JP2008179798A - 冷光放射性高分子材料 - Google Patents
冷光放射性高分子材料 Download PDFInfo
- Publication number
- JP2008179798A JP2008179798A JP2007331572A JP2007331572A JP2008179798A JP 2008179798 A JP2008179798 A JP 2008179798A JP 2007331572 A JP2007331572 A JP 2007331572A JP 2007331572 A JP2007331572 A JP 2007331572A JP 2008179798 A JP2008179798 A JP 2008179798A
- Authority
- JP
- Japan
- Prior art keywords
- monomer
- ligand
- formula
- group
- light
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000002861 polymer material Substances 0.000 title claims abstract description 18
- 239000003446 ligand Substances 0.000 claims abstract description 75
- 239000000178 monomer Substances 0.000 claims abstract description 69
- 229910052751 metal Inorganic materials 0.000 claims abstract description 40
- 239000002184 metal Substances 0.000 claims abstract description 40
- 230000005284 excitation Effects 0.000 claims abstract description 20
- -1 lanthanide acrylate Chemical class 0.000 claims abstract description 20
- 125000006850 spacer group Chemical group 0.000 claims abstract description 17
- 125000000129 anionic group Chemical group 0.000 claims abstract description 15
- 150000002500 ions Chemical class 0.000 claims abstract description 15
- 239000013522 chelant Substances 0.000 claims abstract description 14
- 125000004429 atom Chemical group 0.000 claims abstract description 12
- 230000007935 neutral effect Effects 0.000 claims abstract description 10
- 239000012634 fragment Substances 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 20
- 239000000463 material Substances 0.000 claims description 20
- 229920000642 polymer Polymers 0.000 claims description 19
- 239000000758 substrate Substances 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 12
- 238000006116 polymerization reaction Methods 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 10
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical group C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 claims description 9
- 229910052782 aluminium Inorganic materials 0.000 claims description 9
- 150000001336 alkenes Chemical group 0.000 claims description 8
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical group [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical group C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 claims description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical group [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 6
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical group C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 claims description 6
- 230000005855 radiation Effects 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
- KDVYCTOWXSLNNI-UHFFFAOYSA-N 4-t-Butylbenzoic acid Chemical group CC(C)(C)C1=CC=C(C(O)=O)C=C1 KDVYCTOWXSLNNI-UHFFFAOYSA-N 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- XAAKCCMYRKZRAK-UHFFFAOYSA-N isoquinoline-1-carboxylic acid Chemical group C1=CC=C2C(C(=O)O)=NC=CC2=C1 XAAKCCMYRKZRAK-UHFFFAOYSA-N 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 239000011701 zinc Chemical group 0.000 claims description 4
- 239000005725 8-Hydroxyquinoline Substances 0.000 claims description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 3
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical group [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical group [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 3
- 229910052790 beryllium Inorganic materials 0.000 claims description 3
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical group [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 claims description 3
- 150000004820 halides Chemical class 0.000 claims description 3
- 229910052741 iridium Inorganic materials 0.000 claims description 3
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical group [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-M methacrylate group Chemical group C(C(=C)C)(=O)[O-] CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 229910052762 osmium Inorganic materials 0.000 claims description 3
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical group [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 claims description 3
- 229960003540 oxyquinoline Drugs 0.000 claims description 3
- 229910052697 platinum Inorganic materials 0.000 claims description 3
- 229910052707 ruthenium Chemical group 0.000 claims description 3
