CN100442567C - 高分子半导体溶液,其制备方法以及其应用 - Google Patents
高分子半导体溶液,其制备方法以及其应用 Download PDFInfo
- Publication number
- CN100442567C CN100442567C CNB02816623XA CN02816623A CN100442567C CN 100442567 C CN100442567 C CN 100442567C CN B02816623X A CNB02816623X A CN B02816623XA CN 02816623 A CN02816623 A CN 02816623A CN 100442567 C CN100442567 C CN 100442567C
- Authority
- CN
- China
- Prior art keywords
- solution
- organic
- solvent
- filtration
- polymer
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 229920000642 polymer Polymers 0.000 title claims abstract description 94
- 239000004065 semiconductor Substances 0.000 title claims abstract description 27
- 230000005669 field effect Effects 0.000 claims abstract description 5
- 238000000034 method Methods 0.000 claims description 115
- 238000001914 filtration Methods 0.000 claims description 48
- 239000002904 solvent Substances 0.000 claims description 48
- 238000011282 treatment Methods 0.000 claims description 26
- 238000000576 coating method Methods 0.000 claims description 25
- 238000002360 preparation method Methods 0.000 claims description 23
- 229920002521 macromolecule Polymers 0.000 claims description 21
- 239000011248 coating agent Substances 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 16
- 239000011877 solvent mixture Substances 0.000 claims description 12
- 238000007641 inkjet printing Methods 0.000 claims description 9
- 238000007639 printing Methods 0.000 claims description 9
- 230000000694 effects Effects 0.000 claims description 6
- 238000012856 packing Methods 0.000 claims description 6
- 239000000654 additive Substances 0.000 claims description 4
- 230000010354 integration Effects 0.000 claims description 4
- 239000012528 membrane Substances 0.000 claims description 4
- 238000007650 screen-printing Methods 0.000 claims description 4
- 238000009295 crossflow filtration Methods 0.000 claims description 3
- 238000011118 depth filtration Methods 0.000 claims description 3
- 238000012958 reprocessing Methods 0.000 claims description 3
- 238000010008 shearing Methods 0.000 claims description 3
- 238000010023 transfer printing Methods 0.000 claims description 3
- 238000009472 formulation Methods 0.000 claims description 2
- 230000005499 meniscus Effects 0.000 claims description 2
- 238000012805 post-processing Methods 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 6
- 239000010409 thin film Substances 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 139
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 28
- 239000000463 material Substances 0.000 description 23
- 239000000523 sample Substances 0.000 description 15
- 230000008569 process Effects 0.000 description 14
- 239000004743 Polypropylene Substances 0.000 description 13
- 229920001155 polypropylene Polymers 0.000 description 13
- 238000004220 aggregation Methods 0.000 description 12
- 230000002776 aggregation Effects 0.000 description 12
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical class COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 12
- 230000008859 change Effects 0.000 description 12
- 239000003960 organic solvent Substances 0.000 description 11
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 9
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 9
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical class N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 9
- 230000002349 favourable effect Effects 0.000 description 9
- 239000002245 particle Substances 0.000 description 9
- 239000011521 glass Substances 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- RICKKZXCGCSLIU-UHFFFAOYSA-N 2-[2-[carboxymethyl-[[3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]methyl]amino]ethyl-[[3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]methyl]amino]acetic acid Chemical compound CC1=NC=C(CO)C(CN(CCN(CC(O)=O)CC=2C(=C(C)N=CC=2CO)O)CC(O)=O)=C1O RICKKZXCGCSLIU-UHFFFAOYSA-N 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
- 238000002156 mixing Methods 0.000 description 7
- 239000004810 polytetrafluoroethylene Substances 0.000 description 7
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 7
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical compound CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 6
- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 description 6
- 238000012545 processing Methods 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 238000005516 engineering process Methods 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000004033 plastic Substances 0.000 description 5
- 229920003023 plastic Polymers 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- -1 polyparaphenylene Polymers 0.000 description 5
- 238000007789 sealing Methods 0.000 description 5
- 238000003860 storage Methods 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 239000000428 dust Substances 0.000 description 4
- 125000003983 fluorenyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 4
- 239000013074 reference sample Substances 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical compound CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- 238000000635 electron micrograph Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 150000002894 organic compounds Chemical class 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000004528 spin coating Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- MMZYCBHLNZVROM-UHFFFAOYSA-N 1-fluoro-2-methylbenzene Chemical compound CC1=CC=CC=C1F MMZYCBHLNZVROM-UHFFFAOYSA-N 0.000 description 2
