TWI690519B - 用作分散導電聚合物之功能添加劑的氟化芳香族小分子 - Google Patents
用作分散導電聚合物之功能添加劑的氟化芳香族小分子 Download PDFInfo
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- TWI690519B TWI690519B TW104137504A TW104137504A TWI690519B TW I690519 B TWI690519 B TW I690519B TW 104137504 A TW104137504 A TW 104137504A TW 104137504 A TW104137504 A TW 104137504A TW I690519 B TWI690519 B TW I690519B
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- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
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- 125000006547 cyclononyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
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- SQIFACVGCPWBQZ-UHFFFAOYSA-N delta-terpineol Natural products CC(C)(O)C1CCC(=C)CC1 SQIFACVGCPWBQZ-UHFFFAOYSA-N 0.000 description 1
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- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
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- CWAFVXWRGIEBPL-UHFFFAOYSA-N ethoxysilane Chemical compound CCO[SiH3] CWAFVXWRGIEBPL-UHFFFAOYSA-N 0.000 description 1
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- UAIZDWNSWGTKFZ-UHFFFAOYSA-L ethylaluminum(2+);dichloride Chemical compound CC[Al](Cl)Cl UAIZDWNSWGTKFZ-UHFFFAOYSA-L 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- UQSQSQZYBQSBJZ-UHFFFAOYSA-N fluorosulfonic acid Chemical compound OS(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-N 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- 229930182470 glycoside Natural products 0.000 description 1
- 150000002338 glycosides Chemical class 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
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- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
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- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
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- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 1
- 229910000103 lithium hydride Inorganic materials 0.000 description 1
- FUJCRWPEOMXPAD-UHFFFAOYSA-N lithium oxide Chemical compound [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 1
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- 229920002521 macromolecule Polymers 0.000 description 1
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- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
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- ORUIBWPALBXDOA-UHFFFAOYSA-L magnesium fluoride Chemical compound [F-].[F-].[Mg+2] ORUIBWPALBXDOA-UHFFFAOYSA-L 0.000 description 1
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- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
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- 238000005259 measurement Methods 0.000 description 1
- 150000007974 melamines Chemical class 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 229940095102 methyl benzoate Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- OLXYLDUSSBULGU-UHFFFAOYSA-N methyl pyridine-4-carboxylate Chemical compound COC(=O)C1=CC=NC=C1 OLXYLDUSSBULGU-UHFFFAOYSA-N 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
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- PZYDAVFRVJXFHS-UHFFFAOYSA-N n-cyclohexyl-2-pyrrolidone Chemical compound O=C1CCCN1C1CCCCC1 PZYDAVFRVJXFHS-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
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 150000002791 naphthoquinones Chemical class 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- 239000012299 nitrogen atmosphere Substances 0.000 description 1
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- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
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- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
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- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
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- JGTNAGYHADQMCM-UHFFFAOYSA-N perfluorobutanesulfonic acid Chemical compound OS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F JGTNAGYHADQMCM-UHFFFAOYSA-N 0.000 description 1
