JP5523402B2 - 蛍光ジケトピロロピロール - Google Patents
蛍光ジケトピロロピロール Download PDFInfo
- Publication number
- JP5523402B2 JP5523402B2 JP2011146241A JP2011146241A JP5523402B2 JP 5523402 B2 JP5523402 B2 JP 5523402B2 JP 2011146241 A JP2011146241 A JP 2011146241A JP 2011146241 A JP2011146241 A JP 2011146241A JP 5523402 B2 JP5523402 B2 JP 5523402B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- alkyl
- phenyl
- substituted
- compounds
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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- FYNROBRQIVCIQF-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole-5,6-dione Chemical compound C1=CN=C2C(=O)C(=O)N=C21 FYNROBRQIVCIQF-UHFFFAOYSA-N 0.000 title claims description 46
- 125000000217 alkyl group Chemical group 0.000 claims description 69
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 239000010410 layer Substances 0.000 description 125
- -1 color filters Substances 0.000 description 95
- 238000000034 method Methods 0.000 description 62
- 239000000203 mixture Substances 0.000 description 58
- 239000000463 material Substances 0.000 description 57
- 150000001875 compounds Chemical class 0.000 description 55
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 42
- 230000005525 hole transport Effects 0.000 description 41
- 125000003545 alkoxy group Chemical group 0.000 description 36
- 239000001257 hydrogen Substances 0.000 description 36
- 229910052739 hydrogen Inorganic materials 0.000 description 36
- 125000003118 aryl group Chemical group 0.000 description 34
- 125000000623 heterocyclic group Chemical group 0.000 description 32
- 239000000758 substrate Substances 0.000 description 30
- 125000000753 cycloalkyl group Chemical group 0.000 description 29
- 229910052757 nitrogen Inorganic materials 0.000 description 29
- 239000000976 ink Substances 0.000 description 26
- 150000002431 hydrogen Chemical class 0.000 description 22
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 21
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 20
- 238000002360 preparation method Methods 0.000 description 17
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 16
- 125000004093 cyano group Chemical group *C#N 0.000 description 16
- 239000011368 organic material Substances 0.000 description 16
- 238000007639 printing Methods 0.000 description 16
- 239000007787 solid Substances 0.000 description 16
- 238000001771 vacuum deposition Methods 0.000 description 16
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 15
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 15
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 15
- 229910052736 halogen Inorganic materials 0.000 description 15
- 150000002367 halogens Chemical class 0.000 description 15
- 238000002347 injection Methods 0.000 description 15
- 239000007924 injection Substances 0.000 description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 14
