JP5546070B2 - フルオレニルポルフィリン−アントラセンを含むコポリマー、その製造方法およびその応用 - Google Patents
フルオレニルポルフィリン−アントラセンを含むコポリマー、その製造方法およびその応用 Download PDFInfo
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- JP5546070B2 JP5546070B2 JP2012550292A JP2012550292A JP5546070B2 JP 5546070 B2 JP5546070 B2 JP 5546070B2 JP 2012550292 A JP2012550292 A JP 2012550292A JP 2012550292 A JP2012550292 A JP 2012550292A JP 5546070 B2 JP5546070 B2 JP 5546070B2
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- JP
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- Prior art keywords
- fluorenylporphyrin
- anthracene
- organic
- copolymer
- solvent
- 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
- 229920001577 copolymer Polymers 0.000 title claims description 66
- 238000000034 method Methods 0.000 title claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 42
- 239000002904 solvent Substances 0.000 claims description 30
- 238000004519 manufacturing process Methods 0.000 claims description 28
- 125000000217 alkyl group Chemical group 0.000 claims description 27
- 239000000463 material Substances 0.000 claims description 27
- 239000003054 catalyst Substances 0.000 claims description 26
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 21
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 20
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical group ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 18
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 claims description 14
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 11
- 230000003287 optical effect Effects 0.000 claims description 11
- 238000006116 polymerization reaction Methods 0.000 claims description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 10
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 10
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
- 239000012670 alkaline solution Substances 0.000 claims description 9
- 230000005669 field effect Effects 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- 239000000047 product Substances 0.000 claims description 8
- 238000006467 substitution reaction Methods 0.000 claims description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- -1 fluorenyl porphyrin Chemical class 0.000 claims description 6
- 229920000642 polymer Polymers 0.000 claims description 6
- 239000002244 precipitate Substances 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 5
- 239000000178 monomer Substances 0.000 claims description 5
- 239000007800 oxidant agent Substances 0.000 claims description 5
- 238000007254 oxidation reaction Methods 0.000 claims description 5
- 238000006068 polycondensation reaction Methods 0.000 claims description 5
- 125000001246 bromo group Chemical group Br* 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 229910052763 palladium Inorganic materials 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims 2
- 238000001914 filtration Methods 0.000 claims 1
- 150000003222 pyridines Chemical class 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 14
- 239000004065 semiconductor Substances 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 150000004032 porphyrins Chemical group 0.000 description 10
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 8
