CN105658742A - Polythiophene-containing ink compositions for inkjet printing - Google Patents
Polythiophene-containing ink compositions for inkjet printing Download PDFInfo
- Publication number
- CN105658742A CN105658742A CN201380080634.6A CN201380080634A CN105658742A CN 105658742 A CN105658742 A CN 105658742A CN 201380080634 A CN201380080634 A CN 201380080634A CN 105658742 A CN105658742 A CN 105658742A
- Authority
- CN
- China
- Prior art keywords
- ink
- composition
- organic solvent
- sulfolane
- polymethyl siloxane
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 157
- 238000007641 inkjet printing Methods 0.000 title claims abstract description 45
- 229920000123 polythiophene Polymers 0.000 title claims abstract description 24
- 239000000976 ink Substances 0.000 claims abstract description 153
- 238000000034 method Methods 0.000 claims abstract description 31
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims description 40
- 239000003960 organic solvent Substances 0.000 claims description 31
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical group O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims description 27
- 238000009835 boiling Methods 0.000 claims description 14
- 238000002347 injection Methods 0.000 claims description 14
- 239000007924 injection Substances 0.000 claims description 14
- 230000008569 process Effects 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 239000000010 aprotic solvent Substances 0.000 claims description 5
- MRNHPUHPBOKKQT-UHFFFAOYSA-N indium;tin;hydrate Chemical compound O.[In].[Sn] MRNHPUHPBOKKQT-UHFFFAOYSA-N 0.000 claims description 5
- 239000004020 conductor Substances 0.000 claims description 4
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical group COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 238000001704 evaporation Methods 0.000 claims description 2
- 230000008020 evaporation Effects 0.000 claims description 2
- 238000009472 formulation Methods 0.000 claims description 2
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 claims 4
- 238000004020 luminiscence type Methods 0.000 abstract description 6
- 238000009736 wetting Methods 0.000 abstract description 6
- 230000015572 biosynthetic process Effects 0.000 abstract description 3
- 238000011161 development Methods 0.000 abstract description 3
- 238000000025 interference lithography Methods 0.000 abstract 1
- 239000000463 material Substances 0.000 description 44
- 239000007789 gas Substances 0.000 description 38
- 210000004027 cell Anatomy 0.000 description 34
- 238000007639 printing Methods 0.000 description 32
- 239000002904 solvent Substances 0.000 description 21
- 238000001000 micrograph Methods 0.000 description 15
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 14
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 13
- 239000004094 surface-active agent Substances 0.000 description 12
- -1 methylsiloxane Chemical class 0.000 description 11
- 239000003795 chemical substances by application Substances 0.000 description 7
- 238000010586 diagram Methods 0.000 description 7
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 7
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 239000004205 dimethyl polysiloxane Substances 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 6
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 5
- 239000012530 fluid Substances 0.000 description 5
- 229910052731 fluorine Inorganic materials 0.000 description 5
- 239000011737 fluorine Substances 0.000 description 5
- 150000002334 glycols Chemical class 0.000 description 5
- 230000006698 induction Effects 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- 238000004891 communication Methods 0.000 description 4
- 238000013461 design Methods 0.000 description 4
- 238000007667 floating Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 229910052756 noble gas Inorganic materials 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 238000010926 purge Methods 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical class COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 3
- 239000010405 anode material Substances 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 230000001276 controlling effect Effects 0.000 description 3
- 238000000151 deposition Methods 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000011261 inert gas Substances 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 230000003134 recirculating effect Effects 0.000 description 3
- WGYZMNBUZFHYRX-UHFFFAOYSA-N 1-(1-methoxypropan-2-yloxy)propan-2-ol Chemical compound COCC(C)OCC(C)O WGYZMNBUZFHYRX-UHFFFAOYSA-N 0.000 description 2
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 241001597008 Nomeidae Species 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 238000005276 aerator Methods 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- OCKPCBLVNKHBMX-UHFFFAOYSA-N butylbenzene Chemical compound CCCCC1=CC=CC=C1 OCKPCBLVNKHBMX-UHFFFAOYSA-N 0.000 description 2
- 239000002826 coolant Substances 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000002708 enhancing effect Effects 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 230000005525 hole transport Effects 0.000 description 2
- 238000003384 imaging method Methods 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 210000003411 telomere Anatomy 0.000 description 2
- 102000055501 telomere Human genes 0.000 description 2
- 108091035539 telomere Proteins 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- AUHZEENZYGFFBQ-UHFFFAOYSA-N 1,3,5-trimethylbenzene Chemical compound CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- LHENQXAPVKABON-UHFFFAOYSA-N 1-methoxypropan-1-ol Chemical compound CCC(O)OC LHENQXAPVKABON-UHFFFAOYSA-N 0.000 description 1
- XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 description 1
- CUDYYMUUJHLCGZ-UHFFFAOYSA-N 2-(2-methoxypropoxy)propan-1-ol Chemical compound COC(C)COC(C)CO CUDYYMUUJHLCGZ-UHFFFAOYSA-N 0.000 description 1
- UXFQFBNBSPQBJW-UHFFFAOYSA-N 2-amino-2-methylpropane-1,3-diol Chemical compound OCC(N)(C)CO UXFQFBNBSPQBJW-UHFFFAOYSA-N 0.000 description 1
- CDXFIRXEAJABAZ-UHFFFAOYSA-N 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F CDXFIRXEAJABAZ-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- DELPSTRBSBMRBI-UHFFFAOYSA-N CC(CCC)=O.C1=CC=CC=C1 Chemical compound CC(CCC)=O.C1=CC=CC=C1 DELPSTRBSBMRBI-UHFFFAOYSA-N 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- ONKUXPIBXRRIDU-UHFFFAOYSA-N Diethyl decanedioate Chemical compound CCOC(=O)CCCCCCCCC(=O)OCC ONKUXPIBXRRIDU-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- DJNTZVRUYMHBTD-UHFFFAOYSA-N Octyl octanoate Chemical compound CCCCCCCCOC(=O)CCCCCCC DJNTZVRUYMHBTD-UHFFFAOYSA-N 0.000 description 1
- 229920000144 PEDOT:PSS Polymers 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 1
- JKJWYKGYGWOAHT-UHFFFAOYSA-N bis(prop-2-enyl) carbonate Chemical compound C=CCOC(=O)OCC=C JKJWYKGYGWOAHT-UHFFFAOYSA-N 0.000 description 1
- 230000017531 blood circulation Effects 0.000 description 1
- FFSAXUULYPJSKH-UHFFFAOYSA-N butyrophenone Chemical compound CCCC(=O)C1=CC=CC=C1 FFSAXUULYPJSKH-UHFFFAOYSA-N 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 239000007766 cera flava Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- VNTLIPZTSJSULJ-UHFFFAOYSA-N chromium molybdenum Chemical compound [Cr].[Mo] VNTLIPZTSJSULJ-UHFFFAOYSA-N 0.000 description 1
- 230000004087 circulation Effects 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 239000013256 coordination polymer Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- GUVUOGQBMYCBQP-UHFFFAOYSA-N dmpu Chemical compound CN1CCCN(C)C1=O GUVUOGQBMYCBQP-UHFFFAOYSA-N 0.000 description 1
- 239000012636 effector Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000007772 electrode material Substances 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- IMKMFBIYHXBKRX-UHFFFAOYSA-M lithium;quinoline-2-carboxylate Chemical compound [Li+].C1=CC=CC2=NC(C(=O)[O-])=CC=C21 IMKMFBIYHXBKRX-UHFFFAOYSA-M 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- DCZNSJVFOQPSRV-UHFFFAOYSA-N n,n-diphenyl-4-[4-(n-phenylanilino)phenyl]aniline Chemical compound 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
