TW593405B - Electroactive fluorene polymers having perfluoroalkyl groups, process for preparing such polymers and devices made with such polymers - Google Patents
Electroactive fluorene polymers having perfluoroalkyl groups, process for preparing such polymers and devices made with such polymers Download PDFInfo
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- TW593405B TW593405B TW091109463A TW91109463A TW593405B TW 593405 B TW593405 B TW 593405B TW 091109463 A TW091109463 A TW 091109463A TW 91109463 A TW91109463 A TW 91109463A TW 593405 B TW593405 B TW 593405B
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- 229920000642 polymer Polymers 0.000 title claims abstract description 81
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 title claims description 44
- 125000005010 perfluoroalkyl group Chemical group 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title abstract description 3
- 125000003118 aryl group Chemical group 0.000 claims abstract description 49
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 30
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 30
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 29
- 125000001424 substituent group Chemical group 0.000 claims abstract description 22
- 125000004404 heteroalkyl group Chemical group 0.000 claims abstract description 15
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 13
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 8
- 125000003983 fluorenyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims abstract description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
- 239000001257 hydrogen Substances 0.000 claims abstract description 5
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 5
- 239000000126 substance Substances 0.000 claims description 96
- 239000000178 monomer Substances 0.000 claims description 54
- 238000000034 method Methods 0.000 claims description 17
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 239000003054 catalyst Substances 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 125000005549 heteroarylene group Chemical group 0.000 claims description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 239000003153 chemical reaction reagent Substances 0.000 claims description 3
- 125000005647 linker group Chemical group 0.000 claims description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
- YAYGSLOSTXKUBW-UHFFFAOYSA-N ruthenium(2+) Chemical compound [Ru+2] YAYGSLOSTXKUBW-UHFFFAOYSA-N 0.000 claims description 3
- 229910052786 argon Inorganic materials 0.000 claims description 2
- 125000000732 arylene group Chemical group 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 2
- 101150010802 CVC2 gene Proteins 0.000 claims 1
- 150000001335 aliphatic alkanes Chemical group 0.000 claims 1
- 150000001351 alkyl iodides Chemical class 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims 1
- 125000000524 functional group Chemical group 0.000 claims 1
- 125000006574 non-aromatic ring group Chemical group 0.000 claims 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract description 3
- 125000006163 5-membered heteroaryl group Chemical group 0.000 abstract description 2
- 239000010410 layer Substances 0.000 description 82
- 239000000463 material Substances 0.000 description 16
- -1 poly (1,4-phenylenephenylene) Polymers 0.000 description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- 229920001577 copolymer Polymers 0.000 description 10
- 229910052751 metal Inorganic materials 0.000 description 9
- 239000002184 metal Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 8
- 238000002347 injection Methods 0.000 description 7
- 239000007924 injection Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 230000004913 activation Effects 0.000 description 6
- 150000002739 metals Chemical class 0.000 description 6
- 238000005240 physical vapour deposition Methods 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
