WO2012143109A1 - Amines fluorées en tant que sam dans des del organiques - Google Patents
Amines fluorées en tant que sam dans des del organiques Download PDFInfo
- Publication number
- WO2012143109A1 WO2012143109A1 PCT/EP2012/001631 EP2012001631W WO2012143109A1 WO 2012143109 A1 WO2012143109 A1 WO 2012143109A1 EP 2012001631 W EP2012001631 W EP 2012001631W WO 2012143109 A1 WO2012143109 A1 WO 2012143109A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- layer
- fluorinated
- layer body
- alkyl radical
- body according
- Prior art date
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- 150000001412 amines Chemical class 0.000 title claims abstract description 49
- 108010038083 amyloid fibril protein AS-SAM Proteins 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract description 52
- 229920001940 conductive polymer Polymers 0.000 claims abstract description 38
- 238000004519 manufacturing process Methods 0.000 claims abstract description 13
- 239000010410 layer Substances 0.000 claims description 273
- 238000002347 injection Methods 0.000 claims description 51
- 239000007924 injection Substances 0.000 claims description 51
- -1 poly(3,4- ethylenedioxythiophene) Polymers 0.000 claims description 49
- 229920000123 polythiophene Polymers 0.000 claims description 45
- 239000000758 substrate Substances 0.000 claims description 31
- 239000002253 acid Substances 0.000 claims description 28
- 229920000642 polymer Polymers 0.000 claims description 27
- 239000006185 dispersion Substances 0.000 claims description 22
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 239000004793 Polystyrene Substances 0.000 claims description 9
- 230000008021 deposition Effects 0.000 claims description 9
- 239000002270 dispersing agent Substances 0.000 claims description 9
- 229920002223 polystyrene Polymers 0.000 claims description 9
- 125000001153 fluoro group Chemical group F* 0.000 claims description 8
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 claims description 8
- 239000002356 single layer Substances 0.000 claims description 2
- 238000013086 organic photovoltaic Methods 0.000 claims 2
- 241000577218 Phenes Species 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 230000005525 hole transport Effects 0.000 description 20
- 239000013545 self-assembled monolayer Substances 0.000 description 19
- 239000000243 solution Substances 0.000 description 19
- 239000002094 self assembled monolayer Substances 0.000 description 17
- 229920000144 PEDOT:PSS Polymers 0.000 description 13
- 229920000447 polyanionic polymer Polymers 0.000 description 13
- 239000000463 material Substances 0.000 description 11
- 229910052751 metal Inorganic materials 0.000 description 11
- 239000002184 metal Substances 0.000 description 11
- 125000002091 cationic group Chemical group 0.000 description 8
- 238000000151 deposition Methods 0.000 description 8
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 8
- 150000002739 metals Chemical class 0.000 description 7
- 150000003254 radicals Chemical class 0.000 description 7
- 150000007513 acids Chemical class 0.000 description 6
- 239000011575 calcium Substances 0.000 description 6
- 239000011248 coating agent Substances 0.000 description 6
- 238000000576 coating method Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 5
- 150000001450 anions Chemical class 0.000 description 5
- 239000007800 oxidant agent Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000010414 supernatant solution Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 230000000903 blocking effect Effects 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- AQZYBQIAUSKCCS-UHFFFAOYSA-N perfluorotripentylamine Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)N(C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F AQZYBQIAUSKCCS-UHFFFAOYSA-N 0.000 description 4
- 238000007639 printing Methods 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 239000004411 aluminium Substances 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 3
- 230000015556 catabolic process Effects 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000006731 degradation reaction Methods 0.000 description 3
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 230000000737 periodic effect Effects 0.000 description 3
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- 229920002492 poly(sulfone) Polymers 0.000 description 3
- 229920002098 polyfluorene Polymers 0.000 description 3
- 229910052712 strontium Inorganic materials 0.000 description 3
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- GKWLILHTTGWKLQ-UHFFFAOYSA-N 2,3-dihydrothieno[3,4-b][1,4]dioxine Chemical compound O1CCOC2=CSC=C21 GKWLILHTTGWKLQ-UHFFFAOYSA-N 0.000 description 2
- PFINVJYJNJHTFY-UHFFFAOYSA-N 3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecan-1-amine Chemical compound NCCC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F PFINVJYJNJHTFY-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 229920000089 Cyclic olefin copolymer Polymers 0.000 description 2
- 239000004713 Cyclic olefin copolymer Substances 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical class [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- 229920002125 Sokalan® Polymers 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 230000001680 brushing effect Effects 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 239000003431 cross linking reagent Substances 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 229910002804 graphite Inorganic materials 0.000 description 2
- 239000010439 graphite Substances 0.000 description 2
- 238000005470 impregnation Methods 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 239000011572 manganese Substances 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 2
- 229920002120 photoresistant polymer Polymers 0.000 description 2
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 2
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 229920000128 polypyrrole Polymers 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 150000004756 silanes Chemical class 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
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- 239000000126 substance Substances 0.000 description 2
- 238000010345 tape casting Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
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- 229910001887 tin oxide Inorganic materials 0.000 description 2
- 239000010936 titanium Substances 0.000 description 2
- PYJJCSYBSYXGQQ-UHFFFAOYSA-N trichloro(octadecyl)silane Chemical compound CCCCCCCCCCCCCCCCCC[Si](Cl)(Cl)Cl PYJJCSYBSYXGQQ-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N zinc oxide Inorganic materials [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 1
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical group CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
- HZCZXRSVKNFILZ-UHFFFAOYSA-N 2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluorooctan-1-amine Chemical compound NCC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F HZCZXRSVKNFILZ-UHFFFAOYSA-N 0.000 description 1
- VFBJMPNFKOMEEW-UHFFFAOYSA-N 2,3-diphenylbut-2-enedinitrile Chemical group C=1C=CC=CC=1C(C#N)=C(C#N)C1=CC=CC=C1 VFBJMPNFKOMEEW-UHFFFAOYSA-N 0.000 description 1
- SGTNSNPWRIOYBX-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile Chemical compound C1=C(OC)C(OC)=CC=C1CCN(C)CCCC(C#N)(C(C)C)C1=CC=C(OC)C(OC)=C1 SGTNSNPWRIOYBX-UHFFFAOYSA-N 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 1
- DDTHMESPCBONDT-UHFFFAOYSA-N 4-(4-oxocyclohexa-2,5-dien-1-ylidene)cyclohexa-2,5-dien-1-one Chemical class C1=CC(=O)C=CC1=C1C=CC(=O)C=C1 DDTHMESPCBONDT-UHFFFAOYSA-N 0.000 description 1
- UQRONKZLYKUEMO-UHFFFAOYSA-N 4-methyl-1-(2,4,6-trimethylphenyl)pent-4-en-2-one Chemical group CC(=C)CC(=O)Cc1c(C)cc(C)cc1C UQRONKZLYKUEMO-UHFFFAOYSA-N 0.000 description 1
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 229910052684 Cerium Inorganic materials 0.000 description 1
- MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 description 1
- 229910052693 Europium Inorganic materials 0.000 description 1