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- UWJJYHHHVWZFEP-UHFFFAOYSA-N pentane-1,1-diol Chemical compound CCCCC(O)O UWJJYHHHVWZFEP-UHFFFAOYSA-N 0.000 description 1
- GJWGZSBNFSBUPX-UHFFFAOYSA-N pentyl octanoate Chemical compound CCCCCCCC(=O)OCCCCC GJWGZSBNFSBUPX-UHFFFAOYSA-N 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229920002120 photoresistant polymer Polymers 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229950000845 politef Drugs 0.000 description 1
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 1
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 1
- 229920000548 poly(silane) polymer Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920001843 polymethylhydrosiloxane Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 150000003219 pyrazolines Chemical class 0.000 description 1
- VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical class OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000027756 respiratory electron transport chain Effects 0.000 description 1
- 230000000452 restraining effect Effects 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000000527 sonication Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 210000004722 stifle Anatomy 0.000 description 1
- ILLKMACMBHTSHP-UHFFFAOYSA-N tetradecaethylene glycol Chemical compound OCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCO ILLKMACMBHTSHP-UHFFFAOYSA-N 0.000 description 1
- 238000002207 thermal evaporation Methods 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
- H10K71/10—Deposition of organic active material
- H10K71/12—Deposition of organic active material using liquid deposition, e.g. spin coating
- H10K71/13—Deposition of organic active material using liquid deposition, e.g. spin coating using printing techniques, e.g. ink-jet printing or screen printing
- H10K71/135—Deposition of organic active material using liquid deposition, e.g. spin coating using printing techniques, e.g. ink-jet printing or screen printing using ink-jet printing
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/10—Printing inks based on artificial resins
- C09D11/102—Printing inks based on artificial resins containing macromolecular compounds obtained by reactions other than those only involving unsaturated carbon-to-carbon bonds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
- C09D11/36—Inkjet printing inks based on non-aqueous solvents
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/52—Electrically conductive inks
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D181/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing sulfur, with or without nitrogen, oxygen, or carbon only; Coating compositions based on polysulfones; Coating compositions based on derivatives of such polymers
- C09D181/02—Polythioethers; Polythioether-ethers
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
- H10K71/10—Deposition of organic active material
- H10K71/12—Deposition of organic active material using liquid deposition, e.g. spin coating
- H10K71/15—Deposition of organic active material using liquid deposition, e.g. spin coating characterised by the solvent used
-
- 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
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/17—Carrier injection layers
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Manufacturing & Machinery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Electroluminescent Light Sources (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Ink Jet (AREA)
- Ink Jet Recording Methods And Recording Media Thereof (AREA)
Abstract
Ink compositions comprising polythiophenes and methicone that are formulated for Inkjet printing the hole injecting layer (HIL) of an organic light emitting diode (OLED) are provided. Also provided are methods of inkjet printing the HILs using the ink compositions. Ink compositions for inkjet printing layers in organic light emitting diodes (OLEDs) have been proposed. However, problems associated with inadequate wetting properties of the ink compositions has stifled the development of printable inks because improper wetting leads to non-uniform film formation and, therefore, non-uniform luminescence from organic light emitting diode pixels that incorporate the printed films.
Description
The cross reference of related application
This application claims the priority of the U.S. Provisional Patent Application number 61/898343 that title is the composition for ink comprising polythiophene for ink jet printing that on October 31st, 2013 submits to, in being wholly incorporated into this document by reference. The application is that JIUYUE in 2012 is submitted on the 14th, and require the U.S. Provisional Patent Application number 61/535 of JIUYUE in 2011 submission on the 16th, the title of the priority of 413 is the U.S. Patent Application No. 13/618 of the film-forming agents for base material printing, the cip application of 157, in being wholly incorporated into this document by reference.
Background
Have been proposed for the composition for ink for the ink jet printing layer in Organic Light Emitting Diode (OLED). But, the problem relevant to the insufficient wetting characteristics of composition for ink is restrained and (stifle) development of printable ink, because unsuitable moistening causes that uneven film is formed, and therefore cause the uneven luminescence from the organic light-emitting diode pixel being incorporated to print film. Another challenge having hindered the development of the ink-jet printable compositions for OLED application is keeping sprayable ink formulations while, it is impossible to be incorporated in ink by the living polymer of high concentration.
Summary
Providing the composition for ink comprising polythiophene, it is formulated for the hole injection layer (HIL) of ink jet printing OLED. Some embodiments of composition for ink are characterised by comprising polymethyl siloxane as pining down agent (pinningagent). It is otherwise characterized in that and comprises the aprotic solvent that can be incorporated in ink by the polythiophene of high concentration. Additionally provide the method using this composition for ink ink jet printing HIL.
Forming an embodiment for the method for the HIL of Organic Light Emitting Diode to comprise the following steps: the drop (namely at least one dropping liquid drips) of ink-jet printing inks compositions on the electrode layer in the pixel cell of Organic Light Emitting Diode, described pixel cell is limited by pixel dike (bank); Evaporate with the volatile component allowing composition for ink, thus forming hole injection layer. One embodiment of the composition for ink that can use in the method comprises: the polythiophene of conduction; Water; At least one organic solvent; And polymethyl siloxane, the amount that wherein polymethyl siloxane pins down to provide the contact wire of the drop in pixel cell exists.
Some embodiments of composition for ink comprise: poly-(3,4-ethyldioxythiophene);Water; At least one organic solvent, it has the surface tension being not more than 55 dyne/cm at 25 DEG C, is not more than the viscosity of 15cPs and the boiling point of at least 200 DEG C at 25 DEG C; And polymethyl siloxane. This at least one organic solvent can be such as sulfolane.
When checking the following drawings, detailed description and appending claims, other principal character of the present invention and advantage will become clear and definite for those skilled in the art.
Accompanying drawing is sketched
The exemplary of the present invention will be described in reference to the drawings hereinafter, and wherein identical numeral represents identical element.
Fig. 1 is the block diagram illustrating OLED ink-jet printing system.
Fig. 2 is the schematic diagram of the gas confinement system that can hold the print system shown in FIG.
Fig. 3 is included in the matrix of pixel cell the schematic diagram of the flat faced display of multiple OLED of arrangement, and each pixel cell is limited by pixel dike.
Fig. 4 A is the microphotograph image of the composition for ink pind down in OLED pixel unit of the polymethyl siloxane comprising 0.08wt.%.