- 229910052725 zinc Inorganic materials 0.000 claims description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 2
- JVZRCNQLWOELDU-UHFFFAOYSA-N gamma-Phenylpyridine Natural products C1=CC=CC=C1C1=CC=NC=C1 JVZRCNQLWOELDU-UHFFFAOYSA-N 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 230000001235 sensitizing effect Effects 0.000 claims description 2
- 230000000977 initiatory effect Effects 0.000 claims 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 1
- 229910002651 NO3 Inorganic materials 0.000 claims 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims 1
- 150000007942 carboxylates Chemical class 0.000 claims 1
- 229910052747 lanthanoid Inorganic materials 0.000 abstract description 19
- 125000005842 heteroatom Chemical group 0.000 abstract description 4
- 230000003247 decreasing effect Effects 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 31
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 19
- 150000002602 lanthanoids Chemical class 0.000 description 15
- 239000002904 solvent Substances 0.000 description 14
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 150000004696 coordination complex Chemical class 0.000 description 7
- 239000003999 initiator Substances 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 239000010409 thin film Substances 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 230000008901 benefit Effects 0.000 description 6
- 229910021645 metal ion Inorganic materials 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000004528 spin coating Methods 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 125000005395 methacrylic acid group Chemical group 0.000 description 5
- KKFHAJHLJHVUDM-UHFFFAOYSA-N n-vinylcarbazole Chemical compound C1=CC=C2N(C=C)C3=CC=CC=C3C2=C1 KKFHAJHLJHVUDM-UHFFFAOYSA-N 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 4
- 239000002262 Schiff base Substances 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 150000001735 carboxylic acids Chemical class 0.000 description 4
- 238000007334 copolymerization reaction Methods 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 150000002739 metals Chemical class 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- 150000004753 Schiff bases Chemical class 0.000 description 3
- 229910052771 Terbium Inorganic materials 0.000 description 3
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 125000004494 ethyl ester group Chemical group 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 229910021644 lanthanide ion Inorganic materials 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000007639 printing Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-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
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 230000004913 activation Effects 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- WZJYKHNJTSNBHV-UHFFFAOYSA-N benzo[h]quinoline Chemical compound C1=CN=C2C3=CC=CC=C3C=CC2=C1 WZJYKHNJTSNBHV-UHFFFAOYSA-N 0.000 description 2
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 239000013256 coordination polymer Substances 0.000 description 2
- 229920001795 coordination polymer Polymers 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 238000003618 dip coating Methods 0.000 description 2
- 238000010894 electron beam technology Methods 0.000 description 2
- BYZDRRAHLZZRGC-UHFFFAOYSA-N ethyl 2-(2-methylprop-2-enoylperoxycarbonyl)benzoate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OOC(=O)C(C)=C BYZDRRAHLZZRGC-UHFFFAOYSA-N 0.000 description 2
- 238000000855 fermentation Methods 0.000 description 2
- 230000004151 fermentation Effects 0.000 description 2
- 239000010408 film Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229910001385 heavy metal Inorganic materials 0.000 description 2
- 230000005525 hole transport Effects 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- 125000002524 organometallic group Chemical group 0.000 description 2
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 2
- 229920000767 polyaniline Polymers 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229910052703 rhodium Inorganic materials 0.000 description 2
- 239000010948 rhodium Substances 0.000 description 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- GZCRRIHWUXGPOV-UHFFFAOYSA-N terbium atom Chemical compound [Tb] GZCRRIHWUXGPOV-UHFFFAOYSA-N 0.000 description 2
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 2