- BTQZKHUEUDPRST-UHFFFAOYSA-N 1-fluoro-3-methylbenzene Chemical compound CC1=CC=CC(F)=C1 BTQZKHUEUDPRST-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- 229920000265 Polyparaphenylene Polymers 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 239000003849 aromatic solvent Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 229920000547 conjugated polymer Polymers 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000005350 fused silica glass Substances 0.000 description 2
- 230000004927 fusion Effects 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 2
- 238000003672 processing method Methods 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 150000003222 pyridines Chemical class 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 230000000087 stabilizing effect Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000002562 thickening agent Substances 0.000 description 2
- 125000005259 triarylamine group Chemical group 0.000 description 2
- GETTZEONDQJALK-UHFFFAOYSA-N (trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-UHFFFAOYSA-N 0.000 description 1
- AJCSNHQKXUSMMY-UHFFFAOYSA-N 1-chloro-2,4-difluorobenzene Chemical compound FC1=CC=C(Cl)C(F)=C1 AJCSNHQKXUSMMY-UHFFFAOYSA-N 0.000 description 1
- DGRVQOKCSKDWIH-UHFFFAOYSA-N 1-chloro-2-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1Cl DGRVQOKCSKDWIH-UHFFFAOYSA-N 0.000 description 1
- FNPVYRJTBXHIPB-UHFFFAOYSA-N 1-chloro-3-fluoro-2-methylbenzene Chemical compound CC1=C(F)C=CC=C1Cl FNPVYRJTBXHIPB-UHFFFAOYSA-N 0.000 description 1
- AWLDSXJCQWTJPC-UHFFFAOYSA-N 1-fluoro-2,3-dimethylbenzene Chemical group CC1=CC=CC(F)=C1C AWLDSXJCQWTJPC-UHFFFAOYSA-N 0.000 description 1
- BGVGHYOIWIALFF-UHFFFAOYSA-N 1-fluoro-2-(trifluoromethyl)benzene Chemical compound FC1=CC=CC=C1C(F)(F)F BGVGHYOIWIALFF-UHFFFAOYSA-N 0.000 description 1
- IWFKMNAEFPEIOY-UHFFFAOYSA-N 1-fluoro-3,5-dimethoxybenzene Chemical compound COC1=CC(F)=CC(OC)=C1 IWFKMNAEFPEIOY-UHFFFAOYSA-N 0.000 description 1
- GBOWGKOVMBDPJF-UHFFFAOYSA-N 1-fluoro-3-(trifluoromethyl)benzene Chemical compound FC1=CC=CC(C(F)(F)F)=C1 GBOWGKOVMBDPJF-UHFFFAOYSA-N 0.000 description 1
- UNNNAIWPDLRVRN-UHFFFAOYSA-N 1-fluoro-4-(trifluoromethyl)benzene Chemical compound FC1=CC=C(C(F)(F)F)C=C1 UNNNAIWPDLRVRN-UHFFFAOYSA-N 0.000 description 1
- WRWPPGUCZBJXKX-UHFFFAOYSA-N 1-fluoro-4-methylbenzene Chemical compound CC1=CC=C(F)C=C1 WRWPPGUCZBJXKX-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical class CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- XWCKSJOUZQHFKI-UHFFFAOYSA-N 2-chloro-1,4-difluorobenzene Chemical compound FC1=CC=C(F)C(Cl)=C1 XWCKSJOUZQHFKI-UHFFFAOYSA-N 0.000 description 1
- JTAUTNBVFDTYTI-UHFFFAOYSA-N 2-fluoro-1,3-dimethylbenzene Chemical group CC1=CC=CC(C)=C1F JTAUTNBVFDTYTI-UHFFFAOYSA-N 0.000 description 1
- JZTPKAROPNTQQV-UHFFFAOYSA-N 3-fluorobenzonitrile Chemical compound FC1=CC=CC(C#N)=C1 JZTPKAROPNTQQV-UHFFFAOYSA-N 0.000 description 1
- DAGKHJDZYJFWSO-UHFFFAOYSA-N 4-fluoro-1,2-dimethoxybenzene Chemical compound COC1=CC=C(F)C=C1OC DAGKHJDZYJFWSO-UHFFFAOYSA-N 0.000 description 1
- 102000040350 B family Human genes 0.000 description 1
- 108091072128 B family Proteins 0.000 description 1
- 229920002449 FKM Polymers 0.000 description 1
- CMEWLCATCRTSGF-UHFFFAOYSA-N N,N-dimethyl-4-nitrosoaniline Chemical compound CN(C)C1=CC=C(N=O)C=C1 CMEWLCATCRTSGF-UHFFFAOYSA-N 0.000 description 1
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 206010049040 Weight fluctuation Diseases 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000003570 air Substances 0.000 description 1
- 239000012080 ambient air Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 238000000149 argon plasma sintering Methods 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 238000003287 bathing Methods 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- HHNHBFLGXIUXCM-GFCCVEGCSA-N cyclohexylbenzene Chemical compound [CH]1CCCC[C@@H]1C1=CC=CC=C1 HHNHBFLGXIUXCM-GFCCVEGCSA-N 0.000 description 1
- 238000006704 dehydrohalogenation reaction Methods 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 229910003460 diamond Inorganic materials 0.000 description 1
- 239000010432 diamond Substances 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000002019 doping agent Substances 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 238000013467 fragmentation Methods 0.000 description 1
- 238000006062 fragmentation reaction Methods 0.000 description 1
- 150000002390 heteroarenes Chemical class 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 230000005525 hole transport Effects 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 239000006115 industrial coating Substances 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- 230000000873 masking effect Effects 0.000 description 1
- 239000013528 metallic particle Substances 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 235000012149 noodles Nutrition 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 230000001151 other effect Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- DLRJIFUOBPOJNS-UHFFFAOYSA-N phenetole Chemical compound CCOC1=CC=CC=C1 DLRJIFUOBPOJNS-UHFFFAOYSA-N 0.000 description 1