- 239000000758 substrate Substances 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- 230000002349 favourable effect Effects 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 230000007613 environmental effect Effects 0.000 description 4
- 150000002220 fluorenes Chemical class 0.000 description 4
- 239000011368 organic material Substances 0.000 description 4
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 4
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 229940126062 Compound A Drugs 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- MCEWYIDBDVPMES-UHFFFAOYSA-N [60]pcbm Chemical compound C123C(C4=C5C6=C7C8=C9C%10=C%11C%12=C%13C%14=C%15C%16=C%17C%18=C(C=%19C=%20C%18=C%18C%16=C%13C%13=C%11C9=C9C7=C(C=%20C9=C%13%18)C(C7=%19)=C96)C6=C%11C%17=C%15C%13=C%15C%14=C%12C%12=C%10C%10=C85)=C9C7=C6C2=C%11C%13=C2C%15=C%12C%10=C4C23C1(CCCC(=O)OC)C1=CC=CC=C1 MCEWYIDBDVPMES-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 239000012156 elution solvent Substances 0.000 description 3
- 239000010408 film Substances 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 230000004044 response Effects 0.000 description 3
- 238000010898 silica gel chromatography Methods 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 239000010703 silicon Substances 0.000 description 3
- 230000003595 spectral effect Effects 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- 238000006276 transfer reaction Methods 0.000 description 3
- UCFSYHMCKWNKAH-UHFFFAOYSA-N 4,4,5,5-tetramethyl-1,3,2-dioxaborolane Chemical compound CC1(C)OBOC1(C)C UCFSYHMCKWNKAH-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 150000001347 alkyl bromides Chemical class 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 229910052788 barium Inorganic materials 0.000 description 2
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 229920000547 conjugated polymer Polymers 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000003574 free electron Substances 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 229920002521 macromolecule Polymers 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 238000010791 quenching Methods 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 2
- FXSCJZNMWILAJO-UHFFFAOYSA-N 2-bromo-9h-fluorene Chemical compound C1=CC=C2C3=CC=C(Br)C=C3CC2=C1 FXSCJZNMWILAJO-UHFFFAOYSA-N 0.000 description 1
- MECCSFDHAVAAAW-UHFFFAOYSA-N 4,4,5,5-tetramethyl-2-propan-2-yl-1,3,2-dioxaborolane Chemical compound CC(C)B1OC(C)(C)C(C)(C)O1 MECCSFDHAVAAAW-UHFFFAOYSA-N 0.000 description 1
- BRUOAURMAFDGLP-UHFFFAOYSA-N 9,10-dibromoanthracene Chemical compound C1=CC=C2C(Br)=C(C=CC=C3)C3=C(Br)C2=C1 BRUOAURMAFDGLP-UHFFFAOYSA-N 0.000 description 1
- ILUVPKPCRLBWSK-UHFFFAOYSA-N 9,9-dihexylfluorene-2-carbaldehyde Chemical compound C1=C(C=O)C=C2C(CCCCCC)(CCCCCC)C3=CC=CC=C3C2=C1 ILUVPKPCRLBWSK-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229920000144 PEDOT:PSS Polymers 0.000 description 1
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 125000005577 anthracene group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 230000003139 buffering effect Effects 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 230000000779 depleting effect Effects 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 238000007037 hydroformylation reaction Methods 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000007769 metal material Substances 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 239000003345 natural gas Substances 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000013307 optical fiber Substances 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 238000010248 power generation Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000027756 respiratory electron transport chain Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000011232 storage material Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 1