- 229910001887 tin oxide Inorganic materials 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- IGGDKDTUCAWDAN-UHFFFAOYSA-N 1-vinylnaphthalene Chemical compound C1=CC=C2C(C=C)=CC=CC2=C1 IGGDKDTUCAWDAN-UHFFFAOYSA-N 0.000 description 1
- OKFLKUZAJUNRDN-UHFFFAOYSA-N 2,4,6-triphenylphenol Chemical compound OC1=C(C=2C=CC=CC=2)C=C(C=2C=CC=CC=2)C=C1C1=CC=CC=C1 OKFLKUZAJUNRDN-UHFFFAOYSA-N 0.000 description 1
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- KXTAOXNYQGASTA-UHFFFAOYSA-N 2-benzylidenepropanedioic acid Chemical compound OC(=O)C(C(O)=O)=CC1=CC=CC=C1 KXTAOXNYQGASTA-UHFFFAOYSA-N 0.000 description 1
- XBHOUXSGHYZCNH-UHFFFAOYSA-N 2-phenyl-1,3-benzothiazole Chemical compound C1=CC=CC=C1C1=NC2=CC=CC=C2S1 XBHOUXSGHYZCNH-UHFFFAOYSA-N 0.000 description 1
- QLPKTAFPRRIFQX-UHFFFAOYSA-N 2-thiophen-2-ylpyridine Chemical compound C1=CSC(C=2N=CC=CC=2)=C1 QLPKTAFPRRIFQX-UHFFFAOYSA-N 0.000 description 1
- TXNLQUKVUJITMX-UHFFFAOYSA-N 4-tert-butyl-2-(4-tert-butylpyridin-2-yl)pyridine Chemical group CC(C)(C)C1=CC=NC(C=2N=CC=C(C=2)C(C)(C)C)=C1 TXNLQUKVUJITMX-UHFFFAOYSA-N 0.000 description 1
- BDQGTRWOFVSOQX-UHFFFAOYSA-N 5-(chloromethyl)quinolin-8-ol;hydron;chloride Chemical compound Cl.C1=CN=C2C(O)=CC=C(CCl)C2=C1 BDQGTRWOFVSOQX-UHFFFAOYSA-N 0.000 description 1
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- PIGFYZPCRLYGLF-UHFFFAOYSA-N Aluminum nitride Chemical compound [Al]#N PIGFYZPCRLYGLF-UHFFFAOYSA-N 0.000 description 1
- 229910052684 Cerium Inorganic materials 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- 229910052693 Europium Inorganic materials 0.000 description 1
- 229910052688 Gadolinium Inorganic materials 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- 229910052772 Samarium Inorganic materials 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- CKUAXEQHGKSLHN-UHFFFAOYSA-N [C].[N] Chemical compound [C].[N] CKUAXEQHGKSLHN-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000003926 acrylamides Chemical class 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 229910000410 antimony oxide Inorganic materials 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 150000007860 aryl ester derivatives Chemical class 0.000 description 1
- 150000008378 aryl ethers Chemical class 0.000 description 1
- 230000002238 attenuated effect Effects 0.000 description 1
- 239000010953 base metal Substances 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 229920006037 cross link polymer Polymers 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 150000003983 crown ethers Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 230000005595 deprotonation Effects 0.000 description 1
- 238000010537 deprotonation reaction Methods 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- VILAVOFMIJHSJA-UHFFFAOYSA-N dicarbon monoxide Chemical group [C]=C=O VILAVOFMIJHSJA-UHFFFAOYSA-N 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 1
- 239000007850 fluorescent dye Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 150000005171 halobenzenes Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000003306 harvesting Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 150000002601 lanthanoid compounds Chemical class 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical class CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 230000008832 photodamage Effects 0.000 description 1
- 229920002120 photoresistant polymer Polymers 0.000 description 1
- 125000005498 phthalate group Chemical group 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
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 239000005518 polymer electrolyte Substances 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- HXHCOXPZCUFAJI-UHFFFAOYSA-N prop-2-enoic acid;styrene Chemical compound OC(=O)C=C.C=CC1=CC=CC=C1 HXHCOXPZCUFAJI-UHFFFAOYSA-N 0.000 description 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical compound [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 150000003873 salicylate salts Chemical class 0.000 description 1
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000010421 standard material Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003440 styrenes Chemical group 0.000 description 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- MDDUHVRJJAFRAU-YZNNVMRBSA-N tert-butyl-[(1r,3s,5z)-3-[tert-butyl(dimethyl)silyl]oxy-5-(2-diphenylphosphorylethylidene)-4-methylidenecyclohexyl]oxy-dimethylsilane Chemical compound C1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)C(=C)\C1=C/CP(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 MDDUHVRJJAFRAU-YZNNVMRBSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 239000012780 transparent material Substances 0.000 description 1