- YFSUTJLHUFNCNZ-UHFFFAOYSA-N perfluorooctane-1-sulfonic acid Chemical compound OS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F YFSUTJLHUFNCNZ-UHFFFAOYSA-N 0.000 description 1
- SNGREZUHAYWORS-UHFFFAOYSA-N perfluorooctanoic acid Chemical compound OC(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F SNGREZUHAYWORS-UHFFFAOYSA-N 0.000 description 1
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- 229960005323 phenoxyethanol Drugs 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
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- 239000004033 plastic Substances 0.000 description 1
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- 229920006267 polyester film Polymers 0.000 description 1
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- 229920000098 polyolefin Polymers 0.000 description 1
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- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- IUBQJLUDMLPAGT-UHFFFAOYSA-N potassium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([K])[Si](C)(C)C IUBQJLUDMLPAGT-UHFFFAOYSA-N 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- KCXFHTAICRTXLI-UHFFFAOYSA-N propane-1-sulfonic acid Chemical compound CCCS(O)(=O)=O KCXFHTAICRTXLI-UHFFFAOYSA-N 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- FOWDZVNRQHPXDO-UHFFFAOYSA-N propyl hydrogen carbonate Chemical class CCCOC(O)=O FOWDZVNRQHPXDO-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
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
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- 229910052701 rubidium Inorganic materials 0.000 description 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052706 scandium Inorganic materials 0.000 description 1
- SIXSYDAISGFNSX-UHFFFAOYSA-N scandium atom Chemical compound [Sc] SIXSYDAISGFNSX-UHFFFAOYSA-N 0.000 description 1
- 238000007790 scraping Methods 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- WRIKHQLVHPKCJU-UHFFFAOYSA-N sodium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([Na])[Si](C)(C)C WRIKHQLVHPKCJU-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 1
- 229910001948 sodium oxide Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 229910000018 strontium carbonate Inorganic materials 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
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- 229940116411 terpineol Drugs 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000009210 therapy by ultrasound Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 150000003568 thioethers Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-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
- 238000007738 vacuum evaporation Methods 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-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
- 239000011701 zinc Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D321/00—Heterocyclic compounds containing rings having two oxygen atoms as the only ring hetero atoms, not provided for by groups C07D317/00 - C07D319/00
- C07D321/02—Seven-membered rings
- C07D321/10—Seven-membered rings condensed with carbocyclic rings or ring systems
-
- 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
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/28—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C309/41—Sulfonic acids having 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
- C07C309/43—Sulfonic acids having 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 having at least one of the sulfo groups bound to a carbon atom of a six-membered aromatic ring being part of a condensed ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/257—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings
- C07C43/29—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings containing halogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/02—Halogenated hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/06—Ethers; Acetals; Ketals; Ortho-esters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/17—Amines; Quaternary ammonium compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/37—Thiols