- 238000000576 coating method Methods 0.000 description 14
- 239000010408 film Substances 0.000 description 14
- 239000000049 pigment Substances 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- 125000003710 aryl alkyl group Chemical group 0.000 description 13
- 229910052717 sulfur Inorganic materials 0.000 description 13
- 239000011248 coating agent Substances 0.000 description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 12
- 229910052760 oxygen Inorganic materials 0.000 description 12
- 239000001301 oxygen Substances 0.000 description 12
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 11
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 11
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 11
- 238000004020 luminiscence type Methods 0.000 description 11
- 238000004528 spin coating Methods 0.000 description 11
- 239000011593 sulfur Substances 0.000 description 11
- 238000005266 casting Methods 0.000 description 10
- 239000006185 dispersion Substances 0.000 description 10
- 125000005842 heteroatom Chemical group 0.000 description 10
- 239000003973 paint Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 229910052782 aluminium Inorganic materials 0.000 description 9
- 125000001072 heteroaryl group Chemical group 0.000 description 9
- 229910052751 metal Inorganic materials 0.000 description 9
- 239000002184 metal Substances 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 239000010409 thin film Substances 0.000 description 9
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 8
- 230000001629 suppression Effects 0.000 description 8
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 7
- 125000003172 aldehyde group Chemical group 0.000 description 7
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 description 7
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 7
- 238000005401 electroluminescence Methods 0.000 description 7
- 125000004185 ester group Chemical group 0.000 description 7
- 239000011777 magnesium Substances 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 description 7
- 125000005401 siloxanyl group Chemical group 0.000 description 7
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 239000008096 xylene Substances 0.000 description 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 125000003342 alkenyl group Chemical group 0.000 description 6
- 125000004414 alkyl thio group Chemical group 0.000 description 6
- 239000011230 binding agent Substances 0.000 description 6
- 125000004122 cyclic group Chemical group 0.000 description 6
- 238000005424 photoluminescence Methods 0.000 description 6
- 229920003023 plastic Polymers 0.000 description 6
- 239000004033 plastic Substances 0.000 description 6
- 229920005596 polymer binder Polymers 0.000 description 6
- 239000002491 polymer binding agent Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 125000006413 ring segment Chemical group 0.000 description 6