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- 239000000758 substrate Substances 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- 238000012546 transfer Methods 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 229920001940 conductive polymer Polymers 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 238000000151 deposition Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- VIHDTGHDWPVSMM-UHFFFAOYSA-N ruthenium;triphenylphosphane Chemical compound [Ru].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 VIHDTGHDWPVSMM-UHFFFAOYSA-N 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- DHDHJYNTEFLIHY-UHFFFAOYSA-N 4,7-diphenyl-1,10-phenanthroline Chemical compound C1=CC=CC=C1C1=CC=NC2=C1C=CC1=C(C=3C=CC=CC=3)C=CN=C21 DHDHJYNTEFLIHY-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 2
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 229920000109 alkoxy-substituted poly(p-phenylene vinylene) Polymers 0.000 description 2
- 150000001409 amidines Chemical class 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 2
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 2
- 239000004327 boric acid Substances 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 239000002800 charge carrier Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 229920000547 conjugated polymer Polymers 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 238000005401 electroluminescence Methods 0.000 description 2
- 238000007641 inkjet printing Methods 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 229910003455 mixed metal oxide Inorganic materials 0.000 description 2
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- 229910052763 palladium Inorganic materials 0.000 description 2
- 238000000059 patterning Methods 0.000 description 2
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 2
- 229920002120 photoresistant polymer Polymers 0.000 description 2
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 238000007639 printing Methods 0.000 description 2
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- 229910052707 ruthenium Inorganic materials 0.000 description 2
- 230000003335 steric effect Effects 0.000 description 2
- 125000003107 substituted aryl group Chemical group 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- RRKODOZNUZCUBN-CCAGOZQPSA-N (1z,3z)-cycloocta-1,3-diene Chemical compound C1CC\C=C/C=C\C1 RRKODOZNUZCUBN-CCAGOZQPSA-N 0.000 description 1
- BIWQNIMLAISTBV-UHFFFAOYSA-N (4-methylphenyl)boronic acid Chemical compound CC1=CC=C(B(O)O)C=C1 BIWQNIMLAISTBV-UHFFFAOYSA-N 0.000 description 1
- VYXHVRARDIDEHS-UHFFFAOYSA-N 1,5-cyclooctadiene Chemical compound C1CC=CCCC=C1 VYXHVRARDIDEHS-UHFFFAOYSA-N 0.000 description 1
- 239000004912 1,5-cyclooctadiene Substances 0.000 description 1
- FGRBYDKOBBBPOI-UHFFFAOYSA-N 10,10-dioxo-2-[4-(N-phenylanilino)phenyl]thioxanthen-9-one Chemical compound O=C1c2ccccc2S(=O)(=O)c2ccc(cc12)-c1ccc(cc1)N(c1ccccc1)c1ccccc1 FGRBYDKOBBBPOI-UHFFFAOYSA-N 0.000 description 1
- WSBUZOZAKDVRTK-UHFFFAOYSA-N 2,7-dibromo-9,9-bis(2-ethylhexyl)fluorene Chemical compound C1=C(Br)C=C2C(CC(CC)CCCC)(CC(CC)CCCC)C3=CC(Br)=CC=C3C2=C1 WSBUZOZAKDVRTK-UHFFFAOYSA-N 0.000 description 1
- IQHSSYROJYPFDV-UHFFFAOYSA-N 2-bromo-1,3-dichloro-5-(trifluoromethyl)benzene Chemical group FC(F)(F)C1=CC(Cl)=C(Br)C(Cl)=C1 IQHSSYROJYPFDV-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- VEQPNABPJHWNSG-UHFFFAOYSA-N Nickel(2+) Chemical compound [Ni+2] VEQPNABPJHWNSG-UHFFFAOYSA-N 0.000 description 1
- 206010034972 Photosensitivity reaction Diseases 0.000 description 1
- 229920000265 Polyparaphenylene Polymers 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
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- YCOXTKKNXUZSKD-UHFFFAOYSA-N as-o-xylenol Natural products CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 229920005601 base polymer Polymers 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
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- 235000010290 biphenyl Nutrition 0.000 description 1
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- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
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- JRTIUDXYIUKIIE-UHFFFAOYSA-N cycloocta-1,5-diene;nickel Chemical compound [Ni].C1CC=CCCC=C1.C1CC=CCCC=C1 JRTIUDXYIUKIIE-UHFFFAOYSA-N 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- SUCQPHMWFOCTTR-UHFFFAOYSA-L dichlororuthenium;triphenylphosphane Chemical group Cl[Ru]Cl.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 SUCQPHMWFOCTTR-UHFFFAOYSA-L 0.000 description 1
- JEIRVUFQMXTVDI-UHFFFAOYSA-N diphenylphosphane ruthenium Chemical compound C1(=CC=CC=C1)PC1=CC=CC=C1.[Ru] JEIRVUFQMXTVDI-UHFFFAOYSA-N 0.000 description 1