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L65/00—Compositions of macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain; Compositions of derivatives of such polymers
-
- 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
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Abstract
Description
本發明係關於一種化合物;一種包含此化合物之組成物;一種使用此組成物製備導電層之方法;一種包含根據本發明之化合物的導電層;包含此導電層之電子組件;及根據本發明之化合物用作OLED之電洞注入層中的添加劑之用途。
導電聚合物已用於多種有機電子裝置中,包括發展電致發光(EL)裝置供發光顯示器使用。相對於EL裝置,諸如含有導電聚合物之有機發光二極體(OLED),此類裝置一般具有以下組態:
陽極/電洞注入層/EL聚合物/陰極
陽極典型地為能夠將電洞注入至半導電EL聚合物之另外填充之π-帶中之任何物質,諸如氧化銦錫(ITO)。陽極視情況支撐在玻璃或塑膠基板上。EL聚合物典型地為共軛半導電聚合物,諸如聚(對伸苯基伸乙烯基)或聚茀。陰極典型地為能夠將電子注入至半導電EL聚合物之另外空π *-帶中之任何物質(諸如,Ca或Ba)。
電洞注入層(亦稱為「緩衝層」)典型地為導電聚合物且促進電洞自陽極注入至EL聚合物層中。用作電洞注入層之典型導電聚合物包
括聚苯胺及聚二氧基噻吩。用於製備有機電子裝置中導電層之熟知導電聚合物為聚(3,4-伸乙二氧基噻吩)與聚苯乙烯磺酸之複合物,亦稱為「PEDOT/PSS」。然而,電洞注入層基於PEDOT/PSS之OLED通常鑑定後具有不令人滿意的效能,特定言之相對較短壽命及較低效率及發光。
為提高電洞注入層基於PEDOT/PSS之OLED之效能,先前技術建議添加某些添加劑至用於形成電洞注入層之PEDOT/PSS分散液中。
舉例而言,US 2005/0209388 A1建議用形成膠體之聚合酸(諸如NAFION®)取代聚苯乙烯磺酸,其中根據US 2005/0209388 A1之教示,其中所揭示之組成物藉由在NAFION®存在下氧化聚合噻吩單體來獲得。US 2004/124504 A1建議藉由添加複數個奈米粒子至分散液來提高電洞注入層基於PEDOT/PSS之OLED之效能。US 2004/124504 A1中所揭示之適合奈米粒子為全氟乙烯磺酸鹽,諸如NAFION®。然而,在OLED之電洞注入層中使用NAFION®作為添加劑具有如下缺點:此等氟化磺酸聚合物為昂貴的、不溶於水(其僅形成膠體)及其不溶於有機溶劑。此等缺點限制尤其在較高濃度下其與導電聚合物分散液之相容性。
WO 2009/096352 A1揭示包含特定低分子量氟化磺酸及導電聚合物(諸如聚苯胺)之「電荷傳輸清漆」。此清漆在以薄膜形式施加時可對OLED效能具有有益影響(亦即,低電壓驅動及發光效率)。氟化磺酸可溶於水及高度極性有機溶劑(諸如DMF)。尚未展示此等物質之一般適用性,尤其所述低分子量氟化磺酸在與PEDOT/PSS組合使用時之有益影響。此外,WO 2009/096352 A1中所揭示之氟化磺酸在除水以外的溶劑中之溶解性較低。
因此,本發明之一目標為克服先前技術在有機電子裝置領域,特定言之電洞注入層基於諸如PEDOT/PSS之導電聚合物之OLED中的缺點。
特定言之,本發明之一目標為提供在與導電聚合物(諸如PEDOT/PSS)組合使用時在水或有機溶劑中具有調整之溶解性的低分子量添加劑,用於製備有機電子裝置中導電層,特定言之製備OLED中電洞注入層,有助於提高此等電子裝置之效能。相比於複合聚合物(諸如NAFION®),低分子量添加劑應可由市售前驅體藉由簡單1-2個步驟合成獲得。
形成範疇之獨立申請專利範圍之標的物對以上目標中之至少一者的解決方案提供貢獻,其中來自其的附屬申請專利範圍代表本發明之較佳具體實例,其主題亦對解決至少一個目標作出貢獻。
具體實例
其中K 表示芳香族或雜芳香族基團,其中至少一個氫原子可經選自由磺酸基、硫酸基、銨基及脂族基組成之群的官能基取代;X 選自由C-C鍵、O、S、SO2及NR'組成之群,其中R'表示氫或脂族或芳香族基團;
A 表示氟化或全氟化芳香族基團;n 表示2至6範圍內之整數;m 表示1至3範圍內之整數。
II.如具體實例I之化合物,其中該官能基選自由以下組成之群i)-SO3M,其中M選自由以下組成之群:H+、Na+、K+、Li+、NH4 +、Ca2+及Mg2+,ii)-OSO3M,其中M選自由以下組成之群:H+、Na+、K+、Li+、NH4 +、Ca2+及Mg2+,iii)-CO2M,其中M選自由以下組成之群:H+、Na+、K+、Li+、NH4 +、Ca2+及Mg2+,iv)銨基,其選自由以下組成之群:-N(CH3)4 +、-N(CH2CH3)4 +、-N(C3H7)4 +、-N(C4H9)4 +及-N(C5H11)4 +,及v)烷基,其選自由以下組成之群:-CH3、-C2H5、-C3H7、-C4H9、-C5H11、-C6H13、-C7H15、-C8H17、-C9H19、-C10H21、-C11H23及-C12H25。
III.如具體實例I或II之化合物,其中R'選自由以下組成之群:-CH3、-C2H5、-C3H7及-C4H9。
其中- Y表示S、O或NR",其中R"表示氫原子或具有1至20個碳原子之脂族基,- R選自由以下組成之群:H、-SO3M、-OSO3M、-CO2M、-N(CH3)4 +、-N(CH2CH3)4 +、-N(C3H7)4 +、-N(C4H9)4 +、-N(C5H11)4 +、-CH3、-C2H5、-C3H7、-C4H9、-C5H11、-C6H13、-C7H15、-C8H17、-C9H19、-C10H21、-C11H23及-C12H25,其中M如具體實例II中所定義,及其中點線指示與A之鍵結。
V. 如具體實例IV之化合物,其中X表示O,且其中滿足每個實體K之取代基R之以下組合:n=2,且R=1×-SO3M及3×H或R=2×-SO3M及2×H,
或n=3,及R=3×H或R=3×-SO3M,其中M如具體實例II中所定義。
其中
- Y表示S、O或NR",其中R"表示氫原子或具有1至20個碳原子之脂族基,- R選自由以下組成之群:H、-SO3M、-OSO3M、-CO2M、-N(CH3)4 +、-N(CH2CH3)4 +、-N(C3H7)4 +、-N(C4H9)4 +、-N(C5H11)4 +、-CH3、-C2H5、-C3H7、-C4H9、-C5H11、-C6H13、-C7H15、-C8H17、-C9H19、-C10H21、-C11H23及-C12H25,其中M如具體實例II中所定義,及其中點線指示與A之鍵結。
VII. 如具體實例VI之化合物,其中X表示O,且其中滿足每個實體K之取代基R之以下組合:R=2×-SO3M及4×H,或R=3×-SO3M及3×H,其中M如具體實例II中所定義。
其中R選自由以下組成之群:H、-SO3M、-OSO3M、-CO2M、-N(CH3)4 +、-N(CH2CH3)4 +、-N(C3H7)4 +、-N(C4H9)4 +、-N(C5H11)4 +、-CH3、-C2H5、-C3H7、-C4H9、
-C5H11、-C6H13、-C7H15、-C8H17、-C9H19、-C10H21、-C11H23及-C12H25,其中M如具體實例II中所定義,且其中點線指示與A之鍵結。
其中R選自由以下組成之群:H、-SO3M、-OSO3M、-CO2M、-N(CH3)4 +、
-N(CH2CH3)4 +、-N(C3H7)4 +、-N(C4H9)4 +、-N(C5H11)4 +、-CH3、-C2H5、-C3H7、-C4H9、-C5H11、-C6H13、-C7H15、-C8H17、-C9H19、-C10H21、-C11H23及-C12H25,其中M如具體實例II中所定義,且其中點線指示與A之鍵結。
具有選自由通式VIa至VIe組成之群的一般結構:
其中R選自由以下組成之群:H、-SO3M、-OSO3M、-CO2M、-N(CH3)4 +、-N(CH2CH3)4 +、-N(C3H7)4 +、-N(C4H9)4 +、-N(C5H11)4 +、-CH3、-C2H5、-C3H7、-C4H9、-C5H11、-C6H13、-C7H15、-C8H17、-C9H19、-C10H21、-C11H23及-C12H25,其中M如具體實例II中所定義,且其中點線指示與A之鍵結。
在此R選自由以下組成之群:H、-SO3M、-OSO3M、-CO2M、-N(CH3)4 +、-N(CH2CH3)4 +、-N(C3H7)4 +、-N(C4H9)4 +、-N(C5H11)4 +、-CH3、-C2H5、-C3H7、-C4H9、-C5H11、-C6H13、-C7H15、-C8H17、-C9H19、-C10H21、-C11H23及-C12H25,其中M如具體實例II中所定義,且其中點線指示與A之鍵結。
具有選自由通式VIIIa至VIIIr(對於三環芳香族基團K)組成之群的一般結構或具有通式VIIIs至VIIIu(對於三環雜芳香族基團K):