- WJYIASZWHGOTOU-UHFFFAOYSA-N Heptylamine Chemical compound CCCCCCCN WJYIASZWHGOTOU-UHFFFAOYSA-N 0.000 description 1
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- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
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- MKYBYDHXWVHEJW-UHFFFAOYSA-N N-[1-oxo-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propan-2-yl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(C(C)NC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 MKYBYDHXWVHEJW-UHFFFAOYSA-N 0.000 description 1
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- 229930192627 Naphthoquinone Natural products 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- ATTZFSUZZUNHBP-UHFFFAOYSA-N Piperonyl sulfoxide Chemical compound CCCCCCCCS(=O)C(C)CC1=CC=C2OCOC2=C1 ATTZFSUZZUNHBP-UHFFFAOYSA-N 0.000 description 1
- 208000000474 Poliomyelitis Diseases 0.000 description 1
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- 239000004698 Polyethylene Substances 0.000 description 1
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- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
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- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 229910052769 Ytterbium Inorganic materials 0.000 description 1
- 125000005396 acrylic acid ester group Chemical group 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
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- 150000001447 alkali salts Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
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- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 description 1
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- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 238000000429 assembly Methods 0.000 description 1
- 230000000712 assembly Effects 0.000 description 1
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- OYLGJCQECKOTOL-UHFFFAOYSA-L barium fluoride Chemical compound [F-].[F-].[Ba+2] OYLGJCQECKOTOL-UHFFFAOYSA-L 0.000 description 1
- 229910001632 barium fluoride Inorganic materials 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000005587 carbonate group Chemical group 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- GWXLDORMOJMVQZ-UHFFFAOYSA-N cerium Chemical compound [Ce] GWXLDORMOJMVQZ-UHFFFAOYSA-N 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000002322 conducting polymer Substances 0.000 description 1
- 229920000547 conjugated polymer Polymers 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 150000003950 cyclic amides Chemical class 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 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
- 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 1
- 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
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- AQEFLFZSWDEAIP-UHFFFAOYSA-N di-tert-butyl ether Chemical compound CC(C)(C)OC(C)(C)C AQEFLFZSWDEAIP-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- LAWOZCWGWDVVSG-UHFFFAOYSA-N dioctylamine Chemical compound CCCCCCCCNCCCCCCCC LAWOZCWGWDVVSG-UHFFFAOYSA-N 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000005530 etching Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- LIWAQLJGPBVORC-UHFFFAOYSA-N ethylmethylamine Chemical compound CCNC LIWAQLJGPBVORC-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 150000008376 fluorenones Chemical class 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical class [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 description 1
- 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
- 230000002687 intercalation Effects 0.000 description 1
- 238000009830 intercalation Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 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
- 150000002576 ketones Chemical class 0.000 description 1
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 1
- 229910052808 lithium carbonate Inorganic materials 0.000 description 1
- FUJCRWPEOMXPAD-UHFFFAOYSA-N lithium oxide Chemical compound [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 1
- 229910001947 lithium oxide Inorganic materials 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- ORUIBWPALBXDOA-UHFFFAOYSA-L magnesium fluoride Chemical compound [F-].[F-].[Mg+2] ORUIBWPALBXDOA-UHFFFAOYSA-L 0.000 description 1
- 229910001635 magnesium fluoride Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000003956 methylamines Chemical class 0.000 description 1
- ZQJAONQEOXOVNR-UHFFFAOYSA-N n,n-di(nonyl)nonan-1-amine Chemical compound CCCCCCCCCN(CCCCCCCCC)CCCCCCCCC ZQJAONQEOXOVNR-UHFFFAOYSA-N 0.000 description 1
- JEIFGNLZAYFLFL-UHFFFAOYSA-N n,n-di(undecyl)undecan-1-amine Chemical compound CCCCCCCCCCCN(CCCCCCCCCCC)CCCCCCCCCCC JEIFGNLZAYFLFL-UHFFFAOYSA-N 0.000 description 1
- CLZGJKHEVKJLLS-UHFFFAOYSA-N n,n-diheptylheptan-1-amine Chemical compound CCCCCCCN(CCCCCCC)CCCCCCC CLZGJKHEVKJLLS-UHFFFAOYSA-N 0.000 description 1
- DIAIBWNEUYXDNL-UHFFFAOYSA-N n,n-dihexylhexan-1-amine Chemical compound CCCCCCN(CCCCCC)CCCCCC DIAIBWNEUYXDNL-UHFFFAOYSA-N 0.000 description 1
- DAZXVJBJRMWXJP-UHFFFAOYSA-N n,n-dimethylethylamine Chemical compound CCN(C)C DAZXVJBJRMWXJP-UHFFFAOYSA-N 0.000 description 1
- XTAZYLNFDRKIHJ-UHFFFAOYSA-N n,n-dioctyloctan-1-amine Chemical compound CCCCCCCCN(CCCCCCCC)CCCCCCCC XTAZYLNFDRKIHJ-UHFFFAOYSA-N 0.000 description 1
- OOHAUGDGCWURIT-UHFFFAOYSA-N n,n-dipentylpentan-1-amine Chemical compound CCCCCN(CCCCC)CCCCC OOHAUGDGCWURIT-UHFFFAOYSA-N 0.000 description 1
- DCZNSJVFOQPSRV-UHFFFAOYSA-N n,n-diphenyl-4-[4-(n-phenylanilino)phenyl]aniline Chemical class C1=CC=CC=C1N(C=1C=CC(=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 DCZNSJVFOQPSRV-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- GMTCPFCMAHMEMT-UHFFFAOYSA-N n-decyldecan-1-amine Chemical compound CCCCCCCCCCNCCCCCCCCCC GMTCPFCMAHMEMT-UHFFFAOYSA-N 0.000 description 1
- MJCJUDJQDGGKOX-UHFFFAOYSA-N n-dodecyldodecan-1-amine Chemical compound CCCCCCCCCCCCNCCCCCCCCCCCC MJCJUDJQDGGKOX-UHFFFAOYSA-N 0.000 description 1
- GNVRJGIVDSQCOP-UHFFFAOYSA-N n-ethyl-n-methylethanamine Chemical compound CCN(C)CC GNVRJGIVDSQCOP-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
- NJWMENBYMFZACG-UHFFFAOYSA-N n-heptylheptan-1-amine Chemical compound CCCCCCCNCCCCCCC NJWMENBYMFZACG-UHFFFAOYSA-N 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- PXSXRABJBXYMFT-UHFFFAOYSA-N n-hexylhexan-1-amine Chemical compound CCCCCCNCCCCCC PXSXRABJBXYMFT-UHFFFAOYSA-N 0.000 description 1
- MFHKEJIIHDNPQE-UHFFFAOYSA-N n-nonylnonan-1-amine Chemical compound CCCCCCCCCNCCCCCCCCC MFHKEJIIHDNPQE-UHFFFAOYSA-N 0.000 description 1
- JACMPVXHEARCBO-UHFFFAOYSA-N n-pentylpentan-1-amine Chemical compound CCCCCNCCCCC JACMPVXHEARCBO-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002791 naphthoquinones Chemical class 0.000 description 1
- 125000001624 naphthyl group Chemical group 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
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- FJDUDHYHRVPMJZ-UHFFFAOYSA-N nonan-1-amine Chemical compound CCCCCCCCCN FJDUDHYHRVPMJZ-UHFFFAOYSA-N 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical class C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- 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 1
- 229940100684 pentylamine 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
- 239000002985 plastic film Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000548 poly(silane) polymer Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920006289 polycarbonate film Polymers 0.000 description 1
- 229920000867 polyelectrolyte Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920006267 polyester film Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920001444 polymaleic acid Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 150000003219 pyrazolines Chemical class 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
- 230000002441 reversible effect Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 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
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 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