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000003021 water soluble solvent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/003—Compounds containing elements of Groups 3 or 13 of the Periodic Table without C-Metal linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/06—Aluminium compounds
- C07F5/069—Aluminium compounds without C-aluminium linkages
-
- 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
- H10K85/351—Metal complexes comprising lanthanides or actinides, e.g. comprising europium
-
- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/14—Macromolecular compounds
- C09K2211/1408—Carbocyclic compounds
- C09K2211/1416—Condensed systems
-
- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/14—Macromolecular compounds
- C09K2211/1408—Carbocyclic compounds
- C09K2211/1433—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
-
- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/14—Macromolecular compounds
- C09K2211/1441—Heterocyclic
- C09K2211/1466—Heterocyclic containing nitrogen as the only heteroatom
-
- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/18—Metal complexes
- C09K2211/182—Metal complexes of the rare earth metals, i.e. Sc, Y or lanthanide
-
- 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
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/141—Organic polymers or oligomers comprising aliphatic or olefinic chains, e.g. poly N-vinylcarbazol, PVC or PTFE
-
- 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
- H10K85/321—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
-
- 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
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S428/00—Stock material or miscellaneous articles
- Y10S428/917—Electroluminescent
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Inorganic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Electroluminescent Light Sources (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polymerisation Methods In General (AREA)
- Quinoline Compounds (AREA)
- Pyridine Compounds (AREA)
- Luminescent Compositions (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
【解決手段】励起によって可視領域での冷光放射を行う、次の一般式で表されるモノマー:Mn+(L)n-(CL)x。この式において、n+は、Mの価数を表し、(L)は、1又は2以上の総計n−の価数を有するアニオンリガンドを表し、前記リガンドの少なくとも1つは次の式を有する:Ch−X−Y。この式において、Chは、キレート結合部及びキレート結合部が共役されたリガンドの残りの部分からなるリガンドの断片であるキレート/イオン結合基であり、Yは、オレフィン基を表し、Xは、少なくとも4の炭素及びヘテロ原子の鎖からなるスペーサー又は結合部であり、xは0,1又は2であり、CLは中性コリガンドであり、Mは2,12,13、d−ブロック又はf−ブロックの金属原子を表す。
【選択図】なし
Description
一般的に、金属イオン含有高分子材料には4つのグループがある。
(1)配位高分子材料及び電解質高分子材料
(2)金属錯体をドープした中立極性基を含有する高分子材料
(3)高分子材料の脱プロトン化とこれに続く金属塩との反応により用意された高分子金
属錯体、及び
(4)金属モノマー錯体の重合によって用意された金属高分子錯体
(化6) Mn+(L)n-(CL)x
(化7) Ch−X−Y
−COOHではない。
Yグループは、次の一般式で表すことができる。
この式において、M、CL、n及びxは上記のように定義され、少なくとも1つのリガンドは次の式を有するように、(L)は総計n−価の1又は2以上のアニオンリガンドを表す。
200ml中のモノ−2−(メタクリロキシ)エチルフタレート(MEP)の4.57g (16.4 mmol)が10mlのH2O中のNa2CO3870mg(8.2mmol)と反応させた。次いで、2.2g(1.2当量、6.6mol)のバトフェナントリンがこの反応混合物に溶解され、10mlのH2O中の2g(5.5mmol)のEuCl3×6H2Oが滴下された。製品は、180mlの水の滴下により、ろ過溶液から沈殿された。反応混合物は30分攪拌された。ろ過後、沈殿物は200mlのエタノール/H2O20:80、50mlのH2Oで洗浄され、真空中で一晩乾燥されて5.6g(77%生成)の無色の固体が得られた。
C66H59EuN2O18:予測値/実測値: C 60.05 / 60.16, H 4.5 / 4.52, N 2.1 / 2.3, Eu 11.51 / 11.81. 光冷光放射: 励起: λmax 367 nm; 放射:λmax 613 + 616 nm。
同様の方法が次の実施例2〜7の化合物を用意するために使われた。
C54H47EuN2O18:予測値/実測値: C 55.72 / 54.59, H 4.07 / 3.83, N 2.41 / 2.18. 冷光放射:励起:λ max 270 + 348 nm; 発光:λ max 613 + 617 + 619 nm。
C54H47N2O18Sm:予測値/実測値: C 50.44 / 50.44, H 4.13 / 4.19, Sm 15.04 / 15.44. 冷光放射無し。
C54H47N2O18Tb:予測値/実測値: C 55.39 / 54.75, H 4.05 / 4.09, N 2.39 / 2.20. 冷光放射:励起: λmax 270 + 348 nm; 発光: λmax 613 + 617 + 619 nm。
C54H47N2O18Y:予測値/実測値: C 58.92 / 57.45, H 4.30 / 4.01, N 2.54 / 2.35. 1H-NMR (300 MHz, CDCl3); 9.59 ppm (s, 2H), 8.09 (d, 2H), 7.67 (s, 2H), 7.48 (m, 5H), 7.08 (m, 9H), 5.8 (s, 3H), 5.4 (s, 3H)1.75 (s, 9H).冷光放射無し。
0%)
C52H58N2O18Tb:予測値/実測値: C53.94' 52.56, H 5.05 / 5.08, N 2.42 / 2.21, Tb 13.72 / 14.04. 冷光放射:励起: λmax 287 nm; 発光: λmax 543 nm。
C60H66N2O18Tb:予測値/実測値: C 57.1 / 56.3, H 5.27 / 5.14, N 2.22 / 2.18, Tb 12.59 / 12.64.冷光放射:励起:λ max 296 + 335 nm; 発光: λmax 542 nm。