Fig. 4 B is the black and white line chart of the microphotograph in Fig. 4 A.
Fig. 5 A is free from the microphotograph image of the composition for ink overflowing OLED pixel unit of polymethyl siloxane.
Fig. 5 B is the black and white line chart of the microphotograph in Fig. 5 A.
Fig. 6 A is free from the microphotograph image of the composition for ink of the dewetting OLED pixel unit of polymethyl siloxane.
Fig. 6 B is the black and white line chart of the microphotograph in Fig. 6 A.
Fig. 7 A is by having with comprising the polymethyl siloxane luminous microphotograph as the OLED pixel emission of the HIL of the ink compositions print pining down agent.
Fig. 7 B is the black and white line chart of the microphotograph in Fig. 7 A.
Fig. 8 A is that wherein HIL is with comprising polymethyl siloxane as pining down agent and the sulfolane ink compositions print as organic solvent by the luminous microphotograph of OLED pixel emission.
Fig. 8 B is the black and white line chart of the microphotograph in Fig. 8 A.
Fig. 9 A is that wherein HIL is with comprising polymethyl siloxane as pining down agent and the 1,3-PD ink compositions print as organic solvent by the luminous microphotograph of OLED pixel emission.
Fig. 9 B is the black and white line chart of the microphotograph in Fig. 9 A.
Figure 10 is as described in example 2 above, and before and after 30 minute free time of inkjet printing nozzle, the droplet size of composition for ink is relative to the figure of time.
Figure 11 is as described in example 2 above, and before and after 30 minute free time of inkjet printing nozzle, the liquid drop speed of composition for ink is relative to the figure of time.
Figure 12 is as described in example 2 above, and before and after 30 minute free time of inkjet printing nozzle, the drop angle of composition for ink is relative to the figure of time.
Detailed description
Providing the composition for ink comprising polythiophene, it is formulated for the HIL of ink jet printing OLED. Additionally provide the method using this composition for ink ink jet printing HIL.
Composition for ink is characterised by that the polythiophene of the conduction of high concentration is such as poly-(3,4-ethyldioxythiophene) (PEDOT), additionally provide and make them be very suitable for moistening, injection and the lag characteristic being ink-jet printing on pixelation base material (such as OLED pixel unit). Additionally, this composition for ink provides the thickness with high uniformity and the HIL through printing of homogeneity composition. Therefore, for incorporating them into OLED therein, contribute to the light emittance profile of high uniformity through the HIL of printing.The printability of the enhancing provided by this composition for ink can be at least partially attributed to, and under suitable concentration, polymethyl siloxane can serve as the contact wire of the drop of pixel cell ink inside compositions and pin down the realization of agent. By providing contact wire to pin down, polymethyl siloxane guarantees that the trace (footprint) depositing to the drop of the composition for ink in pixel cell keeps not changing from its original form during dry run.
One basic embodiment of composition for ink is the aqueous solution of the polythiophene, polymethyl siloxane, at least one organic solvent and the water that comprise conduction. Use on the layer of the conductive material (i.e. anode) that the basic embodiment of method of HIL that a kind of composition for ink forms OLED includes making the droplet deposition of composition for ink in the pixel cell of organic LED array, volatile component evaporation with allowing composition for ink, leaves the step of solid HIL. Allow volatile component (such as water and the organic solvent) step evaporated can pass through to make the composition for ink of printing stand decompression (being namely exposed to vacuum), by making the composition for ink of printing be exposed to high temperature or both combinations promote.
Polymethyl siloxane is by the silicone oil of siloxane polymerization. they are also referred to as methyl hydrogen siloxane or methylsiloxane. polymethyl siloxane is commercially available, and is sold as surfactant using trade name Botanisil by Botanigenics (Northridge, CA). these include Botanisil AD-13, AM-14, ATC-21, BPD-100, CD-80, CD-90, CE-35, CM-12, CM-13, CM-70, CP-33, CPM-10, CS-50, CTS-45, DM-60M, DM-85, DM-90, DM-91, DM-92, DM-93, DM-94, DM-95, DM-96, DM-97, DTS-13, DTS-35, GB-19, GB-20, GB-23, GB-25, GB-35, L-23, ME-10, ME-12, PSS-150, PT-100, S-18, S-19, S-20, TSA-16 and TSS-1. the all right trade name SilSense of polymethyl siloxane is available from LubrizolCorporation (Wickliffe, Ohio). these include SilSense Copolyol-1Silicone (PEG-33 (with) PEG-8 polydimethylsiloxane (with) PEG14), SilSense DW-18Silicone (polydimethylsiloxane PEG-7 isostearate), SilSense SW-12Silicone (polydimethylsiloxane PEG-7 cocos nucifera oil acid esters), SilSense IWS (dimethiconol ester dimethiconol stearate), SilSense A-21Silicone (PEG-7 ammonia end polydimethylsiloxane), SilSense PE-100Silicone (polydimethylsiloxane PEG-8 phosphate ester) and Ultrabee WDSilicone (polydimethylsiloxane PEG-8 Cera Flava).
In the composition for ink of the present invention, it is carefully controlled the amount of polymethyl siloxane so that polymethyl siloxane serves as contact wire and pins down agent. This is important, because it prevents the composition for ink drop pind down from departing from (pullaway) (dewetting) from the part dike of pixel cell, it overflows with the other parts at pixel cell sometimes. It also prevents composition for ink be deposited in the side of pixel cell or sprawl beyond pixel cell, as by the generation when more complete wetting.
This composition for ink may be used for formation HIL on multiple OLED electrode material. Most commonly, electrode base material will comprise transparent conductive material, for instance transparent conductive oxide (TCO) or silicon.The suitable concentration range of the polymethyl siloxane in composition for ink will depend upon which the character of following base material. But, for given base material, polymethyl siloxane provides the concentration range that contact wire pins down can be measured by the wetting behavior of the ink droplets that observation has different polymethyl siloxane concentration, and described ink droplets is poured into a mould (casting) method via drop and is applied to surface. By way of illustration, some embodiments of the composition for ink of the present invention comprise and are not more than 0.15 percentage by weight (wt.%), be not more than 0.12wt.% or be not more than the polymethyl siloxane of amount of 0.1wt.%, based on the gross weight gauge of composition for ink. This includes the embodiment of the wherein composition for ink that polymethyl siloxane exists with the amount of 0.02 to 0.15wt.%, farther include the embodiment that wherein polymethyl siloxane exists with the amount of 0.03 to 0.12wt.%, and also farther include the embodiment that wherein polymethyl siloxane exists with the amount of 0.05 to 0.1wt.%, based on the gross weight gauge of composition for ink. By time on HIL ink compositions print to the known anode material used in OLED, such scope is suitable. Such as, launched by anode wherein in the situation of OLED of light (being referred to as bottom-emission), use transparent or semitransparent anode material. Transparent or semitransparent anode material can include Indium sesquioxide., zinc oxide, tin indium oxide (ITO) and indium zinc oxide (IZO) etc. Wherein by the situation of the OLED of cathode luminescence (being referred to as top luminescence), in transparent anode reflecting layer formed below. Reflector material includes silver (Ag), silver-palladium-copper (APC), silver-rubidium-Jin (ARA), molybdenum-chromium (MoCr) etc.