- 229920002120 photoresistant polymer Polymers 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920002959 polymer blend Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000003908 quality control method Methods 0.000 description 1
- 238000000518 rheometry Methods 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 238000000790 scattering method Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
-
- 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
-
- 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
- H10K71/311—Purifying organic semiconductor materials
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
- H10K10/40—Organic transistors
- H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
-
- 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]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
- Electroluminescent Light Sources (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
Abstract
Description
批次 | P-1 | P-2 | P-3 | P-4 | P-5 | P-6 | P-7 |
粘度<sup>1)</sup>在40s<sup>-1</sup>[mPa*s] | ∽25 | ∽22 | ∽18 | ∽26 | ∽21 | 25.3 | 10.5 |
GPC<sup>2)</sup>:Mw/1000 | 1495 | 1440 | 1355 | 1615 | 1550 | 1510 | 1250 |
Mn/1000 | 405 | 420 | 400 | 380 | 420 | 420 | 300 |
EL<sup>3)</sup>(最大效率;在100Cd/m<sup>2</sup>时的U) | 12.3Cd/A3.2V | 11.8Cd/A3.2V | 11.9Cd/A3.6V | 12.4Cd/A3.2V | 11.5Cd/A3.7V | 11.1Cd/A3.7V | 11.8Cd/A3.7V |
标准EL | 10.1Cd/A3.7V | 10.2Cd/A3.9V | 1014Cd/A3.5V | 10.8Cd/A4.0V | 9.9Cd/A3.6V | 9.9Cd/A3.6V | 10.7Cd/A3.7V |
各个聚合物的溶液 | P-1<sup>3)</sup> | P-2<sup>4)</sup> | P-3 | P-4<sup>3)</sup> | P-5<sup>3)</sup> | P-6 | P-7 |
超声处理的使用时间[min] | 102 | 31 | 20 | 82 | 67 | 35 | 10 |
浓度<sup>1)</sup>:[g/l] | 4.49 | 4.42 | 4.45 | 4.24 | 4.33 | 4.46 | 4.63 |
粘度<sup>1)</sup>(在40s<sup>-1</sup>)[mPa*s] | 9.82 | 9.97 | 10.1 | 10.49 | 10.38 | 10.40 | 9.21 |
粘度<sup>1)</sup>(在500s<sup>-1</sup>)[mPa*s] | 8.95 | 8.85 | 9.15 | 9.55 | 8.83 | 9.38 | 8.56 |
GPC<sup>2)</sup>:Mw/1000 | 1210 | 1230 | 1240 | 1250 | 1240 | 1230 | 1180 |
Mn/1000 | 380 | 390 | 400 | 380 | 390 | 400 | 300 |
超声处理时间[h]<sup>1)</sup> | mPa*s,在40s<sup>-1</sup> | mPa*s,在500s<sup>-1</sup> |
0 | 327 | 133 |
12 | 194 | 110 |
22 | 120 | 88 |
30 | 82 | 68 |
41 | 33 | 30 |
52 | 20 | 18.5 |
59 | 17 | 17 |
GPC值<sup>2)</sup> | Mw/1000 | Mn/1000 |
0h US | 1180 | 300 |
59H US | 350 | 150 |
超声处理时间[h]<sup>1)</sup> | mPa*s,在40s<sup>-1</sup> | mPa*s,在500s<sup>-1</sup> |
0 | 115 | 57 |
8 | 15 | 15 |
14 | 11.8 | 11.8 |
17 | 11.0 | 11.0 |
22 | 9.9 | 9.9 |
GPC值<sup>2)</sup> | Mw/1000 | Mn/1000 |
0h US | 1220 | 260 |
22h US | 560 | 260 |
时间 | 萃取物的量[mg] | 萃取物的确定 | 萃取后过滤(EM)<sup>1)</sup> |
10分钟 | 80mg | PP,Mw∽5000 | 没有变化 |
30分钟 | 180mg | PP,Mw∽5000 | 没有变化 |
1小时 | 220mg | PP,Mw∽5000 | 没有变化 |
24小时 | 245mg | PP,Mw∽5000 | 没有变化 |
72小时 | 250mg | PP,Mw∽5000 | 没有变化 |
Claims (21)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE10141624.5 | 2001-08-24 | ||
DE10141624A DE10141624A1 (de) | 2001-08-24 | 2001-08-24 | Lösungen polymerer Halbleiter |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1547780A CN1547780A (zh) | 2004-11-17 |
CN100442567C true CN100442567C (zh) | 2008-12-10 |
Family
ID=7696552
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CNB02816623XA Expired - Fee Related CN100442567C (zh) | 2001-08-24 | 2002-08-22 | 高分子半导体溶液,其制备方法以及其应用 |
Country Status (7)
Country | Link |
---|---|
US (1) | US7252781B2 (zh) |
EP (1) | EP1421635A2 (zh) |
JP (1) | JP4263602B2 (zh) |
KR (1) | KR100924672B1 (zh) |
CN (1) | CN100442567C (zh) |
DE (1) | DE10141624A1 (zh) |
WO (1) | WO2003019694A2 (zh) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN105712986A (zh) * | 2010-07-15 | 2016-06-29 | 默克专利有限公司 | 具有有机配体的金属络合物及其在oled中的用途 |
Families Citing this family (177)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE10318096A1 (de) | 2003-04-17 | 2004-11-11 | Covion Organic Semiconductors Gmbh | Verfahren zur Molekulargewichtskontrolle bei der Synthese von Poly(arylenvinylenen) |
US7767785B2 (en) * | 2003-09-20 | 2010-08-03 | Merck Patent Gmbh | Conjugated polymers, their preparation and use thereof |
DE10343606A1 (de) * | 2003-09-20 | 2005-04-14 | Covion Organic Semiconductors Gmbh | Weiß emittierende Copolymere, deren Darstellung und Verwendung |
US7686978B2 (en) * | 2003-09-24 | 2010-03-30 | E. I. Du Pont De Nemours And Company | Method for the application of active materials onto active surfaces and devices made with such methods |
DE10355786A1 (de) * | 2003-11-26 | 2005-06-30 | Covion Organic Semiconductors Gmbh | Konjugierte Polymere, deren Darstellung und Verwendung |
DE102004020299A1 (de) | 2004-04-26 | 2005-12-01 | Covion Organic Semiconductors Gmbh | Konjugierte Polymere, deren Darstellung und Verwendung |
DE102004020298A1 (de) | 2004-04-26 | 2005-11-10 | Covion Organic Semiconductors Gmbh | Elektrolumineszierende Polymere und deren Verwendung |
DE102004023278A1 (de) * | 2004-05-11 | 2005-12-08 | Covion Organic Semiconductors Gmbh | Elektrolumineszierende Polymere |
DE102004023277A1 (de) * | 2004-05-11 | 2005-12-01 | Covion Organic Semiconductors Gmbh | Neue Materialmischungen für die Elektrolumineszenz |
CN1957484A (zh) | 2004-05-18 | 2007-05-02 | 默克专利股份有限公司 | 包含半导体聚合物的喷墨印刷用配制剂 |
DE102004032527A1 (de) * | 2004-07-06 | 2006-02-02 | Covion Organic Semiconductors Gmbh | Elektrolumineszierende Polymere |