- 0 CC(*)(*)CC(*)=CN=C1C2=NC=C(C)CC=C2C(C)(C)C=CC1=C Chemical compound CC(*)(*)CC(*)=CN=C1C2=NC=C(C)CC=C2C(C)(C)C=CC1=C 0.000 description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- 125000000304 alkynyl group Chemical group 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
- 229910052794 bromium Chemical group 0.000 description 5
- 239000000460 chlorine Chemical group 0.000 description 5
- 239000003086 colorant Substances 0.000 description 5
- 238000004040 coloring Methods 0.000 description 5
- 125000000392 cycloalkenyl group Chemical group 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 229910052731 fluorine Inorganic materials 0.000 description 5
- 239000011737 fluorine Substances 0.000 description 5
- 125000000262 haloalkenyl group Chemical group 0.000 description 5
- 125000001188 haloalkyl group Chemical group 0.000 description 5
- 125000000232 haloalkynyl group Chemical group 0.000 description 5
- 229910052749 magnesium Inorganic materials 0.000 description 5
- 229910001092 metal group alloy Inorganic materials 0.000 description 5
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 5
- 239000004926 polymethyl methacrylate Substances 0.000 description 5
- 239000010453 quartz Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 229910052709 silver Inorganic materials 0.000 description 5
- 239000004332 silver Substances 0.000 description 5
- 125000001544 thienyl group Chemical group 0.000 description 5
- 229910001316 Ag alloy Inorganic materials 0.000 description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
- 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 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- 239000004952 Polyamide Substances 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 4
- KMGBZBJJOKUPIA-UHFFFAOYSA-N butyl iodide Chemical compound CCCCI KMGBZBJJOKUPIA-UHFFFAOYSA-N 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- 229910052802 copper Inorganic materials 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- 238000000151 deposition Methods 0.000 description 4
- 230000008021 deposition Effects 0.000 description 4
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 239000000945 filler Substances 0.000 description 4
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 229910052738 indium Inorganic materials 0.000 description 4
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 4
- 238000007641 inkjet printing Methods 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 125000000468 ketone group Chemical group 0.000 description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- 150000002894 organic compounds Chemical class 0.000 description 4
- 229920002647 polyamide Polymers 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 125000003396 thiol group Chemical group [H]S* 0.000 description 4
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 4