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- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 description 1
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- DNNSSWSSYDEUBZ-UHFFFAOYSA-N krypton atom Chemical compound [Kr] DNNSSWSSYDEUBZ-UHFFFAOYSA-N 0.000 description 1
- 229910052746 lanthanum Inorganic materials 0.000 description 1
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 description 1
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- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
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- BPHQIXJDBIHMLT-UHFFFAOYSA-N perfluorodecane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F BPHQIXJDBIHMLT-UHFFFAOYSA-N 0.000 description 1
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- 229920000767 polyaniline Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- 125000004149 thio group Chemical group *S* 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 238000003631 wet chemical etching Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 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
-
- 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
-
- 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
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
- C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Electroluminescent Light Sources (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US28933301P | 2001-05-07 | 2001-05-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW593405B true TW593405B (en) | 2004-06-21 |
Family
ID=23111073
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW091109463A TW593405B (en) | 2001-05-07 | 2002-05-07 | Electroactive fluorene polymers having perfluoroalkyl groups, process for preparing such polymers and devices made with such polymers |
Country Status (9)
| Country | Link |
|---|---|
| US (3) | US7074886B2 (https=) |
| EP (1) | EP1397410A4 (https=) |
| JP (1) | JP2005513170A (https=) |
| KR (1) | KR20030093334A (https=) |
| CN (1) | CN1507464A (https=) |
| CA (1) | CA2442125A1 (https=) |
| IL (1) | IL158073A0 (https=) |
| TW (1) | TW593405B (https=) |
| WO (1) | WO2002090416A1 (https=) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7250625B2 (en) | 2002-01-11 | 2007-07-31 | Xerox Corporation | Polythiophenes and electronic devices generated therefrom |
| US6770904B2 (en) * | 2002-01-11 | 2004-08-03 | Xerox Corporation | Polythiophenes and electronic devices generated therefrom |
| DE10248876B4 (de) * | 2002-10-18 | 2006-07-06 | H.C. Starck Gmbh | Verfahren zur Herstellung linearer organischer Oligomere |
| JP2007501300A (ja) * | 2003-08-06 | 2007-01-25 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフトング | 位置規則性ポリマーの製造方法 |
| US20060094859A1 (en) * | 2004-11-03 | 2006-05-04 | Marrocco Matthew L Iii | Class of bridged biphenylene polymers |
| US20070082268A1 (en) * | 2005-09-02 | 2007-04-12 | Kurt Star | Chemical protection of metal surface |
| US20090220857A1 (en) * | 2005-09-02 | 2009-09-03 | Toyota Motor Engineering & Manufacturing North America, Inc. | Chemical protection of metal surface |
| JP4935172B2 (ja) * | 2006-04-25 | 2012-05-23 | 富士ゼロックス株式会社 | 有機電界発光素子およびその製造方法、並びに画像表示媒体 |
| US7659410B2 (en) * | 2006-04-25 | 2010-02-09 | Fuji Xerox Co., Ltd. | Thiophene-containing compound and thiophene-containing compound polymer, organic electroluminescent device, production method thereof, and image display medium |
| WO2012008556A1 (ja) * | 2010-07-14 | 2012-01-19 | 住友化学株式会社 | 光電変換素子 |
| GB2483269A (en) * | 2010-09-02 | 2012-03-07 | Cambridge Display Tech Ltd | Organic Electroluminescent Device containing Fluorinated Compounds |
| CN102086338B (zh) * | 2010-12-22 | 2012-12-12 | 浙江工业大学 | 一种乙烯基酯树脂强防腐耐热碳系导电涂料及制备方法 |
Family Cites Families (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2527618A1 (fr) * | 1982-05-25 | 1983-12-02 | Thomson Csf | Polymeres contenant des heterocycles et des noyaux aromatiques et materiaux organiques conducteurs formes a partir de ces polymeres |
| FR2603288B1 (fr) | 1986-09-03 | 1988-12-09 | France Etat | Polyfluorenes 9,9'-disubstitues, leur procede de preparation et leurs applications en electro-optique et electrochimie |
| DE4331401A1 (de) * | 1993-09-15 | 1995-03-16 | Hoechst Ag | Verwendung von Polymeren mit isolierten Chromophoren als Elektrolumineszenzmaterialen |