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 229910052708 sodium 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
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 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
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 125000001174 sulfone group Chemical group 0.000 description 1
- 239000006228 supernatant Substances 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
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- ABVVEAHYODGCLZ-UHFFFAOYSA-N tridecan-1-amine Chemical compound CCCCCCCCCCCCCN ABVVEAHYODGCLZ-UHFFFAOYSA-N 0.000 description 1
- SWZDQOUHBYYPJD-UHFFFAOYSA-N tridodecylamine Chemical compound CCCCCCCCCCCCN(CCCCCCCCCCCC)CCCCCCCCCCCC SWZDQOUHBYYPJD-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
- QFKMMXYLAPZKIB-UHFFFAOYSA-N undecan-1-amine Chemical compound CCCCCCCCCCCN QFKMMXYLAPZKIB-UHFFFAOYSA-N 0.000 description 1
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical class OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 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
Classifications
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
- H01G11/00—Hybrid capacitors, i.e. capacitors having different positive and negative electrodes; Electric double-layer [EDL] capacitors; Processes for the manufacture thereof or of parts thereof
- H01G11/22—Electrodes
- H01G11/30—Electrodes characterised by their material
- H01G11/48—Conductive polymers
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B27/00—Layered products comprising a layer of synthetic resin
- B32B27/06—Layered products comprising a layer of synthetic resin as the main or only constituent of a layer, which is next to another layer of the same or of a different material
- B32B27/08—Layered products comprising a layer of synthetic resin as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B27/00—Layered products comprising a layer of synthetic resin
- B32B27/18—Layered products comprising a layer of synthetic resin characterised by the use of special additives
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B27/00—Layered products comprising a layer of synthetic resin
- B32B27/28—Layered products comprising a layer of synthetic resin comprising synthetic resins not wholly covered by any one of the sub-groups B32B27/30 - B32B27/42
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
- H10K85/113—Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
- H10K85/1135—Polyethylene dioxythiophene [PEDOT]; Derivatives thereof
-
- 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]
- H10K50/17—Carrier injection layers
-
- 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
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
-
- 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
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P70/00—Climate change mitigation technologies in the production process for final industrial or consumer products
- Y02P70/50—Manufacturing or production processes characterised by the final manufactured product
Definitions
- the present invention relates to a layer body, a process for obtaining a layer body, the layer body obtainable by this process, electronic components comprising a layer body as well as the use of a fluorinated amine.
- An electro-luminescent device is characterised in that it gives out light under a flow of electrical current when an electrical voltage is applied.
- Such devices have been known for a long time under the name “light emitting diodes” (LEDs).
- LEDs light emitting diodes
- the emission of light arises when positive charges (holes) and negative charges (electrons) recombine with the emission of light.
- LEDs employed in technology are composed predominantly of inorganic semiconductor materials.
- EL-devices have been known whose fundamental constitu- ents are organic materials.
- These organic EL-devices contain, as a rule, one or more layers of organic charge-transport compounds.
- the fundamental layer composition of an EL-device is, for example, as follows: 1 carrier, substrate
- an EL device consists of two electrodes between which there is an organic layer which performs all of the functions, including the emission of light.
- DE-A-10 2009 031 677 recommends employing func- tionalised polysulphones instead of PSS as the polyanions for balancing the charge of the cati- onic polythiophenes.
- metal oxides such as, for example, ITO and their use in OLEDs.
- the present invention was based on the object of overcoming the disadvantages present in the state of the art in connection with OLEDs, in particular in connection with OLEDs comprising hole injection layers comprising conductive polymers, in particular hole injection layers com- 10 prising polythiophenes and polyanions functionalised with acid groups.
- the present invention was particularly based on the object of providing a layer body comprising conductive polymers, in particular conductive polymers comprising polythiophenes and polyanions functionalised with acid groups, which is, for example, suitable as the hole injection layer in an OLED and which is less susceptible to degradation as compared to the hole 5 injection layers known from the state of the art.
- the present invention was also based on the object of providing a process for the production of such a layer body, which enables the production of more stable (with respect to degradation) hole injection layers, comprising conductive polymers, in particular comprising conductive 0 polymers comprising polythiophenes and polyanions functionalised with acid groups, using the simplest possible process techniques, without thereby adversely influencing the electrical properties of such layers.
- the process should in particular also enable the production of OLEDs with particularly longer life spans.
- the present invention was also based on the object of providing OLEDs which are characterised by a particularly long life span, where the longer life span should, in particular, manifest itself in that the time taken for the light intensity of the OLED at a constant electrical current to halve is as long as possible.
- a layer body at least comprising a first layer comprising a conductive polymer
- fluorinated amines on a surface of a conductive polymer in particular on a surface of a conductive polymer comprising a polythiophene and a polymer functionalised with acid groups, for example on a PEDOT : PSS surface, can form a self as- S0 Marveld monolayer (SAM).
- SAM Self as- S0 Marveld monolayer
- the layer body according to the invention comprises a first layer which comprises a conductive polymer.
- conductive polymers are all those polymers which exhibit an electrical conductivity, such as, for example, conductive polymers based on optionally substituted poly- anilines, optionally substituted polypyrroles or optionally substituted polythiophenes, polymers based on optionally substituted polythiophenes being particularly preferred.
- the conductive polymer in the first layer comprises preferably cationic polythiophene and a preferably anionic polymer functionalised with acid groups.
- the polythiophene is preferably a polythiophene with repeating units of the general formula (I) or (II) or a combination of units of the general formulas (I) and (II), preferably a polythiophene with repeating units of the general formula (II):
- A stands for an optionally substituted C]-C 5 -alkylene radical
- R stands for a linear or branched, optionally substituted Ci-Cis-alkyl radical, an optionally substituted C 5 -Ci 2 -cycloalkyl radical, an optionally substituted C6-Ci 4 -aryl radical, an optionally substituted C 7 -Ci 8 -aralkyl radical, an optionally substituted C1 -C4- hydroxyalkyl radical or a hydroxyl radical,
- x stands for a whole number from 0 to 8 and in the case where multiple radicals R are connected to A, these can be identical or different.
- polythiophenes with repeating units of the general formula (II), wherein A stands for an optionally substituted C 2 -C3-alkylene radical and x stands for 0 or 1.
