910000838 Al alloy Inorganic materials 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- OJDRWZZQYSZHPD-UHFFFAOYSA-N C(CC=C1)C(Cc2c3cccc2)C1=C3C1=C2C=CC=CC2Cc2ccccc12 Chemical compound C(CC=C1)C(Cc2c3cccc2)C1=C3C1=C2C=CC=CC2Cc2ccccc12 OJDRWZZQYSZHPD-UHFFFAOYSA-N 0.000 description 1
- 229910000882 Ca alloy Inorganic materials 0.000 description 1
- RAXXELZNTBOGNW-UHFFFAOYSA-O Imidazolium Chemical compound C1=C[NH+]=CN1 RAXXELZNTBOGNW-UHFFFAOYSA-O 0.000 description 1
- 229910000733 Li alloy Inorganic materials 0.000 description 1
- QUYZZTTYATWSRY-UHFFFAOYSA-N N1C=CC=C2N=CC=C12 Chemical compound N1C=CC=C2N=CC=C12 QUYZZTTYATWSRY-UHFFFAOYSA-N 0.000 description 1
- 241000288049 Perdix perdix Species 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-O Pyrazolium Chemical compound C1=CN[NH+]=C1 WTKZEGDFNFYCGP-UHFFFAOYSA-O 0.000 description 1
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 1
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- RKAGKCQBSWAWSU-UHFFFAOYSA-N acenaphthyleno[1,2-d][1,3]thiazole Chemical class C1=CC(C2=C3N=CS2)=C2C3=CC=CC2=C1 RKAGKCQBSWAWSU-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001515 alkali metal fluoride Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- ILFFFKFZHRGICY-UHFFFAOYSA-N anthracene-1-sulfonic acid Chemical compound C1=CC=C2C=C3C(S(=O)(=O)O)=CC=CC3=CC2=C1 ILFFFKFZHRGICY-UHFFFAOYSA-N 0.000 description 1
- 150000001454 anthracenes Chemical class 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000005235 azinium group Chemical group 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- AMTXUWGBSGZXCJ-UHFFFAOYSA-N benzo[e][1,3]benzoselenazole Chemical compound C1=CC=C2C(N=C[se]3)=C3C=CC2=C1 AMTXUWGBSGZXCJ-UHFFFAOYSA-N 0.000 description 1
- KXNQKOAQSGJCQU-UHFFFAOYSA-N benzo[e][1,3]benzothiazole Chemical compound C1=CC=C2C(N=CS3)=C3C=CC2=C1 KXNQKOAQSGJCQU-UHFFFAOYSA-N 0.000 description 1
- WMUIZUWOEIQJEH-UHFFFAOYSA-N benzo[e][1,3]benzoxazole Chemical compound C1=CC=C2C(N=CO3)=C3C=CC2=C1 WMUIZUWOEIQJEH-UHFFFAOYSA-N 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 1
- 150000004074 biphenyls Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical compound C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- CPCIOUMUZMHAAR-UHFFFAOYSA-N chromen-2-one;sodium Chemical compound [Na].C1=CC=C2OC(=O)C=CC2=C1 CPCIOUMUZMHAAR-UHFFFAOYSA-N 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
- AFYCEAFSNDLKSX-UHFFFAOYSA-N coumarin 460 Chemical compound CC1=CC(=O)OC2=CC(N(CC)CC)=CC=C21 AFYCEAFSNDLKSX-UHFFFAOYSA-N 0.000 description 1