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000004925 Acrylic resin Substances 0.000 description 3
- 229920000178 Acrylic resin Polymers 0.000 description 3
- 229910000838 Al alloy Inorganic materials 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 3
- 239000004743 Polypropylene Substances 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- 239000007983 Tris buffer Substances 0.000 description 3
- 229920000180 alkyd Polymers 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 125000005013 aryl ether group Chemical group 0.000 description 3
- 150000004832 aryl thioethers Chemical group 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 229920001940 conductive polymer Polymers 0.000 description 3
- 239000002274 desiccant Substances 0.000 description 3
- YPLYFEUBZLLLIY-UHFFFAOYSA-N dipropan-2-yl butanedioate Chemical compound CC(C)OC(=O)CCC(=O)OC(C)C YPLYFEUBZLLLIY-UHFFFAOYSA-N 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 239000004973 liquid crystal related substance Substances 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical group 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 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
- 239000012038 nucleophile Substances 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000004014 plasticizer Substances 0.000 description 3
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 3
- 229920001197 polyacetylene Polymers 0.000 description 3
- 229920000767 polyaniline Polymers 0.000 description 3
- 239000004417 polycarbonate Substances 0.000 description 3
- 229920000515 polycarbonate Polymers 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 229920000573 polyethylene Polymers 0.000 description 3
- 229920001155 polypropylene Polymers 0.000 description 3
- 229920000128 polypyrrole Polymers 0.000 description 3
- 229920000123 polythiophene Polymers 0.000 description 3
- 229920000915 polyvinyl chloride Polymers 0.000 description 3
- 239000004800 polyvinyl chloride Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 125000000168 pyrrolyl group Chemical group 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 2
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- 125000001698 2H-pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 2
- 125000002373 5 membered heterocyclic group Chemical group 0.000 description 2
- DMSHUVBQFSNBBL-UHFFFAOYSA-N 5-bromopyridine-2-carbonitrile Chemical compound BrC1=CC=C(C#N)N=C1 DMSHUVBQFSNBBL-UHFFFAOYSA-N 0.000 description 2
- YVVHCBNJWHPMCQ-UHFFFAOYSA-N 5-bromothiophene-2-carbonitrile Chemical compound BrC1=CC=C(C#N)S1 YVVHCBNJWHPMCQ-UHFFFAOYSA-N 0.000 description 2
- 125000004070 6 membered heterocyclic group Chemical group 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 125000005915 C6-C14 aryl group Chemical group 0.000 description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
