TW201811739A - 磺酸酯化合物及其利用 - Google Patents
磺酸酯化合物及其利用 Download PDFInfo
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- TW201811739A TW201811739A TW106120228A TW106120228A TW201811739A TW 201811739 A TW201811739 A TW 201811739A TW 106120228 A TW106120228 A TW 106120228A TW 106120228 A TW106120228 A TW 106120228A TW 201811739 A TW201811739 A TW 201811739A
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- -1 Sulfonic acid ester compound Chemical class 0.000 title claims abstract description 144
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- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Substances O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- 235000008434 ginseng Nutrition 0.000 description 1
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- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
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- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- CECAIMUJVYQLKA-UHFFFAOYSA-N iridium 1-phenylisoquinoline Chemical compound [Ir].C1=CC=CC=C1C1=NC=CC2=CC=CC=C12.C1=CC=CC=C1C1=NC=CC2=CC=CC=C12.C1=CC=CC=C1C1=NC=CC2=CC=CC=C12 CECAIMUJVYQLKA-UHFFFAOYSA-N 0.000 description 1
- BNASDYJRNOLPQY-UHFFFAOYSA-N iridium 2-phenylquinoline Chemical compound [Ir].c1ccc(cc1)-c1ccc2ccccc2n1.c1ccc(cc1)-c1ccc2ccccc2n1.c1ccc(cc1)-c1ccc2ccccc2n1 BNASDYJRNOLPQY-UHFFFAOYSA-N 0.000 description 1
- AOZVYCYMTUWJHJ-UHFFFAOYSA-K iridium(3+) pyridine-2-carboxylate Chemical compound [Ir+3].[O-]C(=O)C1=CC=CC=N1.[O-]C(=O)C1=CC=CC=N1.[O-]C(=O)C1=CC=CC=N1 AOZVYCYMTUWJHJ-UHFFFAOYSA-K 0.000 description 1
- QTRRAHGRSMFAKW-UHFFFAOYSA-N iridium(3+);1-phenylpyrazole Chemical compound [Ir+3].C1=CC=NN1C1=CC=CC=[C-]1.C1=CC=NN1C1=CC=CC=[C-]1.C1=CC=NN1C1=CC=CC=[C-]1 QTRRAHGRSMFAKW-UHFFFAOYSA-N 0.000 description 1
- UEEXRMUCXBPYOV-UHFFFAOYSA-N iridium;2-phenylpyridine Chemical compound [Ir].C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1 UEEXRMUCXBPYOV-UHFFFAOYSA-N 0.000 description 1
- PSLMOSLVUSXMDQ-UHFFFAOYSA-N iridium;pentane-2,4-dione Chemical compound [Ir].CC(=O)CC(C)=O PSLMOSLVUSXMDQ-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 239000005453 ketone based solvent Substances 0.000 description 1
- 229910052746 lanthanum Inorganic materials 0.000 description 1
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 description 1
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- 239000011133 lead Substances 0.000 description 1
- XIXADJRWDQXREU-UHFFFAOYSA-M lithium acetate Chemical compound [Li+].CC([O-])=O XIXADJRWDQXREU-UHFFFAOYSA-M 0.000 description 1
- 239000001989 lithium alloy Substances 0.000 description 1
- 229940031993 lithium benzoate Drugs 0.000 description 1
- LDJNSLOKTFFLSL-UHFFFAOYSA-M lithium;benzoate Chemical compound [Li+].[O-]C(=O)C1=CC=CC=C1 LDJNSLOKTFFLSL-UHFFFAOYSA-M 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- ORUIBWPALBXDOA-UHFFFAOYSA-L magnesium fluoride Chemical compound [F-].[F-].[Mg+2] ORUIBWPALBXDOA-UHFFFAOYSA-L 0.000 description 1
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
- CUONGYYJJVDODC-UHFFFAOYSA-N malononitrile Chemical compound N#CCC#N CUONGYYJJVDODC-UHFFFAOYSA-N 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
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- 229940095102 methyl benzoate Drugs 0.000 description 1
- TUUUUIFSWBEYMP-UHFFFAOYSA-N methyl(diphenyl)phosphane;ruthenium Chemical compound [Ru].C=1C=CC=CC=1P(C)C1=CC=CC=C1 TUUUUIFSWBEYMP-UHFFFAOYSA-N 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
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- YPJRZWDWVBNDIW-MBALSZOMSA-N n,n-diphenyl-4-[(e)-2-[4-[4-[(e)-2-[4-(n-phenylanilino)phenyl]ethenyl]phenyl]phenyl]ethenyl]aniline Chemical group C=1C=C(N(C=2C=CC=CC=2)C=2C=CC=CC=2)C=CC=1/C=C/C(C=C1)=CC=C1C(C=C1)=CC=C1\C=C\C(C=C1)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 YPJRZWDWVBNDIW-MBALSZOMSA-N 0.000 description 1
- NRKQPQQULQMWBV-MBALSZOMSA-N n,n-diphenyl-4-[(e)-2-[6-[(e)-2-[4-(n-phenylanilino)phenyl]ethenyl]naphthalen-2-yl]ethenyl]aniline Chemical compound C=1C=C(N(C=2C=CC=CC=2)C=2C=CC=CC=2)C=CC=1/C=C/C(C=C1C=C2)=CC=C1C=C2\C=C\C(C=C1)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 NRKQPQQULQMWBV-MBALSZOMSA-N 0.000 description 1
- CLTPAQDLCMKBIS-UHFFFAOYSA-N n-[4-[4-(dinaphthalen-1-ylamino)phenyl]phenyl]-n-naphthalen-1-ylnaphthalen-1-amine Chemical compound C1=CC=C2C(N(C=3C=CC(=CC=3)C=3C=CC(=CC=3)N(C=3C4=CC=CC=C4C=CC=3)C=3C4=CC=CC=C4C=CC=3)C=3C4=CC=CC=C4C=CC=3)=CC=CC2=C1 CLTPAQDLCMKBIS-UHFFFAOYSA-N 0.000 description 1
- QKCGXXHCELUCKW-UHFFFAOYSA-N n-[4-[4-(dinaphthalen-2-ylamino)phenyl]phenyl]-n-naphthalen-2-ylnaphthalen-2-amine Chemical compound C1=CC=CC2=CC(N(C=3C=CC(=CC=3)C=3C=CC(=CC=3)N(C=3C=C4C=CC=CC4=CC=3)C=3C=C4C=CC=CC4=CC=3)C3=CC4=CC=CC=C4C=C3)=CC=C21 QKCGXXHCELUCKW-UHFFFAOYSA-N 0.000 description 1
