JP2013525523A - フルオレン類共重合体及びその製造方法並びにその使用 - Google Patents
フルオレン類共重合体及びその製造方法並びにその使用 Download PDFInfo
- Publication number
- JP2013525523A JP2013525523A JP2013505296A JP2013505296A JP2013525523A JP 2013525523 A JP2013525523 A JP 2013525523A JP 2013505296 A JP2013505296 A JP 2013505296A JP 2013505296 A JP2013505296 A JP 2013505296A JP 2013525523 A JP2013525523 A JP 2013525523A
- Authority
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- Japan
- Prior art keywords
- group
- thiophenpyrazine
- copolymer containing
- organic
- fluorene copolymer
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 229920001577 copolymer Polymers 0.000 title claims abstract description 103
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 title claims abstract description 72
- 238000000034 method Methods 0.000 title claims description 13
- 230000008569 process Effects 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 claims abstract description 61
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 35
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims abstract description 28
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 11
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims abstract description 10
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 8
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims abstract description 7
- 238000006243 chemical reaction Methods 0.000 claims description 67
- 150000001875 compounds Chemical class 0.000 claims description 56
- 239000012265 solid product Substances 0.000 claims description 41
- 239000000463 material Substances 0.000 claims description 36
- 239000000243 solution Substances 0.000 claims description 35
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 24
- 239000003960 organic solvent Substances 0.000 claims description 19
- 239000000047 product Substances 0.000 claims description 19
- 238000003756 stirring Methods 0.000 claims description 19
- 239000003054 catalyst Substances 0.000 claims description 16
- 239000005457 ice water Substances 0.000 claims description 15
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 claims description 14
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 claims description 14
- 229940126062 Compound A Drugs 0.000 claims description 13
- 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 claims description 13
- 238000006116 polymerization reaction Methods 0.000 claims description 13
- USDIRSJFHPHMAS-UHFFFAOYSA-N ClC1=NC=C(C=2C1=NC=CN=2)F Chemical compound ClC1=NC=C(C=2C1=NC=CN=2)F USDIRSJFHPHMAS-UHFFFAOYSA-N 0.000 claims description 12
- 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 claims description 10
- 239000007864 aqueous solution Substances 0.000 claims description 7
- 238000005401 electroluminescence Methods 0.000 claims description 7
- 230000005669 field effect Effects 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 6
- 238000013086 organic photovoltaic Methods 0.000 claims description 6
- 229920000642 polymer Polymers 0.000 claims description 6
- 229930192474 thiophene Natural products 0.000 claims description 6
- MRWWWZLJWNIEEJ-UHFFFAOYSA-N 4,4,5,5-tetramethyl-2-propan-2-yloxy-1,3,2-dioxaborolane Chemical compound CC(C)OB1OC(C)(C)C(C)(C)O1 MRWWWZLJWNIEEJ-UHFFFAOYSA-N 0.000 claims description 5
- 239000012670 alkaline solution Substances 0.000 claims description 5
- 230000003287 optical effect Effects 0.000 claims description 5
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 239000003446 ligand Substances 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 3
- 239000000908 ammonium hydroxide Substances 0.000 claims description 3
- 229910052744 lithium Inorganic materials 0.000 claims description 3
- 229910000000 metal hydroxide Inorganic materials 0.000 claims description 3
- 150000004692 metal hydroxides Chemical class 0.000 claims description 3
- 239000012046 mixed solvent Substances 0.000 claims description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 230000004044 response Effects 0.000 abstract description 7
- 230000003595 spectral effect Effects 0.000 abstract description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 69