1.25g(4.5mmol)のモノ−2−(メタクリロイロキシ)エチルフタレン及び1.56g(9mmol)のイソキノリンカルボン(IQA)酸が5molのメタノールに溶解され、50℃で3mlのメタノール/H2O中の1.13g(13.5mmol)のNaHCO3溶液に加えられた。45分間攪拌した後、溶媒はろ過され、6mlメタノール中の1.65g(4.5mmol)のEuCl36H2Oの溶媒に滴下された。真空中での溶媒の蒸発後、THFに2回溶解され、ヘキサン中で沈殿させた。沈殿物は、真空中で一晩乾燥され、3.02g(85%生成)の製品が無色の固体として得られた。
C34H27EuN2O11 予測値/実測値: C 51.59 / 51.79, H 3.44 / 3.26, N 3.54 / 3.66, Eu 19.20 / 18.52. 冷光放射 (CH2Cl2): 発光:λ max 615 nm, excitation: λmax 339 nm。
同様の方法が次の実施例9〜13の化合物を用意するのに用いられた。
C34H27N2O11Sm 予測値/実測値: C 51.69 / 50.58, H 3.44 / 3.20, N 3 Sm 19.04 / 20.13. 冷光放射無し。
C36H29EuO11予測値/実測値: C 54.76 / 55.12, H 3.70 / 3.73, Eu 19.25 / 19.07. 冷光放射 (CH2Cl2): 発光:λmax 613 nm, 励起: λmax 251 nm。
C36H29O11Sm 予測値/実測値: C 54.87 / 55.19, H 3.71 / 3.88, Sm 19.09 / 19.15. 冷光放射無し。
C36H39O10Tb予測値/実測値: C 54.69 / 55.26, H 4.97 / 5.48, Tb 20.10 / 20.12. 冷光放射 (CH2Cl2): 発光: λmax 543 nm, 励起: λmax 253 nm。
C36H39O10Dy 予測値/実測値: C 53.24 / 53.04, H 5.09 / 5.01, Dy 20.01 / 21.12. 冷光放射無し。
[Eu(MEP)3浴]の光重合が、5重量%のジフェニル(2,4,6−トリメチルベンゾイル)ホスフィンオキサイドと共に開始された。トルエン中のヨウロピウムモノマーの溶液(30mg/ml)がガラス基板上にスピンコートされた。ガラス基板に、その後、窒素雰囲気中でUV光を照射した。フォトマスクによって、基板のパターニングがなし遂げられた。露光後、未露光部のモノマーはトルエンによる基板の洗浄で除去され、100nmの厚さの高分子薄膜が得られた。
CHCl3中の10%の1−ヒドロキシクロヘキシル−フェニルケトンと共に[Tb(MEP)3ビピリジル]がガラス上にスピンコートされた。窒素雰囲気中でのフォトマスクを使用したUV露光の後、未反応モノマーはCHCl3により洗浄除去された。10重量%の1−ヒドロキシシクロヘキシル−フェニルケトンと共に[Eu(MEP)浴]がトルエン溶媒からスピンコートされた。露光後、フォトマスクを通じて、未反応モノマーがトルエンにより除去された。
アルゴン雰囲気中で[Eu(MEP)(IQA)2xH2O](5−30%)が抑制剤開放MMAに溶解される。AIBNがラジカル開始剤として添加された。封止されたチューブが60℃の油浴に置かれた。反応が完結(10−30分)された後、製品は真空中で30分間乾燥され無色透明なプラスチックが得られた。
(1)[Eu(MEP)(IQA)2xH2O]とMMA5、10、30重量%との共重合。冷光放射:最大発光:625nm、最大励起:374
(2)[Eu(MEP)(IQA)2xH2O]とスチレン10、30、50重量%との共重合。冷光放射:最大発光614nm、最大励起:365nm
(3)[Eu(MEP)(IQA)2xH2O]とN−ビニルカルバゾール1、5,10重量%との共重合。冷光放射:最大発光615nm、最大励起:390nm
スピンコートと従来の蒸着のコンビネーションにより形成された有機発光ダイオードが発光材料として上記に示された有機ランタニド化合物とともに調査された。
典型的な実施装置は、次のように形成される。
。EL発光波長はccdカメラにより測定され、ヨーロピウムイオンの波長として典型的な発光波長(最大615nm)を生じた。
5−クロロメチル−8−ヒドロキシキノリン塩酸塩(5.0g,21.7mmol)及び2−ヒドロキシメタクリレート(20ml,143mmol)の混合物が2日間真空中60℃で加熱された。室温まで冷却された後、H2O(150ml)が加えられ、溶液は希薄NH3水溶液によってアルカリ化した。製品は沈殿し、フィルター上で回収され、希薄NH3水溶液によって洗浄され、真空中で一晩乾燥させた。この原製品はTHF(250ml)に抽出され不溶性の残留物からろ過された。真空中でのTHFの蒸発から、ヘキサンから2回再結晶された固体が得られ、釘状の純製品の無色の結晶が得られた(4.9g,17mmol,79%)。
Mp: 89 ℃. IR(薄膜): 3055 cm-1, 2955, 2857, 1713 (C=O), 1635 (C=C), 1581 (C=C環).1H-NMR (δ, 300 MHz, DMSO-d6): 8.86 ppm (m, 1H), 8.48 (m, 1H), 7.55 (dd, 1H, 3J= 4.1 ,8.5 Hz), 7.43 (d, 1H, 3J= 7.8 Hz), 7.0 (d, 1H, 3J= 8.2 Hz), 5.95 (m, 1H), 5.64 (m, 1H), 4.84 (s, 2H), 4.23 (m, 2H), 3.69 (m, 2H), 1.83 (s, 3H). 13C [1H] NMR (δ, 300 MHz, DMSO-d6): 166.3 ppm, 153.4, 147.8, 138.7, 135.6, 138.1, 128.5, 127.3, 125.6, 123.9, 121.6, 109.8, 69.9, 67.0, 63.5, 17.8. UV / Vis (CH2Cl2): 245 nm, 323。
窒素雰囲気中−80℃、乾燥トルエン(125ml)中のトリメチルアルミニウム(2.5mmolトルエン中2M溶液1.25ml)が乾燥トルエン(250ml)中メタクリル酸−2−(8−ヒドロキシキノリン−5−ylメトキシ)エチルエステル(2.15g、7.5mmol)に滴下された。混合物は、マイナス20℃で3時間保たれ、その時点でEtOH(3ml)の添加によってクエンチされ、室温まで暖められた。真空中での溶媒の蒸発後、残留物はトルエン(250ml)に溶解され、セライトのパッドを通過させてろ過され、次いで、ヘキサン(400ml)に滴下された。ろ過後、固体がトルエン(10ml)に溶解され、ヘキサン中で沈殿された。これを3回繰り返し、明るい黄色の固体1.54g(69%)が得られた。
C48H48AlN3O12: 予想値/実測値: C 65.08 / 63.68, H 5.46 / 5.32, N 4.74 / 4.81, Al 3.05 / 3.06. M.P.: no m.p., 60℃で重合開始。IR (薄膜): 2954 cm-1, 2864, 1713 (C=O), 1636 (C=C), 1604 (C=C環), 1580 (C=C環). 1H-NMR (δ, 300 MHz, DMSO-d6): 8.64 ppm (m, 6H), 7.49 (m, 6H), 6.75 (dd, 3H), 5.6 (m, 6H), 4.81 (m, 6H), 4.2 (m, 6H), 3.67 (m, 6H), 1.74 (m, 9H). FAB-MS: m/z = 885 (20 %, M+), 599 (100 %). UV / Vis (CH2Cl2): 261 nm, 390. 冷光放射 (CH2Cl2):発光: λmax 534 nm, 励起: λmax 381 nm. 冷光放射 (粉末): 発光: λmax 532 nm, 励起: λmax 381 nm。
パターン化されたITO基板が洗浄液及びDI水中の超音波による通常の方法で予備処理され、炉中で乾燥された。40nmの厚さのPEDOT/PSSの正孔放出/輸送層が基板上のITO面にスピンコートにより積層された。薄膜は、20分間、120℃のホットプレート上で乾燥された。Al(MAEQ)3からなる発光/電子輸送層がトルエン(15mg/ml)からスピンコートにより積層された。1.5nmの厚さを有するLi発光層の上に、厚さ200nmを有するAlカソードが真空中で蒸着された。
Claims (27)
- 励起によって可視領域での冷光放射を行う、次の一般式で表される発光ポリマーの重合に使用されるモノマー。
(化1) Mn+(L)n-(CL)x
この式において、n+は、Mの価数を表し、(L)は、1又は2以上の総計−n価を有するアニオンリガンドを表し、前記リガンドの少なくとも1つは次の式を有する。
(化2) Ch−X−Y
この式において、Chは、キレート結合部及びキレート結合部が共役されたリガンドの残りの部分からなるリガンドの断片であるキレート/イオン結合基であり、Yは、オレフィン基を表し、Xは、少なくとも4つの炭素及び酸素原子を含むスペーサー又は結合部であり、xは0,1又は2であり、CLは中性コリガンドであり、Mはd−ブロック金属である。 - Chが酸素又は窒素電子供与体である請求項1に記載のモノマー。
- Chがカルボン酸、ジカルボン酸、ヒドロキシカルボン酸、β−ジケトネート基又はヒドロキシキノリン基である請求項1又は2に記載のモノマー。
- スペーサーが6から12までの原子からなる請求項1ないし3のいずれかに記載のモノマー。
- スペーサーが電子供与体又は配位基からなる請求項1ないし4のいずれかに記載のモノマー。
- Yがアクリル酸塩の一部又は置換アクリラート基である請求項1ないし5のいずれかに記載のモノマー。
- Yがメタクリラート基である請求項1ないし6のいずれかに記載のモノマー。
- Mがベリリウム、亜鉛、アルミニウム、イリジウム、オスミウム、プラチナ及びルテニウムを表す請求項1ないし7のいずれかに記載のモノマー。