- YUXIBTJKHLUKBD-UHFFFAOYSA-N Dibutyl succinate Chemical compound CCCCOC(=O)CCC(=O)OCCCC YUXIBTJKHLUKBD-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- 229910001218 Gallium arsenide Inorganic materials 0.000 description 2
- 229910007857 Li-Al Inorganic materials 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- 229910008447 Li—Al Inorganic materials 0.000 description 2
- 229920000877 Melamine resin Polymers 0.000 description 2
- 239000004640 Melamine resin Substances 0.000 description 2
- 229910000861 Mg alloy Inorganic materials 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- 239000000020 Nitrocellulose Substances 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 229920000265 Polyparaphenylene Polymers 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- MNLAVFKVRUQAKW-UHFFFAOYSA-N VR nerve agent Chemical compound CCN(CC)CCSP(C)(=O)OCC(C)C MNLAVFKVRUQAKW-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- JFBZPFYRPYOZCQ-UHFFFAOYSA-N [Li].[Al] Chemical compound [Li].[Al] JFBZPFYRPYOZCQ-UHFFFAOYSA-N 0.000 description 2
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- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
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- 150000003335 secondary amines Chemical class 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 229910002076 stabilized zirconia Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 150000001629 stilbenes Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 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
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- GNXPUXGOQIHJLJ-UHFFFAOYSA-N thiadiazolo[4,5-b]pyridine Chemical class C1=CN=C2N=NSC2=C1 GNXPUXGOQIHJLJ-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000006617 triphenylamine group Chemical group 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 229910021642 ultra pure water Inorganic materials 0.000 description 1
- 239000012498 ultrapure water Substances 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 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
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/004—Diketopyrrolopyrrole dyes
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
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- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
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- 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
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- Nitrogen Condensed Heterocyclic Rings (AREA)
- Electroluminescent Light Sources (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
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Description
(a)DPP誘導体及び580〜720nmの範囲に蛍光ピーク波長を有する有機蛍光物質、並びに
(b)ピロロメテン金属錯体(JP2001 257077、JP2001 257078及びJP2001 297881(Toray)も参照すること)
のうちの少なくとも1つを含むELデバイスを開示している。