Aqueous ink composition comprises the polythiophene of one or more conductions further. Such as, the mixture of PEDOT and PEDOT and poly-(styrene sulfonate) (poly (styrenesulfonate)) (PEDOT:PSS) can be comprised in this composition for ink. It is interesting to note that during with suitable solvent (discussing in greater detail below) combination, the concentration that polythiophene can be very high is comprised in composition for ink. Such as, some embodiments of composition for ink comprise the polythiophene of at least polythiophene of the polythiophene of the polythiophene of 30wt.%, at least 40wt.%, at least 50wt.%, at least 55wt.% or the polythiophene of at least 60wt.%, based on the gross weight gauge of composition for ink. In such embodiments, described polythiophene can be PEDOT.
Aqueous ink composition comprises at least one organic solvent. Such as, compositions can comprise the solvent of surface tension and/or the viscosity reducing said composition, increases the solvent of the delay of the composition for ink of printing or the combination of the solvent of these types. Described at least one organic solvent can be the solvent with relatively high boiling point, which increases the delay of the composition for ink of printing. This is advantageous for, because it contributes to preventing composition for ink be dried to during printing in print nozzles and block print nozzles. Such solvent desirably has the boiling point of at least 200 DEG C. Even more desirably, they have the boiling point of at least 230 DEG C, at least 250 DEG C or even at least 280 DEG C. Glycol and glycols (glycols) such as propylene glycol, pentanediol, diethylene glycol and triethylene glycol can be used for increasing the example of the organic solvent postponed. Unfortunately, glycol and glycols tend to have relatively high viscosity and surface tension, and what it can reduce the composition for ink that comprises them can ejection. Therefore, some embodiments of the composition for ink of the present invention are without glycol and glycolic solvents. In these embodiments, it is possible to use have the boiling point of at least 240 DEG C, the viscosity being not more than 15cPs and the capillary aprotic solvent being not more than 55 dyne/cm replace glycol or glycols.This aprotic solvent including there is the viscosity being not more than 12cPs, and farther include to have those of the viscosity that is not more than 10cPs. For the purpose of present disclosure, the boiling point enumerated refers to boiling point at atmosheric pressure. The viscosity enumerated and surface tension refer to the viscosity under printing temperature and surface tension. Such as, if printing occurs at room temperature, then viscosity and surface tension will be those at about 25 DEG C.
Sulfolane, 2,3,4,5-Tetramethylene sulfide-1,1-dioxide, also referred to as tetramethylene sulfone, is relatively high boiling point, an example of the aprotic solvent of relatively low viscosity, and it is not when sacrificing and can provide good delay when ejection. Additionally, while ejection, sulfolane can be comprised and can be incorporated to solvent and the polythiophene of high concentration as the composition for ink of organic solvent keeping good. Such as, this composition for ink can comprise the sulfolane of at least 5wt.%, at least 10wt.% or at least amount of 12wt.%. The suitable concentration range of the sulfolane in composition for ink includes about 3wt.% to about 15wt.%. Under these sulfolane concentration, composition for ink can be incorporated to the PEDOT (such as 35 to 70wt.%) of high concentration. In some composition for ink, sulfolane is main solvent, namely its account for composition for ink total organic solvent content more than 50wt.%. Other suitable solvent includes Allyl carbonate and 1,3-dimethyl-3, and 4,5,6-tetrahydrochysene-2 (1H)-pyrimidones, also referred to as dimethylpropylene urea.
In order to enhancing composition can ejection, composition for ink can comprise the cosolvent serving as surface tension reducer further. Such as, comprise the composition for ink of glycol, glycols, sulfolane or other high boiling solvent to comprise and have compared with low surface tension and typically more lower boiling additional solvent than those solvents. Methyl proxitol or other similar ether may be used for this purpose.
Typically for the composition for ink that can be used for ink jet printing application, it should regulate the surface tension of (tailor) this composition for ink, viscosity, delay and wetting characteristics to allow compositions in temperature (the such as room temperature for printing; ~ 25 DEG C) under when not being dried on nozzle or be assigned with by inkjet printing nozzle when plug nozzle. Therefore, optkmal characteristics will change according to such factor such as jet size, print speed printing speed and printing temperature. Generally, acceptable viscosity by include about 1 to about 20cPs those, and acceptable surface tension will include lower than those of about 50 dyne/cm. In order to eliminate or minimize spray nozzle clogging, the delay of 20 minutes or longer (such as 30 minutes or longer) (at room temperature and not under a vacuum) is desired, wherein postpone to refer to exist performance significantly reduce (such as affecting the reduction of the liquid drop speed of image quality significantly) before, it is possible to make nozzle keep not covering and the idle time.
The ink-jet printer being suitable for printing ink compositions is commercially available, and the print head including drop on demand ink jet, it is available from such as FujifilmDimatix (Lebanon, N.H.), TridentInternational (Brookfield, Conn.), Epson (Torrance, Calif.), HitachiDatasystemsCorporation (SantaClara, Calif.), XaarPLC (Cambridge, UnitedKingdom), and IdanitTechnologies, Limited (RishonLeZion, and RicohPrintingSystemsAmerica Isreal), Inc. (SimiValley, CA).It is, for example possible to use DimatixMaterialsPrinterDMP-3000.
As described in the block diagram of Fig. 1, the various embodiments of OLED ink-jet printing system 100 can be made up of multiple units and system etc., and ink droplet is reliably placed on the ad-hoc location on base material by its permission. Various embodiments according to system and method, print system can include, for instance but it is not limited to base material induction system 110, substrate support 120, motor system 130, print head set component 140, ink delivery system 150 and control system 160.
Base material induction system 110 can be used OLED base material to insert print system 100 and removes from print system 100. Depending on the various embodiments of print system 100, base material induction system 110 can be mechanical conveyor, has base material floating (floatation) platform of clamper molectron, have the automation of end effector, and combination. Additionally, during printing process, it is possible to support base material by a support arrangement 120, described support arrangement is it may be that such as but not limited to chuck (chuck) or floating. Because printing needs the relative motion between print head and base material, so the various embodiments of print system 100 can have motor system 130, it can be such as but not limited to portal frame (gantry) or split axle (splitaxis) XYZ system.
Print head set component 140 can include at least one the print head equipment that can be mounted to motor system 130. At least one the print head equipment included at print head set component 140 can have at least one can pass through the ink jet printing head that the drop of composition for ink is sprayed at least one hole with controlled speed, speed and size. The various embodiments of the print system 100 according to this instruction can have about 1 to about 60 print head equipment. Additionally, the various embodiments of print head equipment can have about 1 to about 30 ink jet printing head in each print head equipment, wherein each ink jet printing head can have about 16 to about 2048 nozzles. Various embodiments according to print head set component 140, each nozzle of each ink jet printing head can discharge the droplet size of about 0.1pL to about 200pL. The print head set component 140 with at least one ink jet printing head can be in fluid communication with composition for ink delivery system 150, and described composition for ink delivery system 150 can by one or more ink jet printing heads of composition for ink supply to print head set component 140.