- L5 Especially preferred as polythiophene is poly(3,4-ethylenedioxythiophene), which is optionally substituted.
- the prefix poly- is to be understood as meaning that more than one identical or different repeating units of the general formulas (I) and/or (II) are contained in
- the polythiophene can also comprise other repeating units, it being preferred that at least 50 %, particularly preferred that at lease 75 % and most preferred that at least 95 % of all repeating units of the polythiophene exhibit the general formula(s) (I) and/or (II), preferably the general formula (II).
- the polythiophenes contain in total n repeating units of the general for-
- the repeating units of the general formula(s) (I) and/or (II), preferably of the general formula (II), within a polythiophene can each be identical or different. Polythiophenes with identical repeating units of the general formula (II) are preferred.
- Ct-C 5 -Alkylene radicals A are preferably methylene, ethylene, n-propylene, n-butylene or n-pentylene.
- 8 -alkyl R preferably stand for linear or branched Ci-C] 8 -alkyl radicals such as methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl, n- pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1-ethylpropyl, 1 ,1-dimethylpropyl, 1 ,2-
- C5-C] 2 -cycloalkyl radicals R stand, for example, for cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl or cyclodecyl.
- C 5 -C 14 -aryl radicals R stand, for example, for phenyl or naphthyl.
- C 7 -Ci 8 - aralkyl radicals R stand, for example, for benzyl, o-, m-, p- tolyl, 2,3-, 2,4-, 2,5-, 2,6-, 3,4-,
- radical A and/or the radical R numerous organic groups are possible, such as, for example, alkyl, cycloalkyl, aryl, aralkyl, alkoxy, halogen, ether, thi- 15 oether, disulphide, sulphoxide, sulphone, sulphonate, amino, aldehyde, ketone, carboxylic acid ester, carboxylic acid, carbonate, carboxylate, cyano, alkylsilane and alkoxysilane groups as well as carboxylamide groups.
- the polythiophenes can be neutral or cationic. In preferred embodiments they are cationic, >0 "cationic" referring only to the charges which reside on the polythiophene main chain.
- the polythiophenes can carry positive and negative charges in the structural unit, the positive charges being on the polythiophene main chain and the negative charges, were applicable, being on the radicals R substituted with sulphonate or carbonate groups.
- the positive charges of the polythiophene chain can thereby be partially or >5 fully balanced by the optionally present anionic groups on the radicals R. Considered as a whole the polythiophenes can be, in these cases, cationic, neutral or even anionic.
- the first layer also comprises a polyanion based on polymers functionalised with acid groups.
- polyanion is anions of polymeric carboxylic acids, such as polyacrylic acids, polymethacrylic acid 5 or polymaleic acids, or polymeric sulphonic acids, such as polystyrene sulphonic acids and polyvinylsulphonic acids.
- the polycarboxylic and polysulphonic acids can also be copolymers of vinylcarboxylic and vinylsulphonic acids with other polymerisable monomers, such as acrylic acid esters and styrene. It is particularly preferable for the first layer to contain an anion of a polymeric carboxylic or sulphonic acid for compensation of the positive charge of the polio ythiophene.
- polyanion is the anion of the polystyrene sulphonic acid (PSS) which, where polythiophene is used, preferably poly(3,4-ethylenedioxythiophene), is preferably present bound as a complex in the form of the PEDOT : PSS complexes known from the state of
- PSS polystyrene sulphonic acid
- Such complexes are obtainable by oxidative polymerisation of the thiophene monomers, preferably 3,4-ethylenedioxythiophene, in an aqueous solution in the presence of the polystyrene sulphonic acid.
- the molecular weight of the polymers functionalised with acid groups which supply the poly- !0 anions is preferably 1,000 to 2,000,000, particularly preferably 2,000 to 500,000.
- the polymers functionalised with acid groups or their alkali salts are commercially available, e.g. polystyrene sulphonic acids and polyacrylic acids, or can be produced by known processes (see e.g. Houben Weyl, Methoden der organischen Chemie, vol. E 20 Makromolekulare Stoffe, Part 2, (1987), p. 1141 et seq.).
- Polymers functionalised with acid groups (polyanions) and polythiophene, in particular polystyrene sulphonic acid and poly(3,4-ethylenedioxythiophene), can be present in the first layer in a weight ratio from 0.5 : 1 to 50 : 1, preferably from 1 : 1 to 30 : 1, particularly preferably from 2 : 1 to 20: 1.
- the weight of the electrically conductive polymers here corresponds to the 10 weight of the monomers employed for the production of the conductive polymers, assuming that complete conversion takes place during the polymerisation.
- the polystyrene sulphonic acid is present in excess by weight compared with the polythiophene, in particular poly(3,4- ethylenedioxythiophene) .
- the first layer consists at least 40 % by weight, particularly preferably at least 55 % by weight and most preferably at least 70 % by weight, of the polythiophene and the polymer functional ised with acid groups, particularly preferably of PEDOT : PSS, the proportion in each case being relative to the total weight of the first layer.
- the layer thickness of the first layer preferably lies in a range from 1 nm to 10 ⁇ , particularly preferably in a range from lO nm to 500 nm and most preferably in a range from 20 nm to 200 nm. s 5
- the layer body according to the invention comprises a further layer following the first layer, which comprises a fluorinated amine, it being particularly preferable according to the invention if this further layer is one which forms a self assembled monolayer (SAM).
- SAM self assembled monolayer
- a self assembled monolayer generally forms spontaneously on dipping a substrate into a fluid comprising the fluorinated amine. It is an organised layer con-
- SAMs exhibit a defined layer thickness, normally a layer thickness in the range from roughly 0.1 to 2 nm.
- the fluorinated amines can be fluorinated or perfluorinated (i.e. the hydrogen atoms in the alkyl chains of the amine can be completely or partially replaced with fluorine atoms). It is preferred, however, for at least 40 %, particularly preferably at least 55 %, and most preferably at least 70 % of the hydrogen atoms in the amine to be replaced with fluorine atoms.
- the amines can be primary, secondary or tertiary amines.
- the fluorinated amine it is particularly preferred for the fluorinated amine to exhibit the general formula (III) R
- R 1 , R 2 and R 3 can, independently of each other, stand for a hydrogen atom, for a C]- C 20 -alkyl radical, preferably for a Ci-Ci 5 -alkyl radical, particularly preferably for a CpCio- alkyl radical, or for a fluorinated CrC ⁇ -alkyl radical, preferably for a fluorinated CrCi 5 -alkyl radical, particularly preferably for a fluorinated d-C 10 -alkyl radical, wherein at least one of the radicals R 1 , R 2 and R 3 stands for a fluorinated Ci-C 20 -alkyl radical, preferably for a fluori- ⁇ nated Ci-Ci 5 -alkyl radical and particularly preferably for a fluorinated Ci-Qo-alkyl radical.
- fluorinated comprises perfluorinated as well as polyfluorinated alkyl radicals.