R1及びR2は、同一又は異なっていてよく、フッ素、塩素又は臭素で置換されていることができるC1〜C25アルキル基、C1〜C4アルキルで1〜3回置換されていることができるアリル基、シクロアルキル基、又はC1〜C4アルキル、ハロゲン、ニトロ若しくはシアノで1〜3回置換されていることができるフェニルにより1又は2回縮合されていることができるシクロアルキル基、アルケニル基、シクロアルケニル基、アルキニル基、ハロアルキル基、ハロアルケニル基、ハロアルキニル基、ケトン若しくはアルデヒド基、エステル基、カルバモイル基、ケトン基、シリル基、シロキサニル基、A3又は−CR3R4−(CH2)m−A3から選択され、ここで、
R3及びR4は、互いに独立して、水素又はC1〜C4アルキル或いはC1〜C4アルキルで1〜3回置換されていることができるフェニルを表し、
A3は、アリール又はヘテロアリール、特にC1〜C8アルキル及び/又はC1〜C8アルコキシで1〜3回置換されていることができるフェニル又は1−若しくは2−ナフチルを表し、そしてmは、0、1、2、3又は4を表し、
A1及びA2は、互いに独立して、窒素、酸素及び硫黄の群から選択される1〜3個のヘテロ原子を含有する5員複素環、又は窒素、酸素及び硫黄の群から選択される1〜3個のヘテロ原子を含有する6員複素環を含む基であり、ここでA1及びA2が、下記式
R5、R6及びR7は、同一又は異なっていてよく、水素原子、C1〜C25アルキル基、シクロアルキル基、アラルキル基、アルケニル基、シクロアルケニル基、アルキニル基、ヒドロキシル基、メルカプト基、アルコキシ基、アルキルチオ基、アリールエーテル基、アリールチオエーテル基、アリール基、複素環基、ハロゲン原子、ハロアルキル基、ハロアルケニル基、ハロアルキニル基、シアノ基、アルデヒド基、カルボキシル基、エステル基、カルバモイル基、ニトロ基、シリル基、シロキサニル基、置換若しくは非置換ビニル基、基NR8R9から選択され、ここでR8及びR9は、互いに独立して、水素原子、アルキル基、シクロアルキル基、アリール基、ヘテロアリール基、複素環基、アラルキル基を表すか、又はR8及びR9は、それらが結合している窒素原子と一緒になって、1又は2個の場合により置換されているフェニル基により縮合されていることができる5員又は6員複素環を形成するか、或いはR5〜R7のうちの少なくとも2つの隣接する置換基が、芳香族又は脂肪族縮合環系を形成し、そして
X1は、水素原子、C1〜C25アルキル基、シクロアルキル基、アラルキル基、アリール基又は複素環基である(但し、下記
R5は、水素原子、C1〜C12アルキル基、C1〜C8アルコキシ基、下記式
R8及びR9は、それらが結合している窒素原子と一緒になって、5員又は6員複素環、例えば下記
X1は、水素又はC1〜C8アルキルを表す。
A4及びA5は、互いに独立して、下式
A9及びA10は、互いに独立して、下記
R38及びR39は、互いに独立して、水素、C1〜C25アルキル、C5〜C12シクロアルキル、−CR11R12−(CH2)m−A6、C6〜C24アリール、特にA6を表すか、又は5〜7個の環原子を含有する飽和若しくは不飽和の複素環基を表し、ここで環は、炭素原子と、窒素、酸素及び硫黄からなる群より選択される1〜3個のヘテロ原子からなり、例えば、A1であり、特に下記
R5′は、水素を除くR5であり、そして
X1は、水素又はC1〜C8アルキルを表す〕で示される化合物がホスト化合物として好ましい。
A1及びA2は、互いに独立して、下記
X1は、水素又はC1〜C8アルキルを表す〕で示される化合物がゲスト化合物として好ましい。
R21及びR22は、同一又は異なっていてよく、C1〜C25アルキル基、C1〜C4アルキルで1〜3回置換されていることができるアリル基、シクロアルキル基、C1〜C4アルキル、ハロゲン、ニトロ又はシアノで1〜3回置換されていることができるフェニルにより1又は2回縮合されていることができるシクロアルキル基、アルケニル基、シクロアルケニル基、アルキニル基、ハロアルキル基、ハロアルケニル基、ハロアルキニル基、ケトン若しくはアルデヒド基、エステル基、カルバモイル基、ケトン基、シリル基、シロキサニル基、A3又は−CR3R4−(CH2)m−A3から選択され、ここで、
R3及びR4は、互いに独立して、水素又はC1〜C4アルキル或いはC1〜C4アルキルで1〜3回置換されていることができるフェニルを表し、
A3は、アリール又はヘテロアリール、特にC1〜C8アルキル及び/又はC1〜C8アルコキシで1〜3回置換されていることができるフェニル又は1−若しくは2−ナフチルを表し、そしてmは、0、1、2、3又は4を表し、
A7及びA8は、互いに独立して、下記
(i)陽極/正孔輸送層/電子輸送層/陰極(ここで、本発明の化合物又は組成物は、発光及び正孔輸送層の形成に利用される正孔輸送化合物若しくは組成物として、又は発光及び電子輸送層の形成に利用されることができる電子輸送化合物若しくは組成物として使用される)、
(ii)陽極/正孔輸送層/発光層/電子輸送層/陰極(ここで、化合物又は組成物は、この構成で正孔輸送特性又は電子輸送特性を示すかどうかに関らず、発光層を形成する)、
(iii)陽極/正孔注入層/正孔輸送層/発光層/電子輸送層/陰極、
(iv)陽極/正孔輸送層/発光層/正孔抑制層/電子輸送層/陰極、
(v)陽極/正孔注入層/正孔輸送層/発光層/正孔阻害層/電子輸送層/陰極、
(vi)陽極/発光層/電子輸送層/陰極、
(vii)陽極/発光層/正孔抑制層/電子輸送層/陰極、
(viii)発光層しか含有しない単層、又は発光材料と正孔輸送層、正孔ブロッキング層及び/若しくは電子輸送層のいずれかの材料との組合せ、並びに
(ix)(ii)〜(vii)で記載された多層構造(ここで、発光層は(viii)で定義された単層である)。
これらの電極材料のうち、金属、金属合金、金属酸化物及び金属化合物は、例えば、スパッタリング法により電極に変えることができる。電極の材料として金属又は金属合金を使用する場合、電極は真空蒸着法によっても形成することができる。電極を形成する材料として金属又は金属合金を使用する場合、電極は、更に化学めっき法により形成することができる(例えば、Handbook of Electrochemistry, pp 383-387, Mazuren, 1985を参照すること)。導電性ポリマーを使用する場合、電極は、導電塗布により予め準備されている基材上に、陽極酸化重合法でフィルムを形成することにより製造することができる。基材上に形成される電極の厚さは特定の値に限定されないが、基材が発光面として使用される場合、電極の厚さは、透明性を確保するために、好ましくは1nm〜300nmの範囲内、より好ましくは5〜200nmの範囲内である。