BRPI0519478A2 (pt) | 2004-12-27 | 2009-02-03 | Quantum Paper Inc | display emissivo endereÇÁvel e imprimÍvel |
GB2424759A (en) * | 2005-04-01 | 2006-10-04 | Seiko Epson Corp | Inkjet deposition of polythiophene semiconductor material dissolved in halogenated aromatic solvents |
DE102005022903A1 (de) * | 2005-05-18 | 2006-11-23 | Merck Patent Gmbh | Lösungen organischer Halbleiter |
US20070201239A1 (en) * | 2005-07-13 | 2007-08-30 | Daniel Rosario | Display Device For A Vehicle |
DE102005037734B4 (de) * | 2005-08-10 | 2018-02-08 | Merck Patent Gmbh | Elektrolumineszierende Polymere, ihre Verwendung und bifunktionelle monomere Verbindungen |
DE102005060473A1 (de) | 2005-12-17 | 2007-06-28 | Merck Patent Gmbh | Konjugierte Polymere, deren Darstellung und Verwendung |
DE102006003710A1 (de) * | 2006-01-26 | 2007-08-02 | Merck Patent Gmbh | Elektrolumineszierende Materialien und deren Verwendung |
DE102006031991A1 (de) * | 2006-07-11 | 2008-01-17 | Merck Patent Gmbh | Elektrolumineszierende Polymere und ihre Verwendung |
US8852467B2 (en) | 2007-05-31 | 2014-10-07 | Nthdegree Technologies Worldwide Inc | Method of manufacturing a printable composition of a liquid or gel suspension of diodes |
US8889216B2 (en) | 2007-05-31 | 2014-11-18 | Nthdegree Technologies Worldwide Inc | Method of manufacturing addressable and static electronic displays |
US8133768B2 (en) | 2007-05-31 | 2012-03-13 | Nthdegree Technologies Worldwide Inc | Method of manufacturing a light emitting, photovoltaic or other electronic apparatus and system |
US9419179B2 (en) | 2007-05-31 | 2016-08-16 | Nthdegree Technologies Worldwide Inc | Diode for a printable composition |
US9425357B2 (en) | 2007-05-31 | 2016-08-23 | Nthdegree Technologies Worldwide Inc. | Diode for a printable composition |
US8674593B2 (en) | 2007-05-31 | 2014-03-18 | Nthdegree Technologies Worldwide Inc | Diode for a printable composition |
US8395568B2 (en) | 2007-05-31 | 2013-03-12 | Nthdegree Technologies Worldwide Inc | Light emitting, photovoltaic or other electronic apparatus and system |
US9534772B2 (en) | 2007-05-31 | 2017-01-03 | Nthdegree Technologies Worldwide Inc | Apparatus with light emitting diodes |
US8809126B2 (en) | 2007-05-31 | 2014-08-19 | Nthdegree Technologies Worldwide Inc | Printable composition of a liquid or gel suspension of diodes |
US9018833B2 (en) | 2007-05-31 | 2015-04-28 | Nthdegree Technologies Worldwide Inc | Apparatus with light emitting or absorbing diodes |
US8415879B2 (en) | 2007-05-31 | 2013-04-09 | Nthdegree Technologies Worldwide Inc | Diode for a printable composition |
US9343593B2 (en) | 2007-05-31 | 2016-05-17 | Nthdegree Technologies Worldwide Inc | Printable composition of a liquid or gel suspension of diodes |
US8877101B2 (en) | 2007-05-31 | 2014-11-04 | Nthdegree Technologies Worldwide Inc | Method of manufacturing a light emitting, power generating or other electronic apparatus |
US8846457B2 (en) | 2007-05-31 | 2014-09-30 | Nthdegree Technologies Worldwide Inc | Printable composition of a liquid or gel suspension of diodes |
CN101689607A (zh) * | 2007-06-28 | 2010-03-31 | 3M创新有限公司 | 结合界面导电簇的薄膜晶体管 |
DE102008045664A1 (de) | 2008-09-03 | 2010-03-04 | Merck Patent Gmbh | Optoelektronische Vorrichtung |
DE102008045662A1 (de) | 2008-09-03 | 2010-03-04 | Merck Patent Gmbh | Optoelektronische Vorrichtung |
WO2009053088A1 (de) | 2007-10-24 | 2009-04-30 | Merck Patent Gmbh | Optoelektronische vorrichtung |
US8127477B2 (en) | 2008-05-13 | 2012-03-06 | Nthdegree Technologies Worldwide Inc | Illuminating display systems |
US7992332B2 (en) | 2008-05-13 | 2011-08-09 | Nthdegree Technologies Worldwide Inc. | Apparatuses for providing power for illumination of a display object |
WO2009155595A2 (en) * | 2008-06-20 | 2009-12-23 | Tempur-Pedic Management, Inc. | Inflatable mattress and method of operating same |
DE102008044868A1 (de) | 2008-08-29 | 2010-03-04 | Merck Patent Gmbh | Elektrolumineszierende Polymere, Verfahren zu ihrer Herstellung sowie ihre Verwendung |
DE102008045663A1 (de) | 2008-09-03 | 2010-03-04 | Merck Patent Gmbh | Fluorverbrückte Assoziate für optoelektronische Anwendungen |
DE102008049037A1 (de) * | 2008-09-25 | 2010-04-22 | Merck Patent Gmbh | Neue Polymere mit niedriger Polydispersität |
US8174000B2 (en) | 2009-02-11 | 2012-05-08 | Universal Display Corporation | Liquid compositions for inkjet printing of organic layers or other uses |
DE102009059985A1 (de) | 2009-12-22 | 2011-07-07 | Merck Patent GmbH, 64293 | Polymer mit Aldehydgruppen, Umsetzung sowie Vernetzung dieses Polymers, vernetztes Polymer sowie Elektrolumineszenzvorrichtung enthaltend dieses Polymer |
DE102009010713A1 (de) | 2009-02-27 | 2010-09-02 | Merck Patent Gmbh | Polymer mit Aldehydgruppen, Umsetzung sowie Vernetzung dieses Polymers, vernetztes Polymer sowie Elektrolumineszenzvorrichtung enthaltend dieses Polymer |
JP5670353B2 (ja) | 2009-02-27 | 2015-02-18 | メルク パテント ゲーエムベーハー | アルデヒド基を含むポリマー、このポリマーの反応および架橋、架橋ポリマー、このポリマー含むエレクトロルミネッセンスデバイス |
DE102009010714A1 (de) | 2009-02-27 | 2010-09-02 | Merck Patent Gmbh | Vernetzbare und vernetzte Polymere, Verfahren zu deren Herstellung sowie deren Verwendung |
CN102378794A (zh) * | 2009-03-31 | 2012-03-14 | Dic株式会社 | 有机半导体墨组合物和使用其的有机半导体图案形成方法 |
DE102009023156A1 (de) | 2009-05-29 | 2010-12-02 | Merck Patent Gmbh | Polymere, die substituierte Indenofluorenderivate als Struktureinheit enthalten, Verfahren zu deren Herstellung sowie deren Verwendung |