- alkyl radicals and fluorinated alkyl radicals can be straight chained or 15 branched and can optionally also comprise cyclic units, straight chain alkyl radicals being particularly preferred.
- fluorinated amines are polyfluorinated or perfluorinated methyla- mine, dimethylamine, trimethylamine, ethylamine, diethylamine, triethylamine, ethylmethyla- mine, ethyldimethylamine, diethylmethyl amine, propylamine, dipropylamine, tripropylamine, >0 butylamine, dibutylamine, tributylamine, pentylamine, dipentylamine, tripentylamine, hexyla- mine, dihexylamine, trihexyl amine, heptylamine, diheptylamine, triheptylamine, octylamine, dioctylamine, trioctylamine, nonylamine, dinonylamine, trinonylamine, decylamine, didecyl- amine, tridecylamine, undecylamine, diund
- fluorinated amines are perfluorotripentylamine, 3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluoro-l-decylamine (also known as ⁇ , ⁇ ,- 2H,2H-perfluorodecylamine) or 2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluoro-l-octylamine (also known as ⁇ , ⁇ -perfluorooctylamine).
- the further layer can also comprise mixtures of at least two different fluorinated amines.
- a contribution to achieving the objects named at the beginning is also made by a process for the production of a layer body comprising the process steps i) the application of a conductive polymer to a substrate to obtain a first layer; ii) the application of a fluorinated amine to the first layer to obtain a further layer.
- a conductive polymer is applied to a substrate to obtain a first layer.
- the substrate can be one which is furnished with a preferably transparent base electrode, the substrate itself preferably also being transparent.
- Glass, PET or other transparent plastics, for example can be employed as transparent substrate, onto which a transparent electrically conductive electrode is then introduced, such as e.g. an electrode made of indium - tin oxide (ITO), doped zinc- or tin oxide or a conductive polymer.
- a transparent electrically conductive electrode such as e.g. an electrode made of indium - tin oxide (ITO), doped zinc- or tin oxide or a conductive polymer.
- transparent plastic substrates are, for example, polycarbonates, polyesters, such as e.g.
- PET and PEN polyethyleneterephthalate and polyeth- ylenenaphthalinedicarboxylate
- copolycarbonates polyacrylates, polysulphones, polyether- sulphones (PES), polyimides, polyethylene, polypropylene, cyclic polyolefins or cyclic olefin copolymers (COC), hydrated styrene polymers or hydrated styrene copolymers.
- Suitable polymer bases can, for example, also be films such as polyester films, PES films from the Sumitomo company or polycarbonate films from the Bayer AG company (Makrofol®). According to the invention, ITO coated glass is particularly preferred as substrate.
- the conductive polymer is deposited onto such a substrate or onto the electrode layer which has been applied to such a substrate to obtain the first layer of the layer body according to the invention, particularly preferred conductive polymers here being those conductive polymers which have already been described at the outset as preferred conductive polymer in connection with the layer body according to the invention.
- particularly preferred according to the invention is a conductive polymer comprising a polythiophene, particularly preferably PEDOT, and a polymer functionalised with acid groups, particularly preferably PSS, the use of PEDOT : PSS complexes as conductive polymer being particularly preferable here also.
- the conductive polymer is preferably introduced to the substrate in the form of a dispersion comprising the conductive polymer and a dispersing agent, particularly preferably in the form of a dispersion comprising polythiophene, a polymer functionalised with acid groups and a dispersing agent, especially preferably in the form of a PEDOT : PSS dispersion, with at least partial subsequent removal of dispersion agent to obtain the first layer.
- a dispersing agent particularly preferably in the form of a dispersion comprising polythiophene, a polymer functionalised with acid groups and a dispersing agent, especially preferably in the form of a PEDOT : PSS dispersion, with at least partial subsequent removal of dispersion agent to obtain the first layer.
- the application of the dispersion can be carried out, for example, using known processes, e.g.
- the at least partial removal of the dispersing agent is preferably effected by drying at a temperature in a range from 20°C to 200°C, in which connection it can be advantageous to at least partially remove the supernatant dispersion prior to the drying processes, for example by spinning off.
- dispersions comprising a polythiophene, a polymer functionalised with acid groups and a dispersing agent is basically described in EP-A-1 122 274 or US 5,11 1,327.
- the polymerisation of the appropriate monomelic compounds is carried out in the presence of polymers functionalised with acid groups, with suitable oxidising agents in suitable solvents.
- Suitable oxidising agents are Iron(III) salts, in particular FeCl 3 and Iron(III) salts of aromatic and aliphatic sulphonic acids, H 2 0 2 , 2 Cr 2 0 7 , 2 S 2 0 8 , Na 2 S 2 0 , KMn0 4 , alkali perborates and alkali or ammonium persulphates or mixtures of these oxidising agents.
- suitable oxidising agents are described, for example, in Handbook of Conducting Polymers (Ed. Skotheim, T.A.), Marcel Dekker: New York, 1986, Vol. 1, 46-57.
- Particularly preferred oxidising agents are FeCl 3 , Na 2 S 2 0 and K 2 S 2 0 8 or mixtures thereof.
- the polymerisation is preferably carried out at a reaction temperature of from -20 to 100°C. Particularly preferable 5 are reaction temperatures of from 20 to 100°C.
- the reaction solution is optionally subsequently treated with at least one ion exchanger.
- Suitable solvents are e.g. polar solvents such as, for example, water, alcohols such as methanol, ethanol, 2-propanol, n-propanol, n-butanol, diacetone alcohol, ethylene glycol, glycerine 0 or mixtures of these.
- polar solvents such as, for example, water, alcohols such as methanol, ethanol, 2-propanol, n-propanol, n-butanol, diacetone alcohol, ethylene glycol, glycerine 0 or mixtures of these.
- aliphatic ketones such as acetone and methylethyl ketone
- aliphatic nitriles such as acetonitrile
- aliphatic and cyclic amides such as N,N- dimethylacetamide, N,N-dimethylformamide (DMF) and 1 -methyl-2-pyrrolidone (NMP)
- ethers such as tetrahydrofuran (THF) as well as sulphoxides such as dimethylsulphoxide (DMSO) or mixture of these with each other or with those solvents previously specified.
- THF tetrahydrofuran
- DMSO dimethylsulphoxide
- the dispersions preferably exhibit a solid content in a range from 0.01 to 20 % by weight, and particularly preferably in a range from 0.2 to 5 % by weight, i.e. they contain in total 0.01 to 20 % by weight, particularly preferably 0.2 to 5 % by weight of polythiophene(s), preferably PEDOT, with polymer functionalised with acid groups, preferably PSS, and optionally further ⁇ components, such as e.g. binding agents, cross-linking agents and/or surfactants, in dissolved and/or dispersed form.
- polythiophene(s) preferably PEDOT
- polymer functionalised with acid groups preferably PSS
- optionally further ⁇ components such as e.g. binding agents, cross-linking agents and/or surfactants, in dissolved and/or dispersed form.