Various embodiments about motor system 130, during printing process, print head set component 140 can move (portal frame type) on fixing base material, or when split axle configures, print head set component 140 and base material both can move. Various embodiments for the configuration of split axle, it is possible to provide the control of Z axis by moving print head set component 140 relative to base material. In the further embodiment of motor system, can fixing printing head molectron 140, and base material can move relative to print head set component 140 on X and Y-axis, moved by the Z axis of print head set component 140 or move offer Z axis motion by the Z axis of base material. During printing process, along with print head set component 140 moves relative to base material, spray the drop of composition for ink when being in orthochronous to be deposited on the desired location on base material.
For the various embodiments of print system 100, control system 160 may be used for controlling the function of printing process.The various embodiments of control system 160 can pass through user interface by end-user access. Control system 180 may be used for controlling, sending data to base material induction system 110, substrate support 120, motor system 130, print head set component 140 and ink delivery system 150, and receives the data from them. Control system 160 can be computer system, microcontroller, special IC (ASIC), field programmable gate array (FPGA), can send and receive control and data message and be able to carry out the electronic circuit of instruction, and combination. Control system 160 can include an electronic circuit or such as the purpose of the communication provided between assembly, multiple electronic circuits of distribution in base material induction system 110, substrate support 120, motor system 130, print head set component 140 and composition for ink delivery system 150.
Additionally, the various embodiments of the control system 160 of print system 100 can provide data to process, show and report preparatory function. All such instrument controlling functions can be exclusively used in print system 100 in this locality, or control system 160 can provide the long-range control of all or part of control, analysis and function of reporting. Finally, the various embodiments of printing equipment 100 can be contained in the closed system 200 of Fig. 2.
According to various embodiments, Fig. 2 is the schematic diagram of the gas confinement system 200 of the print system 100 that can hold Fig. 1. According to this instruction, the various embodiments of gas confinement system 200 can include gas purification loop 230 and at least one heat regulating system 240 of gas confinement molectron 250 and gas confinement molectron 250 fluid communication. Additionally, the various embodiments of gas confinement system can have pressurized inert gas recirculating system 260, it can supply to be applied to operate various equipment, for instance the noble gas of floating of the base material of OLED print system. The various embodiments of pressurized inert gas recirculating system 260 can use the combination source as the various embodiments of noble gas recirculating system 260 of compressor, aerator and both. Additionally, gas confinement system 200 can have filtration and blood circulation (not shown) in the inside of gas confinement system 200, it is together with such as floating printing environment that can provide substantially low granule of other assembly.
As described in figure 2, various embodiments for the gas confinement molectron 200 according to this instruction, gas purification loop 230 can include outlet line 231, and it removes assembly 232 from gas confinement molectron 250 to solvent, and then to gas purge system 234. Then the noble gas that purification removes solvent and other reactant gas material such as oxygen and steam is made to be back to gas confinement molectron 250 by suction line 233. Gas purification loop 230 can also include suitable conduit and connector and sensor, for instance oxygen, steam and solvent vapour sensor. Gas circulation unit such as fan, aerator or motor etc. can be individually provided, or be integrated in such as gas purge system 234 with by gas purification loop 230 recyclegas. Various embodiments according to gas confinement molectron, although the schematic diagram that solvent removal system 232 and gas purge system 234 show in fig. 2 is shown as independent unit, but can using solvent removal system 232 and gas purge system 234 together with single clean unit be contained in.Heat regulating system 240 can include, for instance but it is not limited at least one cooler 241, and it can have the fluid issuing pipeline 243 for being recycled to by coolant in gas confinement molectron, and for making coolant return to the fluid inlet line 245 of cooler.
For the various embodiments of gas confinement molectron 200, gas source can be noble gas, for instance nitrogen, any rare gas, and combination in any. For the various embodiments of gas confinement molectron 200, gas source can be such as the gas source of clean dry air (CDA). For the various embodiments of gas confinement molectron 200, gas source can be supplying inert gas and the source of combination of the gas such as CDA.
Gas confinement system 200 can keep the level of every kind of material of various reactant gas material at 100ppm or lower, such as 10ppm or lower, 1.0ppm or lower or 0.1ppm or lower, described reactant gas material includes various reactive atmospheric gas such as steam and oxygen and organic solvent steam. Additionally, the various embodiments of gas confinement molectron can provide the low particle environments meeting 1 grade of specification limit to the Atmospheric particulates of 5 grades of clean room standards according to ISO14644.
Although what be given above is exemplary OLED ink-jet printing system and gas closed system, but those skilled in the art will be appreciated that and can build such system with the combination in any of one or more equipment of Fig. 1 and Fig. 2 and device and extra equipment and device.
The product of final ink jet printing is the HIL of thickness and the composition with high uniformity. Such as, the layer having the thickness change being not more than 10% across the whole width of layer is possible. Thickness across layer can use metering outfit such as contact pin type contact profile instrument (styluscontactprofilometer) or interferometer microscope to measure. For the suitable interferometer of Through Optical Interference Spectra available commercially from Zygoinstrumentation.
Composition for ink may be used for directly printing in the OLED framework of multilamellar HIL. Typical OLED includes supporting base material, anode, negative electrode, the HIL of configuration on anode and the luminescent layer (EML) configured between HIL and negative electrode. Other layer that can exist in the devices includes providing to assist to make hole transport to the hole transmission layer of luminescent layer between HIL and luminescent layer, and the electron transfer layer (ETL) configured between EML and negative electrode. Base material is usually transparent glass or plastic basis material.
In the framework of these multilamellars, it is possible to form the one or more layers except HIL via ink jet printing, and other film technique can be used to deposit other layer. Typically, various layer will be formed in one or more pixel cells. Each pixel cell includes bottom and is limited by the dike of the circumference limiting unit. It is optionally possible to the surface in surface modification coatings such as surfactant-coated unit. But, in some embodiments, it is absent from such surfactant, because they can the luminescence of cancellation luminescent layer.
Fig. 3 is the schematic diagram of flat faced display, and it includes multiple OLED of arrangement in the matrix of pixel cell. Fig. 3 describes the enlarged drawing 320 in a region of panel 300, and it demonstrates the arrangement 330 of multiple pixel cell, including the pixel cell 332 glowed, the pixel cell 334 of green light and the pixel cell 336 of blue light-emitting.Furthermore, it is possible to form integrated circuit 338 in flat panel display substrates so that for the purpose applying a voltage to each pixel during use in a controlled manner, circuit is adjacent with each pixel cell. The size of pixel cell, shape and aspect ratio can bases, for instance but be not limited to required resolution and change. Such as, the pixel cell density of 100ppi for can be enough for the panel of computer display, wherein for the high-resolution of such as about 300ppi to about 450ppi, may result in the various pixel cells design obeying the effectively picture element density that packaging is higher on substrate surface.