DE102009023154A1 (de) | 2009-05-29 | 2011-06-16 | Merck Patent Gmbh | Zusammensetzung, enthaltend mindestens eine Emitterverbindung und mindestens ein Polymer mit konjugationsunterbrechenden Einheiten |
DE102009030847A1 (de) | 2009-06-26 | 2010-12-30 | Merck Patent Gmbh | Polymere enthaltend substituierte Anthracenyleinheiten, Blends enthaltend diese Polymere sowie Vorrichtungen enthaltend diese Polymere oder Blends |
DE102009030848A1 (de) | 2009-06-26 | 2011-02-03 | Merck Patent Gmbh | Polymere enthaltend Struktureinheiten, die Alkylalkoxygruppen aufweisen, Blends enthaltend diese Polymere sowie optoelektronische Vorrichtungen enthaltend diese Polymere und Blends |
DE102009034194A1 (de) | 2009-07-22 | 2011-01-27 | Merck Patent Gmbh | Materialien für elektronische Vorrichtungen |
DE102009053644B4 (de) | 2009-11-17 | 2019-07-04 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen |
DE102009041414A1 (de) | 2009-09-16 | 2011-03-17 | Merck Patent Gmbh | Metallkomplexe |
DE102009053836A1 (de) | 2009-11-18 | 2011-05-26 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen |
DE102010004803A1 (de) | 2010-01-16 | 2011-07-21 | Merck Patent GmbH, 64293 | Materialien für organische Elektrolumineszenzvorrichtungen |
DE102010006377A1 (de) | 2010-01-29 | 2011-08-04 | Merck Patent GmbH, 64293 | Styrolbasierte Copolymere, insbesondere für die Anwendung in optoelektronischen Bauteilen |
DE102010007938A1 (de) | 2010-02-12 | 2011-10-06 | Merck Patent Gmbh | Elektrolumineszierende Polymere, Verfahren zu ihrer Herstellung sowie ihre Verwendung |
DE102010020567A1 (de) | 2010-05-14 | 2011-11-17 | Merck Patent Gmbh | Metallkomplexe |
DE102010024897A1 (de) | 2010-06-24 | 2011-12-29 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen |
DE102010027320A1 (de) | 2010-07-16 | 2012-01-19 | Merck Patent Gmbh | Polymere Materialien für organische Elektrolumineszenzvorrichtungen |
DE102010032737A1 (de) | 2010-07-29 | 2012-02-02 | Merck Patent Gmbh | Polymere enthaltend substituierte Benzodithiopheneinheiten, Blends enthaltend diese Polymere sowie Vorrichtungen enthaltend diese Polymere oder Blends |
DE102010033080A1 (de) | 2010-08-02 | 2012-02-02 | Merck Patent Gmbh | Polymere mit Struktureinheiten, die Elektronen-Transport-Eigenschaften aufweisen |
DE102010033548A1 (de) | 2010-08-05 | 2012-02-09 | Merck Patent Gmbh | Materialien für elektronische Vorrichtungen |
DE102010033778A1 (de) | 2010-08-09 | 2012-02-09 | Merck Patent Gmbh | Polymere mit Carbazol-Struktureinheiten |
DE102010033777A1 (de) | 2010-08-09 | 2012-02-09 | Merck Patent Gmbh | Polymere mit Carbazol-Struktureinheiten |
DE102010045369A1 (de) | 2010-09-14 | 2012-03-15 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen |
DE102010045405A1 (de) | 2010-09-15 | 2012-03-15 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen |
DE102010046512A1 (de) | 2010-09-24 | 2012-03-29 | Merck Patent Gmbh | Phosphorhaltige Metallkomplexe |
DE102010048498A1 (de) | 2010-10-14 | 2012-04-19 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen |
DE102010048607A1 (de) | 2010-10-15 | 2012-04-19 | Merck Patent Gmbh | Verbindungen für elektronische Vorrichtungen |
JP5980796B2 (ja) | 2010-11-24 | 2016-08-31 | メルク パテント ゲーエムベーハー | 有機エレクトロルミネッセンス素子のための材料 |
DE102010056151A1 (de) | 2010-12-28 | 2012-06-28 | Merck Patent Gmbh | Materiallen für organische Elektrolumineszenzvorrichtungen |
DE102011011539A1 (de) | 2011-02-17 | 2012-08-23 | Merck Patent Gmbh | Verbindungen für elektronische Vorrichtungen |
CN103459391A (zh) | 2011-04-13 | 2013-12-18 | 默克专利有限公司 | 用于电子器件的化合物 |
JP6215192B2 (ja) | 2011-04-18 | 2017-10-18 | メルク パテント ゲーエムベーハー | 有機エレクトロルミネッセンス素子用材料 |
JP6022541B2 (ja) | 2011-04-18 | 2016-11-09 | メルク パテント ゲーエムベーハー | 電子デバイスのための化合物 |
WO2012150001A1 (de) | 2011-05-05 | 2012-11-08 | Merck Patent Gmbh | Verbindungen für elektronische vorrichtungen |
US10177312B2 (en) | 2011-05-05 | 2019-01-08 | Merck Patent Gmbh | Compounds for electronic devices |
DE102011102586A1 (de) | 2011-05-27 | 2012-11-29 | Merck Patent Gmbh | Organische elektronische Vorrichtung |
WO2013007348A1 (de) | 2011-07-11 | 2013-01-17 | Merck Patent Gmbh | Verbindungen für organische elektrolumineszenzvorrichtungen |
JP6100258B2 (ja) | 2011-07-29 | 2017-03-22 | メルク パテント ゲーエムベーハー | 電子素子のための化合物 |
EP3439065B1 (de) | 2011-08-03 | 2022-01-12 | Merck Patent GmbH | Materialien für elektronische vorrichtungen |
KR102077994B1 (ko) | 2011-09-21 | 2020-02-17 | 메르크 파텐트 게엠베하 | 유기 전계발광 소자용 카르바졸 유도체 |
JP6165746B2 (ja) | 2011-10-20 | 2017-07-19 | メルク パテント ゲーエムベーハー | 有機エレクトロルミッセンス素子のための材料 |
DE102011117422A1 (de) | 2011-10-28 | 2013-05-02 | Merck Patent Gmbh | Hyperverzweigte Polymere, Verfahren zu deren Herstellung sowie deren Verwendung in elektronischen Vorrichtungen |
US10008672B2 (en) | 2011-12-12 | 2018-06-26 | Merck Patent Gmbh | Compounds for electronic devices |
DE102012022880A1 (de) | 2011-12-22 | 2013-06-27 | Merck Patent Gmbh | Elektronische Vorrichtungen enthaltend organische Schichten |
JP2015504884A (ja) | 2011-12-27 | 2015-02-16 | メルク パテント ゲーエムベーハー | 1,2,3−トリアゾールを含む金属錯体 |
US9748502B2 (en) | 2012-01-16 | 2017-08-29 | Merck Patent Gmbh | Organic metal complexes |
EP3101088B1 (en) | 2012-02-14 | 2017-11-29 | Merck Patent GmbH | Materials for organic electroluminescent devices |