- the viscosity at 20°C of the dispersions employed for production of the first layer preferably lies between the viscosity of the dispersing agent and 200 mPas, preferably between the vis- :5 cosity of the dispersing agent and 100 mPas.
- the desired amount of dispersing agent can be removed from the dispersion through distillation, preferably in a vacuum or by other processes, e.g. ultra filtration.
- organic, polymeric binding agents and/or organic low-molecular cross-linking agents or surfactants can be added to the dispersion.
- Appropriate binding agents are, for example, described in EP-A 564 91 1. Examples in this regard are polyvinylcarbazole, silanes, such as Silquest ® A187 (Fa. OSi Specialities) or surfactants, such as the fluoro-surfactant FT 248 (Bayer AG).
- a fluorinated amine is then introduced onto the first layer to obtain a further layer, it being particularly preferable if a SAM forms with the application of the fluorinated amine onto the first layer in process step ii).
- Preferred fluorinated amines in this connection are those fluorinated amines which have already been described at the beginning as preferred fluorinated amines in connection with the layer body according to the invention
- the application of the fluorinated amines onto the first layer is preferably effected by dissolving the fluorinated amines in a suitable non-polar solvent, for example in an ether such as tert- butyl ether, and then coating the first layer with the solution so obtained, where the application of the solution onto the first layer can, once more, be carried out using known process, e.g.
- spin coating impregnation, pouring, dripping, spraying, misting on, knife coating, brushing or printing, for example ink-jet, screen, Intaglio, offset or tampon printing.
- an exposure time in a range of 1 second to 120 minutes, particularly preferably 1 to 15 minutes at a temperature in a range preferably from 10 to 60°C, particularly preferably from 20 to 30°C, an excess of fluorinated amine can be removed, for example by spinning off the supernatant solution.
- the process conditions for the application of the fluorinated amine onto the first layer should preferably be selected such that a SAM layer of the fluorinated amine forms on the first, conductive polymer comprising layer, preferably on the layer comprising PEDOT : PSS.
- the concentration of fluorinated amine in the solution employed for introducing the fluorinated amine onto the first layer preferably lies in a range from 0.1 to 20 % by weight, particularly preferably in a range from 1 to 10 % by weight, in each case in relation to the total weight of the solu- tion.
- the process according to the invention can comprise further process steps.
- process step ii such as, for example, iii) the application of a hole transport layer onto the layer obtained in process step ii); iv) the application of an emitter layer onto the hole transport layer; v) the application of an electron injection layer onto the emitter layer; vi) the application of a cathode layer onto the electron injection layer.
- the hole injection layer or the hole transport layer can also be designated as electron blocking layer. If the electron injection layer has the ability to block hole transport, then the electron injection layer can also be designated as hole blocking layer.
- Possible hole transport layers are, for example, layers comprising polyvinylcarbazole or derivatives thereof, polysilane or derivatives thereof, polysiloxane derivatives with aromatic amine in the side or main chain, pyrazoline derivatives, aryl amine derivatives, stilbene derivatives, triphenyldiamine derivatives, polyaniline or derivatives thereof, polythiophene and derivatives thereof, polyarylamine or derivatives thereof, polypyrrole or derivatives thereof, poly p- phenylenevinylene) or derivatives thereof and poly(2,5-thienylenevinylene) or derivatives thereof.
- Particularly preferred as hole transport layer is NPB (N,N'-bis(naphthalene-l-yl)- N,N ' -bis(phenyl)benzidine.
- Suitable materials for the emitter layer are conjugated polymers such as polyphenylene- vinylenes and/or polyfluorenes, for example, the polyparaphenylenevinylene derivatives and polyfluorene derivatives described in WO-A-90/13148, or emitters from the class of low molecular emitters, also termed , mall molecules" in technical circles, such as aluminium com- plexes, such as, for example, tris(8-hydroxyquinolinato)aluminium (Alq 3 ), fluorescence dyes, e.g. quinacridones, or phosphorescent emitters such as, for example, Ir(ppy) 3 .
- Further suitable materials for the emitter layer are described e.g. in DE-A-196 27 071. Particularly preferred as emitter layer, according to the invention, is tris(8-hydroxyquinolinato)aluminium (Alq 3 ).
- the injection layer are single Ca layers or a stack structure consisting of a Ca layer and another layer, which consists of one or more materials selected from the group LA and IIA metals of the periodic table, excluding Ca, which exhibit a work function from 1.5 to 3.0 eV, and oxides, halogenides and carbonates thereof.
- group IA metals of the periodic ⁇ table which exhibit a work function from 1.5 to 3.0 eV, and oxides, halogenides and carbonates thereof are lithium, lithium fluoride, sodium oxide, lithium oxide and lithium carbonate.
- group IIA metals of the periodic table excluding Ca, which exhibit a work function from 1.5 to 3.0 eV, and oxides, halogenides and carbonates thereof, are strontium, magnesium oxide, magnesium fluoride, strontium fluoride, barium fluoride, strontium
- Particularly suitable materials for the cathode layer are transparent or translucent materials with a relatively low work function (preferably lower than 4.0 eV).
- metals such as lithium (Li), sodium (Na), potassium (K), rubidium (Rb), caesium
- Cs Be, magnesium (Mg), calcium (Ca), strontium (Sr), barium (Ba), aluminium (Al), scandium (Sc), vanadium (V), Zn, yttrium (Y), indium (In), cerium (Ce), samarium (Sm), Eu, Tb and ytterbium (Yb); alloys consisting of two or more of these metals; alloys consisting of one or more of these metals and one or more metals selected from Au, Ag, Pt, Cu, manganese (Mn), titanium (Ti), cobalt (Co), nickel (Ni), wolfram (W) and tin (Sn); graphite or graphite
- intercalation compounds such as, for example, ITO and tin oxide.
- metal oxides such as, for example, ITO and tin oxide.
- aluminium is particularly preferable as the cathode layer.
- the application of the further layers, in particular of the hole transport layer, of the emitter layer, of the electron injection layer and of the cathode injection layer can be carried out in a 30 manner known to a person skilled in the art, preferably through vapour coating such as is described, for instance, in WO-A-2009/0170244.
- a contribution to the solution of the objects named at the outset is also made by a layer body, particularly preferably an OLED or an OPV element, which is/are obtainable by the process according to the invention.
- an electronic component comprising a layer body according to the invention or a layer body obtainable by the process according to the invention, this component preferably being an OLED or an OPV element, particularly preferably an OLED.
- the layer formation of the OLED can take any form known to the person skilled in the art, preferably, however, with the hole injecting layer replaced by the layer body according to the invention wherein the further layer of fluorinated amine, preferably the further SAM layer of fluorinated amine, is present in the boundary region between the hole injecting layer and the hole transport layer or, where no separate hole transport layer is present, then in the boundary region between the hole injecting layer and the emitter layer.