- (L)がCh−X−Yではない1又は2のアニオンリガンドを含む請求項1ないし8のいずれかに記載のモノマー。
- 前記Ch−X−Yではないアニオンリガンドがフェニルピリジンである請求項9に記載のモノマー。
- 前記Ch−X−Yではないアニオンリガンドが、イソキノリンカルボン酸、1−ナフトエ酸又は4−t−ブチル安息香酸である請求項9に記載のモノマー。
- 前記Ch−X−Yでないアニオンリガンドが8−ヒドロキシキノリンである請求項9に記載のモノマー。
- 芳香族又はヘテロ芳香族基を有する請求項1ないし12のいずれかに記載のモノマー。
- フェニル増感基を有する請求項13に記載のモノマー。
- xが1又は2である請求項1ないし14のいずれかに記載のモノマー。
- 前記Ch−X−Yが次の式を有する請求項1ないし15のいずれかに記載のモノマー。
(化3)
- 請求項1において定義されるCh−X−Y化合物、及び、選択的に、1又は2の他のアニオンリガンド化合物を脱プロン化し、次いで、脱プロン化された化合物を、選択的に1又は2の中性リガンド化合物の存在下において、請求項1で定義されるMイオン塩と反応させることからなる、請求項1ないし16のいずれかに記載のモノマーを得るための方法。
- 脱プロン化が炭酸塩、硝酸塩、ハロゲン化物又はカルボン酸塩である金属塩によって行われる請求項18に記載の方法。
- 請求項17又は18に記載の方法によって得られるモノマー。
- 次の一般式で表される発光材料に使用されるモノマーをラジカル開始を受けさせることによる発光用高分子材料の製造方法。
(化1) Mn+(L)n-(CL)x
この式において、n+は、Mの価数を表し、(L)は、1又は2以上の総計−n価を有するアニオンリガンドを表し、前記リガンドの少なくとも1つは次の式を有する。
(化2) Ch−X−Y
この式において、Chは、キレート結合部及びキレート結合部が共役されたリガンドの残りの部分からなるリガンドの断片であるキレート/イオン結合基であり、Yは、オレフィン基を表し、Xは、少なくとも4つの炭素及び酸素原子を含むスペーサー又は結合部であり、xは0,1又は2であり、CLは中性コリガンドであり、Mはd−ブロック金属である。 - ラジカル開始がUV光若しくは可視光及び光開始剤によって達成される請求項20に記載の高分子材料の製造方法。
- 化学的放射線にさらすことからなる請求項20又は21に記載の高分子材料の製造方法。
- 高分子の存在が望まれる場所において重合が行われる請求項20ないし22のいずれかに記載の高分子材料の製造方法。
- モノマーの溶液がLED層を形成するためにスピンコートされ、次いで重合される請求項23に記載の高分子材料の製造方法。
- 重合がフォトマスクを用いて行われ、未露光部がモノマーが溶解する有機溶媒を用いて除去される請求項24に記載の高分子材料の製造方法。
- 請求項21ないし25のいずれかに記載の高分子材料の製造方法により高分子材料の層を形成することからなる発光装置の製造方法。
- 前記発光装置が透明な基板層、透明な電極層、発光層及び背面電極を有し、前記発光層が前記高分子材料の層からなる請求項26に記載の発光装置の製造方法。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GBGB0104700.0A GB0104700D0 (en) | 2001-02-26 | 2001-02-26 | Luminescent polymers |
GB0104700.0 | 2001-02-26 |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2002568657A Division JP4672965B2 (ja) | 2001-02-26 | 2002-02-26 | 発光性高分子 |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2014010922A Division JP5753594B2 (ja) | 2001-02-26 | 2014-01-24 | 発光性高分子 |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2008179798A true JP2008179798A (ja) | 2008-08-07 |
JP2008179798A5 JP2008179798A5 (ja) | 2011-01-06 |
JP5535434B2 JP5535434B2 (ja) | 2014-07-02 |
Family
ID=9909517
Family Applications (4)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2002568657A Expired - Fee Related JP4672965B2 (ja) | 2001-02-26 | 2002-02-26 | 発光性高分子 |
JP2007331572A Expired - Lifetime JP5535434B2 (ja) | 2001-02-26 | 2007-12-25 | 発光性高分子 |
JP2010254354A Expired - Lifetime JP5410399B2 (ja) | 2001-02-26 | 2010-11-15 | 発光性高分子 |
JP2014010922A Expired - Lifetime JP5753594B2 (ja) | 2001-02-26 | 2014-01-24 | 発光性高分子 |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2002568657A Expired - Fee Related JP4672965B2 (ja) | 2001-02-26 | 2002-02-26 | 発光性高分子 |
Family Applications After (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2010254354A Expired - Lifetime JP5410399B2 (ja) | 2001-02-26 | 2010-11-15 | 発光性高分子 |
JP2014010922A Expired - Lifetime JP5753594B2 (ja) | 2001-02-26 | 2014-01-24 | 発光性高分子 |
Country Status (7)
Country | Link |
---|---|
US (1) | US7311982B2 (ja) |
EP (1) | EP1363980B1 (ja) |
JP (4) | JP4672965B2 (ja) |
AT (1) | ATE446349T1 (ja) |
DE (1) | DE60234083D1 (ja) |
GB (1) | GB0104700D0 (ja) |
WO (1) | WO2002068560A1 (ja) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2011057815A (ja) * | 2009-09-09 | 2011-03-24 | Toshiba Corp | 蛍光性アモルファス固体を用いた発光材料 |
Families Citing this family (26)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB0104700D0 (en) * | 2001-02-26 | 2001-04-11 | Isis Innovation | Luminescent polymers |
SG92833A1 (en) | 2001-03-27 | 2002-11-19 | Sumitomo Chemical Co | Polymeric light emitting substance and polymer light emitting device using the same |
JP4036018B2 (ja) * | 2001-06-20 | 2008-01-23 | 昭和電工株式会社 | 有機発光素子および発光材料 |
WO2003001616A2 (en) * | 2001-06-20 | 2003-01-03 | Showa Denko K.K. | Light emitting material and organic light-emitting device |
JP5342420B2 (ja) * | 2001-06-21 | 2013-11-13 | 昭和電工株式会社 | 有機発光素子および発光材料 |
GB0120828D0 (en) * | 2001-08-28 | 2001-10-17 | Isis Innovation | Method of driving an electroluminescent device |
US6830833B2 (en) * | 2002-12-03 | 2004-12-14 | Canon Kabushiki Kaisha | Organic light-emitting device based on fused conjugated compounds |
WO2004056839A1 (ja) * | 2002-12-19 | 2004-07-08 | Semiconductor Energy Laboratory Co., Ltd. | 有機金属錯体および前記有機金属錯体を用いた電界発光素子、並びに前記電界発光素子を用いた発光装置 |
CN100503655C (zh) * | 2003-06-02 | 2009-06-24 | 日本轻金属株式会社 | 发光性有机高分子金属配合物和能湿式制膜的发光性有机高分子金属配合物组合物及其制造方法 |
JP4295047B2 (ja) * | 2003-06-02 | 2009-07-15 | 日本軽金属株式会社 | 発光性有機高分子金属錯体及び湿式製膜可能な発光性有機高分子金属錯体組成物並びにその製造方法 |