EP2817350A2 (de) | 2012-02-22 | 2014-12-31 | Merck Patent GmbH | Polymere enthaltend dibenzocycloheptan-struktureinheiten |
KR102040350B1 (ko) | 2012-04-17 | 2019-11-04 | 메르크 파텐트 게엠베하 | 가교성 및 가교된 중합체, 그의 제조 방법 및 그의 용도 |
CN104335377B (zh) | 2012-05-24 | 2017-12-15 | 默克专利有限公司 | 包含稠合杂芳族环的金属络合物 |
DE102012011335A1 (de) | 2012-06-06 | 2013-12-12 | Merck Patent Gmbh | Verbindungen für Organische Elekronische Vorrichtungen |
DE112013002910T5 (de) | 2012-06-12 | 2015-03-19 | Merck Patent Gmbh | Verbindungen für elektronische Vorrichtungen |
JP6422861B2 (ja) | 2012-06-29 | 2018-11-14 | メルク パテント ゲーエムベーハー | 2,7−ピレン構造単位を含むポリマー |
JP6262226B2 (ja) | 2012-07-10 | 2018-01-17 | メルク パテント ゲーエムベーハー | 有機エレクトロルミネッセンスデバイス用の材料 |
WO2014015937A1 (de) | 2012-07-23 | 2014-01-30 | Merck Patent Gmbh | Verbindungen und organische elektrolumineszierende vorrichtungen |
CN108863814A (zh) | 2012-07-23 | 2018-11-23 | 默克专利有限公司 | 芴和含有所述芴的电子器件 |
KR20210097213A (ko) | 2012-07-23 | 2021-08-06 | 메르크 파텐트 게엠베하 | 2-디아릴아미노플루오렌의 유도체 및 이를 함유하는 유기 전자 화합물 |
CN104507932B (zh) | 2012-07-23 | 2016-12-07 | 默克专利有限公司 | 用于有机电致发光器件的材料 |
US11917901B2 (en) | 2012-08-07 | 2024-02-27 | Udc Ireland Limited | Metal complexes |
KR102015270B1 (ko) | 2012-08-10 | 2019-08-28 | 메르크 파텐트 게엠베하 | 유기 전계발광 소자용 물질 |
US10454040B2 (en) | 2012-09-18 | 2019-10-22 | Merck Patent Gmbh | Materials for electronic devices |
EP2917198B1 (de) | 2012-11-12 | 2018-05-16 | Merck Patent GmbH | Materialien für elektronische vorrichtungen |
KR102173856B1 (ko) | 2012-11-30 | 2020-11-04 | 메르크 파텐트 게엠베하 | 전자 소자 |
JP2016506414A (ja) | 2013-01-03 | 2016-03-03 | メルク パテント ゲーエムベーハー | 電子素子のための材料 |
CN104884572B (zh) | 2013-01-03 | 2017-09-19 | 默克专利有限公司 | 用于电子器件的材料 |
WO2014106523A1 (de) | 2013-01-03 | 2014-07-10 | Merck Patent Gmbh | Elektronische vorrichtung |
CN103214900B (zh) * | 2013-04-24 | 2014-08-06 | 南京邮电大学 | 应用于薄膜器件工艺的水基有机纳米墨水及制备和应用 |
DE102013008189A1 (de) | 2013-05-14 | 2014-12-04 | Eberhard Karls Universität Tübingen | Metallkomplexe |
EP3077477B1 (de) | 2013-12-06 | 2018-02-28 | Merck Patent GmbH | Verbindungen und organische elektronische vorrichtungen |
KR101993129B1 (ko) | 2013-12-12 | 2019-06-26 | 메르크 파텐트 게엠베하 | 전자 소자용 물질 |
KR20170091181A (ko) | 2014-04-11 | 2017-08-08 | 메르크 파텐트 게엠베하 | 유기 전계발광 소자용 물질 |
WO2016074755A1 (de) | 2014-11-11 | 2016-05-19 | Merck Patent Gmbh | Materialien für organische elektrolumineszenzvorrichtungen |
CN107112426A (zh) | 2014-12-30 | 2017-08-29 | 默克专利有限公司 | 包含至少一种聚合物和至少一种盐的组合物以及包含所述组合物的电致发光器件 |
US20180006237A1 (en) | 2015-01-30 | 2018-01-04 | Merck Patent Gmbh | Materials for electronic devices |
CN107532013A (zh) | 2015-01-30 | 2018-01-02 | 默克专利有限公司 | 具有低粒子含量的制剂 |
KR102610370B1 (ko) | 2015-05-18 | 2023-12-05 | 메르크 파텐트 게엠베하 | 유기 전계발광 소자용 물질 |
KR102660538B1 (ko) | 2015-07-22 | 2024-04-24 | 메르크 파텐트 게엠베하 | 유기 전계발광 소자용 재료 |
GB201513037D0 (en) | 2015-07-23 | 2015-09-09 | Merck Patent Gmbh | Phenyl-derived compound for use in organic electronic devices |
WO2017016632A1 (en) | 2015-07-29 | 2017-02-02 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
CN107922335B (zh) | 2015-08-13 | 2021-06-04 | 默克专利有限公司 | 六甲基二氢化茚 |
WO2017028940A1 (en) | 2015-08-14 | 2017-02-23 | Merck Patent Gmbh | Phenoxazine derivatives for organic electroluminescent devices |
EP3341448B1 (en) | 2015-08-28 | 2020-02-12 | Merck Patent GmbH | Compounds for electronic devices |
WO2017133829A1 (de) | 2016-02-05 | 2017-08-10 | Merck Patent Gmbh | Materialien für elektronische vorrichtungen |
KR102487147B1 (ko) | 2016-06-03 | 2023-01-11 | 메르크 파텐트 게엠베하 | 유기 전계발광 소자용 재료 |
US11365167B2 (en) | 2016-07-08 | 2022-06-21 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
WO2018065357A1 (en) | 2016-10-06 | 2018-04-12 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
TWI764942B (zh) | 2016-10-10 | 2022-05-21 | 德商麥克專利有限公司 | 電子裝置 |
DE102017008794A1 (de) | 2016-10-17 | 2018-04-19 | Merck Patent Gmbh | Materialien zur Verwendung in elektronischen Vorrichtungen |
WO2018083053A1 (de) | 2016-11-02 | 2018-05-11 | Merck Patent Gmbh | Materialien für elektronische vorrichtungen |
KR102564613B1 (ko) | 2016-11-08 | 2023-08-07 | 메르크 파텐트 게엠베하 | 전자 소자용 화합물 |
TW201833118A (zh) | 2016-11-22 | 2018-09-16 | 德商麥克專利有限公司 | 用於電子裝置之材料 |
EP3544984B1 (en) | 2016-11-25 | 2020-12-23 | Merck Patent GmbH | Bisbenzofuran-fused 2,8-diaminoindeno[1,2-b]fluorene derivatives and related compounds as materials for organic electroluminescent devices (oled) |
EP3544985B1 (en) | 2016-11-25 | 2021-05-12 | Merck Patent GmbH | Bisbenzofuran-fused indeno[1,2-b]fluorene derivatives and related compounds as materials for organic electroluminescent devices (oled) |
CN109983054B (zh) | 2016-11-30 | 2022-10-04 | 默克专利有限公司 | 具有不对称重复单元的聚合物 |
US11261291B2 (en) | 2016-12-22 | 2022-03-01 | Merck Patent Gmbh | Materials for electronic devices |
CN110177855A (zh) | 2017-01-23 | 2019-08-27 | 默克专利有限公司 | 用于有机电致发光器件的材料 |
CN110291064B (zh) | 2017-02-02 | 2023-04-28 | 默克专利有限公司 | 用于电子器件的材料 |
US20200055822A1 (en) | 2017-03-02 | 2020-02-20 | Merck Patent Gmbh | Materials for organic electronic devices |
KR102585423B1 (ko) | 2017-04-25 | 2023-10-05 | 메르크 파텐트 게엠베하 | 전자 디바이스용 화합물 |
TW201920343A (zh) | 2017-06-21 | 2019-06-01 | 德商麥克專利有限公司 | 電子裝置用材料 |
KR20200020841A (ko) | 2017-06-23 | 2020-02-26 | 메르크 파텐트 게엠베하 | 유기 전계발광 디바이스용 재료 |