其中R選自由以下組成之群:H、-SO3M、-OSO3M、-CO2M、-N(CH3)4 +、-N(CH2CH3)4 +、-N(C3H7)4 +、-N(C4H9)4 +、-N(C5H11)4 +、-CH3、-C2H5、-C3H7、-C4H9、-C5H11、-C6H13、-C7H15、-C8H17、-C9H19、-C10H21、-C11H23及-C12H25,其中M如具體實例II中所定義,且其中點線指示與A之鍵結。
其中點線指示與X之鍵結。
XV. 一種組成物,其包含
I)至少一種導電聚合物,II)至少一種溶劑,及III)至少一種如具體實例I至XIV中任一者之化合物。
XVI.如具體實例XV之組成物,其中該導電聚合物I)包含聚噻吩。
XVII.如具體實例XV及XVI中任一者之組成物,其中該溶劑II)為水;有機溶劑,其選自由以下組成之群:醇、脂族烴、芳香族烴、醚、鹵化烴、脂族腈、脂族羧酸、脂族羧酸及酮,或此等溶劑中之至少兩者的混合物。
XVIII.一種製備導電層之方法,其包含以下方法步驟:(P1)用如具體實例XV至XVII中任一者之組成物疊加基板;或首先用包含溶劑及如具體實例I至XIV中任一者之化合物的組成物疊加基板,至少部分移除溶劑,且隨後用如具體實例XV至XVII中任一者之組成物或用包含溶劑及導電聚合物之組成物疊加基板;或首先用包含溶劑及導電聚合物之組成物疊加基板,至少部分移除溶劑,且隨後用如具體實例XV至XVII中任一者之組成物或用包含溶劑、如具體實例I至XIV中任一者之化合物的組成物疊加基板;(P2)至少部分移除溶劑。
XIX.一種導電層,其包含至少一種如具體實例I至XIV中任一者之化合物。
XX.一種電子組件,其包含可藉由如具體實例XVIII之方法獲得之導電層或包含如具體實例XIX之導電層。
XXI.如具體實例XX之電子組件,其中該電子組件為OLED、顯示器、有機太陽能電池、混合太陽能電池、場效電晶體或熱電產生器。
XXII.一種至少一種如具體實例I至XIV中任一者之化合物之用途,其用作OLED之電洞注入層或有機太陽能電池中之添加劑。
其中K 表示芳香族或雜芳香族基團,較佳單環、雙環或三環芳香族或雜芳香族基團,其中至少一個氫原子可經選自由磺酸基、硫酸基、銨基及脂族基組成之群的官能基取代;X 選自由C-C鍵、O、S、SO2及NR'組成之群,較佳選自由O、S、SO2及NR'組成之群,其中R'表示氫或脂族或芳香族基團,較佳烷基且最佳選自由-CH3、-C2H5、-C3H7及-C4H9組成之群的烷基,其中X最佳表示O;A 表示氟化或全氟化芳香族基團;n 表示2至6範圍內之整數,較佳為2或3;m 表示1至3範圍內之整數,較佳為1。
較佳地,在根據本發明之化合物中,官能基(亦即,可取代芳香族基團K之至少一個氫原子之官能基)為選自由以下組成之群的官能
基i)-SO3M,其中M選自由以下組成之群:H+、Na+、K+、Li+、NH4 +、Ca2+及Mg2+,ii)-OSO3M,其中M選自由以下組成之群:H+、Na+、K+、Li+、NH4 +、Ca2+及Mg2+,iii)-CO2M,其中M選自由以下組成之群:H+、Na+、K+、Li+、NH4 +、Ca2+及Mg2+,iv)銨基,其選自由以下組成之群:-N(CH3)4 +、-N(CH2CH3)4 +、-N(C3H7)4 +、-N(C4H9)4 +及-N(C5H11)4 +,及v)烷基,其選自由以下組成之群:-CH3、-C2H5、-C3H7、-C4H9、-C5H11、-C6H13、-C7H15、-C8H17、-C9H19、-C10H21、-C11H23及-C12H25。
官能基i)、ii)、iii)及iv)在根據本發明之化合物用於基於水之組成物時為較佳的,而官能基v)(或無氫原子經此等官能基i)至v)中任一者取代之化合物)對於基於有機溶劑之組成物為較佳的。
根據如本發明化合物之較佳具體實例,雜芳香族或雜芳香族基團K之1、2、3或4個氫原子,較佳1或2個氫原子經以上所提及之選自由磺酸基、硫酸基、銨基及脂族基組成之群的官能基中之一者取代。
如在根據本發明之化合物中,芳香族基團K之兩個或大於兩個氫原子可經以上所提及之官能基中任一者取代,此等基團可相同或不同。然而,根據如本發明化合物之一尤其較佳具體實例,官能基為-SO3M,其中M選自由以下組成之群:H+、Na+、K+、Li+、NH4 +、Ca2+及Mg2+,且若芳香族基團K之大於一個氫原子經官能基取代,則所有此等基團為-SO3M
基團,其中M選自由以下組成之群:H+、Na+、K+、Li+、NH4 +、Ca2+及Mg2+。
根據如本發明化合物之第一具體實例,K表示單環芳香族基團或單環雜芳香族基團,且式Ia之結構次單元Ia'或式Ib之結構次單元Ib'
其中- Y表示S、O或NR",其中R"表示氫原子或具有1至20個碳原子之脂族基,較佳C1-C10烷基,- R選自由以下組成之群:H、-SO3M、-OSO3M、-CO2M、-N(CH3)4 +、
-N(CH2CH3)4 +、-N(C3H7)4 +、-N(C4H9)4 +、-N(C5H11)4 +、-CH3、-C2H5、-C3H7、-C4H9、-C5H11、-C6H13、-C7H15、-C8H17、-C9H19、-C10H21、-C11H23及-C12H25,其中M選自由以下組成之群:H+、Na+、K+、Li+、NH4 +、Ca2+及Mg2+,且其中點線指示與A之鍵結。
根據如本發明之第一具體實例之化合物,尤其較佳化合物為其中X表示O且其中滿足每個實體K之取代基R之以下組合的化合物:n=2,及R=1×-SO3M及3×H或R=2×-SO3M及2×H,或n=3,及R=3×H及3×-SO3M,其中M選自由以下組成之群:H+、Na+、K+、Li+、NH4 +、Ca2+及Mg2+。
根據如本發明化合物之第二具體實例,K表示雙環芳香族基團(亦即,K係基於萘基)或雙環雜芳香族基團。
在第二具體實例化合物之此第一變體為尤其較佳之情形下,其中X表示O,且其中滿足每個實體K之取代基R之以下組合:R=2×-SO3M及4×H,或R=3×-SO3M及3×H,其中M選自由以下組成之群:H+、Na+、K+、Li+、NH4 +、Ca2+及Mg2+。
其中R選自由以下組成之群:H、-SO3M、-OSO3M、-CO2M、-N(CH3)4 +、-N(CH2CH3)4 +、-N(C3H7)4 +、-N(C4H9)4 +、-N(C5H11)4 +、-CH3、-C2H5、-C3H7、-C4H9、-C5H11、-C6H13、-C7H15、-C8H17、-C9H19、-C10H21、-C11H23及-C12H25,其中M選自由以下組成之群:H+、Na+、K+、Li+、NH4 +、Ca2+及Mg2+,且其中點線指示與A之鍵結。
其中R選自由以下組成之群:H、-SO3M、-OSO3M、-CO2M、-N(CH3)4 +、-N(CH2CH3)4 +、-N(C3H7)4 +、-N(C4H9)4 +、-N(C5H11)4 +、-CH3、-C2H5、-C3H7、-C4H9、-C5H11、-C6H13、-C7H15、-C8H17、-C9H19、-C10H21、-C11H23及-C12H25,其中M選自由以下組成之群:H+、Na+、K+、Li+、NH4 +、Ca2+及Mg2+,且其中點線指示與A之鍵結。
其中R選自由以下組成之群:H、-SO3M、-OSO3M、-CO2M、-N(CH3)4 +、-N(CH2CH3)4 +、-N(C3H7)4 +、-N(C4H9)4 +、-N(C5H11)4 +、-CH3、-C2H5、-C3H7、-C4H9、-C5H11、-C6H13、-C7H15、-C8H17、-C9H19、-C10H21、-C11H23及-C12H25,其中M選自由以下組成之群:H+、Na+、K+、Li+、NH4 +、Ca2+及Mg2+,且其中點線指示與A之鍵結。
其中R選自由以下組成之群:H、-SO3M、-OSO3M、-CO2M、-N(CH3)4 +、-N(CH2CH3)4 +、-N(C3H7)4 +、-N(C4H9)4 +、-N(C5H11)4 +、-CH3、-C2H5、-C3H7、-C4H9、-C5H11、-C6H13、-C7H15、-C8H17、-C9H19、-C10H21、-C11H23及-C12H25,其中M選自由以下組成之群:H+、Na+、K+、Li+、NH4 +、Ca2+及Mg2+,且其中點線指示與A之鍵結。
其中- Y表示S、O或NR",其中R"表示氫原子或具有1至20個碳原子之脂族基,較佳C1-C10烷基,- R選自由以下組成之群:H、-SO3M、-OSO3M、-CO2M、-N(CH3)4 +、-N(CH2CH3)4 +、-N(C3H7)4 +、-N(C4H9)4 +、-N(C5H11)4 +、-CH3、-C2H5、-C3H7、-C4H9、
-C5H11、-C6H13、-C7H15、-C8H17、-C9H19、-C10H21、-C11H23及-C12H25,其中M選自由以下組成之群:H+、Na+、K+、Li+、NH4 +、Ca2+及Mg2+,且其中點線指示與A之鍵結。
在第三具體實例化合物為尤其較佳之情形下,其中X表示O,且其中滿足每個實體K之取代基R之以下組合:R=2×-SO3M及6×H,或R=3×-SO3M及5×H,其中M選自由以下組成之群:H+、Na+、K+、Li+、NH4 +、Ca2+及Mg2+。
其中點線指示與X之鍵結。
應注意,儘管在通式Xa至Xg中,官能基展示為-SO3H基團,
此等基團當然亦可部分或完全中和且因此亦可以-SO3M基團形式存在,其中M選自由以下組成之群:H+、Na+、K+、Li+、NH4 +、Ca2+及Mg2+。
根據本發明之化合物可以簡單一步合成,其藉由使單環或多環芳香族或雜芳香族系統K,其中至少一個氫原子可經以上所提及之官能基取代,且其中在連接X之位置存在相應酸形式-XH,亦即- 在X=O之情況下為基團-OH,- 在X=S之情況下為基團-SH,- 在X=SO2之情況下為基團-SO2H,或- 在X=NR'之情況下為基團-NR'H,與氟化或全氟化芳族化合物,較佳具有選自由通式XIa至XIh組成之群的一般結構之全氟化芳族化合物:
在親核性芳香族取代反應中較佳在適合催化劑存在下反應來製備。可用於此目的之催化劑可選自由以下組成之群:鋰、鉀、氫化鋰、氫化鈉、第三丁醇鋰、第三丁醇鈉、第三丁醇鉀、二異丙胺基鋰、正丁基鋰、第二丁基鋰、第三丁基鋰、六甲基二矽烷胺基鋰、六甲基二矽烷胺基鈉、六甲基二矽烷胺基鉀、氫氧化鋰、氫氧化鈉、氫氧化鉀、氫氧化鋇、氧化鋇、碳酸鋰、碳酸鈉、碳酸鉀、碳酸銫、碳酸鈣、碳酸氫鈉、三乙胺、二異丙基乙胺、四甲基乙二胺、三伸乙基二胺、吡啶、二甲胺基吡啶、咪唑及其類似物;及脫水縮合劑,諸如鹽酸、硫酸、五氧化二磷、氯化鋁(III)、三氟化硼二乙基醚複合物、乙基二氯化鋁、二乙基氯化鋁及其類似物。較佳催化劑選自由氫氧化鈉、碳酸鈉及碳酸鉀組成之群。
該反應可在可溶解或分散離析物(亦即,單環或多環芳香族或雜芳香族系統K,其中在連接X之位置使用相應酸形式-XH;及氟化或全氟化芳族化合物)之任何溶劑中進行。較佳使用非質子極性有機溶劑,其較佳選自由以下組成之群:N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基吡咯啶酮、1,3-二甲基-2-咪唑啶酮、二甲亞碸、四氫呋喃及二烷。
可能的反應溫度一般在-50℃至所用溶劑之沸點的範圍內,且較佳在0至140℃範圍內。反應時間通常為0.1至100小時。反應完成後,
可藉由蒸餾掉反應溶劑、藉助於陽離子型交換樹脂使磺酸鹽質子化、用諸如甲醇或其類似物之溶劑操作萃取或藉由沉澱來進行純化。
包含以下之組成物亦對解決以上所提及之目標作出貢獻I)至少一種導電聚合物,II)至少一種溶劑,及III)至少一種根據本發明之化合物,其中該組成物較佳為分散液或溶液,尤其較佳分散液。
導電聚合物I)在本文中應理解為尤其意謂在氧化或還原後具有導電性之共軛聚合物之化合物類別。較佳地,認為此類共軛聚合物為導電聚合物,其在氧化後具有數量級為至少0.01μS cm-1之導電性。
根據本發明之組成物中之導電聚合物I)較佳包含至少一種視情況經取代之聚噻吩、聚吡咯或聚苯胺作為共軛聚合物。
其中z 代表視情況經取代之C1-C5伸烷基,
R 代表直鏈或分支鏈的視情況經取代之C1-C18烷基、視情況經取代之C5-C12環烷基、視情況經取代之C6-C14芳基、視情況經取代之C7-C18芳烷基、視情況經取代之C1-C4羥烷基或羥基,x 代表0至8之整數,且在多個基團R連接至Y之情況下,此等可相同或不同。
通式(A)及(B)因此應理解為x取代基R可連接至伸烷基Y。
尤其較佳為具有通式(B)之重複單元的聚噻吩,其中%代表視情況經取代之C2-C3伸烷基且x代表0或1。尤其較佳聚噻吩為視情況經取代之聚(3,4-伸乙二氧基噻吩)。
在本發明之上下文中,字首聚-應理解為意謂聚合物或聚噻吩中含有通式(A)及/或(B)之大於一個相同或不同重複單元。除通式(A)及/或(B)之重複單元之外,聚噻吩亦可包含其他重複單元,較佳至少50%、尤其較佳至少75%且最佳至少95%之所有聚噻吩重複單元展現通式(A)及/或(B),較佳通式(B)。聚噻吩含有通式(A)及/或(B)、較佳通式(B)之總計n個重複單元,n為2至2000、較佳2至100之整數。聚噻吩內之通式(A)及/或(B)、較佳通式(B)之重複單元可各自相同或不同。具有相同通式(B)重複單元之聚噻吩為較佳的。
聚噻吩較佳在末端基上攜帶H。
在本發明之上下文中,C1-C5伸烷基z較佳為亞甲基、伸乙基、伸正丙基、伸正丁基或伸正戊基。C1-C18烷基R較佳為直鏈或分支鏈C1-C18烷基,諸如甲基、乙基、正丙基或異丙基、正丁基、異丁基、第二丁
基或第三丁基、正戊基、1-甲基丁基、2-甲基丁基、3-甲基丁基、1-乙基丙基、1,1-二甲基丙基、1,2-二甲基丙基、2,2-二甲基丙基、正己基、正庚基、正辛基、2-乙基己基、正壬基、正癸基、正十一烷基、正十二烷基、正十三烷基、正十四烷基、正十六烷基或正十八烷基;C5-C12環烷基R為例如環戊基、環己基、環庚基、環辛基、環壬基或環癸基;C6-C14芳基R為例如苯基或萘基;及C7-C18芳烷基R為例如苄基、鄰甲苯基、間甲苯基、對甲苯基、2,3-二甲苯基、2,4-二甲苯基、2,5-二甲苯基、2,6-二甲苯基、3,4-二甲苯基、3,5-二甲苯基或2,4,6-三甲苯基。以上列舉用於藉助於實例說明本發明且不應視為排他的。
在本發明之上下文中,z基團及/或R基團之任何其他取代基包括許多有機基團,例如烷基、環烷基、芳基、芳烷基、烷氧基、鹵素、醚、硫醚、二硫化物、亞碸、碸、磺酸酯、胺基、醛、酮、羧酸酯(carboxylic ester)、羧酸、碳酸酯、羧酸酯(carboxylate)、氰基、烷基矽烷及烷氧基矽烷之基團以及甲醯胺基。
聚苯胺或聚吡咯之可能取代基包括例如上文所列之z及R基團及/或z及R基團之其他取代基。較佳為未經取代之聚苯胺。
導電聚合物I)中所包含之聚噻吩可為不帶電或陽離子型的。在較佳具體實例中,其為陽離子型,「陽離子型」僅與留存於聚噻吩主鏈上之電荷有關。根據R基團上之取代基,在結構單元中聚噻吩可帶有正電荷及負電荷,在該情況下正電荷位於聚噻吩主鏈上且負電荷(若存在)位於經磺酸酯基或羧酸酯基取代之R基團上。聚噻吩主鏈之正電荷可藉由可存在於R基團上之陰離子型基團部分或完全飽和。總體來看,在此等情
況下,聚噻吩可為陽離子型、不帶電或甚至陰離子型的。然而,在本發明之上下文中,認為所有均為陽離子型聚噻吩,因為聚噻吩主鏈上之正電荷至關重要。正電荷並展未於式中,因為不能明確指出其準確數目及位置。然而,正電荷數為至少1及至多n,其中n為聚噻吩內之所有重複單元(相同或不同)之總數。
為平衡正電荷,若此舉尚未藉由視情況經磺酸酯基或羧酸酯基取代且因此帶負電之R基團實現,則陽離子型聚噻吩需要陰離子作為相對離子。相對離子可為單體或聚合陰離子,聚合陰離子在下文中亦稱為聚陰離子。
聚合陰離子較佳優於單體陰離子,因為其促進膜形成,且由於其大小,會產生更具有熱穩定性之導電膜。在本文中聚合陰離子可為例如以下各酸之陰離子:聚合羧酸,諸如聚丙烯酸、聚甲基丙烯酸或聚順丁烯二酸;或聚合磺酸,諸如聚苯乙烯磺酸及聚乙烯磺酸。此等聚羧酸及聚磺酸亦可為乙烯羧酸及乙烯磺酸與其他可聚合單體(諸如丙烯酸酯及苯乙烯)之共聚物。其他較佳共聚物為聚苯乙烯磺酸、聚烷基苯乙烯及(氫化)異戊二烯/二烯之嵌段共聚物。
較佳聚陰離子為聚合羧酸或磺酸之陰離子。尤其較佳聚陰離子為聚苯乙烯磺酸(PSS)之陰離子。提供聚陰離子之聚酸之分子量較佳為1000至2 000 000,更佳2000至500 000。聚酸或其鹼金屬鹽為市售可得,例如聚苯乙烯磺酸及聚丙烯酸,或者可藉由已知方法製備(參見例如Houben Weyl,Methoden der organischen Chemie[Methods of Organic Chemistry],第E 20卷Makromolekulare Stoffe[Macromolecular Substances],第2部分,(1987),第
1141頁及以下各頁)。
聚陰離子及共軛聚合物(亦即,聚噻吩、聚吡咯或聚苯胺,其視情況經取代)可尤其以0.5:1至50:1、較佳地1:1至30:1、更佳2:1至20:1之重量比存在於根據本發明之組成物中。在本文中共軛聚合物之重量與所用單體之初始重量對應,假定在聚合中完全轉化。
所用單體陰離子為例如C1-C20烷磺酸(諸如甲烷磺酸、乙烷磺酸、丙烷磺酸、丁烷磺酸或高碳磺酸(諸如十二烷磺酸))、脂族全氟磺酸(諸如三氟甲烷磺酸、全氟丁烷磺酸或全氟辛烷磺酸)、脂族C1-C20羧酸(諸如2-乙基己基羧酸)、脂族全氟羧酸(諸如三氟乙酸或全氟辛酸)及視情況經C1-C20烷基取代之芳族磺酸(諸如苯磺酸、鄰甲苯磺酸、對甲苯磺酸或十二烷基苯磺酸)及環烷磺酸(諸如樟腦磺酸)之陰離子;或四氟硼酸根、六氟磷酸根、過氯酸根、六氟銻酸根、六氟砷酸根或六氯銻酸根。較佳單體陰離子為對甲苯磺酸、甲烷磺酸或樟腦磺酸之陰離子。
含有陰離子作為相對離子以平衡電荷之陽離子型聚噻吩在技術領域中通常亦稱為聚噻吩/(聚)陰離子複合物。因此,尤其較佳為在根據本發明之組成物中導電聚合物I)包含聚噻吩與單陰離子或聚陰離子或兩者之組合的複合物,較佳聚(3,4-伸乙二氧基噻吩)(PEDOT)與聚苯乙烯磺酸(PSS)之複合物,亦稱為「PEDOT/PSS」複合物。在用於製備聚噻吩(如3,4-伸乙二氧基噻吩)之單體在聚陰離子存在下在適合溶劑(如水)中氧化聚合時可獲得此類複合物,如例如揭示於EP 0 440 957 A2中。聚噻吩與聚陰離子之複合物,特定言之PEDOT/PSS複合物較佳以粒子形式存在於根據本發明之組成物中。
根據本發明之組成物亦包含至少一種溶劑II)作為另一組分。
較佳溶劑為- 水,- 選自由脂族烴組成之群的有機溶劑,諸如庚烷、己烷、戊烷、辛烷,- 萜烯或石油醚,- 芳香族烴,諸如苯、甲苯、二甲苯、1,3,5-三甲苯、聯苯,- 醚,諸如二***、二異丙醚、甲基第三丁醚、二丁醚、二苯醚、苯甲醚及乙二醇醚,諸如聚乙二醇(PEG)、乙二醇單甲醚、乙二醇單***、乙二醇單丁醚、乙二醇單苯醚、二乙二醇單甲醚、二乙二醇單***、乙二醇二甲醚、乙二醇二***、丙二醇單丙醚、二丙二醇單甲醚、二丙二醇二甲醚、二乙二醇單甲醚或乙二醇二丁醚,- 酯,諸如乙酸甲酯、乙酸乙酯、乙酸丙酯或乙酸丁酯、苯甲酸甲酯、苯甲酸乙酯、苯甲酸丙酯、苯甲酸丁酯、γ-丁內酯、δ-戊內酯、γ-戊內酯、乙二醇甲醚乙酸酯、乙二醇單***乙酸酯、乙二醇單丁醚乙酸酯、丙二醇甲醚乙酸酯,- 鹵化烴,諸如二氯甲烷、二氯乙烷、氯苯、氯仿、四氯甲烷、三氯乙烷或三氯乙烯,- 脂族腈,諸如乙腈,- 脂族亞碸及碸,諸如二甲亞碸或環丁碸,- 脂族羧酸,諸如乙酸,- 脂族羧酸醯胺,諸如乙醯胺、二甲基乙醯胺或二甲基甲醯胺,及酮,