US7279234B2 (en) * | 2003-08-22 | 2007-10-09 | E.I. Du Pont De Nemours And Company | Methods for identity verification using transparent luminescent polymers |
DE10361385B4 (de) * | 2003-12-29 | 2011-07-28 | OSRAM Opto Semiconductors GmbH, 93055 | Polymere, phosphoreszierende, organisch halbleitende Emittermaterialien auf Basis perarylierter Borane, Verfahren zu deren Herstellung und Verwendungen davon |
SG144706A1 (en) * | 2004-02-04 | 2008-08-28 | Agency Science Tech & Res | Red emission organic phosphor with broad excitation band |
GB0423506D0 (en) * | 2004-10-22 | 2004-11-24 | Univ Belfast | Light emitting complex salts |
JP4902381B2 (ja) * | 2007-02-07 | 2012-03-21 | 昭和電工株式会社 | 重合性化合物の重合体 |
FR2917226B1 (fr) * | 2007-06-06 | 2009-09-11 | Inst Nat Sciences Appliq | Procede de marquage de materiaux a base de matrices organiques polymeriques thermoplastiques ou thermodurcissables |
US8441003B2 (en) | 2007-06-28 | 2013-05-14 | Showa Denko K.K. | Phosphorescent polymer compound based on iridium polymer complex and organic electroluminescent device utilizing the same |
US8177978B2 (en) | 2008-04-15 | 2012-05-15 | Nanoh20, Inc. | Reverse osmosis membranes |
WO2011008549A2 (en) | 2009-06-29 | 2011-01-20 | NanoH2O Inc. | Improved hybrid tfc ro membranes with nitrogen additives |
EP2637773B1 (en) | 2010-11-10 | 2019-10-30 | NanoH2O Inc. | Improved hybrid tfc ro membranes with non-metallic additives |
KR101359799B1 (ko) * | 2011-11-08 | 2014-02-10 | 재단법인대구경북과학기술원 | 전계발광소자 및 그 제조 방법 |
CN104498032A (zh) * | 2014-12-16 | 2015-04-08 | 武汉工程大学 | 侧挂型聚甲基丙烯酸甲酯稀土配合物发光材料及其制备方法 |
US9861940B2 (en) | 2015-08-31 | 2018-01-09 | Lg Baboh2O, Inc. | Additives for salt rejection enhancement of a membrane |
US9737859B2 (en) | 2016-01-11 | 2017-08-22 | Lg Nanoh2O, Inc. | Process for improved water flux through a TFC membrane |
US10155203B2 (en) | 2016-03-03 | 2018-12-18 | Lg Nanoh2O, Inc. | Methods of enhancing water flux of a TFC membrane using oxidizing and reducing agents |
CN108586768B (zh) * | 2018-06-11 | 2021-02-23 | 上海大学 | 二维锌配位聚合物及其制备方法 |
Family Cites Families (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS4815628B1 (ja) | 1969-02-25 | 1973-05-16 | ||
JPS552423B2 (ja) * | 1973-02-09 | 1980-01-19 | ||
JPS5647458B2 (ja) | 1973-12-17 | 1981-11-10 | ||
DE2407307A1 (de) | 1974-02-15 | 1975-08-28 | Bayer Ag | 8-hydroxychinolin-gruppen enthaltende polymerisate |
JPH0252072A (ja) | 1988-08-17 | 1990-02-21 | Bunzo Hirano | 塗装前処理工程などの水洗処理装置 |
JPH05210273A (ja) | 1992-01-30 | 1993-08-20 | Ricoh Co Ltd | 画像形成方法及びその装置 |
DE69305262T2 (de) | 1992-07-13 | 1997-04-30 | Eastman Kodak Co | Einen inneren Übergang aufweisende organisch elektrolumineszierende Vorrichtung mit einer neuen Zusammensetzung |
DE4305959A1 (de) * | 1993-02-26 | 1994-09-01 | Bayer Ag | Lumineszierende Copolymere |
JPH07101441A (ja) | 1993-09-30 | 1995-04-18 | Tsuchida Kibutsu Kogyosho:Kk | 金属製二重容器の製造方法 |
JPH07252475A (ja) | 1994-03-16 | 1995-10-03 | Mitsubishi Chem Corp | 有機電界発光素子 |
DE19500912A1 (de) | 1995-01-13 | 1996-07-18 | Basf Ag | Elektrolumineszierende Anordnung |
JP3474334B2 (ja) | 1995-10-31 | 2003-12-08 | ヤマハ発動機株式会社 | モータ制御装置 |
JPH1155905A (ja) | 1997-07-31 | 1999-02-26 | Asmo Co Ltd | モータの整流子及びその製造方法 |
JPH1169281A (ja) | 1997-08-15 | 1999-03-09 | Media Rinku Syst:Kk | 要約生成装置及び映像表示装置 |
JP2000252072A (ja) * | 1999-03-03 | 2000-09-14 | Honda Motor Co Ltd | 有機エレクトロルミネッセンス素子とその製造方法 |
JP3505425B2 (ja) | 1999-03-15 | 2004-03-08 | 株式会社東芝 | 光電変換素子および光電変換素子用の光増感色素 |
JP3959928B2 (ja) * | 2000-04-19 | 2007-08-15 | 株式会社デンソー | 有機el素子及び有機el素子の製造方法 |
IL154960A0 (en) | 2000-10-10 | 2003-10-31 | Du Pont | Polymers having attached luminescent metal complexes and devices made with sych polymers |
GB0104700D0 (en) * | 2001-02-26 | 2001-04-11 | Isis Innovation | Luminescent polymers |
-
2001
- 2001-02-26 GB GBGB0104700.0A patent/GB0104700D0/en not_active Ceased
-
2002
- 2002-02-26 WO PCT/GB2002/000821 patent/WO2002068560A1/en active Application Filing
- 2002-02-26 DE DE60234083T patent/DE60234083D1/de not_active Expired - Lifetime
- 2002-02-26 JP JP2002568657A patent/JP4672965B2/ja not_active Expired - Fee Related
- 2002-02-26 AT AT02700479T patent/ATE446349T1/de not_active IP Right Cessation
- 2002-02-26 US US10/469,205 patent/US7311982B2/en not_active Expired - Lifetime
- 2002-02-26 EP EP02700479A patent/EP1363980B1/en not_active Expired - Lifetime
-
2007