- BLFVVZKSHYCRDR-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-2-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-2-amine Chemical compound C1=CC=CC=C1N(C=1C=C2C=CC=CC2=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C3C=CC=CC3=CC=2)C=C1 BLFVVZKSHYCRDR-UHFFFAOYSA-N 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 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 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- QEFYFXOXNSNQGX-UHFFFAOYSA-N neodymium atom Chemical compound [Nd] QEFYFXOXNSNQGX-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910052758 niobium Inorganic materials 0.000 description 1
- 239000010955 niobium Substances 0.000 description 1
- GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 238000009832 plasma treatment Methods 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 229920000734 polysilsesquioxane polymer Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 229910001414 potassium ion Inorganic materials 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- VQMWBBYLQSCNPO-UHFFFAOYSA-N promethium atom Chemical compound [Pm] VQMWBBYLQSCNPO-UHFFFAOYSA-N 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000005372 silanol group Chemical group 0.000 description 1
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- FVRNDBHWWSPNOM-UHFFFAOYSA-L strontium fluoride Chemical compound [F-].[F-].[Sr+2] FVRNDBHWWSPNOM-UHFFFAOYSA-L 0.000 description 1
- 229910001637 strontium fluoride Inorganic materials 0.000 description 1
- DIORMHZUUKOISG-UHFFFAOYSA-N sulfoformic acid Chemical compound OC(=O)S(O)(=O)=O DIORMHZUUKOISG-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- 150000003613 toluenes Chemical class 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- XSVXWCZFSFKRDO-UHFFFAOYSA-N triphenyl-(3-triphenylsilylphenyl)silane Chemical compound C1=CC=CC=C1[Si](C=1C=C(C=CC=1)[Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 XSVXWCZFSFKRDO-UHFFFAOYSA-N 0.000 description 1
- DETFWTCLAIIJRZ-UHFFFAOYSA-N triphenyl-(4-triphenylsilylphenyl)silane Chemical compound C1=CC=CC=C1[Si](C=1C=CC(=CC=1)[Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 DETFWTCLAIIJRZ-UHFFFAOYSA-N 0.000 description 1
- LNQMQGXHWZCRFZ-UHFFFAOYSA-N triphenyl-[4-(4-triphenylsilylphenyl)phenyl]silane Chemical group C1=CC=CC=C1[Si](C=1C=CC(=CC=1)C=1C=CC(=CC=1)[Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 LNQMQGXHWZCRFZ-UHFFFAOYSA-N 0.000 description 1
- HITRWHKLCHWBNZ-UHFFFAOYSA-N triphenyl-[4-(9-phenylfluoren-9-yl)phenyl]silane Chemical compound C1=CC=CC=C1C1(C=2C=CC(=CC=2)[Si](C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)C2=CC=CC=C2C2=CC=CC=C21 HITRWHKLCHWBNZ-UHFFFAOYSA-N 0.000 description 1
- RFDGVZHLJCKEPT-UHFFFAOYSA-N tris(2,4,6-trimethyl-3-pyridin-3-ylphenyl)borane Chemical compound CC1=C(B(C=2C(=C(C=3C=NC=CC=3)C(C)=CC=2C)C)C=2C(=C(C=3C=NC=CC=3)C(C)=CC=2C)C)C(C)=CC(C)=C1C1=CC=CN=C1 RFDGVZHLJCKEPT-UHFFFAOYSA-N 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
- 238000001132 ultrasonic dispersion Methods 0.000 description 1
- 238000007738 vacuum evaporation Methods 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
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- HTPBWAPZAJWXKY-UHFFFAOYSA-N zinc;quinolin-8-ol Chemical compound [Zn+2].C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1 HTPBWAPZAJWXKY-UHFFFAOYSA-N 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/63—Esters of sulfonic acids
- C07C309/72—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C309/75—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing singly-bound oxygen atoms bound to the carbon skeleton
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- C09D201/00—Coating compositions based on unspecified macromolecular compounds
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/20—Diluents or solvents
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/16—Electron transporting layers
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
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- 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
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
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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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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/18—Metal complexes
- C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
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- H10K50/17—Carrier injection layers
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Abstract