- UIMOXRDVWDLOHW-UHFFFAOYSA-N coumarin 481 Chemical compound FC(F)(F)C1=CC(=O)OC2=CC(N(CC)CC)=CC=C21 UIMOXRDVWDLOHW-UHFFFAOYSA-N 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000000295 emission spectrum Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- ZFRKEVMBGBIBGT-UHFFFAOYSA-N ethenyl benzenesulfonate Chemical compound C=COS(=O)(=O)C1=CC=CC=C1 ZFRKEVMBGBIBGT-UHFFFAOYSA-N 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 125000001207 fluorophenyl group Chemical group 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-O hydron;1,3-oxazole Chemical compound C1=COC=[NH+]1 ZCQWOFVYLHDMMC-UHFFFAOYSA-O 0.000 description 1
- KAESVJOAVNADME-UHFFFAOYSA-O hydron;1h-pyrrole Chemical compound [NH2+]1C=CC=C1 KAESVJOAVNADME-UHFFFAOYSA-O 0.000 description 1
- SMWDFEZZVXVKRB-UHFFFAOYSA-O hydron;quinoline Chemical compound [NH+]1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-O 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- AWJUIBRHMBBTKR-UHFFFAOYSA-O isoquinolin-2-ium Chemical compound C1=[NH+]C=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-O 0.000 description 1
- DZFWNZJKBJOGFQ-UHFFFAOYSA-N julolidine Chemical class C1CCC2=CC=CC3=C2N1CCC3 DZFWNZJKBJOGFQ-UHFFFAOYSA-N 0.000 description 1
- 229910052747 lanthanoid Inorganic materials 0.000 description 1
- 150000002602 lanthanoids Chemical class 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 150000004880 oxines Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- VDNSHGNZYOIMOW-UHFFFAOYSA-N oxygen(2-) zirconium(4+) Chemical compound [O--].[O--].[O--].[O--].[Zr+4].[Zr+4] VDNSHGNZYOIMOW-UHFFFAOYSA-N 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000447 polyanionic polymer Polymers 0.000 description 1
- 229920005547 polycyclic aromatic hydrocarbon Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
- WVIICGIFSIBFOG-UHFFFAOYSA-N pyrylium Chemical compound C1=CC=[O+]C=C1 WVIICGIFSIBFOG-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 239000011593 sulfur Chemical group 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- 150000003755 zirconium compounds Chemical class 0.000 description 1
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- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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Abstract
【選択図】
なし
Description
「US Patent 3,995,299 (Partridge)」には、アノード、有機正孔導入・輸送領域(an organic hole injecting and transporting zone)、ルミネセンス領域(a luminescent zone)、電子輸送領域(an electron transporting zone)、ならびにカソードを順に含む、エレクトロルミネセンスデバイスが開示されている。ルミネセンス領域は、ペリレンもしくはアクリジンなどの蛍光色素(fluorescent dye)をドープしたポリビニルカルバゾールのような有機ポリマーとすることができる。
特許出願「PCT/GB03/05573」では、ジルコニウムキノラートを含む金属キノラートの使用について開示しており、ジルコニウム2-メチルキノラート(zirconium 2-methyl quinolate)の使用を開示している。
ZrL4 + 4(q-2Me) → Zr(q-2Me)2L2
(1) ZrL44(q-2Me) → Zr(q-2Me)2L2
(2) 2 Zr(q-2Me)2+ 4 acac → Zrq-2Me)4 + Zr(acac)4
ここで2-メチル-8-ヒドロキシキノリンは以下の構造で、
その2-メチルジルコニウムキノラート(2-methyl zirconium quinolate)にドーパントをドープすることもできる。
参照することによって本明細書に含まれている「US 4769292」で考察しているように、蛍光物質が存在すると、発光波長を広い範囲から選択することができる。
好ましいドーパントには以下のような構造のクマリン類である。