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 1
- LPSKDVINWQNWFE-UHFFFAOYSA-M tetrapropylazanium;hydroxide Chemical compound [OH-].CCC[N+](CCC)(CCC)CCC LPSKDVINWQNWFE-UHFFFAOYSA-M 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- PYJJCSYBSYXGQQ-UHFFFAOYSA-N trichloro(octadecyl)silane Chemical compound CCCCCCCCCCCCCCCCCC[Si](Cl)(Cl)Cl PYJJCSYBSYXGQQ-UHFFFAOYSA-N 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/22—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains four or more hetero rings
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y10/00—Nanotechnology for information processing, storage or transmission, e.g. quantum computing or single electron logic
-
- 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
- C08G61/123—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 derived from five-membered heterocyclic compounds
- C08G61/124—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 derived from five-membered heterocyclic compounds with a five-membered ring containing one nitrogen atom in the ring
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/151—Copolymers
-
- 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
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/10—Definition of the polymer structure
- C08G2261/14—Side-groups
- C08G2261/148—Side-chains having aromatic units
-
- 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
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/31—Monomer units or repeat units incorporating structural elements in the main chain incorporating aromatic structural elements in the main chain
- C08G2261/314—Condensed aromatic systems, e.g. perylene, anthracene or pyrene
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Description
本開示は、有機材料に関連し、特に、フルオレニルポルフィリン−アントラセンを含むコポリマー、その製造方法およびその応用に関連する。
今日の世界経済は主として石炭、石油および天然ガスなどの化石エネルギーに根差している。しかしながら、これらの再生不可能な化石エネルギーは枯渇しつつある。21世紀初頭から、世界的規模のエネルギー問題、結果として生じる環境汚染および地球温暖化はますます明白かつ深刻なものとなっている。太陽エネルギーは、広大かつ広範な配電、豊富な資源量、無公害、低汚染、安全、接続が容易であるといった、数多くの利点を備えている。したがって、太陽エネルギーは、最も期待される再生可能なエネルギー源のひとつであると考えられている。
本開示の一態様において、広いスペクトル応答性および良好な安定性を有する、フルオレニルポルフィリン−アントラセンを含むコポリマーが提供され、簡単な合成経路および低コストである、フルオレニルポルフィリン−アントラセンを含むコポリマーの製造方法もまた提供される。
によって表される化合物A、B、CおよびDを供給する工程;
溶媒、触媒および酸化剤を含む系中で、化合物A、BおよびCの重縮合酸化反応を行い、フルオレニルポルフィリン化合物を製造する工程;
溶媒および触媒を含む系中で、前記フルオレニルポルフィリン化合物の臭素置換反応を行い、二臭素置換フルオレニルポルフィリン化合物を製造する工程;および
触媒、溶媒およびアルカリ性溶液の存在下で、前記二臭素置換フルオレニルポルフィリン化合物および前記化合物Dの鈴木重合反応を行い、式(1):
によって表されるポリマーを製造する工程;
を含む、フルオレニルポルフィリン−アントラセンを含むコポリマーの製造方法。
図面中の構成要素は必ずしも一定の縮尺であるわけではなく、代わりに、本開示の原理を明瞭に図示することに重点が置かれている。さらに、図面において、同様の参照符号は、全図にわたって該当部分を示す。
開示は例示としてものであって、添付の図面の形状により制限されるものではなく、図面中、類似の参照番号は類似の要素を示す。本開示における「一」または「1つの」実施形態の参照は、必ずしも同じ実施形態を参照するものではなく、このような参照は、少なくとも1つを意味するものであると認められる。
工程S01において、式:
によって表される化合物A、B、CおよびDが供給され;
工程S02において、溶媒、触媒および酸化剤を含む系中で、化合物A、BおよびCの重縮合酸化反応が行われ、フルオレニルポルフィリン化合物が製造され;
工程S03において、溶媒および触媒を含む系中で、フルオレニルポルフィリン化合物の臭素置換反応が行われ、二臭素置換フルオレニルポルフィリン化合物が製造され;
工程S04において、触媒、溶媒およびアルカリ性溶液の存在下で、二臭素置換フルオレニルポルフィリン化合物および化合物Dの鈴木重合反応が行われ、式(1):