本発明の好ましい実施態様において、発光層は、正孔輸送層と電子輸送層の間で使用することができる。通常、発光層は、正孔輸送層上に薄膜を形成することにより調製される。
J. Appl. Phys. 65(9) (1989) 3610で開示されている化合物:
ヒドラゾンに基づく化合物:
等を使用することができる。
正孔を輸送する性質を有するあらゆる化合物が、正孔輸送材料として使用されることができ、例えば、トリアゾール誘導体、オキサジアゾール誘導体、イミダゾール誘導体、ポリアリールアルカン誘導体、ピラゾリン誘導体、ピラゾロン誘導体、フェニレンジアミン誘導体、アリールアミン誘導体、アミノ置換カルコン誘導体、オキサゾール誘導体、スチルベニルアントラセン誘導体、フルオレノン誘導体、ヒドラゾン誘導体、スチルベン誘導体、アニリン誘導体のコポリマー、PEDOT(ポリ(3,4−エチレンジオキシ−チオフェン))及びその誘導体、導電性オリゴマー、特にチオフェンオリゴマー、ポルフィリン化合物、芳香族第三級アミン化合物、スチルベニルアミン化合物等である。
正孔輸送層は、陽極に少なくとも1個の正孔輸送材料を含有する有機膜を調製することにより形成できる。正孔輸送層は、真空蒸着法、スピンコート法、流延法、インクジェットプリント法、LB法等により形成することができる。これらの方法のなかで、真空蒸着法、スピンコート法及び流延法が、容易さ及び費用の観点から特に好ましい。
正孔輸送層をスピンコート法又は流延法で形成する場合、層は、発光層の形成で記載された条件(上記参照)で形成することができる。
正孔注入層は、少なくとも1つの正孔注入材料を陽極層と正孔輸送層の間に含有する有機膜を調製することにより形成できる。正孔注入層は、真空蒸着法、スピンコート法、流延法、LB法等により形成することができる。層の厚さは、好ましくは5nm〜5μm、より好ましくは10nm〜100nmである。
一般にホスト発色団は、500〜720nm、好ましくは520nm〜630nm、最も好ましくは540〜600nmでフォトルミネセンス発光ピークを有するジケトピロロピロールである。ホスト発色団は、好ましくは式IIのジケトピロロピロールである。
フレキソ印刷、スクリーン印刷、パッケージング印刷、セキュリティインク印刷、凹版印刷又はオフセット印刷の印刷工程における印刷インク用、予備プレス工程用及び捺染用、オフィス、家庭又はグラフィック用途用、例えば紙製品用、例としてはボールペン、フェルトチップ、ファイバーチップ、カード、木材、(木材)ステイン、金属、インクパッド用インクの調製、又はインパクトプリント法(インパクトプレッシャーインクリボンを用いる)用インクの調製、
塗布材料用、工業及び商業用途用、織物装飾及び工業用マーク用、ローラー塗り若しくは粉末被覆用、又は自動車の仕上げ塗装用、ハイソリッド(低溶剤)、含水若しくは金属被覆材料用、又は水性塗料着色配合物用着色剤の調製、
被覆、繊維、円盤、又は成形型担体用着色プラスチックの調製、
デジタルプリント用、昇華型熱転写印刷工程用、インクジェットプリント工程用、又は熱転写印刷工程用ノンインパクトプリント材料の調製、また
特に400〜700nmの範囲の可視光線用、液晶ディスプレー(LCD)、若しくは電荷結合素子(CCD)用のカラーフィルタの調製、又は
化粧品の調製、又は
ポリマーインク粒子、トナー、色素レーザー、乾燥コピートナー、液体コピートナー又は電子写真用トナー及びエレクトロルミネセンスデバイスの調製に使用することができる。
(i)エレクトロルミネセンスにより発生された三原色の青、緑及び赤を使用すること、
(ii)エレクトロルミネセンスの青色又は白色を、上記の青色のエレクトロルミネセンスと、緑色及び赤色の蛍光とを吸収する色変化媒体(CCM)によりフォトルミネセンスの緑色及び赤色に変換すること、
(iii)白色のルミネセンス発光を、カラーフィルタにより青色、緑色及び赤色に変換すること。
(a)本発明の式Iの蛍光ジケトピロロピロール又は組成物を、着色された高分子量有機材料の総重量に基づき、0.01〜50、好ましくは0.01〜5、特に好ましくは0.01〜2重量%、及び
(b)高分子有機材料を、着色された高分子量有機材料の総重量に基づき、99.99〜50、好ましくは99.99〜95、特に好ましくは99.99〜98重量%、及び
(c)場合により、レオロジー向上剤、分散剤、充填剤、塗料助剤、乾燥剤、可塑剤、UV安定剤のような慣用の添加剤及び/又は追加の顔料若しくは対応する前駆体の有効量、例えば(a)と(b)の総量に基づき、0〜50重量%
含む組成物に関する。
カラーフィルタの特に好ましい製造は、非水性溶媒又はポリマーの分散媒体を有する、本発明の化合物又は組成物を含む顔料分散体で示される。
更に本発明は、本発明の化合物又は組成物を含有する顔料分散体、又は本発明の組成物の彩色上有効な量で着色されている高分子量有機材料を含むトナーに関する。
更に本発明は、本発明の組成物を含む、好ましくは分散体の形態の着色剤、着色プラスチック、ポリマーインク粒子又はノンインパクトプリント(non-impact-printing)材料、或いは本発明の組成物の彩色上有効な量で着色されている高分子量有機材料に関する。
本発明の組成物を含む、本発明の顔料分散体の彩色上有効な量とは、一般的に、着色されている材料の総量に基づき、0.0001〜99.99重量%、好ましくは0.001〜50重量%、特に好ましくは0.01〜50重量%を意味する。
本発明の組成物は、ポリアミドに組み込む間に分解しないため、カラーポリアミドに適用することができる。更に、特にプラスチックにおいて著しく良好な耐光性、優れた熱安定性を示す。
ナトリウム3.8g及びtert−アミルアルコール300mlを窒素雰囲気下で100℃まで加熱し、15時間撹拌した。反応混合物を室温に冷ました。2−シアノ−5−ブロモピリジン27.7gを加え、110℃まで加熱した。この温度に達すると直ちに、コハク酸ジイソプロピル16.2gとtert−アミルアルコール100mlの溶液を、滴加漏斗を使用して1時間かけて加えた。添加が完了したとき、反応混合物を100℃で20時間保持し、65℃に冷却した。次に水300mlを加え、得られた顔料懸濁液を室温で濾過し、メタノール及び水で洗浄液が無色になるまで洗浄し、真空下、100℃で乾燥して、1,4−ジケト−3,6−ビス−2−(5−ブロモピリジン−イル)−ピロロ−(3,4−c)−ピロール6.6g(コハク酸ジブチルに基づき、理論値の9.8%)を得た。