諸如丙酮或甲基第三丁基酮,- 醇,諸如甲醇、乙醇、丙醇、丁醇、己醇、萜品醇、1,2-丙二醇、乙二醇或十二醇,- 縮醛,諸如乙二醇二甲醚(二甲氧基乙烷)、二乙二醇二甲醚、四乙二醇二甲醚或二氧戊環,- 碳酸酯,諸如碳酸伸丙酯或碳酸伸乙酯- 及其他溶劑類,如寡聚矽氧烷或聚矽氧烷,- 及此等溶劑中之至少兩者的混合物。
根據本發明之組成物包含至少一種根據本發明之化合物作為組分III),其中根據本發明之組成物較佳包含量以組成物之總重量計在各情況下為0.01至10wt.-%、較佳0.1至7.5wt.-%且最佳0.5至5wt.-%之至少一種化合物III)。至少一種化合物III)與導電聚合物I)之重量比(在聚噻吩/(聚)陰離子複合物之情況下,至少一種化合物III)及聚噻吩與聚陰離子之總重量之重量比)較佳在1:100至100:1範圍內,更佳在1:10至10:1範圍內且最佳在1:5至5:1範圍內。
除至少一種導電聚合物I)、至少一種溶劑II)及至少一種根據本發明之化合物III)之外,根據本發明之組成物可包含不同於組分I)、II)及III)之其他添加劑IV),諸如- 表面活性物質,例如陰離子界面活性劑,諸如烷基苯磺酸及鹽、石蠟磺酸鹽、醇磺酸鹽、醚磺酸鹽、磺基丁二酸鹽、磷酸酯、烷基醚羧酸或羧酸鹽,陽離子界面活性劑,諸如四級烷基銨鹽,非離子界面活性劑,諸如直鏈醇乙氧基化物、含氧醇乙氧基化物、烷基酚乙氧基化物或烷基聚葡
糖苷,- 黏著促進劑,諸如有機官能性矽烷或其水解產物,例如3-縮水甘油氧丙基三烷氧基矽烷、3-胺丙基三乙氧基矽烷、3-巰基丙基三甲氧基矽烷、3-甲基丙烯醯氧丙基三甲氧基矽烷、乙烯基三甲氧基矽烷或辛基三乙氧基矽烷,或- 交聯劑,諸如三聚氰胺化合物、遮蔽異氰酸酯、官能性矽烷(例如四乙氧基矽烷)、烷氧基矽烷水解產物(例如基於四乙氧基矽烷)、環氧矽烷(諸如3-縮水甘油氧丙基三烷氧基矽烷)、環氧化物或環氧丙烷、胺、四級胺、多元胺或四級多元胺,- 黏合劑,諸如聚伸烷基二醇、聚丙烯酸酯、聚胺基甲酸酯、聚酯、聚醚、聚醯胺或聚乙烯醇,或- 提高導電性之添加劑,諸如:聚伸烷基二醇,特定言之聚乙二醇或聚丙二醇、聚丙三醇或此等之混合物;多元醇,諸如丙二醇及乙二醇;亞碸,諸如二甲亞碸;羧酸醯胺,諸如甲基乙醯胺、二甲基乙醯胺、二甲基甲醯胺;N-甲基吡咯啶酮;N-環己基吡咯啶酮;離子液體;糖,諸如山梨糖醇。
此等添加劑之量當然將視添加劑性質而定,但以組成物之總重量計通常在0至20wt.-%、更佳1至15wt.-%且最佳2.5至10wt.-%之範圍內。
較佳地,根據本發明之組成物在各情況下包含以組成物之總重量計
I)0.01至10wt.-%、更佳0.1至7.5wt.-%且最佳0.5至5wt.-%之導電聚
合物;III)0.01至10wt.-%、更佳0.1至7.5wt.-%且最佳0.2至5wt.-%之至少一種根據本發明之化合物;IV)0至20wt.-%、更佳1至15wt.-%且最佳2.5至10wt.-%之不同於組分I)、II)及III)之其他添加劑IV),其中其餘物為溶劑II)。
根據本發明之組成物此外較佳在25℃溫度下具有在1至12範圍內,尤其較佳在4至8範圍內之pH。根據本發明之組成物在20℃下之黏度較佳小於1,000mPas,較佳小於400mPas。
根據本發明之組成物之固體含量較佳在0.1至10wt.%範圍內,尤其較佳在0.5至7.5wt.%範圍內且最佳在1至5wt.%範圍內。
根據本發明之組成物可藉由各種方法獲得。
- 根據第一具體實例,根據本發明之組成物可藉由在根據本發明之化合物III)存在下在適當溶劑中將用於製備導電聚合物I)之單體(諸如3,4-伸乙二氧基噻吩)氧化聚合來獲得。用於聚合反應之溶劑可為存在於根據本發明之組成物中的溶劑II),然而,亦有可能用不同溶劑取代用於聚合反應之溶劑(此類方法揭示於例如US 6,692,662 B2中)或添加另一溶劑至用於聚合反應之溶劑中以獲得溶劑混合物。
- 根據第二(且較佳)具體實例,根據本發明之組成物可藉由僅添加根據本發明之化合物III)至已包含導電聚合物I)之組成物,較佳PEDOT/PSS水性分散液中來獲得。在此情況下,亦有可能的是用於聚合反應之溶劑可為存在於根據本發明之組成物中的溶劑II),或用於聚合反應之溶劑經不同
溶劑取代,如揭示於例如US 6,692,662 B2中,或添加另一溶劑至用於聚合反應之溶劑中以獲得溶劑混合物。在此情況下
在必要時,將藉由以上所提及之方法中之一者獲得的組分I)、II)及III)之混合物加熱直至所有組分溶解,其中最高溫度當然將視所用溶劑之沸點而定。
製備導電層之方法亦對解決以上所提及之目標作出貢獻,該方法包含以下方法步驟:(P1)用根據本發明之組成物疊加基板或首先用包含溶劑及根據本發明之化合物的組成物(但不一定包含導電聚合物)疊加基板,至少部分移除溶劑,且隨後用根據本發明之組成物或用包含溶劑及導電聚合物之組成物(但不一定包含根據本發明之化合物)疊加基板;或首先用包含溶劑及導電聚合物之組成物(但不一定包含根據本發明之化合物)疊加基板,至少部分移除溶劑,且隨後用根據本發明之組成物或用包含溶劑、根據本發明之化合物的組成物(但不一定包含導電聚合物)疊加基板;(P2)至少部分移除溶劑。
在方法步驟(P1)中,基板用根據本發明之組成物(或用包含溶劑及導電聚合物I)或根據本發明之化合物III)之組成物)疊加。可用於電子組件,諸如OLED中之所有層適合作為基板。因此,特定言之,基
板可為裝備有較佳透明底部電極之基板,基板自身較佳亦為透明的。舉例而言,玻璃、PET或其他透明塑膠可用作透明基板,隨後在其上引入透明導電電極,諸如由氧化銦錫(ITO)製成、摻雜有氧化鋅或氧化錫或導電聚合物之電極。尤其適合之透明塑膠基板為例如聚碳酸酯、聚酯(諸如聚對苯二甲酸伸乙酯及聚萘二甲酸伸乙酯(PET及PEN))、共聚碳酸酯、聚丙烯酸酯、聚碸、聚醚碸(PES)、聚醯亞胺、聚乙烯、聚丙烯、環狀聚烯烴或環狀烯烴共聚物(COC)、水合苯乙烯聚合物或水合苯乙烯共聚物。適合聚合物基質亦可例如為膜,諸如聚酯膜、來自Sumitomo公司之PES膜或來自Bayer AG公司之聚碳酸酯膜(Makrofol®)。根據本發明,經ITO塗佈之玻璃尤其較佳作為基板。
用根據本發明之組成物或用包含溶劑及導電聚合物或根據本發明之化合物之組成物疊加基板可隨後藉由已知方法實現,例如藉由以0.1μm至250μm濕膜厚度、較佳0.5μm至50μm濕膜厚度旋塗、浸漬、澆注、滴加、注入、噴塗、刮塗、鋪展或印刷(例如噴墨、網板、凹版、平版或移印),且隨後在20℃至200℃之溫度下乾燥。
在方法步驟(P2)中,隨後至少部分移除已塗覆組成物中所含之溶劑,獲得包含導電聚合物I)及根據本發明之化合物III)之導電層,該移除較佳藉由簡單蒸發進行。
根據如本發明方法之一尤其較佳具體實例,方法步驟(P1)及(P2)僅為製造OLED之兩個步驟。如上所述,OLED通常包含陽極電洞注入層
發光體層,及陰極,其中電洞注入層較佳藉由根據本發明之方法製備。OLED可包含其他層,諸如位於電致發光層與陰極之間的電子注入層。
已使用根據本發明之組成物製備電洞注入層之OLED可例如展現以下層結構(a)至(h)中任一者:
(a)陽極/
電洞注入層/
至少一個發光體層/
陰極;
(b)陽極/
電洞注入層/
電洞傳輸層/
至少一個發光體層/
陰極;
(c)陽極/
電洞注入層/
至少一個發光體層/
電子注入層/
陰極;
(d)陽極/
電洞注入層/
電洞傳輸層/
至少一個發光體層/
電子注入層/
陰極;
(e)陽極/
電洞注入層/
至少一個發光體層/
電子傳輸層/
陰極;
(f)陽極/
電洞注入層/
電洞傳輸層/
至少一個發光體層/
電子傳輸層/
陰極;
(g)陽極/
電洞注入層/
至少一個發光體層/
電子傳輸層/
電子注入層/
陰極;
(h)陽極/
電洞注入層/
電洞傳輸層/
至少一個發光體層/
電子傳輸層/
電子注入層/
陰極。
層結構(a)至(h)可藉由位於基板(該基板為例如玻璃或透明塑膠膜)附近之陽極或位於基板附近之陰極實施。
陽極層較佳基於氧化銦錫、氧化銦鋅、摻雜氟之氧化錫、三氧化鎢、二氧化鈦、三氧化鉬、氧化鋁鋅、氧化鎵銦鋅、鋁、銀、鈀、銅、金、鉑及其合金,例如銀-鈀-銅及鉬-鉻。
適用於發光體層之物質為共軛聚合物,諸如聚伸苯基-伸乙烯基及/或聚茀,例如WO-A-90/13148中所述之聚對伸苯基伸乙烯基衍生物及聚茀衍生物;或來自低分子量發光體類別之發光體,在技術界亦稱為「小分子」,諸如鋁錯合物(諸如參(8-羥基喹啉根基)鋁(Alq3))、螢光染料(例如喹吖啶酮)或磷光發光體(諸如Ir(ppy)3)。其他適用於發光體層之物質描述於例如DE-A-196 27 071中。根據本發明,尤其較佳作為發發光體的為參(8-羥基喹啉根基)鋁(Alq3)。
較佳作為注入層的為單個Ca層或由Ca層及另一層組成之堆疊結構,該另一層由選自群IA及IIA之一或多種物質組成。較佳作為注入層的為單個Ca層或由Ca層及另一層組成之堆疊結構,該另一層由選自週期表之展現1.5至3.0eV功函數的IA及IIA族金屬(不包括Ca)及氧化
物、鹵化物及其碳酸鹽之一或多種物質組成。週期表之展現1.5至3.0eV功函數的IA族金屬及氧化物、鹵化物及其碳酸鹽之實例為鋰、氟化鋰、氧化鈉、氧化鋰及碳酸鋰。週期表之展現1.5至3.0eV功函數的IIA族金屬(不包括Ca)及氧化物、鹵化物及其碳酸鹽之實例為鍶、氧化鎂、氟化鎂、氟化鍶、氟化鋇、氧化鍶及碳酸鎂。