本發明係提供一種磺酸酯化合物,其係以下述式(1)表示,
(式中,R1及R2各自獨立表示氫原子、或直鏈狀或分枝狀之1價脂肪族烴基,R3表示直鏈狀或分枝狀之1價脂肪族烴基,但是R1、R2及R3之碳數之合計為6以上;A1表示-O-或-S-,A2表示(n+1)價之芳香族基,A3表示含有1個以上之芳香環之取代或非取代之m價的烴基;m表示滿足2≦m≦4之整數,n表示滿足1≦n≦4之整數)。
Description
本發明係有關磺酸酯化合物及其利用。
有機電致發光(EL)元件使用作為發光層或電荷注入層之由有機化合物所成的電荷傳輸性薄膜。特別是電洞注入層擔任在陽極與電洞傳輸層或發光層之電荷授受,為了達成有機EL元件之低電壓驅動及高亮度,而完成重要的功能。
近年,有發現將低分子寡聚苯胺系材料或寡聚噻吩系材料溶解於有機溶劑中之由均勻系溶液所成的電荷傳輸性清漆,藉由將由此清漆所得的電洞注入層插入有機EL元件中,可得到底層基板之平坦化效果或優異的有機EL元件特性的報告(專利文獻1~3)。此外,也有藉由使用作為電子接受性物質之1,4-苯並二噁烷磺酸化合物(專利文獻4),可降低有機EL元件之驅動電壓的報告。
但是磺酸化合物通常對有機溶劑的溶解性低,故調製有機溶液時所使用的溶劑容易受限定,必須以高比率使用N,N-二甲基乙醯胺、N-甲基吡咯烷酮等之溶解力高的高極性有機溶劑。以高比率含有高極性有機溶劑的 有機溶液,有時會使噴墨塗佈裝置之一部分或、形成於基板上之絕緣膜及隔牆等的有機構造物受傷。而且,磺酸化合物係因高極性,故藉由矽膠管柱層析之純化、藉由分液萃取、及水洗等的操作除去鹽類困難。
另外,提出磺酸酯化合物對於各種有機溶劑之溶解性高,因加熱或化學作用等之外在刺激產生有機強酸的材料已為人知。以加熱產生磺酸之化合物的具體例,有磺酸環己酯等的報告(非專利文獻1),此磺酸酯化合物在熱酸增殖劑的概念也受矚目(專利文獻5、非專利文獻2)。但是特別是芳香族二磺酸等之在缺電子(electron deficient)之芳香環上進行取代的磺酸酯化合物,僅以少許的熱或、與水、鹼性物質等之反應容易產生分解,故期望製造安定性高的磺酸酯化合物。
[專利文獻1]日本特開2002-151272號公報
[專利文獻2]國際公開第2004/043117號
[專利文獻3]國際公開第2005/043962號
[專利文獻4]國際公開第2005/000832號
[專利文獻5]日本特開平7-134416號公報
[專利文獻6]日本專利第5136795號公報
[非專利文獻1]Chemische Berichte, 90, pp. 585-592 (1957)
[非專利文獻2]機能材料、24卷、pp. 72-82、2004年
本發明人等為了解決前述問題點,因此提出具有高安定性,同時對廣範圍之有機溶劑具有高溶解性的磺酸酯化合物的報告(專利文獻6)。但是前述磺酸酯化合物係以往使用之磺酸化合物或相較於磺酸酯化合物,安定性或對有機溶劑之溶解性更優異,但是欲使溶解於低極性溶劑時,必須在高溫下且長時間攪拌,又,製成溶液時,在長期間保存時,有析出的情形,對有機溶劑之溶解性或安定性仍有改良的餘地。
本發明有鑑於前述的情形而完成者,本發明之目的係提供對低極性溶劑之溶解性或清漆之安定性優異,使用於有機EL元件時,可實現優異之元件特性的磺酸酯化合物。
本發明人等為了達成前述目的,精心研究的結果發現特定之磺酸化合物與脂肪族醇化合物的酯,相較於以往磺酸酯化合物,對低極性溶劑之溶解性更優異,此外,作為溶液時之保存安定性也優異,而完成本發明。
因此,本發明係提供下述磺酸酯化合物及其利用。
1.一種磺酸酯化合物,其係以下述式(1)表示,
(式中,R1及R2各自獨立表示氫原子、或直鏈狀或分枝狀之1價脂肪族烴基,R3表示直鏈狀或分枝狀之1價脂肪族烴基,R1、R2及R3之碳數之合計為6以上;A1表示-O-或-S-,A2表示(n+1)價之芳香族基,A3表示含有1個以上之芳香環之取代或非取代之m價的烴基;m表示滿足2≦m≦4之整數,n表示滿足1≦n≦4之整數)。
2.如1項之磺酸酯化合物,其中R1為氫原子,R2及R3各自獨立為碳數1~6之烷基。
3.如1或2項之磺酸酯化合物,其中A2為由萘或蒽所衍生之基。
4.如3項之磺酸酯化合物,其中A2為由萘所衍生之基。
5.如1~4中任一項之磺酸酯化合物,其中A3為由全氟聯苯所衍生之基。
6.如1~5中任一項之磺酸酯化合物,其中m為2。
7.如1~6中任一項之磺酸酯化合物,其中n為2。
8.一種電子接受性物質前驅物,其係由如1~7中任一項之磺酸酯化合物所成。
9.一種電荷傳輸性清漆,其係包含如8項之電子接受性物質前驅物、電荷傳輸性物質及有機溶劑。
10.如9項之電荷傳輸性清漆,其中前述有機溶劑為低極性有機溶劑。
11.如9或10項之電荷傳輸性清漆,其中前述電荷傳輸性物質為苯胺衍生物。
12.一種電荷傳輸性薄膜,其係使用如9~11中任一項之電荷傳輸性清漆所製作。
13.一種有機電致發光元件,其係具備如12項之電荷傳輸性薄膜。
本發明之磺酸酯化合物係對於含有低極性溶劑之廣範圍的有機溶劑,顯示高溶解性,故使用低極性溶劑,或即使降低高極性溶劑之比率,也可調製電荷傳輸性清漆。又,製成溶液時之保存安定性也優異。低極性有機溶劑系的電荷傳輸性清漆,不僅可以在溶劑耐性有問題的噴墨塗佈裝置進行塗佈,而且在基板上存在有絕緣膜或隔牆等之耐溶劑性有問題之構造物的情形也可使用,結果可無問題地製造具有高平坦性的非晶質固體薄膜。
又,由本發明之電荷傳輸性清漆所得的薄膜因顯示高電荷傳輸性,故作為電洞注入層或電洞傳輸層使 用的情形時,可使有機EL元件之驅動電壓降低。利用此薄膜之高平坦性及高電荷傳輸性,也可應用於太陽能電池之電洞傳輸層、燃料電池用電極、電容器電極保護膜、抗靜電膜。
本發明之磺酸酯化合物係以下述式(1)表示者。
式(1)中,R1及R2各自獨立表示氫原子、或直鏈狀或分枝狀之1價脂肪族烴基,R3表示直鏈狀或分枝狀之1價脂肪族烴基。但是R1、R2及R3之碳數之合計為6以上。R1、R2及R3之碳數之合計的上限,無特別限定,較佳為20以下,更佳為10以下。
前述直鏈狀或分枝狀之1價脂肪族烴基,無特別限定,可列舉甲基、乙基、n-丙基、異丙基、n-丁基、異丁基、tert-丁基、n-己基、n-辛基、2-乙基己基、癸基等之碳數1~18之烷基;乙烯基、1-丙烯基、2-丙烯基、異丙烯基、1-甲基-2-丙烯基、1-丁烯基、2-丁烯基、3-丁烯基、己烯基等之碳數2~18之烯基等。
R1較佳為氫原子,R2及R3較佳為碳數1~6之烷基。此時,R2及R3可相同或相異。
式(1)中,A1表示-O-或-S-,但是較佳為-O-。A2表示(n+1)價之芳香族基。A3表示含有1個以上之芳香環之取代或非取代之m價的烴基。
A2表示之(n+1)價之芳香族基係自芳香族化合物之芳香環上去除(n+1)個之氫原子所得之基。前述芳香族化合物,可列舉苯、甲苯、二甲苯、萘、蒽、菲等。此等之中,A2較佳為由萘或蒽所衍生之基,更佳為由萘所衍生之基。
A3表示之含有1個以上之芳香環之取代或非取代之m價的烴基係自含有1個以上之芳香環之取代或非取代之烴中,去除m個鍵結於碳骨架之原子或原子團所得之基。前述烴可列舉苯、甲苯、二甲苯、乙基苯、聯苯、萘、蒽、菲等或此等之基之氫原子之一部分或全部,再經羥基、胺基、矽烷醇基、巰基、羧基、磺酸酯基、磷酸基、磷酸酯基、酯基、硫酯基、醯胺基、硝基、一價烴基、有機氧基、有機胺基、有機甲矽烷基、有機基硫醇基、醯基、磺酸基、鹵素原子等取代者。
考慮式(1)表示之磺酸酯化合物之耐久性提昇及電荷傳輸性提昇時,A3較佳為由1,3,5-三嗪所衍生之2價或3價基、由取代或非取代之苯所衍生之2價或3價基、由取代或非取代之甲苯所衍生之2價或3價基、由取代或非取代之p-二甲苯所衍生之2價基、由取代或非取代之萘所衍 生之2價或3價基、由全氟聯苯所衍生之2~4價基等,更佳為2價之全氟聯苯基。
式(1)中,m表示滿足2≦m≦4之整數,但是較佳為2。n表示滿足1≦n≦4之整數,但是較佳為2。
本發明之磺酸酯化合物,可藉由例如下述(Scheme)所示,使式(1”)表示之磺酸鹽化合物與鹵化劑反應,合成下述式(1’)表示之磺醯鹵化合物(以下也稱為步驟1),使該磺醯鹵化合物與式(2)表示之醇化合物反應(以下也稱為步驟2)可合成。
(式中,A1~A3、R1~R3、m及n係與前述相同。M+表示鈉離子、鉀離子、吡啶鎓離子、四級銨離子等之一價的陽離子。Hal表示氯原子、溴原子等之鹵素原子。)
式(1”)表示之磺酸鹽化合物,可依據習知的方法來合成。
步驟1中使用的鹵化劑,可列舉亞硫醯氯(Thionyl Chloride)、乙二醯氯(oxalyl chloride)、氧氯化磷 (Phosphorus oxychloride)、氯化磷(V)等之鹵化劑,較佳為亞硫醯氯。鹵化劑的使用量係相對於磺酸鹽化合物,只要是1倍莫耳以上時,無特別限定,相對於磺酸鹽化合物,以質量比使用2~10倍量為佳。
步驟1中使用的反應溶劑,較佳為與鹵化劑不會反應的溶劑,可列舉氯仿、二氯乙烷、四氯化碳、己烷、庚烷等,較佳為無溶劑。又,以無溶劑進行反應的情形,反應終了時,以成為均勻系溶液的量以上,使用鹵化劑為佳。反應溫度可為0~150℃左右,但是較佳為20~100℃,且使用之鹵化劑的沸點以下。反應終了後,一般而言,將藉由減壓濃縮等所得之粗產物用於次步驟。
式(2)表示之醇化合物,較佳為2-乙基-1-己醇、2-丁基-1-辛醇、1-辛醇、3-壬醇等,更佳為2-乙基-1-己醇、2-丁基-1-辛醇、1-辛醇。
步驟2中,也可併用鹼。可使用的鹼,可列舉氫化鈉、吡啶、三乙基胺、二異丙基乙基胺等,較佳為氫化鈉、吡啶、三乙基胺。鹼的使用量係相對於磺醯鹵化合物(1’),較佳為1倍莫耳~溶劑量。
步驟2中,使用的反應溶劑,可使用各種有機溶劑,但是較佳為四氫呋喃、二氯乙烷、氯仿、吡啶。反應溫度無特別限定,較佳為0~80℃。反應終了後,使用減壓濃縮、分液萃取、水洗、再沉澱、再結晶、管柱層析法等的常法,進行後處理、純化,可得到純粹的磺酸酯化合物。又,藉由對所得之純粹的磺酸酯化合物施予熱處理 等,也可得到高純度的磺酸化合物。
式(1)表示之磺酸酯化合物係藉由加熱處理等產生磺酸,及此磺酸化合物顯示電子接受性,故適合作為酸產生劑或電子接受性物質前驅物使用。在此,電子接受性物質係指提高電子傳輸層能及成膜均勻性所用者,與電子接受性摻雜劑同義。
式(1)表示之磺酸酯化合物係因對於含有低極性溶劑之廣範圍的溶劑,顯示高溶解性,故可使用各種各樣的溶劑,調製溶液的物性,塗佈特性高。因此,以磺酸酯的狀態進行塗佈,在塗膜之乾燥時或煅燒時,產生磺酸為佳。由磺酸酯產生磺酸的溫度,在室溫下安定,且煅燒溫度以下為佳,故可為40~260℃。此外,考慮清漆內之高的安定性與煅燒時之脫離容易性時,較佳為80~230℃,更佳為120~180℃。
式(1)表示之磺酸酯化合物係藉由與電荷傳輸機構本體的電荷傳輸性物質一同溶解或分散於有機溶劑,可作為電荷傳輸性清漆。
本發明之電荷傳輸性清漆係包含以式(1)表示之化合物所成之電子接受性物質前驅物、電荷傳輸性物質、及有機溶劑。又,本發明中,電荷傳輸性係與導電性同義。電 荷傳輸性清漆可為其本身具有電荷傳輸性者,也可為藉此所得之固形膜為具有電荷傳輸性者。
