JP2008538218A5 - - Google Patents
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- JP2008538218A5 JP2008538218A5 JP2007556432A JP2007556432A JP2008538218A5 JP 2008538218 A5 JP2008538218 A5 JP 2008538218A5 JP 2007556432 A JP2007556432 A JP 2007556432A JP 2007556432 A JP2007556432 A JP 2007556432A JP 2008538218 A5 JP2008538218 A5 JP 2008538218A5
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- JP
- Japan
- Prior art keywords
- polymer
- aryl
- group
- substituted
- alkyl
- 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
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- 229920000642 polymer Polymers 0.000 claims description 159
- 125000003118 aryl group Chemical group 0.000 claims description 68
- 125000001072 heteroaryl group Chemical group 0.000 claims description 50
- 125000000217 alkyl group Chemical group 0.000 claims description 49
- 239000000203 mixture Substances 0.000 claims description 41
- -1 perfluoro Chemical group 0.000 claims description 37
- 125000004104 aryloxy group Chemical group 0.000 claims description 26
- 125000003545 alkoxy group Chemical group 0.000 claims description 25
- 125000004407 fluoroaryl group Chemical group 0.000 claims description 25
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 24
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 21
- 125000001153 fluoro group Chemical group F* 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 19
- 229910052799 carbon Inorganic materials 0.000 claims description 17
- 230000005525 hole transport Effects 0.000 claims description 17
- 239000000178 monomer Substances 0.000 claims description 17
- 150000001875 compounds Chemical class 0.000 claims description 15
- 229920001577 copolymer Polymers 0.000 claims description 15
- 239000000463 material Substances 0.000 claims description 15
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 13
- 229910052751 metal Inorganic materials 0.000 claims description 12
- 239000002184 metal Substances 0.000 claims description 12
- 101710134784 Agnoprotein Proteins 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 239000011159 matrix material Substances 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 9
- 150000002148 esters Chemical class 0.000 claims description 9
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 8
- 238000002484 cyclic voltammetry Methods 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 230000003647 oxidation Effects 0.000 claims description 8
- 238000007254 oxidation reaction Methods 0.000 claims description 8
- 230000002441 reversible effect Effects 0.000 claims description 8
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 7
- 230000007935 neutral effect Effects 0.000 claims description 7
- 238000000926 separation method Methods 0.000 claims description 7
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 6
- 125000000732 arylene group Chemical group 0.000 claims description 6
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 6
- 238000004132 cross linking Methods 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 5
- 229910052698 phosphorus Inorganic materials 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 239000010409 thin film Substances 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 238000006116 polymerization reaction Methods 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- FNQJDLTXOVEEFB-UHFFFAOYSA-N 1,2,3-benzothiadiazole Chemical compound C1=CC=C2SN=NC2=C1 FNQJDLTXOVEEFB-UHFFFAOYSA-N 0.000 claims description 3
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 claims description 3
- 239000005964 Acibenzolar-S-methyl Substances 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 150000003949 imides Chemical class 0.000 claims description 3
- 229910052759 nickel Inorganic materials 0.000 claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 3
- 229910052763 palladium Inorganic materials 0.000 claims description 3
- 125000004001 thioalkyl group Chemical group 0.000 claims description 3
- 125000005000 thioaryl group Chemical group 0.000 claims description 3
- 229910052723 transition metal Inorganic materials 0.000 claims description 3
- 150000003624 transition metals Chemical class 0.000 claims description 3
- 229910052725 zinc Inorganic materials 0.000 claims description 3
- 239000011701 zinc Substances 0.000 claims description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 229910052744 lithium Inorganic materials 0.000 claims description 2
- 150000002739 metals Chemical class 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 229910052710 silicon Inorganic materials 0.000 claims description 2
- 239000010410 layer Substances 0.000 claims 43
- 125000000547 substituted alkyl group Chemical group 0.000 claims 12