ポリアニリンは、例えば以下のようなオクタマー単位(octamer unit)、すなわちpが4であるようなもの、を形成する可能性がある。
芳香族環は非置換であるか、もしくは例えばエチル基のようなC1から20のアルキル基などで置換されている可能性がある。
前述のポリアニリン類などのアミノ置換芳香族化合物のポリマーは、他の正孔輸送物質とともに、もしくは組み合わせて、バッファー層としても用いることができる。
本発明は実施例中で説明されている。
〈 テトラキス(8-ヒドロキシキナルジナト)ジルコニウム(IV)の合成 〉
元素分析結果:理論値は、C, 66.36, H, 4.46, N, 7.74であり、実測値は、C, 66.17, H 4.33, N, 7.76であった。
〈 エレクトロルミネセンスデバイス 〉
あらかじめエッチングしたITO被覆ガラス片(pre-etched ITO coated glass piece)(10 x 10cm2)を用いた。デバイスはSolciet Machine(株式会社アルバック、茅ヶ崎、日本)を用いた真空蒸発により、逐次的にITO上に構成して加工された。個々のピクセルの活性領域(active area)は3mm x 3mmで、以下の層を含む。
ここで、ITOはインジウム-スズ酸化物被覆ガラス、Dは以下に示したもの、α-NPBは図8に示したもので、Zrq4-2Me は実施例1に従って調製したテトラキス(8-ヒドロキシキナルジナト)ジルコニウム(IV)、DPQAはジフェニルキンアクリジン(diphenylquinacridine)、そしてHfq4はハフニウムキノラートである。
Zrq4-2Me : DPQA層は、DPQAをドープした2-Meジルコニウムキノラートを生成するために同時に真空蒸着することにより形成した。Zrq4-2MeとDPQAとの重量比は相対的な厚みの計測で簡単に示される。
Claims (32)
- 置換もしくは非置換ジルコニウム2-メチルキノラートを製造する方法であって、
ジルコニウム塩ZnL4(ここでLはアニオン)と置換もしくは非置換2-メチル-8-ヒドロキシキノリンを反応させる、混合塩Zr(q-2Me)2L2を生成させるためのステップ、ならびに、
その後、前記混合塩をベータジケトンと反応させる、ジルコニウム2-メチルキノラートを生成するためのステップ、
を含むことを特徴とする方法。 - Lがアルコキシドであることを特徴とする、請求項1記載の方法。
- 前記ベータジケトンが2,4-ペンタンジオンであることを特徴とする、請求項1もしくは2記載の方法。
- 前記反応が有機溶媒中で起こることを特徴とする、請求項1から3のいずれかに記載の方法。
- 請求項1から5のいずれかに記載の方法によって作られたことを特徴とする、置換もしくは非置換ジルコニウム2-メチルキノラート。
- (i) 第一電極、(ii) 請求項6記載の、置換もしくは非置換2-メチルジルコニウムキノラートを含むエレクトロルミネセンス物質の層、および(iii) 第二電極を含むことを特徴とする、エレクトロルミネセンスデバイス。
- (i) 第一電極、(ii) 請求項6記載の、置換もしくは非置換2-メチルジルコニウムキノラート、および、ドーパントを含むエレクトロルミネセンス物質の層、(iii) 第二電極を含むことを特徴とする、エレクトロルミネセンスデバイス。
- 前記ドーパントが、ジフェニルアクリジン、クマリン類、ペリレン、キノラート類、ポルホリン(porphoryin)、ポルフィン類、ピラザロン類(pyrazalones)およびそれらの誘導体から選択されることを特徴とする、請求項8記載のエレクトロルミネセンスデバイス。
- ジルコニウム2-メチルキノラートのモル数に基づいて、蛍光物質が最大で10モルパーセントまで存在することを特徴とする、請求項8もしくは9記載のエレクトロルミネセンスデバイス。
- ジルコニウム2-メチルキノラートのモル数に基づいて、蛍光物質が最大で1モルパーセントまで存在することを特徴とする、請求項8もしくは9記載のエレクトロルミネセンスデバイス。
- ジルコニウム2-メチルキノラートのモル数に基づいて、蛍光物質が10-3モルパーセント未満存在することを特徴とする、請求項8もしくは9記載のエレクトロルミネセンスデバイス。
- 前記ドーパントのバンドギャップがジルコニウム2-メチルキノラートのバンドギャップよりも大きくなく、かつ、還元電位がジルコニウム2-メチルキノラートの還元電位よりも負ではないことを特徴とする、請求項8から12のいずれかに記載のエレクトロルミネセンス組成物。
- 前記ドーパントが存在しないときのジルコニウム2-メチルキノラートによる発光が最大である波長が、前記置換アントラセン化合物の最大吸収波長から25nm以内に存在することを特徴とする、請求項8から13のいずれかに記載のエレクトロルミネセンス組成物。
- 前記ドーパントが構造式(A)、(B)および(C)の化合物、ならびに、図9から13の図の化合物から選択されることを特徴とする、請求項8から14のいずれかに記載のエレクトロルミネセンス組成物。
- 前記第一電極と前記エレクトロルミネセンス層の間に正孔輸送物質の層があることを特徴とする、請求項7から15のいずれかに記載のエレクトロルミネセンスデバイス。
- 前記正孔輸送物質が芳香族アミン錯体(aromatic amine complex)であることを特徴とする、請求項14記載のエレクトロルミネセンスデバイス。
- 前記正孔輸送物質がポリ芳香族アミン錯体(polyaromatic amine complex)であることを特徴とする、請求項14記載のエレクトロルミネセンスデバイス。
- 前記正孔輸送物質が、ポリ(ビニルカルバゾール)、N,N'-ジフェニル-N,N'-ビス(3-メチルフェニル)-1,1'-ビフェニル-4,4'-ジアミン(TPD)、ポリアニリン、置換ポリアニリン類、ポリチオフェン類、置換ポリチオフェン類、ポリシラン類および置換ポリシラン類から選択された、ポリマーの膜であることを特徴とする、請求項14記載のエレクトロルミネセンスデバイス。
- 前記正孔輸送物質が、本明細書の構造式(I)もしくは(II)の化合物、または図4から8の図のような化合物の膜であることを特徴とする、請求項14記載のエレクトロルミネセンスデバイス。