| US5770070A (en) * | 1994-10-03 | 1998-06-23 | Genomyx Corporation | Radioactive waste disposal cartridge |
| DE4436773A1 (de) * | 1994-10-14 | 1996-04-18 | Hoechst Ag | Konjugierte Polymere mit Spirozentren und ihre Verwendung als Elektrolumineszenzmaterialien |
| TW334474B (en) * | 1995-02-01 | 1998-06-21 | Sumitomo Kagaku Kk | Method for making a polymeric fluorescent substrate and organic electrolumninescent element |
| CN1229415C (zh) | 1995-07-28 | 2005-11-30 | 陶氏环球技术公司 | 2,7－芳基－9－取代的芴和9－取代的芴的低聚物和聚合物 |
| US5708130A (en) * | 1995-07-28 | 1998-01-13 | The Dow Chemical Company | 2,7-aryl-9-substituted fluorenes and 9-substituted fluorene oligomers and polymers |
| WO1997009394A1 (de) * | 1995-09-04 | 1997-03-13 | Hoechst Research & Technology Deutschland Gmbh & Co. Kg | Polymere mit triarylamin-einheiten als elektrolumineszenzmaterialien |
| WO1997033323A1 (en) * | 1996-03-04 | 1997-09-12 | Uniax Corporation | Polyfluorenes as materials for photoluminescence and electroluminescence |
| US6300465B1 (en) | 1997-01-30 | 2001-10-09 | Jsr Corporation | Process for producing phenylene-containing polymer and film-forming material |
| US6309763B1 (en) * | 1997-05-21 | 2001-10-30 | The Dow Chemical Company | Fluorene-containing polymers and electroluminescent devices therefrom |
| US5998045A (en) * | 1997-07-03 | 1999-12-07 | International Business Machines Corporation | Polymeric light-emitting device |
| US5777070A (en) * | 1997-10-23 | 1998-07-07 | The Dow Chemical Company | Process for preparing conjugated polymers |
| KR100697861B1 (ko) | 1998-03-13 | 2007-03-22 | 캠브리지 디스플레이 테크놀로지 리미티드 | 전장 발광 디바이스들 |
| WO1999054943A1 (en) | 1998-04-21 | 1999-10-28 | The Dow Chemical Company | Organic electroluminescent devices with improved stability in air |
| DE19846766A1 (de) * | 1998-10-10 | 2000-04-20 | Aventis Res & Tech Gmbh & Co | Konjugierte Polymere, enthaltend spezielle Fluorenbausteine mit verbesserten Eigenschaften |
| DE19846768A1 (de) * | 1998-10-10 | 2000-04-20 | Aventis Res & Tech Gmbh & Co | Konjugierte Polymere enthaltend 2,7-Fluorenyleinheiten mit verbesserten Eigenschaften |
| WO2000042668A1 (en) * | 1999-01-15 | 2000-07-20 | The Dow Chemical Company | Semiconducting polymer field effect transistor |
| CA2360644A1 (en) * | 1999-02-04 | 2000-08-10 | The Dow Chemical Company | Fluorene copolymers and devices made therefrom |
| WO2000053656A1 (en) | 1999-03-05 | 2000-09-14 | Cambridge Display Technology Limited | Polymer preparation |
| FR2790815B1 (fr) | 1999-03-08 | 2001-04-27 | Jean Michel Pretceille | Procede de raccordement, ensemble a compteur et robinet sur console, et raccord pour sa mise en oeuvre |
| GB9917356D0 (en) | 1999-07-24 | 1999-09-22 | Univ Cambridge Tech | Aromatic monomers and polymers for optoelectronic devices |
| WO2001042331A1 (en) * | 1999-12-09 | 2001-06-14 | Cambridge Display Technology Limited | Fluorene-perylene copolymers and uses thereof |
-
2002
- 2002-05-03 US US10/139,002 patent/US7074886B2/en not_active Expired - Fee Related
- 2002-05-06 IL IL15807302A patent/IL158073A0/xx unknown
- 2002-05-06 JP JP2002587490A patent/JP2005513170A/ja active Pending
- 2002-05-06 CN CNA028094476A patent/CN1507464A/zh active Pending
- 2002-05-06 WO PCT/US2002/018399 patent/WO2002090416A1/en not_active Ceased
- 2002-05-06 CA CA002442125A patent/CA2442125A1/en not_active Abandoned
- 2002-05-06 KR KR10-2003-7014231A patent/KR20030093334A/ko not_active Withdrawn
- 2002-05-06 EP EP02744278A patent/EP1397410A4/en not_active Withdrawn
- 2002-05-07 TW TW091109463A patent/TW593405B/zh not_active IP Right Cessation
-
2004
- 2004-04-01 US US10/816,153 patent/US7183365B2/en not_active Expired - Lifetime
- 2004-04-01 US US10/816,160 patent/US7259229B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| US7074886B2 (en) | 2006-07-11 |
| CN1507464A (zh) | 2004-06-23 |
| KR20030093334A (ko) | 2003-12-06 |
| WO2002090416A1 (en) | 2002-11-14 |
| US7259229B2 (en) | 2007-08-21 |
| US20020177679A1 (en) | 2002-11-28 |
| US20040219391A1 (en) | 2004-11-04 |
| EP1397410A1 (en) | 2004-03-17 |
| US7183365B2 (en) | 2007-02-27 |
| US20040186255A1 (en) | 2004-09-23 |
| EP1397410A4 (en) | 2005-03-16 |
| IL158073A0 (en) | 2004-03-28 |
| CA2442125A1 (en) | 2002-11-14 |
| JP2005513170A (ja) | 2005-05-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Annulment or lapse of patent due to non-payment of fees |