- 125000003107 substituted aryl group Chemical group 0.000 claims 11
- 150000002431 hydrogen Chemical class 0.000 claims 9
- 230000000903 blocking effect Effects 0.000 claims 8
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims 7
- 239000012044 organic layer Substances 0.000 claims 5
- 239000013110 organic ligand Substances 0.000 claims 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims 4
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims 4
- 125000002947 alkylene group Chemical group 0.000 claims 4
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 claims 4
- 239000012964 benzotriazole Substances 0.000 claims 4
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims 4
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims 4
- 125000005415 substituted alkoxy group Chemical group 0.000 claims 4
- 239000000654 additive Substances 0.000 claims 3
- 125000005418 aryl aryl group Chemical group 0.000 claims 3
- 239000004973 liquid crystal related substance Substances 0.000 claims 3
- 238000006467 substitution reaction Methods 0.000 claims 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 2
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims 2
- 230000000996 additive effect Effects 0.000 claims 2
- 150000004982 aromatic amines Chemical class 0.000 claims 2
- 229920001940 conductive polymer Polymers 0.000 claims 2
- 150000004696 coordination complex Chemical class 0.000 claims 2
- 230000005669 field effect Effects 0.000 claims 2
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims 2
- 239000002245 particle Substances 0.000 claims 2
- KALYBUBHFPSGGQ-UHFFFAOYSA-N pyrido[3,2-h][1,2,3]benzotriazine Chemical compound N1=NN=CC2=CC=C3C=CC=NC3=C12 KALYBUBHFPSGGQ-UHFFFAOYSA-N 0.000 claims 2
- OUTISQSDRYHMII-UHFFFAOYSA-N pyrido[3,2-h]cinnoline Chemical compound C1=NN=C2C3=NC=CC=C3C=CC2=C1 OUTISQSDRYHMII-UHFFFAOYSA-N 0.000 claims 2
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims 2
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims 2
- UMHFSEWKWORSLP-UHFFFAOYSA-N thiophene 1,1-dioxide Chemical compound O=S1(=O)C=CC=C1 UMHFSEWKWORSLP-UHFFFAOYSA-N 0.000 claims 2
- 150000003852 triazoles Chemical class 0.000 claims 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- 239000010405 anode material Substances 0.000 claims 1
- 239000011575 calcium Substances 0.000 claims 1
- 229910052791 calcium Inorganic materials 0.000 claims 1
- 150000001721 carbon Chemical group 0.000 claims 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims 1
- 239000010406 cathode material Substances 0.000 claims 1
- 239000011248 coating agent Substances 0.000 claims 1
- 238000000576 coating method Methods 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 125000000524 functional group Chemical group 0.000 claims 1
- 239000011777 magnesium Substances 0.000 claims 1
- 229910052749 magnesium Inorganic materials 0.000 claims 1
- 239000002105 nanoparticle Substances 0.000 claims 1
- 230000005693 optoelectronics Effects 0.000 claims 1
- 150000003003 phosphines Chemical class 0.000 claims 1
- 229910052700 potassium Inorganic materials 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- 239000004065 semiconductor Substances 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 claims 1
- 230000005281 excited state Effects 0.000 description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
- 229920000265 Polyparaphenylene Polymers 0.000 description 6
- 150000001502 aryl halides Chemical class 0.000 description 6
- 239000003153 chemical reaction reagent Substances 0.000 description 6
- 230000021615 conjugation Effects 0.000 description 6
- 238000000295 emission spectrum Methods 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 6
- 229910052796 boron Inorganic materials 0.000 description 5
- 229920000412 polyarylene Polymers 0.000 description 5
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 4
- 238000006069 Suzuki reaction reaction Methods 0.000 description 4
- 150000001450 anions Chemical class 0.000 description 4
- 150000001768 cations Chemical class 0.000 description 4
- 230000008878 coupling Effects 0.000 description 4
- 238000010168 coupling process Methods 0.000 description 4
- 238000005859 coupling reaction Methods 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- 238000010348 incorporation Methods 0.000 description 4
- 238000004020 luminiscence type Methods 0.000 description 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 4
- 229920002098 polyfluorene Polymers 0.000 description 4
- 150000005839 radical cations Chemical class 0.000 description 4
- 230000002829 reductive effect Effects 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000000950 dibromo group Chemical group Br* 0.000 description 3