によって表されるポリマーが製造される。
化合物Aは、以下の工程を含む方法に従って製造される:
工程1、9,9−ジアルキル−2−ブロモ−フルオレンを得る触媒および溶媒の条件における置換反応において、2−ブロモ−フルオレンを臭素化アルキルと作用させた。触媒は、テトラブチルアンモニウムブロミドまたはベンジルトリエチルアンモニウムクロリド、溶媒はトルエン、ジメチルスルホキシド、テトラヒドロフラン等を用いた。臭素化アルキルは、R1およびR2としてのアルキル基をそれぞれ有する二臭素化アルキルを用いた。以下のスキームに図示されるように、この反応は2段階すなわち、工程iおよび工程iiで行われ、二種類の臭素化アルキルが置換反応に用いられた。
ホルムアルデヒド、触媒およびピロールを含む系中における縮合反応により、化合物Cを得た。反応式は以下の通りである:
以下のスキームに図示されるように、置換反応において、ブチルリチウムをボロン酸エステルと作用させた。
5,15−ビス(9,9−ヘキシル−フルオレニル)ポルフィリンをクロロホルムに溶解させ、少量のピリジンを加えた。反応物の温度を0℃まで下げ、適当な量のN−ブロモスクシンイミドを加え、混合物を0.5時間撹拌し、室温に戻した。その後、混合物を4時間撹拌し、アセトンを加えることによって反応を終結させ、溶媒を除去し、ジエチルエーテル/メタノールで再結晶させることにより、生成物を得た。
本実施形態において、フルオレニルポルフィリン−アントラセンを含むコポリマーは、下記の式で表される:
Claims (10)
- 式(1)によって表されるポリマーを含む、フルオレニルポルフィリン−アントラセンを含むコポリマー:
- R1およびR3は同一のC1−C16アルキル基であり;R2およびR4は同一のC1−C16アルキル基である、請求項1に記載のフルオレニルポルフィリン−アントラセンを含むコポリマー。
- R1、R2、R3およびR4は同一のC1−C16アルキル基である、請求項1または2に記載のフルオレニルポルフィリン−アントラセンを含むコポリマー。
- nは5〜50の整数である、請求項1〜3のいずれか1項に記載のフルオレニルポルフィリン−アントラセンを含むコポリマー。
- 式:
によって表される化合物A、B、CおよびDを供給する工程;
溶媒、触媒および酸化剤を含む系中で、化合物A、BおよびCの重縮合酸化反応を行い、フルオレニルポルフィリン化合物を製造する工程;
溶媒および触媒を含む系中で、前記フルオレニルポルフィリン化合物の臭素置換反応を行い、二臭素置換フルオレニルポルフィリン化合物を製造する工程;および
触媒、溶媒およびアルカリ性溶液の存在下で、前記二臭素置換フルオレニルポルフィリン化合物および前記化合物Dの鈴木重合反応を行い、式(1):
によって表されるポリマーを製造する工程;
を含む、フルオレニルポルフィリン−アントラセンを含むコポリマーの製造方法。 - 前記重縮合酸化反応に用いられる前記触媒は、トリフルオロ酢酸であり;かつ前記重縮合酸化反応に用いられる前記酸化剤は、ジクロロ−ジシアノ−ベンゾキノンである、請求項5に記載の製造方法。
- 前記鈴木重合反応に用いられる前記触媒は、有機パラジウム触媒であり;かつ前記鈴木重合反応に用いられる前記アルカリ性溶液は、無機アルカリ性水溶液または有機アルカリ性水溶液であり、前記鈴木重合反応に用いられる前記溶媒は、極性の弱い非プロトン性有機溶媒、極性の非プロトン性有機溶媒またはこれらの混合物である、請求項5または6に記載の製造方法。
- 前記臭素置換反応に用いられる前記触媒は、ピリジン、ピリジン誘導体またはトリエチルアミンであり;かつ前記溶媒はクロロホルムまたはテトラヒドロフランである、請求項5〜7のいずれか1項に記載の製造方法。
- 前記鈴木重合反応の後に、
前記鈴木重合反応の生成物をメタノールに注ぐ工程;
沈殿物を濾過および分離する工程;
前記沈殿物を洗浄する工程;
ソックスレー抽出器中、モノマーおよび触媒残渣を除去するために得られた固体をアセトンで洗浄し、フルオレニルポルフィリン−アントラセンを含むコポリマーを得る工程;を含む精製工程をさらに含む、請求項5〜8のいずれか1項に記載の製造方法。 - 請求項1〜4のいずれか1項に記載のフルオレニルポルフィリン−アントラセンを含むコポリマーまたは、請求項5〜9のいずれか1項に記載の製造方法により得られるフルオレニルポルフィリン−アントラセンを含むコポリマーを用いた、太陽電池素子、有機電界効果トランジスタ、有機エレクトロルミネッセント素子、有機光学式記憶素子、有機非線形材料または有機レーザー素子の製造方法。
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US7795452B2 (en) | 2003-10-31 | 2010-09-14 | Nissan Chemical Industries, Ltd. | Charge-transporting organic material containing compound having 1,4-dithiin ring |
JP4883898B2 (ja) * | 2004-11-18 | 2012-02-22 | パナソニック株式会社 | 電子デバイスおよびそれを用いた電子機器 |
FR2892723B1 (fr) * | 2005-11-03 | 2009-04-24 | Biomerieux Sa | Nouveaux monomeres electropolymerisables, solubles en solution aqueuse, comportant une metalloporphyrine. |
-
2010
- 2010-01-30 JP JP2012550292A patent/JP5546070B2/ja not_active Expired - Fee Related
- 2010-01-30 CN CN2010800481069A patent/CN102686592B/zh not_active Expired - Fee Related
- 2010-01-30 US US13/575,684 patent/US8598301B2/en active Active
- 2010-01-30 WO PCT/CN2010/070435 patent/WO2011091607A1/zh active Application Filing
- 2010-01-30 EP EP10844385.4A patent/EP2530084B1/en not_active Not-in-force
Also Published As
Publication number | Publication date |
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US20120302717A1 (en) | 2012-11-29 |
WO2011091607A1 (zh) | 2011-08-04 |
JP2013518151A (ja) | 2013-05-20 |
CN102686592A (zh) | 2012-09-19 |
US8598301B2 (en) | 2013-12-03 |
CN102686592B (zh) | 2013-11-27 |
EP2530084B1 (en) | 2014-03-12 |
EP2530084A1 (en) | 2012-12-05 |
EP2530084A4 (en) | 2013-06-12 |
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