前述電荷傳輸性物質,可使用在以往有機EL之領域使用者,具體而言,可列舉苯胺衍生物、噻吩衍生物、吡咯衍生物等之電荷傳輸性寡聚物。前述電荷傳輸性寡聚物的分子量,通常為200~8,000,但是從調製提供高電荷傳輸性薄膜之清漆的觀點,較佳為300以上,更佳為400以上,又更佳為500以上,從調製提供高平坦性薄膜之均勻清漆的觀點,較佳為6,000以下,更佳為5,000以下,又較佳為4,000以下,又更佳為3,000以下。
前述電荷傳輸性寡聚物之中,考慮對有機溶劑之溶解性與所得薄膜之電荷傳輸性之平衡時,較佳為苯胺衍生物。苯胺衍生物,可列舉日本特開2002-151272號公報所記載的寡聚苯胺衍生物、國際公開第2004/105446號所記載的寡聚苯胺化合物、國際公開第2008/032617號所記載的寡聚苯胺化合物、國際公開第2008/032616號所記載的寡聚苯胺化合物、國際公開第2013/042623號記載之芳基二胺化合物等。
又,也可使用以下述式(3)表示之苯胺衍生物。
式(3)中,X1表示-NY1-、-O-、-S-、-(CR107R108)L-或單鍵,但是k1或k2為0時,表示-NY1-。
Y1各自獨立表示氫原子、可被Z1取代之碳數1~20之烷基、碳數2~20之烯基或碳數2~20之炔基、或可被Z2取代之碳數6~20之芳基或碳數2~20之雜芳基。
碳數1~20之烷基,可為直鏈狀、分枝狀、環狀之任一,其具體例可列舉甲基、乙基、n~丙基、異丙基、n-丁基、異丁基、s-丁基、tert-丁基、n-戊基、n-己基、n-庚基、n-辛基、n-壬基、n-癸基等之碳數1~20之直鏈狀或分枝狀烷基;環丙基、環丁基、環戊基、環己基、環庚基、環辛基、環壬基、環癸基、雙環丁基、雙環戊基、雙環己基、雙環庚基、雙環辛基、雙環壬基、雙環癸基等之碳數3~20之環狀烷基。
碳數2~20之烯基,可為直鏈狀、分枝狀、環狀之任一,其具體例可列舉乙烯基、n-1-丙烯基、n-2-丙烯基、1-甲基乙烯基、n-1-丁烯基、n-2-丁烯基、n-3-丁烯基、2-甲基-1-丙烯基、2-甲基-2-丙烯基、1-乙基乙烯基、1-甲基-1-丙烯基、1-甲基-2-丙烯基、n-1-戊烯基、n-1-癸烯基、n-1-二十烯基等。
碳數2~20之炔基,可為直鏈狀、分枝狀、環 狀之任一,其具體例可列舉乙炔基、n-1-丙炔基、n-2-丙炔基、n-1-丁炔基、n-2-丁炔基、n-3-丁炔基、1-甲基-2-丙炔基、n-1-戊炔基、n-2-戊炔基、n-3-戊炔基、n-4-戊炔基、1-甲基-n-丁炔基、2-甲基-n-丁炔基、3-甲基-n-丁炔基、1,1-二甲基-n-丙炔基、n-1-己炔基、n-1-癸炔基、n-1-十五炔基、n-1-二十炔基等。
碳數6~20之芳基之具體例,可列舉苯基、1-萘基、2-萘基、1-蒽基、2-蒽基、9-蒽基、1-菲基、2-菲基、3-菲基、4-菲基、9-菲基等。
碳數2~20之雜芳基之具體例,可列舉2-噻吩基、3-噻吩基、2-呋喃基、3-呋喃基、2-噁唑基、4-噁唑基、5-噁唑基、3-異噁唑基、4-異噁唑基、5-異噁唑基、2-噻唑基、4-噻唑基、5-噻唑基、3-異噻唑基、4-異噻唑基、5-異噻唑基、2-咪唑基、4-咪唑基、2-吡啶基、3-吡啶基、4-吡啶基等。
R107及R108各自獨立表示氫原子、氯原子、溴原子、碘原子、硝基、氰基、胺基、醛基、羥基、巰基、磺酸基、羧酸基、可被Z1取代之碳數1~20之烷基、碳數2~20之烯基或碳數2~20之炔基、可被Z2取代之碳數6~20之芳基或碳數2~20之雜芳基、或-NHY2、-NY3Y4、-C(O)Y5、-OY6、-SY7、-SO3Y8、-C(O)OY9、-OC(O)Y10、-C(O)NHY11或-C(O)NY12Y13基。
Y2~Y13各自獨立表示可被Z1取代之碳數1~20之烷基、碳數2~20之烯基或碳數2~20之炔基、或可被Z2取代 之碳數6~20之芳基或碳數2~20之雜芳基。
Z1表示氯原子、溴原子、碘原子、硝基、氰基、胺基、醛基、羥基、巰基、磺酸基、羧酸基、或可被Z3取代之碳數6~20之芳基或碳數2~20之雜芳基。
Z2表示氯原子、溴原子、碘原子、硝基、氰基、胺基、醛基、羥基、巰基、磺酸基、羧酸基、或可被Z3取代之碳數1~20之烷基、碳數2~20之烯基或碳數2~20之炔基。
Z3表示氯原子、溴原子、碘原子、硝基、氰基、胺基、醛基、羥基、巰基、磺酸基、或羧酸基。
R107、R108及Y2~Y13之烷基、烯基、炔基、芳基及雜芳基,可列舉與前述同樣者。
此等之中,R107及R108較佳為氫原子或可被Z1取代之碳數1~20之烷基,更佳為氫原子或可被Z1取代之甲基,最佳為氫原子。
L表示以-(CR107R108)-表示之2價基之數,為1~20之整數,較佳為1~10,更佳為1~5,又更佳為1~2,最佳為1。又,L為2以上時,複數之R107彼此可相同或相異,複數之R108也彼此可相同或相異。
特別是X1較佳為-NY1~或單鍵。又,Y1較佳為氫原子或可被Z1取代之碳數1~20之烷基,更佳為氫原子或可被Z1取代之甲基,最佳為氫原子。
式(3)中,R101~R106各自獨立表示氫原子、氯原子、溴原子、碘原子、硝基、氰基、胺基、醛基、羥 基、巰基、磺酸基、羧酸基、可被Z1取代之碳數1~20之烷基、碳數2~20之烯基或碳數2~20之炔基、可被Z2取代之碳數6~20之芳基或碳數2~20之雜芳基、或-NHY2、-NY3Y4、-C(O)Y5、-OY6、-SY7、-SO3Y8、-C(O)OY9、-OC(O)Y10、-C(O)NHY11或-C(O)NY12Y13(Y2~Y13係表示與前述相同意義)。此等烷基、烯基、炔基、芳基及雜芳基,可列舉與前述同樣者。
特別是式(3)中,R101~R104較佳為氫原子、鹵素原子、可被Z1取代之碳數1~10之烷基、或可被Z2取代之碳數6~14之芳基,更佳為氫原子、或碳數1~10之烷基,最佳為全部為氫原子。
又,R105及R106較佳為氫原子、氯原子、溴原子、碘原子、可被Z1取代之碳數1~10之烷基、可被Z2取代之碳數6~14之芳基、或可被Z2取代之二苯基胺基(Y3及Y4為可被Z2取代之苯基的-NY3Y4基),更佳為氫原子、或二苯基胺基,同時氫原子或二苯基胺基為又更佳。
此等之中,R101~R104為氫原子或碳數1~10之烷基、R105及R106為氫原子或二苯基胺基,X1為-NY1-或單鍵,且Y1為氫原子或甲基之組合為佳,R101~R104為氫原子,R105及R106同時為氫原子或二苯基胺基,X1為-NH-或單鍵之組合為更佳。
式(3)中,k1及k2各自獨立表示0以上之整數,滿足1≦k1+k2≦20,但是考慮所得之薄膜之電荷傳輸性與苯胺衍生物之溶解性之平衡時,較佳為滿足 2≦k1+k2≦8,更佳為滿足2≦k1+k2≦6,又更佳為滿足2≦k1+k2≦4。
Y1~Y13及R101~R108中,Z1較佳為氯原子、溴原子、碘原子、或可被Z3取代之碳數6~20之芳基,更佳為氯原子、溴原子、碘原子、或可被Z3取代之苯基,最佳為不存在(即,非取代)。
Z2較佳為氯原子、溴原子、碘原子、或可被Z3取代之碳數1~20之烷基,更佳為氯原子、溴原子、碘原子、或可被Z3取代之碳數1~4之烷基,最佳為不存在(即,非取代)。
Z3較佳為氯原子、溴原子或碘原子,最佳為不存在(即,非取代)。
Y1~Y13及R101~R108中,烷基、烯基及炔基之碳數,較佳為10以下,更佳為6以下,又更佳為4以下。又,芳基及雜芳基之碳數,較佳為14以下,更佳為10以下,又更佳為6以下。
又,前述苯胺衍生物之合成法,無特別限定,可列舉Bulletin of Chemical Society of Japan,67,pp.1749-1752(1994)、Synthetic Metals,84,pp.119-120(1997)、Thin Solid Films,520(24),pp.7157-7163(2012)、國際公開第2008/032617號、國際公開第2008/032616號、國際公開第2008/129947號、國際公開第2013/084664號等所記載的方法。
式(3)表示之苯胺衍生物之具體例,可列舉下 述式表示者,但是不限定於此等。又,下述式中,DPA表示二苯基胺基,Ph表示苯基,TPA表示p-(二苯基胺基)苯基。
調製本發明之電荷傳輸性清漆時所用的有機溶劑,可使用可良好溶解前述苯胺衍生物及本發明之磺酸酯化合物的高溶解性溶劑。特別是本發明之磺酸酯化合物,即使對於低極性溶劑,也為溶解性高,故低極性溶劑也可作為高溶解性溶劑使用。
高溶解性溶劑之中,低極性溶劑,可列舉例如氯仿、氯苯等之氯系溶劑;甲苯、二甲苯、四氫萘、環己基苯、3-苯氧基甲苯等之芳香族烴系溶劑等。又,極性 溶劑可列舉N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N,N-二甲基異丁基醯胺、N-甲基吡咯烷酮、1,3-二甲基-2-咪唑啉酮等之醯胺系溶劑;異佛爾酮、環己酮等之酮系溶劑;乙酸乙酯、苯甲酸甲基等之酯系溶劑;乙二醇、二乙二醇等之多元醇系溶劑;四氫呋喃、二噁烷、苯甲醚等之醚系溶劑;二甲基亞碸等之亞碸系溶劑。此等之溶劑可1種單獨使用或混合2種以上使用,其使用量係在清漆所使用的全溶劑中可為5~100質量%。
又,電荷傳輸性物質均完全溶解於前述溶劑中,或成為均勻分散的狀態為佳,更佳為完全溶解。
又,前述有機溶劑可含有至少一種於25℃下具有10~200mPa.s,特別是35~150mPa.s的黏度,於常壓(大氣壓)下沸點為50~300℃,特別是150~250℃之高黏度有機溶劑為佳。藉由添加這種溶劑,可調製清漆黏度之調整變得容易,可提供再現性佳之高平坦性薄膜,配合使用之塗佈方法的清漆調製。
高黏度有機溶劑,可列舉例如環己醇、乙二醇、乙二醇二環氧丙醚、1,3-辛二醇、二乙二醇、二丙二醇、三乙二醇、三丙二醇、1,3-丁二醇、2,3-丁二醇、1,4-丁二醇、丙二醇、己二醇等,但是不限定於此等。高黏度有機溶劑可兼為高溶解性溶劑,此等係以主體(host)的種類而定。
提高高黏度有機溶劑時的添加比例,以固體不會析出之範圍內為佳,於固體不會析出之範圍時,清漆 所使用之全溶劑中5~90質量%為佳。
此外,為了提高對基板之濕潤性、調整溶劑之表面張力、調整極性、調整沸點等之目的,其他的溶劑,在清漆所使用的全溶劑中,以1~90質量%、較佳為1~50質量%之比例混合為佳。
這種溶劑可列舉例如丙二醇單甲醚、乙二醇單丁醚、二乙二醇二乙醚、二乙二醇單甲醚、二乙二醇二甲醚、二乙二醇單乙醚乙酸酯、二乙二醇單丁醚乙酸酯、二丙二醇單甲醚、丙二醇單甲醚乙酸酯、二乙二醇單乙醚、二丙酮醇、γ-丁內酯、乙基乳酸酯、n-己基乙酸酯等,但是不限定於此等。此等之溶劑可1種單獨使用或混合2種以上使用。此等之溶劑可兼高溶解性溶劑,此等係以主體的種類而定。
本發明中,電荷傳輸性清漆從可再現性佳得到更高平坦性之薄膜的觀點,將電荷傳輸性物質溶解於有機溶劑後,使用次微米(Sub-micro)等級的過濾器等進行過濾為佳。