- 230000005283 ground state Effects 0.000 description 3
- 238000005424 photoluminescence Methods 0.000 description 3
- 238000010791 quenching Methods 0.000 description 3
- 150000005838 radical anions Chemical class 0.000 description 3
- 150000003384 small molecules Chemical class 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 235000021286 stilbenes Nutrition 0.000 description 3
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 2
- WGLLSSPDPJPLOR-UHFFFAOYSA-N 2,3-dimethylbut-2-ene Chemical group CC(C)=C(C)C WGLLSSPDPJPLOR-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 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
- 150000005347 biaryls Chemical group 0.000 description 2
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 2
- 239000002800 charge carrier Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 239000003792 electrolyte Substances 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 229920002959 polymer blend Polymers 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 230000000171 quenching effect Effects 0.000 description 2
- 238000006578 reductive coupling reaction Methods 0.000 description 2
- 238000012552 review Methods 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 150000001629 stilbenes Chemical class 0.000 description 2
- 230000000638 stimulation Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- 125000005259 triarylamine group Chemical group 0.000 description 2
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- MDRUKDLYOLTXBU-UHFFFAOYSA-N 2,3,4-tribromoaniline Chemical compound NC1=CC=C(Br)C(Br)=C1Br MDRUKDLYOLTXBU-UHFFFAOYSA-N 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- KIGVOJUDEQXKII-UHFFFAOYSA-N 4-bromo-n-(4-bromophenyl)-n-phenylaniline Chemical compound C1=CC(Br)=CC=C1N(C=1C=CC(Br)=CC=1)C1=CC=CC=C1 KIGVOJUDEQXKII-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- WSNMPAVSZJSIMT-UHFFFAOYSA-N COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 Chemical compound COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 WSNMPAVSZJSIMT-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 150000000918 Europium Chemical class 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 238000006411 Negishi coupling reaction Methods 0.000 description 1
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 1
- 238000006619 Stille reaction Methods 0.000 description 1
- XBDYBAVJXHJMNQ-UHFFFAOYSA-N Tetrahydroanthracene Natural products C1=CC=C2C=C(CCCC3)C3=CC2=C1 XBDYBAVJXHJMNQ-UHFFFAOYSA-N 0.000 description 1
- UATOFRZSCHRPBG-UHFFFAOYSA-N acetamide;hydrate Chemical compound O.CC(N)=O UATOFRZSCHRPBG-UHFFFAOYSA-N 0.000 description 1
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical group CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000000149 argon plasma sintering Methods 0.000 description 1
- 150000001543 aryl boronic acids Chemical class 0.000 description 1
- 238000005801 aryl-aryl coupling reaction Methods 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 238000012661 block copolymerization Methods 0.000 description 1
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 210000001072 colon Anatomy 0.000 description 1
- 230000000112 colonic effect Effects 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000005094 computer simulation Methods 0.000 description 1
- 229920000547 conjugated polymer Polymers 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 description 1
- VBXDEEVJTYBRJJ-UHFFFAOYSA-N diboronic acid Chemical compound OBOBO VBXDEEVJTYBRJJ-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005518 electrochemistry Effects 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 230000027721 electron transport chain Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 229920000578 graft copolymer Polymers 0.000 description 1
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 238000009815 homocoupling reaction Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 230000008520 organization Effects 0.000 description 1
- 238000005691 oxidative coupling reaction Methods 0.000 description 1
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical class CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Applications Claiming Priority (3)
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| US65567805P | 2005-02-22 | 2005-02-22 | |
| US60/655,678 | 2005-02-22 | ||
| PCT/US2006/006565 WO2006091799A2 (en) | 2005-02-22 | 2006-02-22 | High bandgap arylene polymers |
Publications (3)
| Publication Number | Publication Date |
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| JP2008538218A JP2008538218A (ja) | 2008-10-16 |
| JP2008538218A5 true JP2008538218A5 (https=) | 2010-03-11 |
| JP5308676B2 JP5308676B2 (ja) | 2013-10-09 |