- the further layer of fluorinated amine preferably the further SAM layer of fluorinated amine
- the OLED according to the invention can, for example, exhibit any of the following layer structures (a) to (h):
- hole injection layer/ hole transport layer/ 0 at least one emitter layer/ electron injection layer/ cathode
- hole injection layer at least one emitter layer/ SO electron transport layer/ electron injection layer/ cathode;
- the hole injection layer corresponding in each case to the layer body according to the invention or the layer body obtainable by the process according to the invention and in each case arranged in a such a way, that the further layer of fluorinated amine, preferably the further SAM of fluorinated amine is facing the hole injection layer or emitter layer.
- the layer structures (a) to (h) can be embodied either with the anode located next to the substrate, the substrate being, for example, glass or a transparent plastic film, or with the cathode located next to the substrate.
- anode layer hole transport layer, emitter layer, electron injection layer and cathode layer, those layers already mentioned at the outset in connection with the process according to the invention as preferred anode layer, hole transport layer, emitter layer, electron injection layer and cathode layer are again preferred.
- the electron transport layer can consist of materials such as, for example, oxadiazol derivatives, anthraquinodimethane or derivatives thereof, benzoquinone or derivatives thereof, naphthoquinone or derivatives thereof, anthraquinone or derivatives thereof, tetracyanoan- thraquinodimethane or derivatives thereof, fluorenone derivatives, diphenyldicyanoethylene or derivatives thereof, diphenoquinone derivatives and metal complexes of 8-hydroxyquinoline or
- an OLED which is formed of the following layers: anode layer/first layer of the layer body according to the invention or of the layer body obtainable using the process according to the invention/further layer 5 of the layer body according to the invention or of the layer body obtainable according to the invention/optional hole transport layer/optional emitter layer/optional electron injection layer/cathode layer.
- a contribution to the solution of the objects named at the outset is also made by the use of a 0 fluorinated amine for the improvement of the life span of electronic components which comprise layers of a conductive polymer, preferably layers comprising PEDOT : PSS complexes, the electronic component preferably being an OLED, especially preferably an OLED formed of the following layers: anode/hole injection layer/layer of the fluorinated amine, preferably SAM layer of the fluorinated amine/hole transport layer/emitter layer/electron injection lay- 5 er/cathode.
- the hole injection layer preferably comprises a conductive polymer, particularly preferably complexes of PEDOT : PSS.
- the time taken for the light intensity of the OLEDs at a constant electrical current to halve serves as a measure of the life span of the OLEDs.
- Preferred fluorinated amines in this connection are similarly those fluorinated amines which !0 have already been described at the outset as preferred fluorinated amines in connection with the layer body according to the invention.
- Example 1 SAM layer of lH,lH,2H,2H-perfluorodecylamine (according to the invention)
- SAM-1 will be used for building an organic light emitting diode (OLED).
- OLED organic light emitting diode
- ITO-coated glass is cut into 50 mm ⁇ 50 mm pieces (substrates) and structured into four parallel lines, each 2 mm wide and 5 cm long with Photoresist and an etching solution. Then the substrates are freed from the remains of the Photoresist, cleaned in an ultrasonic bath with 0.3 % Mucasol solution, rinsed with distilled water and centrifuged dry in a centrifuge. Directly before coating the ITO-coated sides are cleaned in a UV/Ozone reac-
- the aqueous dispersion, Clevios ® P AI4083 (Heraeus Clevios GmbH, Leverkusen), is 5 filtered through a syringe filter (Millipore HV, 0.45 ⁇ ).
- the cleaned ITO-coated substrate is placed on a spin coater (Carl Siiss, RC13) and approximately 5 ml of the filtered solution are distributed over the ITO-coated side of the substrate. Subsequently, the supernatant solution is spun off by rotating the plate at 1000 U/min over a period of 30 s. Then the thusly coated substrate is dried for 5 minutes at 200 °C on a hotplate.
- the layer !0 thickness is 50 nm (Tencor, Alphastep 500).
- the thusly coated substrate is transferred into a vapour deposition apparatus (Univex 350, Leybold).
- a vapour deposition apparatus Univex 350, Leybold.
- 60 nm of a hole transport layer of NPB (N,N'-bis(naphthalene-l- yl)-N,N'-bis(phenyl)benzidine) and then 50 nm of an emitter layer of A1Q3 (tris-(8- hydroxyquinoline)aluminum) (Sensient, Bitterfeld) are sequentially vapour deposited at a pressure of 10-3 Pa and at a vapour deposition rate of 1 A/sec.
- the layer system is transferred into a glove box with an N 2 atmosphere and an integrated vapour deposition apparatus (Edwards) and metal electrodes are applied by
- the substrate is placed on a shadow mask with the layer system facing downwards.
- the shadow mask contains rectangular slits with a width of 2 mm which are orientated perpendicular to the ITO stripes.
- a 0.5 nm thick LiF layer and subsequently a 200 nm thick Al layer are sequentially vapour deposited.
- the vapour deposition rates are 1 A/s for LiF and 10 A s
- the surface area of the individual OLEDs is 4.0 mm 2 .
- the two electrodes of the organic LED are connected to a power supply with electric !0 leads (contacted).
- the positive terminal is connected to the ITO electrode, the negative terminal with the metal electrode.
- the procedure is as that for example 1 with the difference that in point 1.3 ap- proximately 5 ml of the solution SAM-2 consisting of 0.1 g perfluorotripentylamine (Fluroinert FC 70, Sigma Aldrich) in 10 g tert.- butylmethyl ether is distributed onto the coated substrate which now lies, once again, on the spin coater. After an exposure time of approximately 3 min the supernatant solution is spun off at 3000 U/min for 30 s. The layer thickness of the entire coating remains unchanged after this process step and is 50 nm.
- SAM-2 consisting of 0.1 g perfluorotripentylamine (Fluroinert FC 70, Sigma Aldrich) in 10 g tert.- butylmethyl ether
- Table 1 shows an evaluation of the characteristic curves as well as the life span of the OLEDs produced in example 1-4.
- the characteristic curves were evaluated at a light intensity of 1000 cd/m 2 and show that the voltage is significantly lower when SAM layers SAM-1 and SAM-2 are used than in the con- trol test or with the material SAM-3.
- the life span test which is carried out at a constant current density of 3.84 mA/cm 2 , shows that the OLEDs with the SAM layers SAM-1 and SAM-2 according to the invention are significantly more stable than those without.
- the value t 2 gives the time at which half of the original light intensity (L0) is reached.