Although disclosure above has been concentrated on preparing for the ink jet printing aqueous ink composition based on the HIL of polythiophene, but the another aspect of this technology provide prepare HIL or HTL for ink jet printing OLED non-aqueous, based on the composition for ink of organic solvent. This organic HIL/HTL composition for ink comprises routine and is considered the component of wetting agent, but is incorporated in HTL ink with the amount carefully controlled so that uncontrolled the sprawling that it is actually prevented from occurring possibly as the result of moistening is overflowed with pixel cell. In some embodiments, organic inks comprises: (1) hole-injecting material or hole mobile material; (2) one or more organic solvents, it makes hole inject or hole mobile material dissolves; (3) fluorine-containing surfactant. Described hole is injected or hole mobile material is typically to be not more than about 5wt.%, is more typically not more than 2wt.% and also is more typically not more than the amount existence of about 1wt.% (such as about 0.1 to about 1wt.%), based on the gross weight gauge of composition for ink. Organic solvent typically accounts for about the 95 to about 99.8wt.% of composition for ink. Fluorinated surfactant is typically to be not more than the amount existence of about 0.15wt.%. Such as, in some embodiments of the composition for ink based on organic solvent, fluorinated surfactant exists with the amount of about 0.03wt.% to about 0.1wt.%.
As it has been described above, the suitable hole-injecting material for the composition for ink based on organic solvent includes polythiophene. suitable hole mobile material includes polyvinylcarbazole or derivatives thereof, polysilane or derivatives thereof, side chain or main chain have the polyorganosiloxane ramification of aromatic amine, pyrazoline derivative, arylamine derivatives, derivant, triphenyl diamine derivant, polyaniline or derivatives thereof, polythiophene or derivatives thereof, polyarylamine or derivatives thereof, polypyrrole or derivatives thereof, poly-(to phenylene vinylidene) (poly (p-phenylenevinylene)) or derivatives thereof, or poly-(2, 5-Asia thienyl ethenylidene) (poly (2, 5thienylenevinylene)) or derivatives thereof.
For the suitable organic solvent of HIL/HTL composition for ink include alkoxyl alcohol, alkylol, alkylbenzene, benzoic acid Arrcostab, alkylnaphthalene, amyl octylate, methyl phenyl ethers anisole, aryl alcohol, benzylalcohol, butyl benzene, butyrophenone, cis naphthalane, dipropylene glycol methyl ether, detergent alkylate, sym-trimethylbenzene., methoxypropanol, essence of Niobe, methyl naphthalene, methyl pyrrolidone, phenyl phenol, 1, ammediol, ketopyrrolidine, trans naphthalane, benzene pentanone (valerophenon), and mixture.
Fluorine-containing surfactant is the surfactant comprising fluorinated alkyl chain. E.I.duPontdeNemoursandCompany (Wilmington, Delaware) merchandising name is called the fluorinated surfactant of Capstone and Zonyl.Fluorine-containing surfactant can be such as fluorine-containing telomer (such as telomere (telomere) B monoether and Polyethylene Glycol or 2-perfluoroalkyl ethanol). commercially available fluorine-containing surfactant includes Zonyl FS1033D, Zonyl FS1176, Zonyl FSG, Zonyl FS-300, Zonyl FSN, Zonyl FSH, Zonyl FSN, Zonyl FSO, Zonyl FSN-100, Zonyl FSO-100, Zonyl FSH, Zonyl FSN, Zonyl FSO, Zonyl FSH, Zonyl FSN, Zonyl FSO, Zonyl FS500, Zonyl FS510, Zonyl FSJ, Zonyl FS-610, Zonyl 9361, Zonyl FSA, FSP, FSE, FSJ, Zonyl FSP, Zonyl 9361, Zonyl FSE, Zonyl FSA, Zonyl UR, Zonyl 8867L, Zonyl FSG, Zonyl 8857A, Foraperle 225, Forafac 1268, Forafac 1157, Forafac 1183, Zonyl 8929B, Zonyl 9155, Zonyl 9815, Zonyl 9933LX, Zonyl 9938, Zonyl PFBI, Zonyl PFBEI, Zonyl PFBE, Zonyl PFHI, Zonyl BA,-8-Zonyl PFHEI, Zonyl TM, Zonyl 8932, Zonyl 7910, Zonyl 7040, Foraperle 321/325, Zonyl 9464, Zonyl NF, Zonyl RP, Zonyl 321, Zonyl 8740, Zonyl 225, Zonyl 227, Zonyl 9977, Zonyl 9027, Zonyl 9671, Zonyl 9338 and Zonyl 9582, Capstone ST-500, Capstone ST-300, Capstone ST-200, Capstone ST-110, Capstone P-640, Capstone P-623, Capstone P-620, Capstone P-600, Capstone FS-10, Capstone FS-17, Capstone FS-22, Capstone FS-30, Capstone FS-31, Capstone FS-3100, Capstone FS-34, Capstone FS-35, Capstone FS-50, Capstone FS-51, Capstone FS-60, Capstone FS-61, Capstone FS-63, Capstone FS-64, Capstone FS-64, Capstone FS-65, Capstone FS-66, Capstone FS-81, Capstone FS-83, Capstone LPA, Capstone 1460, Capstone 1157, Capstone 1157D, Capstone 1183, Capstone CPS, Capstone E, Capstone LMC, Capstone CP, Capstone PSB, Capstone 4-I, Capstone 42-I, Capstone 42-U, Capstone 6-I, Capstone 62-AL, Capstone 62-I, Capstone 62-MA, Capstone TC, Capstone TR and Capstone TS.
Embodiment
Embodiment 1: polymethyl siloxane is on the impact of uniformity in pixel
The improvement of contact wire restraining function and the produced uniformity of luminance provided by the polymethyl siloxane in HIL ink jet ink composition is be provided.
Material and method.
The preparation of HIL composition for ink:
HIL composition for ink A and B is prepared by component displayed in Table 1 and concentration. Compositions A and B both comprises the polymethyl siloxane of indicated concentration. As a comparison case, preparation comprises the composition listed in table 2 but lacks the composition for ink (Comparative composition) of polymethyl siloxane.
Table 1
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Table 2
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By being placed on balance by clean bottle and using Pasteur pipet to be transferred to by the desired amount of BotanisilS-18, bottle is prepared described composition for ink.Taring (tare) balance, and successively 1,3-PD, water and DPGME are pipetted in bottle. Then bottle is removed from balance, add a cover and rotate to mix the aqueous solution of gained. Then bottle is back to balance, and the desired amount of PEDOT dispersion (HaraeusCleviosTMPVPA14083) is pipetted in bottle. Then bottle is removed from balance, add a cover and rotate so that PEDOT mixes with other component of mixture. Then filter the PEDOT composition for ink of gained with politef (PTFE) filter membrane (2.0 ��m), and filtered compositions is collected in amber bottle. Finally, before the use by this bottle of sonication 15 minutes.
When there is no BotanisilS-18, use identical program preparation contrast composition for ink.
Viscosity and stalagmometry:
DV-IPrimeBrookfield flow graph is used to carry out viscosity measurement. Adopt SITA pressure in bubbles tonometer surface tension. Provide composition for ink A and the B comprising polymethyl siloxane and the measured value of contrast composition for ink (Comparative composition) in tables 1 and 2.