KR102661058B1 (ko) | 2017-06-28 | 2024-04-25 | 메르크 파텐트 게엠베하 | 전자 디바이스용 재료 |
CN110914244A (zh) | 2017-07-28 | 2020-03-24 | 默克专利有限公司 | 用于电子器件中的螺二芴衍生物 |
EP3679024B1 (de) | 2017-09-08 | 2022-11-02 | Merck Patent GmbH | Materialien für elektronische vorrichtungen |
TWI815831B (zh) | 2017-11-23 | 2023-09-21 | 德商麥克專利有限公司 | 用於電子裝置之材料 |
US20200308129A1 (en) | 2017-12-15 | 2020-10-01 | Merck Patent Gmbh | Substituted aromatic amines for use in organic electroluminescent devices |
US20210036245A1 (en) | 2017-12-20 | 2021-02-04 | Merck Patent Gmbh | Heteroaromatic compounds |
WO2019170729A1 (en) | 2018-03-09 | 2019-09-12 | Merck Patent Gmbh | Compounds for electronic devices |
US20210020850A1 (en) | 2018-03-09 | 2021-01-21 | Merck Patent Gmbh | Compounds for electronic devices |
KR20200132912A (ko) | 2018-03-16 | 2020-11-25 | 메르크 파텐트 게엠베하 | 유기 전계발광 디바이스용 재료 |
EP3820965B1 (de) | 2018-07-09 | 2023-01-25 | Merck Patent GmbH | Materialien für elektronische vorrichtungen |
EP3877443A1 (de) | 2018-11-07 | 2021-09-15 | Merck Patent GmbH | Polymere mit amingruppenhaltigen wiederholungseinheiten |
EP3898603A1 (en) | 2018-12-20 | 2021-10-27 | Merck Patent GmbH | Materials for electronic devices |
EP3898604A2 (en) | 2018-12-20 | 2021-10-27 | Merck Patent GmbH | Materials for electronic devices |
TW202035345A (zh) | 2019-01-17 | 2020-10-01 | 德商麥克專利有限公司 | 用於有機電致發光裝置之材料 |
US20220127286A1 (en) | 2019-03-04 | 2022-04-28 | Merck Patent Gmbh | Ligands for nano-sized materials |
TW202110935A (zh) | 2019-04-16 | 2021-03-16 | 德商麥克專利有限公司 | 含有可交聯聚合物之調配物 |
WO2021048244A1 (en) | 2019-09-13 | 2021-03-18 | Merck Patent Gmbh | Semiconducting nanoparticle |
CN115003654A (zh) | 2020-02-06 | 2022-09-02 | 默克专利有限公司 | 用于电子器件的材料 |
KR20240075872A (ko) | 2021-09-28 | 2024-05-29 | 메르크 파텐트 게엠베하 | 전자 디바이스용 재료 |
WO2023052275A1 (de) | 2021-09-28 | 2023-04-06 | Merck Patent Gmbh | Materialien für elektronische vorrichtungen |
WO2023052313A1 (de) | 2021-09-28 | 2023-04-06 | Merck Patent Gmbh | Materialien für elektronische vorrichtungen |
WO2023052314A1 (de) | 2021-09-28 | 2023-04-06 | Merck Patent Gmbh | Materialien für elektronische vorrichtungen |
WO2023094412A1 (de) | 2021-11-25 | 2023-06-01 | Merck Patent Gmbh | Materialien für elektronische vorrichtungen |
WO2023117835A1 (en) | 2021-12-21 | 2023-06-29 | Merck Patent Gmbh | Electronic devices |
CN118355092A (zh) | 2021-12-21 | 2024-07-16 | 默克专利有限公司 | 电子器件 |
WO2023152346A1 (de) | 2022-02-14 | 2023-08-17 | Merck Patent Gmbh | Materialien für elektronische vorrichtungen |
WO2023213759A1 (de) | 2022-05-04 | 2023-11-09 | Merck Patent Gmbh | Polymere enthaltend speziell substituierte triarylamin-einheiten sowie elektrolumineszenzvorrichtungen enthaltend diese polymere |
WO2024013004A1 (de) | 2022-07-11 | 2024-01-18 | Merck Patent Gmbh | Materialien für elektronische vorrichtungen |
WO2024115426A1 (de) | 2022-12-01 | 2024-06-06 | Merck Patent Gmbh | Polymere enthaltend spirotruxenderivate als wiederholungseinheit sowie elektrolumineszenzvorrichtungen enthaltend diese polymere |
WO2024132993A1 (de) | 2022-12-19 | 2024-06-27 | Merck Patent Gmbh | Materialien für elektronische vorrichtungen |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5278213A (en) * | 1991-04-22 | 1994-01-11 | Allied Signal Inc. | Method of processing neutral polyanilines in solvent and solvent mixtures |
US5618469A (en) * | 1994-05-23 | 1997-04-08 | Al-Coat Ltd. | Polyaniline-containing solution, articles coated therewith, and methods for the preparation of same |
Family Cites Families (18)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4025463A (en) * | 1974-06-25 | 1977-05-24 | Eastman Kodak Company | Organic semiconductor compositions |
DE3625154A1 (de) | 1986-07-25 | 1988-01-28 | Horst Dr Rer Nat Kutsch | Verfahren zur herstellung eines organischen halbleiters |
US5160457A (en) * | 1987-08-07 | 1992-11-03 | Allied-Signal Inc. | Thermally stable forms of electrically conductive polyaniline |
US5281363A (en) * | 1991-04-22 | 1994-01-25 | Allied-Signal Inc. | Polyaniline compositions having a surface/core dopant arrangement |
US5624605A (en) * | 1991-06-12 | 1997-04-29 | Uniax Corporation | Processible forms of electrically conductive polyaniline |
US5232631A (en) * | 1991-06-12 | 1993-08-03 | Uniax Corporation | Processible forms of electrically conductive polyaniline |
JPH0980824A (ja) * | 1995-09-12 | 1997-03-28 | Toyobo Co Ltd | 電子写真式直描型記録媒体およびそれを用いた電子写真式直描型平版印刷版 |
WO1999012395A1 (fr) * | 1997-09-02 | 1999-03-11 | Seiko Epson Corporation | Procede de fabrication d'un element electroluminescent organique et element electroluminescent organique correspondant |
DE19806037A1 (de) * | 1998-02-13 | 1999-08-19 | Aventis Res & Tech Gmbh & Co | Triptycen-Polymere und -Copolymere |
US6313288B1 (en) * | 1998-11-18 | 2001-11-06 | Ricoh Company, Ltd. | Mixture of titanyltetraazaporphyrin compounds and electrophotographic photoconductor using the same |
WO2001017040A1 (en) * | 1999-08-31 | 2001-03-08 | E Ink Corporation | A solvent annealing process for forming a thin semiconductor film with advantageous properties |
GB9920543D0 (en) | 1999-08-31 | 1999-11-03 | Cambridge Display Tech Ltd | A formulation for depositing a light-emitting polymer layer |
JP2001072763A (ja) * | 1999-09-02 | 2001-03-21 | Mitsubishi Gas Chem Co Inc | ポリフェニレンエーテルの製造方法 |