本發明之清漆中之固體成分濃度,從抑制電荷傳輸性物質之析出,確保充分的膜厚的觀點,通常為0.1~20質量%左右,較佳為0.5~10質量%。又,在此所謂的固體成分係指自清漆所含之成分中去除溶劑後殘留的成分。本發明之清漆的黏度,通常在25℃下為1~50mPa.s。
又,前述固體成分中,電子接受性物質前驅物之含量係以莫耳比表示,相對於電荷傳輸性物質1,較 佳為0.01~20左右,更佳為0.05~10左右。
藉由將本發明之電荷傳輸性清漆塗佈於基材上使乾燥,可在基材上形成電荷傳輸性薄膜。
清漆之塗佈方法,可列舉浸漬法、旋轉塗佈法、轉印印刷法、輥塗法、刷毛塗佈、噴墨法、噴霧法、狹縫塗佈法等,但是不限定於此等。配合塗佈方法,調節清漆之黏度及表面張力為佳。
又,使用本發明之清漆的情形,液膜之乾燥條件也無特別限定,例如有使用加熱板之加熱煅燒。通常為100~260℃左右的範圍內,以1分鐘~1小時左右的加熱煅燒,可得到乾燥膜。又,煅燒環境也無特別限定。
電荷傳輸性薄膜之膜厚,無特別限定,作為有機EL元件之機能層使用時,較佳為5~200nm。改變膜厚的方法,例如有改變清漆中之固體成分濃度,或改變塗佈時之基板上之溶液量等的方法。
本發明之有機EL元件係具有一對電極,在此等電極之間,具備前述本發明之電荷傳輸性薄膜者。
有機EL元件之代表的構成,可列舉下述(a)~(f),但是不限定於此等。又,下述構成中,必要時,可在發光層與陽極之間設置電子阻擋層等,在發光層與陰 極之間設置電洞(hole)阻擋層等。又,電洞注入層、電洞傳輸層或電洞注入傳輸層也可兼具作為電子阻擋層(electron blocking layer)等的功能,電子注入層、電子傳輸層或電子注入傳輸層,也可兼具作為電洞阻擋層等的功能。
(a)陽極/電洞注入層/電洞傳輸層/發光層/電子傳輸層/電子注入層/陰極
(b)陽極/電洞注入層/電洞傳輸層/發光層/電子注入傳輸層/陰極
(c)陽極/電洞注入傳輸層/發光層/電子傳輸層/電子注入層/陰極
(d)陽極/電洞注入傳輸層/發光層/電子注入傳輸層/陰極
(e)陽極/電洞注入層/電洞傳輸層/發光層/陰極
(f)陽極/電洞注入傳輸層/發光層/陰極
「電洞注入層」、「電洞傳輸層」及「電洞注入傳輸層」係指在發光層與陽極之間所形成的層,具有將電洞由陽極傳輸至發光層之機能者。在發光層與陽極之間,設置僅1層電洞傳輸性材料層的情形,此為「電洞注入傳輸層」,在發光層與陽極之間,設置2層以上之電洞傳輸性材料層的情形,接近陽極的層為「電洞注入層」,此以外的層為「電洞傳輸層」。特別是電洞注入層及電洞注入傳輸層,可使用不僅來自陽極之電洞接受性,且各自對電洞傳輸層及發光層之電洞注入性也優異的薄膜。
「電子注入層」、「電子傳輸層」及「電子注入傳輸層」係指在發光層與陰極之間所形成的層,具有將電子自陰極傳輸至發光層之機能者。發光層與陰極之間,設置僅1層電子傳輸層性材料層的情形,此為「電子注入傳輸層」,在發光層與陰極之間設置2層以上之電子傳輸層性材料層的情形,接近陰極的層為「電子注入層」,此外的層為「電子傳輸層」。
「發光層」係指具有發光機能之有機層,於採用摻雜系統的情形,含有主體材料與摻雜劑材料。此時,主體材料主要為促進電子與電洞之再結合,具有使激子關閉於發光層內之機能,摻雜劑材料為具有使再結合所得之激子有效率地發光的機能。磷光元件的情形,主體材料主要為具有以摻雜劑生成之激子關閉於發光層內的機能。
使用本發明之電荷傳輸性清漆製作有機EL元件時的使用材料或製作方法,可列舉如下述者,但並不限定於此等。
使用的電極基板,預先以洗劑、醇、純水等進行液體洗淨淨化為佳,例如陽極基板係在使用前,進行UV臭氧處理、氧-電漿處理等的表面處理為佳。但是陽極材料以有機物為主成份時,亦可不進行表面處理。
由本發明之電荷傳輸性清漆所得的薄膜為電洞注入層時之本發明之有機EL元件之製作方法之一例,如下述。
藉由前述方法,於陽極基板上塗佈本發明之電荷傳輸性清漆,進行煅燒,在電極上製作電洞注入層。此電洞注入層之上,依序設置電洞傳輸層、發光層、電子傳輸層、電子注入層、陰極。電洞傳輸層、發光層、電子傳輸層及電子注入層係配合使用之材料的特性等,以蒸鍍法或塗佈法(濕式製程)之任一方法形成即可。
陽極材料可列舉以銦錫氧化物(ITO)、銦鋅氧化物(IZO)為代表的透明電極,或以鋁為代表的金屬或此等合金等所構成的金屬陽極,以進行平坦化處理者為佳。亦可使用具有高電荷傳輸性之聚噻吩衍生物或聚苯胺衍生物。
又,構成金屬陽極的其他金屬,可列舉鈧、鈦、釩、鉻、錳、鐵、鈷、鎳、銅、鋅、鎵、釔、鋯、鈮、鉬、釕、銠、鈀、鎘、銦、鈧、鑭、鈰、鐠、釹、鉅(promethium)、釤、銪、釓、鋱、鏑、鈥、鉺、銩、鐿、鉿、鉈、鎢、錸、鋨、銥、鉑、金、鈦、鉛、鉍或此等的合金等。
形成電洞傳輸層的材料,可列舉(三苯基胺)二聚物衍生物、[(三苯基胺)二聚物]螺二聚物、N,N’-雙(萘-1-基)-N,N’-雙(苯基)-聯苯胺(α-NPD)、N,N’-雙(萘-2-基)-N,N’-雙(苯基)-聯苯胺、N,N’-雙(3-甲基苯基)-N,N’-雙(苯基)-聯苯胺、N,N’-雙(3-甲基苯基)-N,N’-雙(苯基)-9,9-旋環雙茀、N,N’-雙(萘-1-基)-N,N’-雙(苯基)-9,9-旋環雙茀、N,N’-雙(3-甲基苯基)-N,N’-雙(苯基)-9,9-二甲基-茀、 N,N’-雙(萘-1-基)-N,N’-雙(苯基)-9,9-二甲基-茀、N,N’-雙(3-甲基苯基)-N,N’-雙(苯基)-9,9-二苯基-茀、N,N’-雙(萘-1-基)-N,N’-雙(苯基)-9,9-二苯基-茀、N,N’-雙(萘-1-基)-N,N’-雙(苯基)-2,2’-二甲基聯苯胺、2,2’,7,7’-四(N,N-二苯基胺基)-9,9-旋環雙茀、9,9-雙[4-(N,N-雙-聯苯基-4-基-胺基)苯基]-9H-茀、9,9-雙[4-(N,N-雙-萘-2-基-胺基)苯基]-9H-茀、9,9-雙[4-(N-萘-1-基-N-苯基胺基)-苯基]-9H-茀、2,2’,7,7’-四[N-萘基(naphthalenyl)(苯基)-胺基]-9,9-旋環雙茀、N,N’-雙(菲-9-基)-N,N’-雙(苯基)-聯苯胺、2,2’-雙[N,N-雙(聯苯基-4-基)胺基]-9,9-旋環雙茀、2,2’-雙(N,N-二苯基胺基)-9,9-旋環雙茀、二-[4-(N,N-二(p-甲苯基)胺基)-苯基]環己烷、2,2’,7,7’-四(N,N-二(p-甲苯基)胺基)-9,9-旋環雙茀、N,N,N’,N’-四-萘-2-基-聯苯胺、N,N,N’,N’-四-(3-甲基苯基)-3,3’-二甲基聯苯胺、N,N’-二(萘基)-N,N’-二(萘-2-基)-聯苯胺、N,N,N’,N’-四(萘基)-聯苯胺、N,N’-二(萘-2-基)-N,N’-二苯基聯苯胺-1,4-二胺、N1,N4-二苯基-N1,N4-二(m-甲苯基)苯-1,4-二胺、N2,N2,N6,N6-四苯基萘-2,6-二胺、參(4-(喹啉-8-基)苯基)胺、2,2’-雙(3-(N,N-二(p-甲苯基)胺基)苯基)聯苯、4,4’,4”-三[3-甲基苯基(苯基)胺基]三苯基胺(m-MTDATA)、4,4’,4”-三[1-萘基(苯基)胺基]三苯基胺(1-TNATA)等之三芳基胺類、5,5”-雙-{4-[雙(4-甲基苯基)胺基]苯基}-2,2’:5’,2”-第三噻吩(BMA-3T)等之寡聚噻吩類等之電洞傳輸性低分子材料等。
形成發光層之材料,可列舉三(8-羥基喹啉(hydroxyquinolinato))鋁(III)(Alq3)、雙(8-羥基喹啉)鋅(II)(Znq2)、雙(2-甲基-8-羥基喹啉)-4-(p-苯基苯酚)鋁(III)(BAlq)、4,4’-雙(2,2-二苯基乙烯基)聯苯、9,10-二(萘-2-基)蒽、2-t-丁基-9,10-二(萘-2-基)蒽、2,7-雙[9,9-二(4-甲基苯基)-茀-2-基]-9,9-二(4-甲基苯基)茀、2-甲基-9,10-雙(萘-2-基)蒽、2-(9,9-旋環雙茀(spirobifluorene)-2-基)-9,9-旋環雙茀、2,7-雙(9,9-旋環雙茀-2-基)-9,9-旋環雙茀、2-[9,9-二(4-甲基苯基)-茀-2-基]-9,9-二(4-甲基苯基)茀、2,2’-二芘基-9,9-旋環雙茀、1,3,5-三(芘-1-基)苯、9,9-雙[4-(芘基)苯基]-9H-茀、2,2’-二(9,10-二苯基蒽)、2,7-二芘基-9,9-旋環雙茀、1,4-二(芘-1-基)苯、1,3-二(芘-1-基)苯、6,13-二(聯苯-4-基)稠五苯(pentacene)、3,9-二(萘-2-基)苝、3,10-二(萘-2-基)苝、三[4-(芘基)-苯基]胺、10,10’-二(聯苯-4-基)-9,9’-二蒽、N,N’-二(萘-1-基)-N,N’-二苯基-[1,1’:4,1”:4’,1'''-聯四苯(Quaterphenyl)]-4,4'''-二胺、4,4’-二[10-(萘-1-基)蒽-9-基]聯苯、二苯并{[f,f’]-4,4’,7,7’-四苯基}二茚並[1,2,3-cd:1’,2’,3’-lm]苝、1-(7-(9,9’-二蒽-10-基)-9,9-二甲基-9H-茀-2-基)芘、1-(7-(9,9’-二蒽-10-基)-9,9-二己基-9H-茀-2-基)芘、1,3-雙(咔唑-9-基)苯、1,3,5-三(咔唑-9-基)苯、4,4’,4”-三(咔唑-9-基)三苯胺、4,4’-雙(咔唑-9-基)聯苯(CBP)、4,4’-雙(咔唑-9-基)-2,2’-二甲基聯苯、2,7-雙(咔唑-9-基)-9,9-二甲基茀、2,2’,7,7’-四(咔唑-9-基)-9,9-旋環雙茀、2,7-雙(咔唑- 9-基)-9,9-二(p-甲苯基)茀、9,9-雙[4-(咔唑-9-基)-苯基]茀、2,7-雙(咔唑-9-基)-9,9-旋環雙茀、1,4-雙(三苯基矽烷基)苯、1,3-雙(三苯基矽烷基)苯、雙(4-N,N-二乙胺基-2-甲基苯基)-4-甲基苯基甲烷、2,7-雙(咔唑-9-基)-9,9-二辛基茀、4,4”-二(三苯基矽烷基)-p-聯三苯、4,4’-二(三苯基矽烷基)聯苯、9-(4-t-丁基苯基)-3,6-雙(三苯基矽烷基)-9H-咔唑、9-(4-t-丁基苯基)-3,6-二(三苯甲基(trityl))-9H-咔唑、9-(4-t-丁基苯基)-3,6-雙(9-(4-甲氧基苯基)-9H-茀-9-基)-9H-咔唑、2,6-雙(3-(9H-咔唑-9-基)苯基)吡啶、三苯基(4-(9-苯基-9H-茀-9-基)苯基)矽烷、9,9-二甲基-N,N-二苯基-7-(4-(1-苯基-1H-苯并[d]咪唑-2-基)苯基)-9H-茀-2-胺、3,5-雙(3-(9H-咔唑-9-基)苯基)吡啶、9,9-旋環雙茀-2-基-二苯基-膦(phosphine)氧化物、9,9’-(5-(三苯基矽烷基)-1,3-伸苯基)雙(9H-咔唑)、3-(2,7-雙(磷酸二苯基(Diphenylphosphoryl))-9-苯基-9H-茀-9-基)-9-苯基-9H-咔唑、4,4,8,8,12,12-六(p-甲苯基)-4H-8H-12H-12C-氮雜二苯并[cd,mn]芘、4,7-二(9H-咔唑-9-基)-1,10-啡繞啉(phenanthroline)、2,2’-雙(4-(咔唑-9-基)苯基)聯苯、2,8-雙(磷酸二苯基)二苯并[b,d]噻吩、雙(2-甲基苯基)二苯基矽烷、雙[3,5-二(9H-咔唑-9-基)苯基]二苯基矽烷、3,6-雙(咔唑-9-基)-9-(2-乙基-己基)-9H-咔唑、3-(磷酸二苯)-9-(4-(磷酸二苯)苯基)-9H-咔唑、3,6-雙[(3,5-二苯基)苯基]-9-苯基咔唑等,可藉由此等材料與發光性摻雜物進行共蒸鍍,而形成發光層。