HIL ink jet printing and OLED manufacture:
By on the ito anode in HIL ink compositions print to OLED framework. The base material of OLED is the glass of the thickness with 0.5mm, makes the anode pattern (pattern) of 60nmITO (tin indium oxide) thereon. Then dike material (being also referred to as pixel confining layers) is made to pattern on ITO, the unit of deposition ink jet printing layer formed in which. Dike material is to design the negative work photoresist for ink jet printing. The unit of gained has highly for the dike of about 0.5 to 2 ��m, and it is 45�� angle relative to the bottom of unit so that the opening of each unit is more wider than bottom it. 45�� angle is the representative of typical dike angle, and its scope is at about 5 �� to about 70 ��. The width of unit and length dimension are about 60x175 ��m. Then the composition for ink using table 1 and 2 will, in HIL layer ink jet printing to unit, dry and at high temperature toast to remove water and solvent from layer under vacuo.
At room temperature it is used in the ink-jet printing system printing HIL composition for ink described in PCT application publication No. WO2013/158310, by reference the complete disclosure of described WO2013/158310 is incorporated herein. Ink jet printing is carried out in pixel cell by filling overall (bulk) ink housing tube with HIL composition for ink. This entirety ink housing tube and main distribution bin fluid communication, and during printing, HIL composition for ink without interruption is provided to main distribution bin. Then HIL composition for ink is fed in the print head including multiple nozzle, by described nozzle, HIL composition for ink is ejected in pixel cell. During printing, typical droplet size is about 10pl, and is printed onto in each unit by about 3 to 10 to form the drop of composition for ink in the cells.
It is made by being incorporated to the OLED of the HIL with composition for ink A printing. Htl layer is ink-jet printing on HIL layer, dries under vacuo subsequently and at high temperature toast remove solvent and cause crosslinking in crosslinkable polymer. Then EML layer is ink-jet printing on htl layer, dries under vacuo subsequently and at high temperature toast to remove solvent. Use above-mentioned printer ink jet printing HTL and EML layer. Described HTL composition for ink is by forming based on the hole transport polymer material in the dicyandiamide solution (it is made up of the mixture through distillation and degassed sad diethylester and octyl octanoate of the weight ratio of 1:1) of ester.Described EML composition for ink is made up of the electroluminescent organic material in ethyl sebacate.
Then pass through vacuum thermal evaporation and apply ETL layer, with after-applied cathode layer. ETL material includes quinoline and closes lithium (lithiumquinolate) (LiQ) as emissive material, and cathode layer is made up of the aluminum of 100nm.
Result.
The drop of compositions A and the B being printed onto in pixel cell is pind down to pixel dike, and had not both experienced spilling also without experience disengaging. The image of HIL layer prepared by compositions A (polymethyl siloxane of 0.1wt.%) that is that be used in pixel cell printing and that pin down to pixel cell is shown in Fig. 4 A. On the contrary, the image (Fig. 5 and 6) of the Comparative composition being printed onto pixel cell demonstrates when being absent from polymethyl siloxane, composition for ink is uncontrollably sprawled and overflows the side 500 (Fig. 5 A) of pixel cell or the dike with pixel cell departs from (dewetting), produces to overflow the dewetting regions 602 (Fig. 6 A) on the bottom of unit of 600 combinations with some pixel cells.
For display in above-mentioned Fig. 4 A-6A and in following Fig. 7 A-9A each microphotograph of display, it is provided that black and white line chart and be marked as corresponding " B " figure.
It is investigated the electroluminescence characters of the OLED pixel including the HIL with the compositions A ink jet printing prepared. Once manufacture OLED, by applying electric current at diode two ends and making light emission imaging study its electroluminescent uniformity. The luminescence display of gained is in the microphotograph of Fig. 7 A. In the figure, it can be seen that with composition for ink A printing HIL layer contribute to OLED pixel (by as described in HIL layer be incorporated in) uniformly light-emitting.
Embodiment 2: the sulfolane impact on printing characteristic
Following examples merely illustrate the printing characteristic of the improvement being given HIL composition for ink by sulfolane.
Material and method.
The preparation of HIL composition for ink:
Preparation comprises the HIL composition for ink of polymethyl siloxane, sulfolane and other composition listed in table 3.
Table 3
| Composition | Wt.% |
| PEDOT | 59.9 |
| DPGME | 5 |
| Sulfolane | 10 |
| H2O | 25 |
| Surfactant (S18) | 0.1 |
| Viscosity [cP] | 5.9 |
| ST [dyne/cm] | 45.0 |
Prepare composition for ink as described in example 1 above, replace 1,3-PD except with sulfolane.
Viscosity and stalagmometry:
Viscosity and stalagmometry is carried out in embodiment 1.
HIL ink jet printing and OLED manufacture:
As described in example 1 above, the OLED pixel that printing HIL composition for ink and formation are tested for electroluminescent.
Delay measurements:
It is used in the ink-jet printing system described in PCT application publication No. WO2013/158310 and carries out the delay measurements of ink. By making nozzle injection (fire) and measuring 300 data points of volume, speed and directivity and measure. Then nozzle is made idle 30 minutes. Restart nozzle after 30 minutes, and record more than 300 data point.
Injection (the end of the first data set compared to steady statue, before 30 minute free time), when the second data set starts (after 30 minute free time), draw and compare data set to find any Set-out slide effect (usually speed declines and stereomutation).
DimatixFujifilmDMP-2831 printer is also used to carry out the delay measurements of ink. In observing the arranging of drop, open all 16 nozzles and confirm that all nozzles are all in injection. Then injection is stopped 5 minutes.Restart injection and check that all nozzles of confirmation remain in work. Then, injection 15 and 30 minutes continuously are carried out. By delay time measurement be the ink terminated in injection and (uncapped) nozzle of not adding a cover start dry between time, described drying causes that unsuitable drop penetrates. In order to measure when composition for ink is drying, white light and fluorescence mode test under microscope they.
Result.
Once manufacture OLED, by applying electric current at each diode two ends and making light emission imaging study their electroluminescent uniformity. OLED for having the OLED and the HIL having with the ink compositions print of table 1 of the HIL of the ink compositions print with table 3 measures electroluminescent. The sulfolane that the contrast of the microphotograph of Fig. 8 and 9 demonstrates in HIL composition for ink provides pixel light emission (Fig. 8 A) evenly than propylene glycol (Fig. 9 A).
Additionally, the maximum stable injection frequency (1000Hz) of the composition for ink comprising sulfolane is higher than the maximum stable injection frequency of the composition for ink comprising glycol. Finally, compared to only 15 minutes of the composition for ink comprising glycol, comprise the time delay of composition for ink of sulfolane for more than 30 minutes. The result being used in the delayed test that the ink-jet printing system described in PCT application publication No. WO2013/158310 is measured is shown in Figure 10 to 12. In these figures, the ink called after P113 of sulfolane will be comprised. Figure 10 is before the free time and after 30 minute free time, and composition for ink is through the figure of the droplet size of 14 minutes. Figure 11 is before the free time and after 30 minute free time, and composition for ink is through the figure of the liquid drop speed of 14 minutes. As in the figure, it can be seen that the liquid drop speed when restarting is only low than the liquid drop speed before the free time by 4%. Figure 12 is before the free time and after 30 minute free time, and composition for ink is through the figure of the drop angle of 14 minutes. Before and after the free time, do not observe the significant difference of drop angle.