電子傳輸層可由以下物質組成:諸如二唑衍生物、蒽醌二甲烷或其衍生物、苯醌或其衍生物、萘醌或其衍生物、蒽醌或其衍生物、四氰基蒽醌二甲烷或其衍生物、茀酮衍生物、二苯基二氰乙烯或其衍生物、聯苯醌衍生物,及8-羥基喹啉或其衍生物、聚喹啉或其衍生物、聚喹喏啉或其衍生物或聚茀或其衍生物之金屬錯合物。
尤其適用於陰極層之物質為具有相對較低功函數(較佳低於4.0eV)之透明或半透明物質。此類型物質之實例為金屬,諸如鋰(Li)、鈉(Na)、鉀(K)、銣(Rb)、銫(Cs)、Be、鎂(Mg)、鈣(Ca)、鍶(Sr)、鋇(Ba)、鋁(Al)、鈧(Sc)、釩(V)、Zn、釔(Y)、銦(In)、鈰(Ce)、釤(Sm)、Eu、Tb及鐿(Yb);由此等金屬中之兩者或大於兩者組成之合金;由此等金屬中之一或多者及選自Au、Ag、Pt、Cu、錳(Mn)、鈦(Ti)、鈷(Co)、鎳(Ni)、鎢(W)及錫(Sn)之一或多種金屬組成的合金;石墨或石墨插層化合物;及金屬氧化物,諸如ITO及氧化錫。尤其較佳為使用鋁作為陰極層。
可以熟習此項技術者已知之方式,較佳經由諸如描述於例如WO-A-2009/0170244中之蒸氣塗佈進行發光體層、電子注入層及陰極注入層之塗覆。
包含至少一種根據本發明之化合物之導電層亦對解決以上所提及之目標作出貢獻。根據如本發明導電層之一較佳具體實例,導電層進一步包含至少一種導電聚合物,其中彼等導電聚合物較佳已關於根據本發明之組成物提及為較佳導電聚合物I)。在此情形下,亦較佳的為導電層中至少一種根據本發明之化合物與至少一種導電聚合物之重量比(在聚噻吩/(聚)陰離子複合物之情況下,至少一種根據本發明之化合物及聚噻吩與聚陰離子之總重量之重量比)較佳在1:100至100:1範圍內,更佳在1:10至10:1範圍內且最佳在1:5至5:1範圍內。
包含可藉由根據本發明之方法獲得的導電層或包含根據本發明之導電層的電子組件亦對解決以上所提及之目標作出貢獻。根據如本發明電子組件之一較佳具體實例,此電子組件為OLED、顯示器、有機太陽能電池、混合太陽能電池、場效電晶體或熱電產生器。在OLED之情況下,此外較佳的為OLED之電洞注入層可藉由根據本發明之方法獲得或對應於根據本發明之導電層。
使用至少一種根據本發明之化合物作為OLED之電洞注入層中的添加劑亦對解決以上所提及之目標作出貢獻。
現將藉助於非限制性實施例進一步說明本發明。
實施例
實施例1A:合成化合物Xa
將變色酸二鈉鹽(2.00g,0.005mol)、碳酸鉀(2.76g,0.005mol)、十氟聯苯(8.35g,0.025mol)及50ml DMSO在120-130℃下加熱下攪拌歷經40小時。藉由1H-NMR光譜學控制反應。反應完成後,將其冷卻至室溫且過濾固體,含有其餘K2CO3及副產物KF。使來自濾液之DMSO在真空(1毫巴)下蒸發,且使過量十氟聯苯昇華。添加20mL水至殘餘物中,且沉澱出呈白色固體狀之產物,過濾其且用冷水洗滌。濾餅在真空下乾燥,得到2.27g純化合物Xa,其對應於69%分離產率。
1H NMR(300MHz,DMSO-d6)δ=8.12(s,2H),7.65(d,J=15.9Hz,2H);19F NMR(282MHz,DMSO-d6)δ=-55.6(m),-59.5(m),-60.2(m),-70.0(m),-78.7(m),-82.7(m)。
在調配之前,使化合物Xa再結晶。將其溶解於H2O(固體含量1%)中且加熱至90℃。熱溶液經由針筒過濾器(PVDF,0.8μm)過濾,且濃縮。
實施例1B:合成化合物Xe
使3,6-二羥基萘-2,7-二磺酸二鈉鹽與六氟苯及碳酸鉀(1:4:10莫耳比)在DMF(濃度為每1L DMF 40g 3,6-二羥基萘-2,7-二磺酸二鈉鹽)中在130℃下反應。藉由1H-NMR光譜學控制反應。在120-130℃下加熱20h後,根據1H-NMR光譜學,反應完成。將混合物冷卻至室溫且過濾固體,含有其餘K2CO3及副產物KF。將來自濾液之DMSO及過量六氟苯在真空(1毫巴)下蒸發。添加水(每25mL初始量DMSO 10mL)至殘餘物中,且沉澱出呈白色固體狀之產物,過濾其,用水洗滌且在真空(1毫巴)下乾燥,得到第一部分化合物Xe。將所形成之濾液蒸發至其初始體積之大約50%,且在冷凍機中在4℃下冷卻隔夜。沉澱出呈白色固體狀之新產物部分,再次過濾其,用水洗滌且在真空(1毫巴)中乾燥,得到呈白色固體狀之第二部分化合物Xe。化合物Xe之總產率為67%。
1H NMR(300MHz,DMSO)δ 8.31(s,2H),7.07(s,2H);19F NMR(282MHz,DMSO)δ=-76.0(m),-83.0(m),-84.3(m)。
實施例1C:合成化合物Xg(可溶於有機溶劑)
將K2CO3(1.1g,0.008mol)及十氟聯苯(3g,0.009mol)懸浮於無水N,N-二甲基乙醯胺(10ml)中且加熱至100℃。在92-97℃下緩慢添加溶解於DMAc(10ml)中之1,3,5-三羥基苯(0.25g,0.002mol)歷經4h時段。完成添加後,將反應混合物加熱至120℃直至TLC證實起始物質完全消耗。將混合物濃縮,且向殘餘物中緩慢添加稀NH4Cl溶液(1g NH4Cl/20ml H2O)。用MTBE萃取水相3次。合併之有機層用鹽水洗滌且經Na2SO4脫水。蒸發溶劑後,澄清黃色高黏性油狀物藉由管柱層析經SiO2(沖提劑:甲苯)純化。分離出呈淡黃色高黏性油狀之產物(2.1g,0.002mol,數量)。
LC-MS(ESI;H2O/MeCN梯度0.8g/L NH4OAc)M=1068;1H
NMR(400MHz,CDCl3):δ=6.49。
實施例2:調配PEDOT:PSS與化合物Xa之分散液
實施例2A(化合物Xa之固體含量=0.7%):
將0.42g化合物Xa溶解於30g Clevios P VPAI 4083(Heraeus Precious Metals GmbH & Co.KG,1.5%固體含量)中。添加24g水,且在室溫下攪拌混合物30min,且隨後加熱(1h,40℃)直至所有固體完全溶解。將混合物冷卻至室溫(1h),添加6g乙醇且再攪拌混合物30min。老化3h後,分散液隨後經由0.8μm及0.45μm針筒過濾器(PVDF)過濾。
實施例2B(化合物Xa之固體含量=0.47%):
將0.28g化合物Xa溶解於40g Clevios P VPAI 4083(Heraeus Precious Metals GmbH & Co.KG,1.5%固體含量)中。添加14g水,且在室溫下攪拌混合物30min,且隨後加熱(1h,40℃)直至所有固體完全溶解。將混合物冷卻至室溫(1h),添加6g乙醇且再攪拌混合物30min。老化3h後,分散液隨後經由0.8μm及0.45μm針筒過濾器(PVDF)過濾。
實施例2C(化合物Xa之固體含量=0.3%):
將0.18g化合物Xa溶解於40g Clevios P VPAI 4083(Heraeus
Precious Metals GmbH & Co.KG,1.5%固體含量)中。添加14g水,且在室溫下攪拌混合物30min,且隨後加熱(1h,40℃)直至所有固體完全溶解。將混合物冷卻至室溫(1h),添加6g乙醇且再攪拌混合物30min。老化3h後,分散液隨後經由0.8μm及0.45μm針筒過濾器(PVDF)過濾。
實施例2D(化合物Xa之固體含量=1.05%):
將0.63g化合物Xa溶解於30g Clevios P VPAI 4083(Heraeus Precious Metals GmbH & Co.KG,1.5%固體含量)中。添加24g水,且在室溫下攪拌混合物30min,且隨後加熱(1h,55℃)直至所有固體完全溶解。將混合物冷卻至室溫(1h),添加6g乙醇且再攪拌混合物30min。老化3h後,分散液經由0.8μm針筒過濾器(PVDF)過濾。對於經由0.45μm針筒過濾器過濾,在過濾之前有必要進行3h超音波處理(Sonorex R1028,Bandelin)。
實施例3:製造具有含有化合物Xa之導電層之OLED
使用實施例2A至2B中所獲得之分散液來建構有機發光二極體(OLED)。製造OLED之程序為如下:
i)製備基板
將經ITO塗佈之玻璃切成大小為50mm×50mm之片(基板),且用光阻建構出8根接觸線-在其末端各2mm寬。其後,將基板在超音波浴中在0.3%強度Mucasol溶液中清潔,用蒸餾水沖洗且以離心旋乾。緊接著在塗佈之前,將經ITO塗佈之側在UV/臭氧反應器(PR-100,UVP Inc.,Cambridge,GB)中活化10min。
ii)塗覆電洞注入層
將根據實施例2A至2D之約5ml分散液過濾(Millipore HV,0.45μm)。將清潔的經ITO塗佈之基板放於旋塗機(Carl Süss RC8)上,且將經過濾溶液分佈於基板之經ITO塗佈之側上。隨後藉由旋轉板30sec甩掉過量溶液。調整旋轉速度以始終獲得用觸針式表面輪廓儀(Dektak 150,Bruker)測定之為50nm(乾膜)之層厚度。其後,使以此方式塗佈之基板在加熱板上在200℃下乾燥5min。
iii)塗覆電洞傳輸層及發射極層
將用來自實施例2A至2D之分散液塗佈之ITO基板轉移至氣相沉積單元(Univex 350,Leybold)中。在低於10-3Pa壓力下,以1Å/sec氣相沉積速率連續氣相沉積首先N,N'-雙(萘-1-基)-N,N'-雙(苯基)-聯苯胺(N,N'-bis(naphthalen-1-yl)-N,N'-bis(phenyl)-benzidine;NPB)之60nm電洞傳輸層且隨後參-(8-羥基喹啉)-鋁(tris-(8-hydroxyquinoline)-aluminium;AlQ3)之50nm發光體層。
iv)塗覆金屬陰極