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| JP2007556432A Expired - Fee Related JP5308676B2 (ja) | 2005-02-22 | 2006-02-22 | 高バンドギャップアリーレンポリマー |
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| JP (1) | JP5308676B2 (https=) |
| KR (1) | KR101274442B1 (https=) |
| CN (2) | CN101870766B (https=) |
| DE (1) | DE112006000379T5 (https=) |
| GB (1) | GB2436766B (https=) |
| WO (1) | WO2006091799A2 (https=) |
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|---|---|---|---|---|
| DE102007005090A1 (de) * | 2007-02-01 | 2008-08-07 | Leonhard Kurz Gmbh & Co. Kg | Organische Solarzelle |
| JO3598B1 (ar) | 2006-10-10 | 2020-07-05 | Infinity Discovery Inc | الاحماض والاسترات البورونية كمثبطات اميد هيدروليز الحامض الدهني |
| TW201000107A (en) | 2008-04-09 | 2010-01-01 | Infinity Pharmaceuticals Inc | Inhibitors of fatty acid amide hydrolase |
| WO2010118155A1 (en) | 2009-04-07 | 2010-10-14 | Infinity Pharmaceuticals, Inc. | Inhibitors of fatty acid amide hydrolase |
| CA2757622A1 (en) | 2009-04-07 | 2010-10-14 | Infinity Pharmaceuticals, Inc. | Inhibitors of fatty acid amide hydrolase |
| KR101601269B1 (ko) * | 2009-05-13 | 2016-03-08 | 엘지이노텍 주식회사 | 전기전도성 조성물 및 그로부터 제작된 ｐｖ용 전지 |
| MX361692B (es) | 2010-02-03 | 2018-12-13 | Infinity Pharmaceuticals Inc | Inhibidores de amida hidrolasa de ácido graso. |
| JP5793878B2 (ja) * | 2010-02-10 | 2015-10-14 | 三菱化学株式会社 | 重合体、有機電界発光素子材料、有機電界発光素子用組成物、有機電界発光素子、表示装置及び照明装置 |
| CN104093689A (zh) | 2012-01-31 | 2014-10-08 | 剑桥显示技术有限公司 | 聚合物 |
| GB2508409B (en) * | 2012-11-30 | 2015-11-25 | Cambridge Display Tech Ltd | Organic light-emitting composition, device and method |
| KR20230159629A (ko) | 2016-12-12 | 2023-11-21 | 벡톤 디킨슨 앤드 컴퍼니 | 수용성 중합체 염료 |
| CN119286279A (zh) | 2017-12-26 | 2025-01-10 | 贝克顿·迪金森公司 | 深紫外线可激发的水溶剂化聚合物染料 |
| US12517088B2 (en) | 2019-05-15 | 2026-01-06 | Lg Chem, Ltd. | Method for selecting material for organic light-emitting device |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4382138A (en) * | 1981-09-28 | 1983-05-03 | Standard Oil Company (Indiana) | Polyamide containing 4,4'-diamino-2,2', 6,6'-tetramethylbiphenyl moieties |
| CA2115143C (en) | 1991-08-19 | 2002-11-19 | Robert R. Gagne | Macromonomers having reactive end groups |
| US5869592A (en) | 1991-08-19 | 1999-02-09 | Maxdem Incorporated | Macromonomers having reactive side groups |
| US6723811B1 (en) | 1994-12-28 | 2004-04-20 | Cambridge Display Technology Ltd. | Polymers for use in optical device |
| DE19509451A1 (de) * | 1995-03-20 | 1996-09-26 | Hoechst Ag | Poly((oligo-p-phenylen)-vinylen)-Derivate, Verfahren zu ihrer Herstellung sowie ihre Verwendung |
| EP0745658A1 (en) * | 1995-05-30 | 1996-12-04 | Stichting Scheikundig Onderzoek In Nederland (Son) | Light-emitting copolymers |
| DE19606511A1 (de) * | 1996-02-22 | 1997-09-04 | Hoechst Ag | Teilkonjugierte Polymere mit Spirozentren und ihre Verwendung als Elektrolumineszenzmaterialien |
| US6309763B1 (en) | 1997-05-21 | 2001-10-30 | The Dow Chemical Company | Fluorene-containing polymers and electroluminescent devices therefrom |
| US6560290B2 (en) | 1998-01-20 | 2003-05-06 | Silicon Image, Inc. | CMOS driver and on-chip termination for gigabaud speed data communication |
| CA2360644A1 (en) | 1999-02-04 | 2000-08-10 | The Dow Chemical Company | Fluorene copolymers and devices made therefrom |
| TWI293964B (en) | 2001-02-05 | 2008-03-01 | Sumitomo Chemical Co | Polymeric fluorescent substance, production thereof and polymer light-emitting device |
| JP4259875B2 (ja) | 2001-03-24 | 2009-04-30 | メルク パテント ゲーエムベーハー | スピロビフルオレン単位およびフルオレン単位を含む共役ポリマーおよびその使用 |
| US7629429B2 (en) | 2001-05-11 | 2009-12-08 | Cambridge Display Technology Limited | Substituted fluorene polymers their preparation and uses |
| TW588105B (en) | 2001-07-19 | 2004-05-21 | Sumitomo Chemical Co | Polymeric fluorescent substance and polymer light-emitting device using the same |
| JP3902993B2 (ja) * | 2002-08-27 | 2007-04-11 | キヤノン株式会社 | フルオレン化合物及びそれを用いた有機発光素子 |
| JP4429149B2 (ja) * | 2004-11-26 | 2010-03-10 | キヤノン株式会社 | フルオレン化合物及び有機発光素子 |
-
2006
- 2006-02-22 GB GB0713745.8A patent/GB2436766B/en not_active Expired - Fee Related
- 2006-02-22 CN CN201010217383XA patent/CN101870766B/zh not_active Expired - Fee Related
- 2006-02-22 CN CNA200680009357XA patent/CN101146843A/zh active Pending
- 2006-02-22 KR KR1020077019097A patent/KR101274442B1/ko not_active Expired - Fee Related
- 2006-02-22 US US11/816,911 patent/US8822633B2/en active Active
- 2006-02-22 JP JP2007556432A patent/JP5308676B2/ja not_active Expired - Fee Related
- 2006-02-22 WO PCT/US2006/006565 patent/WO2006091799A2/en not_active Ceased
- 2006-02-22 DE DE112006000379T patent/DE112006000379T5/de not_active Withdrawn
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