Word " exemplary " is used herein to mean that as embodiment, example or illustration. Any aspect or design here depicted as " exemplary " are not necessarily to be construed as more preferred than other side or design or favourable. Additionally, for the purpose of present disclosure, unless specifically stated otherwise, " with " or the use of "or" be intended to include "and/or".
For the purpose illustrated and describe, present the above description of the exemplary of the present invention. It is not intended to be exhaustive or limits the invention to exact form disclosed, and according to instruction above, amendment and variant are possible, maybe can be obtained from the practice of the present invention. Select and describe embodiment to explain principles of the invention and the practical application as the present invention, so that the various amendments that those skilled in the art can be suitable for intended special-purpose in various embodiments with employing use the present invention. It is intended to be limited the scope of the present invention by appending claims and their equivalent.
Claims (19)
1. the method forming the hole injection layer for Organic Light Emitting Diode, described method includes:
The drop of ink-jet printing inks compositions on electrode layer in the pixel cell of Organic Light Emitting Diode, described pixel cell is limited by pixel dike, and described composition for ink comprises:
The polythiophene of conduction;
Water:
At least one organic solvent;With
Polymethyl siloxane, the amount that wherein polymethyl siloxane pins down to provide the contact wire of the drop in pixel cell exists; With
Allow the volatile component evaporation of composition for ink, thus forming hole injection layer.
2. the process of claim 1 wherein that the polythiophene of described conduction is PEDOT.
3. the method for claim 2, wherein said PEDOT exists with the amount of at least 50wt.%.
4. the method for claim 2, wherein said electrode layer comprises transparent conductive material.
5. the method for claim 4, wherein said transparent conductive material is tin indium oxide, and polymethyl siloxane exists with the amount of about 0.03wt.% to about 0.12wt.%.
6. the process of claim 1 wherein that described at least one organic solvent is the aprotic solvent of the viscosity having the surface tension being not more than 55 dyne/cm at 25 DEG C with being not more than 15cPs.
7. the method for claim 6, wherein said at least one organic solvent has the boiling point of 240 DEG C or higher at atmosheric pressure.
8. the process of claim 1 wherein that described at least one organic solvent is sulfolane.
9. the method for claim 8, wherein said sulfolane is main organic solvent in composition for ink.
10. the method for claim 8, wherein said sulfolane exists with the amount of at least 5wt.%.
11. the method for claim 3, wherein said electrode layer comprises tin indium oxide, and polymethyl siloxane exists with the amount of about 0.05wt.% to about 0.1wt.%, and described at least one organic solvent is sulfolane, and it exists with the amount of about 5 to about 12wt.%.
12. the method for claim 8, wherein said composition for ink comprises second organic solvent than sulfolane with less surface tension and less boiling point further.
13. the method for claim 12, wherein said second organic solvent is methyl proxitol.
14. the process of claim 1 wherein ink formulations there is the surface tension being not more than 47 dyne/cm at 25 DEG C, the viscosity that is not more than 15cPs at 25 DEG C and the time delay of at least 20 minutes at 25 DEG C.
15. composition for ink, it comprises:
PEDOT:
Water:
At least one organic solvent, its have at 25 DEG C, be not more than 55 dyne/cm surface tension, at 25 DEG C, be not more than the viscosity of 15cPs and the boiling point of at least 200 DEG C; With
Polymethyl siloxane.
16. the composition for ink of claim 15, wherein said at least one organic solvent is sulfolane.
17. the composition for ink of claim 16, it comprises second organic solvent than sulfolane with less surface tension and less boiling point further.
18. the composition for ink of claim 17, wherein said second organic solvent is methyl proxitol.
19. the composition for ink of claim 17, it comprises:
The PEDOT of about 50 to about 70wt.%;
The sulfolane of about 3wt.% to about 10wt.%; With
The polymethyl siloxane of about 0.3 to 0.12wt.%.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810153650.8A CN108219588A (en) | 2013-10-31 | 2013-12-04 | For the composition for ink for including polythiophene of ink jet printing |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361898343P | 2013-10-31 | 2013-10-31 | |
| US61/898343 | 2013-10-31 | ||
| PCT/US2013/073175 WO2015065499A2 (en) | 2013-10-31 | 2013-12-04 | Polythiophene-containing ink compositions for inkjet printing |
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| EP (1) | EP3063800A4 (en) |
| JP (2) | JP6438041B2 (en) |
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| WO2023070618A1 (en) * | 2021-10-30 | 2023-05-04 | 华为技术有限公司 | Light-emitting element ink and application of polymer in same, and display apparatus and manufacturing method therefor |
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| US20180248122A1 (en) * | 2015-08-24 | 2018-08-30 | Dic Corporation | Ink composition for organic semiconductor device and organic semiconductor device including the same |
| CN108291105B (en) * | 2015-11-12 | 2021-09-10 | 广州华睿光电材料有限公司 | Composition for printing electronic devices and use thereof in electronic devices |
| CN105440802B (en) * | 2015-12-22 | 2017-12-12 | 江南大学 | It is a kind of can ultraviolet photodimerization PEDOT conductive inks and preparation method thereof |
| US20200303648A1 (en) * | 2017-11-28 | 2020-09-24 | Sakai Display Products Corporation | Organic el light-emitting element and method for manufacturing same |
| KR102316066B1 (en) * | 2018-07-27 | 2021-10-21 | 주식회사 엘지화학 | Ink composition, organic light emitting device using the same and method of manufacturing the same |
| KR102156301B1 (en) * | 2018-09-06 | 2020-09-15 | (주)에스티아이 | Method of inkjet printing and inkjet printing apparatus |
| KR102170962B1 (en) * | 2018-12-10 | 2020-10-28 | (주)에스티아이 | Method of inkjet printing and inkjet printing apparatus |
| KR102243003B1 (en) * | 2020-12-22 | 2021-04-21 | 코오롱인더스트리 주식회사 | Composition for forming hole transport layer and semitransparent organic photovoltaics comprising the same |
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Also Published As
| Publication number | Publication date |
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| CN105658742B (en) | 2018-03-30 |
| WO2015065499A3 (en) | 2015-07-16 |
| EP3063800A2 (en) | 2016-09-07 |
| KR20180108917A (en) | 2018-10-04 |
| WO2015065499A2 (en) | 2015-05-07 |
| JP2017502485A (en) | 2017-01-19 |
| JP2018119164A (en) | 2018-08-02 |
| KR20160078973A (en) | 2016-07-05 |
| JP6438041B2 (en) | 2018-12-12 |
| CN108219588A (en) | 2018-06-29 |
| EP3063800A4 (en) | 2017-06-21 |
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