- 前記正孔輸送物質が、アニリンの共重合体、アニリンとo-アニシジン、m-スルファニル酸、もしくはo-アミノフェノールとの共重合体、またはo-トルイジンとo-アミノフェノール、o-エチルアニリン、o-フェニレンジアミンもしくはアミノアントラセンとの共重合体であることを特徴とする、請求項14記載のエレクトロルミネセンスデバイス。
- 前記正孔輸送物質が、共役高分子であることを特徴とする、請求項14記載のエレクトロルミネセンスデバイス。
- 前記共役高分子がポリ(p-フェニレンビニレン)(PPV)、ならびに、PPV、ポリ(2,5-ジアルコキシフェニレンビニレン)、ポリ(2-メトキシ-5-(2-メトキシペンチルオキシ-1,4-フェニレンビニレン)、ポリ(2-メトキシペンチルオキシ)-1,4-フェニレンビニレン)、ポリ(2-メトキシ-5-(2-ドデシルオキシ-1,4-フェニレンビニレン) および、長鎖可溶化性アルコキシ基であるアルコキシ基、ポリフルオレン類およびオリゴフルオレン類、ポリフェニレン類およびオリゴフェニレン類、ポリアントラセン類およびオリゴアントラセン類、ポリチオフェン類(ploythiophenes)およびオリゴチオフェン類のうちの少なくとも一つを含む、他のポリ(2,5-ジアルコキシフェニレンビニレン類) を含む共重合体から選択された共役高分子であることを特徴とする、請求項22記載のエレクトロルミネセンスデバイス。
- 前記エレクトロルミネセンス化合物が前記正孔輸送物質に混合されていることを特徴とする、請求項14から23のいずれかに記載のエレクトロルミネセンスデバイス。
- 前記カソードと前記エレクトロルミネセンス化合物の層との間に、電子輸送物質の層があることを特徴とする、請求項7から24のいずれかに記載のエレクトロルミネセンスデバイス。
- 前記電子輸送物質が、金属キノラートであることを特徴とする、請求項25記載のエレクトロルミネセンスデバイス。
- 前記金属キノラートが、アルミニウムキノラート、ジルコニウムキノラート、ハフニウムキノラート、バナジウムキノラート、チタニウムキノラート、バナジウムキノラート、ニオビウムキノラート、もしくはタンタル(tantulum)キノラートまたはリチウムキノラートであることを特徴とする、請求項26記載のエレクトロルミネセンスデバイス。
- 前記電子輸送物質がMx(DBM)nの構造であることを特徴とし、
ここでMxは金属で、DBMはジベンゾイルメタンであり、nはMxの価数である、
請求項25記載のエレクトロルミネセンスデバイス。 - 前記電子輸送物質が9,10-ジシアノアントラセンのようなシアノアントラセン、ポリスチレンスルホン酸(polystyrene sulphonate)、もしくは図2もしくは3の図で示された構造式の化合物であることを特徴とする、請求項25記載のエレクトロルミネセンスデバイス。
- 前記電子輸送物質が前記エレクトロルミネセンス化合物と混合されていることを特徴とする、請求項25から29のいずれかに記載のエレクトロルミネセンスデバイス。
- 前記第一電極が透明電気伝導ガラス電極であることを特徴とする、請求項7から30のいずれかに記載のエレクトロルミネセンスデバイス。
- 前記第二電極が、アルミニウム、カルシウム、リチウム、マグネシウム、および、それらの合金、ならびに銀/マグネシウム合金から選択されたものであることを特徴とする、請求項7から31のいずれかに記載のエレクトロルミネセンスデバイス。
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JPH06145146A (ja) * | 1992-11-06 | 1994-05-24 | Chisso Corp | オキシネイト誘導体 |
JPH09272865A (ja) * | 1996-04-08 | 1997-10-21 | Toyo Ink Mfg Co Ltd | 有機エレクトロルミネッセンス素子用電子注入材料およびそれを用いた有機エレクトロルミネッセンス素子 |
US6210814B1 (en) * | 1998-04-10 | 2001-04-03 | The University Of Southern California | Color-tunable organic light emitting devices |
WO2004046275A1 (ja) * | 2002-11-21 | 2004-06-03 | Semiconductor Energy Laboratory Co., Ltd | 電界発光素子および発光装置 |
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GB0230072D0 (en) * | 2002-12-24 | 2003-01-29 | Elam T Ltd | Electroluminescent materials and devices |
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2004
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JPH06145146A (ja) * | 1992-11-06 | 1994-05-24 | Chisso Corp | オキシネイト誘導体 |
JPH09272865A (ja) * | 1996-04-08 | 1997-10-21 | Toyo Ink Mfg Co Ltd | 有機エレクトロルミネッセンス素子用電子注入材料およびそれを用いた有機エレクトロルミネッセンス素子 |
US6210814B1 (en) * | 1998-04-10 | 2001-04-03 | The University Of Southern California | Color-tunable organic light emitting devices |
WO2004046275A1 (ja) * | 2002-11-21 | 2004-06-03 | Semiconductor Energy Laboratory Co., Ltd | 電界発光素子および発光装置 |
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GB2423302B8 (en) | 2006-10-27 |
US20070254183A1 (en) | 2007-11-01 |
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