發光性摻雜劑,可列舉3-(2-苯并噻唑基)-7-(二乙胺基)香豆素、2,3,6,7-四氫-1,1,7,7-四甲基-1H,5H,11H-10-(2-苯并噻唑基)喹嗪基(quinolizino)[9,9a,1gh]香豆素、喹吖啶酮、N,N’-二甲基-喹吖啶酮、三(2-苯基吡啶)銥(III)(Ir(ppy)3)、雙(2-苯基吡啶)(乙醯丙酮(acetylacetonate))銥(III)(Ir(ppy)2(acac))、三[2-(p-甲苯基)吡啶]銥(III)(Ir(mppy)3)、9,10-雙[N,N-二(p-甲苯基)胺基]蒽、9,10-雙[苯基(m-甲苯基)胺基]蒽、雙[2-(2-羥基苯基)苯並噻唑(benzothiazolato)]鋅(II)、N10,N10,N10,N10-四(p-甲苯基)-9,9’-二蒽-10,10’-二胺、N10,N10,N10,N10-四苯基-9,9’-二蒽-10,10’-二胺、N10,N10-二苯基-N10,N10-二萘基-9,9’-二蒽-10,10’-二胺、4,4’-雙(9-乙基-3-咔唑乙烯基(carbazovinylene))-1,1’-聯苯、苝、2,5,8,11-四-t-丁基苝、1,4-雙[2-(3-N-乙基咔唑基)乙烯基]苯、4,4’-雙[4-(二-p-甲苯胺基)苯乙烯基]聯苯、4-(二-p-甲苯胺基)-4’-[(二-p-甲苯胺基)苯乙烯基]茋、雙[3,5-二氟-2-(2-吡啶基)苯基-(2-羧基吡啶基)]銥(III)、4,4’-雙[4-(二苯胺基)苯乙烯基]聯苯、雙(2,4-二氟苯基吡啶(pyridinato))四(1-吡唑基)硼酸銥(III)、N,N’-雙(萘-2-基)-N,N’-雙(苯基)-三(9,9-二甲基伸茀基(fluorenylene))、2,7-雙{2-[苯基(m-甲苯基)胺基]-9,9-二甲基-茀-7-基}-9,9-二甲基-茀、N-(4-((E)-2-(6((E)-4-(二苯胺基)苯乙烯基)萘-2-基)乙烯基)苯基)-N-苯基苯胺、fac-銥(III)三(1-苯基-3-甲基苯并咪唑啉-2-亞基-C,C2)、mer-銥(III)三(1-苯基-3-甲基苯并咪唑啉-2- 亞基-C,C2)、2,7-雙[4-(二苯胺基)苯乙烯基]-9,9-旋環雙茀、6-甲基-2-(4-(9-(4-(6-甲基苯并[d]噻唑-2-基)苯基)蒽-10-基)苯基)苯并[d]噻唑、1,4-二[4-(N,N-二苯基)胺基]苯乙烯基苯、1,4-雙(4-(9H-咔唑-9-基)苯乙烯基)苯、(E)-6-(4-(二苯胺基)苯乙烯基)-N,N-二苯基萘-2-胺、雙(2,4-二氟苯基吡啶)(5-(吡啶-2-基)-1H-四唑鹽)銥(III)、雙(3-三氟甲基-5-(2-吡啶基)吡唑)((2,4-二氟苄基)二苯基磷酸酯)銥(III)、雙(3-三氟甲基-5-(2-吡啶基)吡唑鹽)(苄基二苯基磷酸酯)銥(III)、雙(1-(2,4-二氟苄基)-3-甲基苯并咪唑鹽)(3-(三氟甲基)-5-(2-吡啶基)-1,2,4-三唑(triazolate))銥(III)、雙(3-三氟甲基-5-(2-吡啶基)吡唑鹽)(4’,6’-二氟苯基吡啶鹽(pyridinate)銥(III)、雙(4’,6’-二氟苯基吡啶(pyridinato))(3,5-雙(三氟甲基)-2-(2’-吡啶基)吡咯鹽)銥(III)、雙(4’,6’-二氟苯基吡啶)(3-(三氟甲基)-5-(2-吡啶基)-1,2,4-三唑)銥(III)、(Z)-6-三甲苯基-N-(6-三甲苯基喹啉-2(1H)-亞基)喹啉-2-胺-BF2、(E)-2-(2-(4-(二甲胺基)苯乙烯基)-6-甲基-4H-吡喃-4-亞基)丙二腈、4-(二氰基伸甲基)-2-甲基-6-久洛尼啶基-9-二烯基-4H-吡喃、4-(二氰基亞甲基)-2-甲基-6-(1,1,7,7-四甲基久洛尼啶基-9-二烯基)-4H-吡喃、4-(二氰基亞甲基)-2-t-丁基-6-(1,1,7,7-四甲基久洛尼啶-4-基-乙烯基)-4H-吡喃、三(二苯甲醯基甲烷)啡繞啉(phenanthroline)銪(III)、5,6,11,12-四苯基稠四苯、雙(2-苯并[b]噻吩-2-基-吡啶)(乙醯丙酮)銥(III)、三(1-苯基異喹啉)銥(III)、雙(1-苯基異喹啉)(乙醯丙酮)銥(III)、雙 [1-(9,9-二甲基-9H-茀-2-基)-異喹啉](乙醯丙酮)銥(III)、雙[2-(9,9-二甲基-9H-茀-2-基)喹啉](乙醯丙酮)銥(III)、三[4,4’-二-t-丁基-(2,2’)-聯吡啶]釕(III).雙(六氟磷酸酯)、三(2-苯基喹啉)銥(III)、雙(2-苯基喹啉)(乙醯丙酮)銥(III)、2,8-二-t-丁基-5,11-雙(4-t-丁基苯基)-6,12-二苯基稠四苯、雙(2-苯基苯并偶氮(benzodiazoleate))(乙醯丙酮)銥(III)、5,10,15,20-四苯基四苯并卟啉鉑、鋨(II)雙(3-三氟甲基-5-(2-吡啶)-吡唑鹽)二甲基苯基膦(phosphine)、鋨(II)雙(3-(三氟甲基)-5-(4-t-丁基吡啶基)-1,2,4-三唑)二苯基甲基膦、鋨(II)雙(3-(三氟甲基)-5-(2-吡啶基)-1,2,4-三唑)二甲基苯基膦、鋨(II)雙(3-(三氟甲基)-5-(4-t-丁基吡啶基)-1,2,4-三唑)二甲基苯基膦、雙[2-(4-n-己基苯基)喹啉](乙醯丙酮)銥(III)、三[2-(4-n-己基苯基)喹啉]銥(III)、三[2-苯基-4-甲基喹啉]銥(III)、雙(2-苯基喹啉)(2-(3-甲基苯基)吡啶鹽)銥(III)、雙(2-(9,9-二乙基-茀-2-基)-1-苯基-1H-苯并[d]咪唑鹽)(乙醯丙酮)銥(III)、雙(2-苯基吡啶)(3-(吡啶-2-基)-2H-苯并哌喃-2-酮)銥(III)、雙(2-苯基喹啉)(2,2,6,6-四甲基庚烷-3,5-二酮)銥(III)、雙(苯基異喹啉)(2,2,6,6-四甲基庚烷-3,5-二酮)銥(III)、銥(III)雙(4-苯基噻吩并[3,2-c]吡啶(pyridinato)-N,C2)乙醯丙酮、(E)-2-(2-t-丁基-6-(2-(2,6,6-三甲基-2,4,5,6-四氫-1H-吡咯[3,2,1-ij]喹啉-8-基)乙烯基)-4H-吡喃-4-亞基)丙二腈、雙(3-三氟甲基-5-(1-異喹啉基)吡唑鹽)(甲基二苯基膦)釕、雙[(4-n-己基苯基)異喹啉](乙醯丙酮)銥(III)、鉑(II)八乙基卟吩、雙(2-甲基二苯 并[f,h]喹喔啉(quinoxaline))(乙醯丙酮)銥(III)、三[(4-n-己基苯基)氧代喹啉]銥(III)等。
形成電子傳輸層的材料,可列舉8-羥基喹啉(quinolinato)-鋰、2,2’,2”-(1,3,5-石油醚(benzine)甲苯基)-三(1-苯基-1-H-苯并咪唑)、2-(4-聯苯)5-(4-tert-丁基苯基)-1,3,4-噁二唑、2,9-二甲基-4,7-二苯基-1,10-啡繞啉、4,7-二苯基-1,10-啡繞啉、雙(2-甲基-8-喹啉)-4-(苯基苯酚(Phenolato))鋁、1,3-雙[2-(2,2’-聯吡啶-6-基)-1,3,4-氧雜重氮-5-基]苯、6,6’-雙[5-(聯苯-4-基)-1,3,4-氧雜重氮-2-基]-2,2’-聯吡啶、3-(4-聯苯基)-4-苯基-5-tert-丁基苯基-1,2,4-三唑、4-(萘-1-基)-3,5-二苯基-4H-1,2,4-三唑、2,9-雙(萘-2-基)-4,7-二苯基-1,10-啡繞啉、2,7-雙[2-(2,2’-聯吡啶-6-基)-1,3,4-氧雜重氮-5-基]-9,9-二甲基茀、1,3-雙[2-(4-tert-丁基苯基)-1,3,4-氧雜重氮-5-基]苯、三(2,4,6-三甲基-3-(吡啶-3-基)苯基)硼烷、1-甲基-2-(4-(萘-2-基)苯基)-1H-咪唑并[4,5f][1,10]啡繞啉、2-(萘-2-基)-4,7-二苯基-1,10-啡繞啉、苯基-二芘基膦氧化物、3,3’,5,5’-四[(m-吡啶基)-酚-3-基]聯苯、1,3,5-三[(3-吡啶基)-酚-3-基]苯、4,4’-雙(4,6-二苯基-1,3,5-三嗪-2-基)聯苯、1,3-雙[3,5-二(吡啶-3-基)苯基]苯、雙(10-羥基苯并[h]喹啉)鈹、二苯基雙(4-(吡啶-3-基)苯基)矽烷、3,5-二(芘-1-基)吡啶等。
形成電子注入層之材料,可列舉氧化鋰(Li2O)、氧化鎂(MgO)、氧化鋁(Al2O3)、氟化鋰(LiF)、氟化鈉(NaF)、氟化鎂(MgF2)、氟化銫(CsF)、氟化鍶 (SrF2)、三氧化鉬(MoO3)、鋁、乙醯丙酮鋰(Li(acac))、乙酸鋰、苯甲酸鋰等。
陰極材料可列舉鋁、鎂-銀合金、鋁-鋰合金、鋰、鈉、鉀、銫等。
又,由本發明之電荷傳輸性清漆所得的薄膜為電洞注入層時,本發明之有機EL元件之製作方法之其他的例,如下述。
前述有機EL元件製作方法中,取代進行電洞傳輸層、發光層、電子傳輸層、電子注入層之真空蒸鍍操作,而藉由依序形成電洞傳輸層、發光層,可製作具有以本發明之電荷傳輸性清漆形成之電荷傳輸性薄膜的有機EL元件。具體而言,在陽極基板上,塗佈本發明之電荷傳輸性清漆,藉由前述方法製作電洞注入層,其上依序形成電洞傳輸層、發光層,進一步蒸鍍陰極材料,作為有機EL元件。
使用的陰極及陽極材料,可使用與前述同樣者,可進行同樣的洗凈處理、表面處理。
電洞傳輸層及發光層之形成方法,可列舉在電洞傳輸性高分子材料或發光性高分子材料、或此等中添加有摻雜劑的材料中,添加溶劑進行溶解,或均勻地分散,分別塗佈於電洞注入層或電洞傳輸層上後,藉由煅燒進行成膜的方法。
電洞傳輸性高分子材料,可列舉聚[(9,9-二己基茀基-2,7-二基)-co-(N,N’-雙{p-丁基苯基}-1,4-二胺基伸 苯基)]、聚[(9,9-二辛基茀基-2,7-二基)-co-(N,N’-雙{p-丁基苯基}-1,1’-亞聯苯基-4,4-二胺)]、聚[(9,9-雙{1’-戊烯-5’-基}茀基-2,7-二基)-co-(N,N’-雙{p-丁基苯基}-1,4-二胺基伸苯基)]、聚[N,N’-雙(4-丁基苯基)-N,N’-雙(苯基)-聯苯胺]-聚倍半矽氧烷封端、聚[(9,9-雙(二辛基茀基)-2,7-二基)-co-(4,4’-(N-(p-丁基苯基))二苯基胺)]等。
發光性高分子材料,可列舉聚(9,9-二烷基茀)(PDAF)等之聚茀衍生物、聚(2-甲氧基-5-(2’-乙基己氧基)-1,4-苯乙烯)(MEH-PPV)等之聚苯乙烯衍生物、聚(3-烷基噻吩)(PAT)等之聚噻吩衍生物、聚乙烯基咔唑(PVCz)等。