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
- 239000010410 layer Substances 0.000 description 35
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 26
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 26
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 238000012360 testing method Methods 0.000 description 22
- 238000004440 column chromatography Methods 0.000 description 19
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 17
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 16
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
- 229910052757 nitrogen Inorganic materials 0.000 description 13
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 13
- 239000011521 glass Substances 0.000 description 11
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 10
- 239000004065 semiconductor Substances 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- CZDVJGBXKADLCY-UHFFFAOYSA-N thieno[3,4-b]pyrazine Chemical compound N1=CC=NC2=CSC=C21 CZDVJGBXKADLCY-UHFFFAOYSA-N 0.000 description 8
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 6
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 6
- 239000012299 nitrogen atmosphere Substances 0.000 description 6
- 239000011368 organic material Substances 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 238000011160 research Methods 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 5
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 5
- MUQHZJJWUBYMIK-UHFFFAOYSA-N CC1(C(OBO1)(C)C)C.CC1(C2=CC=CC=C2C=2C=CC=CC12)C Chemical compound CC1(C(OBO1)(C)C)C.CC1(C2=CC=CC=C2C=2C=CC=CC12)C MUQHZJJWUBYMIK-UHFFFAOYSA-N 0.000 description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-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
- 239000002585 base Substances 0.000 description 4
- 230000007613 environmental effect Effects 0.000 description 4
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 4
- 229910052763 palladium Inorganic materials 0.000 description 4
- 230000003014 reinforcing effect Effects 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- 238000001771 vacuum deposition Methods 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- -1 C 4 lithium compounds Chemical class 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000012267 brine Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000005034 decoration Methods 0.000 description 3
- GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical compound C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 description 3
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- QOKIQMPCYLIXOF-UHFFFAOYSA-N 2,5-dibromo-3,6-dimethylthieno[3,2-b]thiophene Chemical compound CC1=C(Br)SC2=C1SC(Br)=C2C QOKIQMPCYLIXOF-UHFFFAOYSA-N 0.000 description 2
- PYRYRMKKDOKMAN-UHFFFAOYSA-N 2,5-dibromo-3,6-dioctylthieno[3,2-b]thiophene Chemical compound CCCCCCCCC1=C(Br)SC2=C1SC(Br)=C2CCCCCCCC PYRYRMKKDOKMAN-UHFFFAOYSA-N 0.000 description 2
- KBVDUUXRXJTAJC-UHFFFAOYSA-N 2,5-dibromothiophene Chemical compound BrC1=CC=C(Br)S1 KBVDUUXRXJTAJC-UHFFFAOYSA-N 0.000 description 2
- HKUVNSRUEGOMBY-UHFFFAOYSA-N 3,6-di(icosyl)thieno[3,2-b]thiophene Chemical compound CCCCCCCCCCCCCCCCCCCCC1=CSC2=C1SC=C2CCCCCCCCCCCCCCCCCCCC HKUVNSRUEGOMBY-UHFFFAOYSA-N 0.000 description 2
- GDEWXFQKAYEKLX-UHFFFAOYSA-N 3,6-dimethylthieno[3,2-b]thiophene Chemical compound CC1=CSC2=C1SC=C2C GDEWXFQKAYEKLX-UHFFFAOYSA-N 0.000 description 2
- QFZLOYZIBDWMLB-UHFFFAOYSA-N 3,6-dioctylthieno[3,2-b]thiophene Chemical compound CCCCCCCCC1=CSC2=C1SC=C2CCCCCCCC QFZLOYZIBDWMLB-UHFFFAOYSA-N 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- TVYDLYUASALTRG-UHFFFAOYSA-N C(CCCCCCC)C1(C2=CC=CC=C2C=2C=CC=CC12)CCCCCCCC.CC1(OBOC1(C)C)C Chemical compound C(CCCCCCC)C1(C2=CC=CC=C2C=2C=CC=CC12)CCCCCCCC.CC1(OBOC1(C)C)C TVYDLYUASALTRG-UHFFFAOYSA-N 0.000 description 2
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical compound CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 2
- NWCVSQQUZHZMOT-UHFFFAOYSA-N S1C=CC=C1.BrC=1SC=CC1CCCCCCCCCCCCCCCCCCCC Chemical compound S1C=CC=C1.BrC=1SC=CC1CCCCCCCCCCCCCCCCCCCC NWCVSQQUZHZMOT-UHFFFAOYSA-N 0.000 description 2