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Abstract
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EP12716243.6A EP2700112A1 (fr) | 2011-04-21 | 2012-04-16 | Amines fluorées en tant que sam dans des del organiques |
KR1020137030843A KR20140032406A (ko) | 2011-04-21 | 2012-04-16 | OLEDs에서 SAM으로서 불소화 아민 |
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DE102011018480A DE102011018480A1 (de) | 2011-04-21 | 2011-04-21 | Fluorierte Amine als SAM in OLEDs |
US201161480433P | 2011-04-29 | 2011-04-29 | |
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WO1990013148A1 (fr) | 1989-04-20 | 1990-11-01 | Cambridge Research And Innovation Limited | Dispositifs electroluminescents |
EP0440957A2 (fr) | 1990-02-08 | 1991-08-14 | Bayer Ag | Dispersions de polythiophènes nouvelles, leur préparation et leur utilisation |
US5111327A (en) | 1991-03-04 | 1992-05-05 | General Electric Company | Substituted 3,4-polymethylenedioxythiophenes, and polymers and electro responsive devices made therefrom |
EP0564911A2 (fr) | 1992-04-06 | 1993-10-13 | Agfa-Gevaert AG | Pièces antistatiques en matière plastique |
DE19627071A1 (de) | 1996-07-05 | 1998-01-08 | Bayer Ag | Elektrolumineszierende Anordnungen |
EP1122274A1 (fr) | 2000-02-03 | 2001-08-08 | Bayer Ag | Méthode de production de polymeres pi-conjugués solubles dans l'eau |
EP1227529A2 (fr) | 2001-01-26 | 2002-07-31 | Bayer Ag | Dispositifs électroluminescents |
DE102004006583A1 (de) | 2004-02-10 | 2005-09-01 | H.C. Starck Gmbh | Polythiophenformulierungen zur Verbesserung von organischen Leuchtdioden |
DE102004010811A1 (de) | 2004-03-05 | 2005-09-22 | H.C. Starck Gmbh | Polythiophenformulierung zur Verbesserung von organischen Leuchtdioden |
US20070259476A1 (en) * | 2006-05-04 | 2007-11-08 | Samsung Electronics Co., Ltd. | Compositions for forming organic insulating films, methods for forming organic insulating films using the compositions and organic thin film transistors comprising an organic insulating film formed by such a method |
WO2009017024A1 (fr) | 2007-07-31 | 2009-02-05 | Sumitomo Chemical Company, Limited | Procédé de fabrication d'un dispositif électroluminescent organique |
US20100025703A1 (en) * | 2004-12-29 | 2010-02-04 | Cambridge Display Technology Limited | Conductive Polymer Compositions in Opto-Electrical Devices |
DE102009012163A1 (de) | 2009-03-06 | 2010-09-09 | Siemens Aktiengesellschaft | Monolagen organischer Verbindungen auf Metalloxidoberflächen oder oxidhaltigen Metalloberflächen und damit hergestelltes Bauelement auf Basis organischer Elektronik |
DE102009031677A1 (de) | 2009-07-02 | 2011-01-05 | H.C. Starck Clevios Gmbh | Neue Polyelektrolyt-Komplexe und deren Verwendung |
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EP0781075B1 (fr) * | 1994-09-08 | 2001-12-05 | Idemitsu Kosan Company Limited | Procede d'enrobage d'un element electroluminescent organique et d'un autre element electroluminescent organique |
JPH1012380A (ja) * | 1996-06-25 | 1998-01-16 | Idemitsu Kosan Co Ltd | 多色発光装置およびその製造方法 |
JPH10275682A (ja) * | 1997-02-03 | 1998-10-13 | Nec Corp | 有機el素子 |
CN1869277B (zh) * | 2002-08-02 | 2010-09-29 | 出光兴产株式会社 | 溅射靶、烧结体及利用它们制造的导电膜、有机el元件及其所用的衬底 |
JP2008210788A (ja) * | 2007-02-02 | 2008-09-11 | Toppan Printing Co Ltd | 有機el素子 |
DE102009037691A1 (de) * | 2009-08-17 | 2011-03-03 | Siemens Aktiengesellschaft | Dielektrische Schutzschicht für eine selbstorganisierende Monolage (SAM) |
-
2011
- 2011-04-21 DE DE102011018480A patent/DE102011018480A1/de not_active Ceased
-
2012
- 2012-04-16 KR KR1020137030843A patent/KR20140032406A/ko not_active Application Discontinuation
- 2012-04-16 EP EP12716243.6A patent/EP2700112A1/fr not_active Withdrawn
- 2012-04-16 WO PCT/EP2012/001631 patent/WO2012143109A1/fr active Application Filing
- 2012-04-18 TW TW101113733A patent/TW201307062A/zh unknown
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WO1990013148A1 (fr) | 1989-04-20 | 1990-11-01 | Cambridge Research And Innovation Limited | Dispositifs electroluminescents |
EP0440957A2 (fr) | 1990-02-08 | 1991-08-14 | Bayer Ag | Dispersions de polythiophènes nouvelles, leur préparation et leur utilisation |
US5111327A (en) | 1991-03-04 | 1992-05-05 | General Electric Company | Substituted 3,4-polymethylenedioxythiophenes, and polymers and electro responsive devices made therefrom |
EP0564911A2 (fr) | 1992-04-06 | 1993-10-13 | Agfa-Gevaert AG | Pièces antistatiques en matière plastique |
DE19627071A1 (de) | 1996-07-05 | 1998-01-08 | Bayer Ag | Elektrolumineszierende Anordnungen |
EP1122274A1 (fr) | 2000-02-03 | 2001-08-08 | Bayer Ag | Méthode de production de polymeres pi-conjugués solubles dans l'eau |
EP1227529A2 (fr) | 2001-01-26 | 2002-07-31 | Bayer Ag | Dispositifs électroluminescents |
DE102004006583A1 (de) | 2004-02-10 | 2005-09-01 | H.C. Starck Gmbh | Polythiophenformulierungen zur Verbesserung von organischen Leuchtdioden |
DE102004010811A1 (de) | 2004-03-05 | 2005-09-22 | H.C. Starck Gmbh | Polythiophenformulierung zur Verbesserung von organischen Leuchtdioden |
US20100025703A1 (en) * | 2004-12-29 | 2010-02-04 | Cambridge Display Technology Limited | Conductive Polymer Compositions in Opto-Electrical Devices |
US20070259476A1 (en) * | 2006-05-04 | 2007-11-08 | Samsung Electronics Co., Ltd. | Compositions for forming organic insulating films, methods for forming organic insulating films using the compositions and organic thin film transistors comprising an organic insulating film formed by such a method |
WO2009017024A1 (fr) | 2007-07-31 | 2009-02-05 | Sumitomo Chemical Company, Limited | Procédé de fabrication d'un dispositif électroluminescent organique |
DE102009012163A1 (de) | 2009-03-06 | 2010-09-09 | Siemens Aktiengesellschaft | Monolagen organischer Verbindungen auf Metalloxidoberflächen oder oxidhaltigen Metalloberflächen und damit hergestelltes Bauelement auf Basis organischer Elektronik |
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YONG KYUN LEE ET AL: "Self-assembled monolayer modification of PEDOT:PSS interface to improve the device performance in blue PLED", PROCEEDINGS OF SPIE, vol. 6655, 1 January 2007 (2007-01-01), pages 66551E - 66551E-9, XP055027500, ISSN: 0277-786X, DOI: 10.1117/12.731980 * |
Also Published As
Publication number | Publication date |
---|---|
EP2700112A1 (fr) | 2014-02-26 |
TW201307062A (zh) | 2013-02-16 |
KR20140032406A (ko) | 2014-03-14 |
DE102011018480A1 (de) | 2012-10-25 |
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