溶劑可列舉甲苯、二甲苯、氯仿等。溶解或均勻分散法,可列舉攪拌、加熱攪拌、超音波分散等的方法。
塗佈方法無特別限定,可列舉噴墨法、噴霧法、浸漬法、旋轉塗佈法、轉印印刷法、輥塗法、刷毛塗佈等。又,塗佈係在氮、氬等的惰性氣體下進行為佳。
煅燒方法可列舉在惰性氣體下或真空中,以烤箱或加熱板加熱的方法。
由本發明之電荷傳輸性清漆所得的薄膜為電洞注入傳輸層時,本發明之有機EL元件之製作方法之一例如下述。
陽極基板上形成電洞注入傳輸層,在此電洞注入傳輸層上,依序設置發光層、電子傳輸層、電子注入 層、陰極。發光層、電子傳輸層及電子注入層之形成方法及具體例,可列舉與前述同樣者。
陽極材料、形成發光層、發光性摻雜劑、電子傳輸層及電子阻擋層的材料、陰極材料,可列舉與前述同樣者。
又,電極及前述各層間之任意之間,必要時可設置電洞阻擋層(hole blocking layer)、電子阻擋層(electron blocking layer)等。例如形成電子阻擋層的材料,可列舉三(苯基吡唑)銥等。
構成陽極與陰極及此等之間所形成之層的材料係因製造具備底部發光(Bottom Emission)構造、頂部發光(Top Emission)構造之任一的元件而異,故考慮該點來選擇適宜材料。
通常,底部發光構造的元件,在基板側使用透明陽極,由基板側取出光,而頂部發光構造的元件則是使用由金屬所成的反射陽極,由與基板相反方向之透明電極(陰極)側取出光。因此,例如就陽極材料而言,製造底部發光構造的元件時,使用ITO等的透明陽極,而製造頂部發光構造的元件時,使用Al/Nd等的反射陽極。
本發明之有機EL元件,為了防止特性惡化,可使用通常方法,必要時與捕水劑等一同封裝。
以下,舉實施例及比較例,更具體地說明本發明,但本發明並不受限於下述實施例。又,實施例中,試料調製及物性分析用的裝置係如以下所示。
(1)1H-NMR測量:Bruker公司製、Ascend 500
(2)基板洗凈:長州產業(股)製、基板洗凈裝置(減壓電漿方式)
(3)清漆之塗佈:三傘(股)製、旋轉塗佈機MS-A100
(4)膜厚測量:(股)小坂研究所製、微細形狀測量機Surfaccoda ET-4000
(5)有機EL元件之製作:長州產業(股)製、多機能蒸鍍裝置系統C-E2L1G1-N
(6)有機EL元件之亮度等之測量:(有)Tech-world製、I-V-L測量系統
依據國際公開第2006/025342號所記載的方法,合成下述式表示的磺酸化合物NSO-2。
依據專利文獻6所記載的方法,合成下述式表示之磺酸酯化合物NSO-2-PGME。
依據下述圖示,合成磺酸酯化合物NSO-2-EH。
在1-萘酚-3,6-二磺酸鈉11g(31.59mmol)中,於氮環境下,依序添加全氟聯苯4.8g(14.36mol)、碳酸鉀4.2g(30.15mol)及N,N-二甲基甲醯胺100mL,將反應系進行氮取代後,於內溫100℃下攪拌6小時。放置冷卻至室溫後,藉由過濾除去碳酸鉀殘渣,進行減壓濃縮。為了除去殘存之雜質,而在殘渣中加入甲醇100mL,於室溫下攪拌30分鐘。然後,過濾懸浮溶液,得到磺酸鈉鹽A 11.8g(收率83%)。
在磺酸鈉鹽A 2g(2mmol)中,加入亞硫醯氯(8mL)及DMF(0.1mL),進行1小時加熱迴流後,餾除亞硫 醯氯,得到含有磺酸氯化物A的固體。本化合物未進行進一步純化,而使用於下一步驟。
在前述固體中,加入氯仿(12mL)及吡啶(8mL),於0℃下添加2-乙基-1-己醇3.13g(24mmol)。昇溫至室溫,然後攪拌3小時。餾除溶劑後添加水,以乙酸乙酯萃取,以硫酸鈉使有機層乾燥。過濾、濃縮後,將所得之粗產物以矽膠管柱層析(己烷/乙酸乙酯)純化,得到磺酸酯化合物NSO-2-EH 1.25g的白色固體(收率46%(自磺酸鈉鹽A之2階段收率))。1H-NMR之測量結果如以下所示。
1H-NMR(500MHz,CDCl3):δ 0.78-0.85(m,24H),1.15-1.39(m,32H),1.58-1.62(m,4H),4.02-4.10(m,8H),7.34(s,2H),8.21(dd,J=1.5,9.0Hz,2H),8.44(s,2H),8.67(d,J=9.0Hz,2H),8.69(d,J=1.5Hz,2H)。
除了使用2-丁基-1-辛醇4.47g(24mmol)取代2-乙基-1-己醇外,與實施例1-1同樣的方法合成,得到下述式表示之磺酸酯化合物NSO-2-BO 1.50g的白色固體(收率48%(自磺酸鈉鹽A之2階段收率))。1H-NMR之測量結果如以下所示。
1H-NMR(500MHz,CDCl3):δ 0.79-0.87(m,24H),1.17-1.28(m,64H),1.62-1.68(m,4H),4.02(d,J=5.0Hz,4H),4.08(d,J=5.0Hz,4H),7.36(s,2H),8.21(dd,J=1.5,9.0Hz,2H),8.44(s,2H),8.67(d,J=9.0Hz,2H),8.69(d,J=1.5Hz, 2H)。
除了使用1-辛醇3.13g(24mmol)取代2-乙基-1-己醇外,與實施例1-1同樣的方法合成,得到下述式表示之磺酸酯化合物NSO-2-OC 0.13g的白色固體(收率5%(自磺酸鈉鹽A之2階段收率))。1H-NMR之測量結果如以下所示。
1H-NMR(500MHz,CDCl3):δ 0.82-0.87(m,12H),1.20-1.36(m,40H),1.64-1.74(m,8H),4.11-4.19(m,8H),7.35(s,2H),8.21(dd,J=2.0,9.0Hz,2H),8.44(s,2H),8.67(d,J=9.0Hz,2H),8.68(d,J=2.0Hz,2H)。
將NSO-2-EH(393mg)及寡聚苯胺化合物1(133mg)添加於3-苯氧基甲苯(5g)及四氫萘(5g)之混合溶劑中,於50℃下,以400rpm加熱攪拌5分鐘。藉此,NSO-2-EH完全溶解於溶劑。將所得之溶液使用孔徑0.2μm的PTFE製過濾器過濾,得到電荷傳輸性清漆A。又,寡聚苯胺化合物1係依據國際公開第2013/084664號記載的方法合成。
將NSO-2-BO(408mg)及寡聚苯胺化合物1(118mg)添加於3-苯氧基甲苯(5g)及四氫萘(5g)之混合溶劑中,於50℃下,以400rpm加熱攪拌5分鐘。藉此,NSO-2-BO完全溶解於溶劑。將所得之溶液使用孔徑0.2μm的PTFE製過濾器過濾,得到電荷傳輸性清漆B。
將NSO-2-OC(393mg)及寡聚苯胺化合物1(133mg)添加於3-苯氧基甲苯(5g)及四氫萘(5g)之混合溶劑中,於50℃下,以400rpm加熱攪拌5分鐘。藉此,NSO-2-OC完全溶解於溶劑。將所得之溶液使用孔徑0.2μm的PTFE製過濾器過濾,得到電荷傳輸性清漆C。
將NSO-2-PGME(384mg)及寡聚苯胺化合物1(142mg)添加於3-苯氧基甲苯(5g)及四氫萘(5g)之混合溶劑中,於50℃下,以400rpm加熱攪拌30分鐘,但是產生溶解殘餘。藉由於70℃下,以400rpm加熱攪拌20分鐘,NSO-2-PGME完全溶解於溶劑。將所得之溶液使用孔徑0.2μm的PTFE製過濾器過濾,得到電荷傳輸性清漆D。
將NSO-2(349mg)及寡聚苯胺化合物1(177mg)加入於3-苯氧基甲苯(5g)及四氫萘(5g)之混合溶劑中,於90℃下以400rpm加熱攪拌30分鐘,但是NSO-2完全未溶解。
將NSO-2(349mg)及寡聚苯胺化合物1(177mg)加入於1,3-二甲基-2-咪唑啉酮(3.3g)、2,3-丁二醇(4g)及二丙二醇單甲醚(2.7g)之混合溶劑中,於50℃下,以400rpm加熱攪拌5分鐘。因此,NSO-2完全溶解於溶劑。將所得之溶液使用孔徑0.2μm的PTFE製過濾器過濾,得到電荷傳輸性清漆E。
NSO-2-EH、NSO-2-BO及NSO-2-OC係在50℃下,以400rpm加熱攪拌5分鐘的條件下,完全溶解於低極性溶劑的3-苯氧基甲苯及四氫萘之混合溶劑中,然而NSO- 2-PGME為了完全溶解於前述混合溶劑時,必須在70℃下,以400rpm加熱攪拌20分鐘的條件,又,NSO-2未溶解於前述混合溶劑。亦即,本發明之磺酸酯化合物對於低極性溶劑的溶解性優異。
將電荷傳輸性清漆A~D以2℃冷藏保存,觀測保存開始後,經過下述表1所示時間之時點有無析出物。結果如表1所示。
如表1所示,含有本發明之磺酸酯化合物的電荷傳輸性清漆係保存安定性優異。
以下實施例及比較例中,ITO基板係使用ITO在表面上,且膜厚150nm,經圖型化之25mm×25mm×0.7t的玻璃基板,使用在使用前藉由O2電漿洗凈裝置(150W、30秒鐘)除去表面上之雜質者。
使用旋轉塗佈機,將電荷傳輸性清漆A塗佈於ITO基板後,在大氣下,以120℃預煅燒1分鐘,接著於200℃下進行本煅燒30分鐘,在ITO基板上形成30nm的薄膜。
其上,使用蒸鍍裝置(真空度2.0×10-5Pa),依序層合α-NPD及鋁的薄膜,得到HOD。以蒸鍍速率0.2nm/秒的條件進行蒸鍍。α-NPD及鋁之薄膜的膜厚,分別為30nm及80nm。
又,為了防止因空氣中之氧、水等的影響造成特性劣化,HOD係以封裝基板封裝後,評價其特性。依以下順序進行封裝。
氧濃度2ppm以下、露點-85℃以下的氮環境中,將HOD收納於封裝基板之間,藉由接著材((股)MORESCO製Moresco Moisture cut WB90US(P))貼合封裝基板。此時,將捕水劑(Dynic(股)製HD-071010W-40)與HOD一同收納於封裝基板內。對於貼合後的封裝基板,照射UV光(波長365nm、照射量6,000mJ/cm2)後,於80℃下進行1小時退火處理,使接著材硬化。
除了使用電荷傳輸性清漆B取代電荷傳輸性清漆A外,與實施例4-1同樣的方法製作HOD。
除了使用電荷傳輸性清漆D取代電荷傳輸性清漆A外,與實施例4-1同樣的方法製作HOD。
除了使用電荷傳輸性清漆E取代電荷傳輸性清漆A,以80℃預煅燒1分鐘,以230℃本煅燒15分鐘外,與實施例4-1同樣的方法製作HOD。
對於前述實施例及比較例製作之各HOD,測量驅動電壓3V之電流密度。結果如表2所示。
如表2所示,含有本發明之磺酸酯化合物的電荷傳輸性清漆,相較於以往者,顯示同等或同等以上的電洞傳輸性。
以下實施例及比較例中,ITO基板係使用ITO在表面上,且膜厚150nm,經圖型化之25mm×25mm×0.7t的玻璃基板,使用在使用前藉由O2電漿洗凈裝置(150W、30秒鐘) 除去表面上的雜質者。
使用旋轉塗佈機,將電荷傳輸性清漆A塗佈於ITO基板後,以120℃乾燥1分鐘,在大氣環境下,於200℃下進行煅燒30分鐘,在ITO基板上形成30nm之均勻的薄膜。