隨後將層系統轉移至具有N2氛圍及整合式氣相沉積單元(Auto306 Vacuum Coater,Edwards)之手套箱中,且氣相沉積金屬電極。為此,將基板以層系統向下放於陰影遮罩上。陰影遮罩包含2mm寬矩形槽,其與ITO長條相交且定向為垂直於此長條。在p<=10-3Pa壓力下由兩個氣相沉積舟連續氣相沉積0.5nm厚LiF層及隨後200nm厚Al層。氣相沉積速率對於LiF為1Å/s且對於Al為10Å/s。個別OLED之面積為4.0mm2。
v)層堆疊概述
實施例3A:ITO//來自實施例2A之調配物(50nm)//NPB//ALQ//LiF//Al
實施例3B:ITO//來自實施例2B之調配物(50nm)//NPB//ALQ//LiF//Al
實施例3C:ITO//來自實施例2C之調配物(50nm)//NPB//ALQ//LiF//Al
實施例3D:1TO//來自實施例2D之調配物(50nm)//NPB//ALQ//LiF//Al
vi)OLED特性鑑定
有機LED之兩個電極經由電導線與源極/量測單元(Keithley 2400)連接(接觸)。正極連接至ITO電極且負極連接至金屬電極。標繪出OLED電流及電致發光強度(用光電二極體(EG&G C30809E)+靜電計(Keithley 6415)進行偵測)對電壓之依賴性。隨後藉由使I=3.84mA恆定電流流經配置且監測隨時間變化之電壓及光強度來測定OLED裝置之壽命。
OLED之特性資料概述於表1中。
比較實施例4:製造不含化合物Xa之OLED
程序與實施例3中相同,不同之處在於在第二方法步驟中,被視為OLED構造中之標準的Clevios P VP AI4083(Heraeus Precious Metals GmbH & Co.KG)單獨用作夾層而非來自實施例2A至2D之根據本發明的分散液。根據實施例3沉積Clevios © P VP AI4083。膜厚度為50nm。
OLED之特性資料概述於表1中。
層堆疊:
比較實施例4 ITO//Clevios P VP AI4083(50nm)//NPB//ALQ//LiF//Al
實施例5:測定電阻率
藉由量測膜之薄層電阻及其層厚度來測定CleviosTM膜之電阻率。藉由將1-2ml聚合物分散液沉積於50mm×50mm玻璃基板上來製備膜。在沉積前,將1mm厚度玻璃基板在超音波浴中在0.3%強度Mucasol溶
液中澈底清潔,用蒸餾水沖洗且以離心旋乾。作為最後一步,藉由UV/臭氧曝曬(PR-100UV/臭氧UVP,Cambridge,GB)持續15min使待塗佈之表面活化。隨後,將玻璃基板置於旋塗機(Carl Süss RC8)之夾盤中。藉由在1000rpm下旋轉玻璃板30sec來移除覆蓋分散液。獲得薄而均勻之膜。將膜傳送至設置為130℃之加熱板且在此處放置5min至乾燥。
在下一步驟中,用陰影遮罩覆蓋膜。該遮罩由大小為50mm×50mm之100μm厚鋼片製成,展現在中心加工之6個平行縫隙(長度L:25.0mm,寬度b:3.0mm,縫隙間距:a=500μm)。遮罩由磁鐵自經塗佈之基板的背面固持。基板安裝在具有電熱加熱舟之用於Ag蒸發的真空蒸鍍機(Univex 350,Leybold)中。將容器抽空至6×10-4Pa壓力。在達到此壓力時,以20Å/sec速率熱蒸鍍Ag直至達到2000Å之最終電極厚度。
用靜電計(Keithley 616)在自製裝置中量測相鄰Ag電極之間的電阻R,在該裝置中,樣品安裝在真空腔室中且Au觸針壓於Ag電極上。
藉由用刀片將膜刮下基板且在刮膜上掃描機械表面輪廓儀(Dektak 150,Bruker)之觸針來測定膜厚度d。
最後,根據ro=R×L/b×d藉由薄層電阻乘以層厚度來計算電阻率「ro」。
由根據實施例2A至2D之分散液製成的膜之電阻率展示於表1中。
實施例6:比較來自實施例3及4之OLED
比較標繪出來自實施例3及4的OLED之電流及電致發光對
比電壓及壽命量測值的圖表。
可觀測到所有實施例3A至3D與標準(比較實施例4)相比之壽命顯著增加。
Claims (6)
- 一種製備導電層之方法,其包含以下方法步驟:(P1)用如申請專利範圍第1項之組成物疊加基板;或首先用包含該溶劑II)及如申請專利範圍第1項所定義之化合物III)的組成物疊加基板,至少部分移除該溶劑II),且隨後用如申請專利範圍第1項之組成物或用包含該溶劑II)及如申請專利範圍第1項所定義之該導電聚合物I)之組成物疊加該基板;或首先用包含該溶劑II)及如申請專利範圍第1項所定義之該導電聚合物I)之組成物疊加基板,至少部分移除該溶劑II),且隨後用如申請專利範圍第1項之組成物或用包含該溶劑II)及如申請專利範圍第1項所定義之化合物III)的組成物疊加該基板;(P2)至少部分移除該溶劑II)。
- 一種導電層,其包含至少一種如申請專利範圍第1項所定義之化合物III)。
- 一種電子組件,其包含可藉由如申請專利範圍第2項之方法獲得之導電層或包含如申請專利範圍第3項之導電層。
- 如申請專利範圍第4項之電子組件,其中該電子組件為OLED、顯示器、有機太陽能電池、混合太陽能電池、場效電晶體或熱電產生器。
- 一種至少一種如申請專利範圍第1項所定義之化合物之用途,其用作OLED之電洞注入層或有機太陽能電池中之添加劑。
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2014
- 2014-11-18 EP EP21174566.6A patent/EP3886194A3/en not_active Withdrawn
- 2014-11-18 EP EP14193716.9A patent/EP3024049B1/en active Active
-
2015
- 2015-11-13 TW TW104137504A patent/TWI690519B/zh not_active IP Right Cessation
- 2015-11-17 CN CN201580062284.XA patent/CN107112422B/zh not_active Expired - Fee Related
- 2015-11-17 US US15/525,202 patent/US10658598B2/en not_active Expired - Fee Related
- 2015-11-17 JP JP2017523941A patent/JP6820846B2/ja active Active
- 2015-11-17 KR KR1020177016661A patent/KR20170086078A/ko not_active Application Discontinuation
- 2015-11-17 WO PCT/EP2015/076868 patent/WO2016079144A1/en active Application Filing
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1405849A1 (en) * | 2002-10-04 | 2004-04-07 | Corning Incorporated | Halogenated styrene compounds and low-absorption-loss polymers obtainable therefrom |
EP1640372A1 (en) * | 2003-06-25 | 2006-03-29 | Nissan Chemical Industries, Ltd. | 1,4-benzodioxane sulfonic acid compound and use thereof as electron-acceptor material |
JP2007176921A (ja) * | 2005-07-01 | 2007-07-12 | Nippon Shokubai Co Ltd | ベンゾニトリル化合物、その製造方法及び用途 |
US20100320422A1 (en) * | 2008-01-29 | 2010-12-23 | Naoki Nakane | Arylsulfonic acid compound and use thereof as electron-acceptor material |
Also Published As
Publication number | Publication date |
---|---|
EP3886194A2 (en) | 2021-09-29 |
JP2017537077A (ja) | 2017-12-14 |
EP3886194A3 (en) | 2021-10-20 |
CN107112422B (zh) | 2020-03-03 |
EP3024049B1 (en) | 2021-08-25 |
EP3024049A1 (en) | 2016-05-25 |
US10658598B2 (en) | 2020-05-19 |
KR20170086078A (ko) | 2017-07-25 |
CN107112422A (zh) | 2017-08-29 |
WO2016079144A1 (en) | 2016-05-26 |
TW201630893A (zh) | 2016-09-01 |
JP6820846B2 (ja) | 2021-01-27 |
US20170365798A1 (en) | 2017-12-21 |
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