US6621098B1 (en) * | 1999-11-29 | 2003-09-16 | The Penn State Research Foundation | Thin-film transistor and methods of manufacturing and incorporating a semiconducting organic material |
US20020038999A1 (en) * | 2000-06-20 | 2002-04-04 | Yong Cao | High resistance conductive polymers for use in high efficiency pixellated organic electronic devices |
EP1339772B1 (de) * | 2000-11-22 | 2011-01-12 | H.C. Starck Clevios GmbH | Dispergierbare polymerpulver |
GB0028867D0 (en) * | 2000-11-28 | 2001-01-10 | Avecia Ltd | Field effect translators,methods for the manufacture thereof and materials therefor |
JP4307839B2 (ja) * | 2001-03-10 | 2009-08-05 | メルク パテント ゲーエムベーハー | 有機半導体の溶液および分散液 |
-
2001
- 2001-08-24 DE DE10141624A patent/DE10141624A1/de not_active Withdrawn
-
2002
- 2002-08-22 JP JP2003523035A patent/JP4263602B2/ja not_active Expired - Fee Related
- 2002-08-22 WO PCT/EP2002/009382 patent/WO2003019694A2/de active Application Filing
- 2002-08-22 EP EP02796263A patent/EP1421635A2/de not_active Ceased
- 2002-08-22 KR KR1020047002743A patent/KR100924672B1/ko active IP Right Grant
- 2002-08-22 CN CNB02816623XA patent/CN100442567C/zh not_active Expired - Fee Related
- 2002-08-22 US US10/487,665 patent/US7252781B2/en not_active Expired - Lifetime
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5278213A (en) * | 1991-04-22 | 1994-01-11 | Allied Signal Inc. | Method of processing neutral polyanilines in solvent and solvent mixtures |
US5618469A (en) * | 1994-05-23 | 1997-04-08 | Al-Coat Ltd. | Polyaniline-containing solution, articles coated therewith, and methods for the preparation of same |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN105712986A (zh) * | 2010-07-15 | 2016-06-29 | 默克专利有限公司 | 具有有机配体的金属络合物及其在oled中的用途 |
CN105712986B (zh) * | 2010-07-15 | 2019-01-01 | 默克专利有限公司 | 具有有机配体的金属络合物及其在oled中的用途 |
Also Published As
Publication number | Publication date |
---|---|
US7252781B2 (en) | 2007-08-07 |
WO2003019694A2 (de) | 2003-03-06 |
US20040206939A1 (en) | 2004-10-21 |
DE10141624A1 (de) | 2003-03-06 |
WO2003019694A3 (de) | 2003-10-09 |
KR20040049304A (ko) | 2004-06-11 |
EP1421635A2 (de) | 2004-05-26 |
CN1547780A (zh) | 2004-11-17 |
JP2005532412A (ja) | 2005-10-27 |
KR100924672B1 (ko) | 2009-11-03 |
JP4263602B2 (ja) | 2009-05-13 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN100442567C (zh) | 高分子半导体溶液,其制备方法以及其应用 | |
CN100357370C (zh) | 有机半导体的溶液与分散液 | |
Dössel et al. | Synthesis and controlled self-assembly of covalently linked hexa-peri-hexabenzocoronene/perylene diimide dyads as models to study fundamental energy and electron transfer processes | |
CN104114672B (zh) | 用于有机电致发光器件的螺二芴化合物 | |
US8038903B2 (en) | Organic semiconductor solutions | |
CN104756273B (zh) | 用于制造电子器件的高纯度溶剂中的制剂 | |
JP2007527624A (ja) | 有機半導体の溶液 | |
CN101918491B (zh) | 组合物和有机光电转换元件 | |
Kempf et al. | Amphiphilic poly (alkylthiophene) block copolymers prepared via externally initiated GRIM and click coupling | |
Feng et al. | Revealing the Side‐Chain‐Dependent Ordering Transition of Highly Crystalline Double‐Cable Conjugated Polymers | |
CN105431214A (zh) | 真空纯化方法 | |
CN102421858A (zh) | 导电制剂 | |
Liang et al. | Developing perylene diimide based acceptor polymers for organic photovoltaics | |
KR20170108116A (ko) | 낮은 입자 함유량을 갖는 조성물 | |
Zhao et al. | High performance n-type thermoelectric material based on naphthalenediimide radical anions | |
EP3380541B1 (en) | Degradable conjugated polymers | |
CN1252132C (zh) | 含涂布增强剂的旋布介电层组合物 | |
An et al. | Synergistic Contribution of Oligo (ethylene glycol) and Fluorine Substitution of Conjugated Polymer Photocatalysts toward Solar Driven Sacrificial Hydrogen Evolution | |
Guo et al. | Scandium‐catalyzed synthesis of Si–H‐containing syndiotactic polystyrene and its functionalized polymer carrying pendant perylene bisimide units | |
EP3626802A1 (en) | Method for producing liquid composition | |
Jeon et al. | Hybrid effect of Ag ions and polarized Ag nanoparticles in poly (ethylene oxide)/AgBF4/ionic liquid composites for long‐term stable membranes | |
Lin et al. | Supramolecular block copolymer photovoltaics through ureido-pyrimidinone hydrogen bonding interactions | |
Yasseen et al. | Electronic structures and photovoltaic properties of a novel phthalocyanine and titanium dioxide phthalocyanine for dye sensitized-solar cells | |
EP2200103A1 (en) | Methods for controlling the crystalline nanofibre content of organic layers used in organic electronic devices | |
Wolfe et al. | A series of perylene diimide cathode interlayer materials for green solvent processing in conventional organic photovoltaics |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
ASS | Succession or assignment of patent right |
Owner name: MERCK PATENT GMBH Free format text: FORMER OWNER: MERCK ODED MATERIALS CO., LTD. Effective date: 20060915 |
|
C41 | Transfer of patent application or patent right or utility model | ||
TA01 | Transfer of patent application right |
Effective date of registration: 20060915 Address after: Darmstadt Applicant after: MERCK PATENT GmbH Address before: Frankfurt, Germany Applicant before: Merck Olide Materials Co.,Ltd. |
|
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
CF01 | Termination of patent right due to non-payment of annual fee | ||
CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20081210 Termination date: 20210822 |