接著,對於形成有薄膜的ITO基板,使用蒸鍍裝置(真空度1.0×10-5Pa),將α-NPD以0.2nm/秒形成30nm薄膜。其次,將CBP與Ir(PPy)3進行共蒸鍍。共蒸鍍係控制蒸鍍速率使Ir(PPy)3之濃度成為6%,使層合40nm。接著,依序層合Alq3、氟化鋰及鋁的薄膜,製作有機EL元件。此時,蒸鍍速率係針對Alq3及鋁為0.2nm/秒,針對氟化鋰為0.02nm/秒的條件下分別進行,膜厚分別為20nm、0.5nm及80nm。
又,為了防止因空氣中之氧、水等的影響造成特性劣化,有機EL元件係以封裝基板封裝後,評價其特性。封裝係與前述同樣的方法進行。
除了使用電荷傳輸性清漆B取代電荷傳輸性清漆A外,與實施例4-1同樣的方法,製作有機EL元件。
除了使用電荷傳輸性清漆D取代電荷傳輸性清漆A外,與實施例4-1同樣的方法,製作有機EL元件。
除了使用電荷傳輸性清漆E取代電荷傳輸性清漆A外,預煅燒為80℃下1分鐘,本煅燒為230℃下15分鐘外,與實施例4-1同樣的方法,製作有機EL元件。
對於此等的元件,測量亮度1,000cd/m2時之電壓及電流效率。結果如表3所示。又,各元件之發光面尺寸的面積為2mm×2mm。
如表3所示,含有本發明之磺酸酯化合物的電荷傳輸性清漆,相較於以往者,顯示同等的有機EL特性。
Claims (13)
- 一種磺酸酯化合物,其係以下述式(1)表示,
- 如請求項1之磺酸酯化合物,其中R 1為氫原子,R 2及R 3各自獨立為碳數1~6之烷基。
- 如請求項1或2之磺酸酯化合物,其中A 2為由萘或蒽所衍生之基。
- 如請求項3之磺酸酯化合物,其中A 2為由萘所衍生之基。
- 如請求項1~4中任一項之磺酸酯化合物,其中A 3為由全氟聯苯所衍生之基。
- 如請求項1~5中任一項之磺酸酯化合物,其中m為2。
- 如請求項1~6中任一項之磺酸酯化合物,其中n為2。
- 一種電子接受性物質前驅物,其係由如請求項1~7中任一項之磺酸酯化合物所成。
- 一種電荷傳輸性清漆,其係包含如請求項8之電子接受性物質前驅物、電荷傳輸性物質及有機溶劑。
- 如請求項9之電荷傳輸性清漆,其中前述有機溶劑為低極性有機溶劑。
- 如請求項9或10之電荷傳輸性清漆,其中前述電荷傳輸性物質為苯胺衍生物。
- 一種電荷傳輸性薄膜,其係使用如請求項9~11中任一項之電荷傳輸性清漆所製作。
- 一種有機電致發光元件,其係具備如請求項12之電荷傳輸性薄膜。
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TW106120228A TWI746578B (zh) | 2016-06-16 | 2017-06-16 | 磺酸酯化合物及其利用 |
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EP (1) | EP3473614A4 (zh) |
JP (1) | JP6443588B2 (zh) |
KR (1) | KR102392403B1 (zh) |
CN (1) | CN109415310B (zh) |
TW (1) | TWI746578B (zh) |
WO (1) | WO2017217457A1 (zh) |
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CN109415309B (zh) * | 2016-06-16 | 2022-02-25 | 日产化学株式会社 | 磺酸酯化合物及其利用 |
WO2018230548A1 (ja) * | 2017-06-15 | 2018-12-20 | Dic株式会社 | 機能層形成用インク |
EP3730477A4 (en) * | 2017-12-20 | 2021-09-15 | Nissan Chemical Corporation | SULPHONIC ACID ESTER COMPOUND AND ASSOCIATED USE |
KR20200098661A (ko) * | 2017-12-20 | 2020-08-20 | 닛산 가가쿠 가부시키가이샤 | 전하 수송성 바니시 |
KR20210039404A (ko) | 2018-08-03 | 2021-04-09 | 닛산 가가쿠 가부시키가이샤 | 아닐린 유도체 |
WO2020027259A1 (ja) | 2018-08-03 | 2020-02-06 | 日産化学株式会社 | 電荷輸送性ワニス |
WO2020066979A1 (ja) | 2018-09-25 | 2020-04-02 | 日産化学株式会社 | 有機機能膜付き基板の製造方法 |
CN112789298B (zh) | 2018-09-28 | 2024-04-30 | 日产化学株式会社 | 聚合物及其利用 |
WO2020196154A1 (ja) | 2019-03-27 | 2020-10-01 | 日産化学株式会社 | アリールアミン化合物およびその利用 |
KR20210151082A (ko) | 2019-03-29 | 2021-12-13 | 닛산 가가쿠 가부시키가이샤 | 전하수송성 바니시 |
JP7484901B2 (ja) | 2019-04-26 | 2024-05-16 | 日産化学株式会社 | アリールスルホン酸エステル化合物の製造方法 |
CN113874352A (zh) | 2019-05-31 | 2021-12-31 | 日产化学株式会社 | 芳基胺化合物及其利用 |
WO2020262418A1 (ja) * | 2019-06-26 | 2020-12-30 | 日産化学株式会社 | 電荷輸送性ワニス |
TW202115202A (zh) * | 2019-06-26 | 2021-04-16 | 日商日產化學股份有限公司 | 電荷輸送性塗料 |
CN114105838A (zh) * | 2021-11-19 | 2022-03-01 | 北京大学深圳研究生院 | 一种柔性热电材料及其制备方法 |
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JPS5136795B2 (zh) | 1971-11-12 | 1976-10-12 | ||
US4143023A (en) | 1977-06-29 | 1979-03-06 | General Electric Company | Plasticized polycarbonate composition |
DE3216455A1 (de) * | 1982-05-03 | 1983-11-17 | Bayer Ag, 5090 Leverkusen | Anthrachinonfarbstoffe, ihre herstellung und verwendung sowie dichtroitisches material enthaltend diese anthrachinonfarbstoffe |
JPH07134416A (ja) | 1993-06-28 | 1995-05-23 | Oki Electric Ind Co Ltd | 放射線感応性樹脂組成物 |
JP4868099B2 (ja) * | 2000-11-09 | 2012-02-01 | 日産化学工業株式会社 | 電界発光素子 |
EP1589788B1 (en) | 2002-11-07 | 2014-07-09 | Nissan Chemical Industries, Ltd. | Charge-transporting varnish |
TW200504046A (en) | 2003-06-25 | 2005-02-01 | Nissan Chemical Ind Ltd | 1,4-Benzodioxane sulfonic acid compound and use thereof as electron-acceptor material |
WO2005043962A1 (ja) | 2003-10-31 | 2005-05-12 | Nissan Chemical Industries, Ltd. | 1,4−ジチイン環を有する化合物を含む電荷輸送性有機材料 |
TW200615254A (en) * | 2004-08-31 | 2006-05-16 | Nissan Chemical Ind Ltd | Arylsulfonic acid compound and use thereof as electron-acceptor material |
WO2006049045A1 (ja) * | 2004-11-01 | 2006-05-11 | Nissan Chemical Industries, Ltd. | スルホン酸エステルを含有するリソグラフィー用反射防止膜形成組成物 |
JP5136795B2 (ja) | 2006-02-23 | 2013-02-06 | 日産化学工業株式会社 | スルホン酸エステル化合物からなる電子受容性物質前駆体およびその利用 |
TWI643913B (zh) * | 2013-10-04 | 2018-12-11 | 日產化學工業股份有限公司 | Charge transport varnish, charge transporting film and organic electroluminescent element |
CN106463636B (zh) | 2014-06-05 | 2020-04-03 | 日产化学工业株式会社 | 电荷传输性清漆 |
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- 2017-06-14 CN CN201780037111.1A patent/CN109415310B/zh active Active
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EP3473614A4 (en) | 2020-02-26 |
WO2017217457A1 (ja) | 2017-12-21 |
KR20190018499A (ko) | 2019-02-22 |
TWI746578B (zh) | 2021-11-21 |
US10513491B2 (en) | 2019-12-24 |
US20190169120A1 (en) | 2019-06-06 |
EP3473614A1 (en) | 2019-04-24 |
CN109415310B (zh) | 2022-03-01 |
CN109415310A (zh) | 2019-03-01 |
JPWO2017217457A1 (ja) | 2018-09-27 |
KR102392403B1 (ko) | 2022-04-29 |
JP6443588B2 (ja) | 2018-12-26 |
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