- 2007-12-25 JP JP2007331572A patent/JP5535434B2/ja not_active Expired - Lifetime
-
2010
- 2010-11-15 JP JP2010254354A patent/JP5410399B2/ja not_active Expired - Lifetime
-
2014
- 2014-01-24 JP JP2014010922A patent/JP5753594B2/ja not_active Expired - Lifetime
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2011057815A (ja) * | 2009-09-09 | 2011-03-24 | Toshiba Corp | 蛍光性アモルファス固体を用いた発光材料 |
Also Published As
Publication number | Publication date |
---|---|
ATE446349T1 (de) | 2009-11-15 |
US7311982B2 (en) | 2007-12-25 |
WO2002068560A1 (en) | 2002-09-06 |
JP2004526024A (ja) | 2004-08-26 |
DE60234083D1 (de) | 2009-12-03 |
JP5535434B2 (ja) | 2014-07-02 |
US20040113124A1 (en) | 2004-06-17 |
JP5753594B2 (ja) | 2015-07-22 |
EP1363980A1 (en) | 2003-11-26 |
JP4672965B2 (ja) | 2011-04-20 |
EP1363980B1 (en) | 2009-10-21 |
JP5410399B2 (ja) | 2014-02-05 |
GB0104700D0 (en) | 2001-04-11 |
JP2014140037A (ja) | 2014-07-31 |
JP2011080071A (ja) | 2011-04-21 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP5753594B2 (ja) | 発光性高分子 | |
JP2008179798A5 (ja) | ||
JP2004526024A5 (ja) | ||
US7060372B2 (en) | Polymers having attached luminescent metal complexes and devices made with such polymers | |
KR100752464B1 (ko) | 고분자 화합물 및 전계발광소자 | |
JP4971034B2 (ja) | 赤橙色または赤色発光を有するエレクトロルミネセンスイリジウム化合物及びかかる化合物で製造されたデバイス | |
US7517594B2 (en) | Electroluminescent platinum compounds and devices made with such compounds | |
KR101255233B1 (ko) | 유기 금속 착물 및 이를 이용한 유기 전계 발광 소자 | |
TW200415226A (en) | Compounds comprising phosphorus-containing metal complexes | |
JP2008137994A (ja) | イリジウム錯体化合物、それを用いた有機エレクトロルミネッセンス素子およびその用途 | |
JP2010525111A (ja) | ポリカルバゾリル(メタ)アクリレート発光組成物 | |
EP1516901A1 (en) | Phosphors and process for production thereof, luminescent compositions, and organic electroluminescent devices and processes for production thereof | |
JP4256625B2 (ja) | ヘテロ環化合物及びそれを用いた発光素子 | |
EP1484381A1 (en) | Phosphors, process for production thereof, phosphorescent compositions and articles made by using the same | |
JP2010525112A (ja) | ポリカルバゾリル(メタ)アクリレート発光組成物 | |
US7402345B2 (en) | Electroluminescent iridium compounds with fluorinated phenylpyridine ligands, and devices made with such compounds | |
WO2006041056A1 (ja) | 金属含有配位化合物、配位化合物残基含有高分子化合物、有機エレクトロルミネッセンス材、白色有機エレクトロルミネッセンス材、白色発光素子及び発光素子 | |
JPWO2014157470A1 (ja) | リン光発光材料及び発光素子 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20101110 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20111206 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20120302 |
|
A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20120307 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20120330 |
|
A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20120404 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20120424 |
|
A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20120427 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20120529 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20121211 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20130301 |
|
A02 | Decision of refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 20130924 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20140124 |
|
A911 | Transfer to examiner for re-examination before appeal (zenchi) |
Free format text: JAPANESE INTERMEDIATE CODE: A911 Effective date: 20140218 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20140325 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20140423 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 5535434 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
RD02 | Notification of acceptance of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: R3D02 |
|
S531 | Written request for registration of change of domicile |
Free format text: JAPANESE INTERMEDIATE CODE: R313531 |
|
S533 | Written request for registration of change of name |
Free format text: JAPANESE INTERMEDIATE CODE: R313533 |
|
R350 | Written notification of registration of transfer |
Free format text: JAPANESE INTERMEDIATE CODE: R350 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
S111 | Request for change of ownership or part of ownership |
Free format text: JAPANESE INTERMEDIATE CODE: R313113 |
|
R350 | Written notification of registration of transfer |
Free format text: JAPANESE INTERMEDIATE CODE: R350 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
EXPY | Cancellation because of completion of term |