2,5−ジ−ブチル−1,4−ジケト−3,6−ビス−2−(5−ブロモピリジン−イル)ピロロ(3,4−c)ピロール200mg、ジフェニルアミン151mg、酢酸パラジウム(II)6mg、ビス−ジフェニルホスフィノフェロセン20mg、炭酸セシウム233mg及び無水キシレン50mlを、三首フラスコに入れ、窒素雰囲気下、150℃で7時間撹拌した。反応が完了した後、キシレンを減圧下で除去し、残渣をカラムクロマトグラフィー(シリカゲル、溶離剤としてジクロロメタン)により精製した。乾燥した後、目的生成物0.12g(46%)を赤色の固体として得た。
ヨウ化メチルをヨウ化ブチルの代わりに使用する以外は、実施例1を繰り返した。赤色の固体(収率:18%)を得た。
2,5−ジメチル−1,4−ジケト−3,6−ビス−2−(5−ブロモピリジン−イル)ピロロ(3,4−c)ピロール220mg、ジトリルアミン228mg、酢酸パラジウム(II)6mg、ビス−ジフェニルホスフィノフェロセン20mg、炭酸セシウム300mg及び無水キシレン10mlを、三首フラスコに入れ、窒素雰囲気下、150℃で4時間撹拌した。反応が完了した後、キシレンを減圧下で除去し、残渣をカラムクロマトグラフィー(シリカゲル、溶離剤としてジクロロメタン)により精製した。乾燥した後、目的生成物0.08g(24%)を赤色の固体として得た。
ナトリウム6.01g及びtert−アミルアルコール400mlを窒素雰囲気下で100℃まで加熱し、18時間撹拌した。反応混合物を室温に冷まし、2−シアノ−5−ブロモチオフェン44.66gを加え、110℃まで加熱した。この温度に達すると直ちに、コハク酸ジイソプロピル24.3gとtert−アミルアルコール100mlの溶液を、滴加漏斗を使用して5時間かけて加えた。添加が完了したとき、反応混合物を120℃で20時間保持し、65℃に冷却した。次に水300ml及び酢酸20mlを加え、得られた顔料懸濁液を室温で濾過し、メタノール及び水で洗浄液が無色になるまで洗浄し、乾燥して、1,4−ジケト−3,6−ビス−2−(5−ブロモピリジン−イル)−ピロロ−(3,4−c)−ピロール8.0g(コハク酸ジブチルに基づき、理論値の7.3%)を得た。
A−5 200mg、3,5−ジメチルフェニルボロン酸150mg、テトラキス−(トリフェニルホスフィノ)パラジウム10mg、炭酸カリウム166mg及び無水キシレン10mlを三首フラスコに入れ、130℃で1時間撹拌した。キシレンを除去し、得られた生成物をカラムクロマトグラフィー(シリカゲル、溶離剤としてジクロロメタン)により精製した。乾燥した後、目的生成物(A−8)0.02gを紫色の固体として得た。
2−シアノ−3,4−エチレンジオキシチオフェンを2−シアノ−5−ブロモチオフェンの代わりに使用する以外は実施例5を繰り返し、それにより暗紫色の固体を得た(収率:15%)。
A−5をA−3の代わりに使用する以外は実施例4を繰り返し、それにより赤紫色の固体を得た(収率:10%)。
ヨウ化n−ドデシルをヨウ化ブチルの代わりに使用する以外は、実施例1を繰り返した。赤色の固体(収率:13%)を得た。
A−10及びジフェニルアミンをそれぞれA−3及び次トリルアミンの代わりに使用する以外は実施例4を繰り返し、それにより紫色の固体を得た(収率:21%)。
2−シアノピリジンを2−シアノ−5−ブロモピリジンの代わりに使用する以外は実施例1を繰り返し、それにより赤色の固体を得た(収率:32%)。
ルミネセンス素子1
ITO透明導電性膜が厚さ約120nmまで付着したガラス基材(Geomatek Co製、電子線蒸着法で調製された製品)を、30×40mmの寸法に切断し、エッチングした。このようにして得られた基板をSemikoklin(登録商標)56で15分間超音速洗浄に付し、次に高温の超純水で洗浄した。続いて基材をアセトンで15分間超音速洗浄に付し、次に乾燥した。基材が素子になる直前に、そのようにして得られた基材を空気プラズマ処理に半時間付して、真空蒸着装置の中へ入れた。装置を内部圧が1×10-5Pa以下になるまで排気した。次に抵抗加熱法に従って、フタロシアニン銅錯体(CuPc)を、厚さ20nmまで蒸着して、正孔注入層を形成した。N,N′−ジ(ナフタレンー1−イル)−N,N′−ジフェニル−ベンジジン(α−NPD)を厚さ40nmまで蒸着して、正孔輸送層を形成した。続いてホストとしてDPP化合物H−2及びゲストとして(実施例4で得られた)DPP化合物G−13を、発光層として厚さ30nmまで共付着し、DPP化合物の比率を、付着速度により調節して(H−2:G−13=100:1〜0.5)、均一の発光層を形成した。続いて厚さ30nmを有するAlq3層を蒸着して、電子輸送層を形成した。厚さ0.5nmのフッ化リチウム(LiF)を電子注入材料として蒸着した。電子注入材料の上に、厚さ150nmのアルミニウム(Al)を蒸着して陰極を形成し、2×2mm2の大きさを有する素子を調製した。
このようにして得られたルミネセンス素子1のルミネセンスピーク波長及び発光強度を表1にまとめた。
蛍光染料A−12及びPMMAをジクロロメタンに溶解し、直径3mmの石英ロッドを溶液中に浸漬して、石英ロッドの周りに薄膜を形成した。試料を乾燥炉で6時間乾燥した。PPMフィルム中のA−12の濃度は、2mM/lであった。調製した石英ロッドを薄膜リングレーザーシステムのリング共振器及び光増幅器として使用した。
ヨウ化n−ヘキシルをヨウ化ブチルの代わりに使用する以外は、実施例1を繰り返した(収率:6%)。融点=196〜199℃。
A−13をA−3の代わりに使用する以外は実施例4を繰り返した(収率:45%)。融点=268〜270℃。
適用例1を繰り返して、ルミネセンス素子5及び6調製した。使用した発光材料を下記の表3に示す。
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BRPI1013566A2 (pt) | 2009-03-23 | 2016-04-12 | Basf Se | polímero, composto, material, camada ou componente orgânicos semi condutores, dispositivo semicondutor, processos para a preparação de um dispositivo semicondutor orgânico, de um composto, e de um polímero, e, uso do polímero, do composto e/ou do material, camada ou componente orgânicos semi condutores |
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