- BMBNVJRQUFXOKT-UHFFFAOYSA-N S1C=CC=C1.C(CCCCCCCCCCCCCCCCCCC)C1=CSC=C1 Chemical compound S1C=CC=C1.C(CCCCCCCCCCCCCCCCCCC)C1=CSC=C1 BMBNVJRQUFXOKT-UHFFFAOYSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000005210 alkyl ammonium group Chemical group 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 238000007664 blowing Methods 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 239000003574 free electron Substances 0.000 description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 150000003949 imides Chemical class 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000002861 polymer material Substances 0.000 description 2
- 238000010248 power generation Methods 0.000 description 2
- COHIZWAIFCLIDY-UHFFFAOYSA-N pyrazine;thiophene Chemical group C=1C=CSC=1.C1=CN=CC=N1 COHIZWAIFCLIDY-UHFFFAOYSA-N 0.000 description 2
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 2
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 2
- HMPFMHMEQPWCNR-UHFFFAOYSA-N 2,7-dibromo-9,9-di(icosyl)fluorene Chemical compound C1=C(Br)C=C2C(CCCCCCCCCCCCCCCCCCCC)(CCCCCCCCCCCCCCCCCCCC)C3=CC(Br)=CC=C3C2=C1 HMPFMHMEQPWCNR-UHFFFAOYSA-N 0.000 description 1
- LONBOJIXBFUBKQ-UHFFFAOYSA-N 2,7-dibromo-9,9-dimethylfluorene Chemical compound C1=C(Br)C=C2C(C)(C)C3=CC(Br)=CC=C3C2=C1 LONBOJIXBFUBKQ-UHFFFAOYSA-N 0.000 description 1
- CYKLQIOPIMZZBZ-UHFFFAOYSA-N 2,7-dibromo-9,9-dioctylfluorene Chemical compound C1=C(Br)C=C2C(CCCCCCCC)(CCCCCCCC)C3=CC(Br)=CC=C3C2=C1 CYKLQIOPIMZZBZ-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- 0 C*(C)C(C)(C)c1ccc2-c3ccc(*)cc3C(*)(*)c2c1 Chemical compound C*(C)C(C)(C)c1ccc2-c3ccc(*)cc3C(*)(*)c2c1 0.000 description 1
- LAFRCZDAGGUVPB-UHFFFAOYSA-N CCCCCCCCCCCCCCCCCCCC[Zn]CCCCCCCCCCCCCCCCCCCC.Br Chemical compound CCCCCCCCCCCCCCCCCCCC[Zn]CCCCCCCCCCCCCCCCCCCC.Br LAFRCZDAGGUVPB-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- 229920000144 PEDOT:PSS Polymers 0.000 description 1
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- YLHMUQYQPDRKAH-UHFFFAOYSA-M [Br-].CCCCCCCC[Zn+] Chemical compound [Br-].CCCCCCCC[Zn+] YLHMUQYQPDRKAH-UHFFFAOYSA-M 0.000 description 1
- SOHOYYHPFIUFDH-UHFFFAOYSA-M [Br-].[Zn+]C Chemical compound [Br-].[Zn+]C SOHOYYHPFIUFDH-UHFFFAOYSA-M 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- TXMQVANOCNIJMZ-UHFFFAOYSA-N dotetracontane-21,22-dione Chemical compound CCCCCCCCCCCCCCCCCCCCC(=O)C(=O)CCCCCCCCCCCCCCCCCCCC TXMQVANOCNIJMZ-UHFFFAOYSA-N 0.000 description 1
- 238000000295 emission spectrum Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N o-dimethylbenzene Natural products CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 229940005642 polystyrene sulfonic acid Drugs 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UFBAKNJSYGCXMB-UHFFFAOYSA-N pyrazine thiophene Chemical group S1C=CC=C1.N1=CC=NC=C1.S1C=CC=C1 UFBAKNJSYGCXMB-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- LPSKDVINWQNWFE-UHFFFAOYSA-M tetrapropylazanium;hydroxide Chemical compound [OH-].CCC[N+](CCC)(CCC)CCC LPSKDVINWQNWFE-UHFFFAOYSA-M 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 230000002463 transducing effect Effects 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
Classifications
-
- H—ELECTRICITY
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Abstract
【解決手段】本発明に係るチオフェンピラジンユニットを含有するフルオレン類共重合体は、下記一般式(I)で表される共重合体を含む。
【化1】
(式中、R1、R2、R5、R6、R7及びR8は、H又はC1〜C20のアルキル基からなる群から選ばれ、R3及びR4は、H、C1〜C20のアルキル基、C1〜C20のアルコキシ基、フェニル基又はフェノキシ基からなる群から選ばれ、x+y=1,x≠0,y≠0であり、nは1〜200の整数を示し、Ar1はチオフェンユニットを含有する基である。)
【選択図】図1
Description
また、本発明に係るチオフェンピラジンユニットを含有するフルオレン類共重合体の製造方法は、下記一般式で表される化合物A、B、Cをそれぞれ提供するステップと、
触媒、アルカリ溶液及び有機溶剤の条件下で前記化合物A、B、CをSuzuki重合反応させて、下記一般式(I)で表される共重合体を得るステップと、を含む。
また、上記の共重合体において、R1及びR2は同じアルキル基であり、R3及びR4は同じアルキル基であり、R5及びR6は同じアルキル基であり、R7及びR8は同じアルキル基であることが好ましい。R5、R6、R7及びR8は、同じアルキル基であることがより好ましい。R1、R2、R5、R6、R7及びR8はアルキル基であることが好ましく、例えば、C8以上のアルキル基であってもよい。R3及びR4は、アルキル基、アルコキシ基、フェニル基又はフェノキシ基であることが好ましい。例えば、R3及びR4はC8以上のアルキル基又はC8以上のアルコキシ基であってもよい。前記共重合体の中にアルキル基、アルコキシ基、フェニル基又はフェノキシ基を導入することによって、該共重合体の溶解性及び分子量を高めることができ、スピンコート可能なポリマー又はオリゴマーを得られる。また、nは5〜100の整数であることが好ましい。
上記のチオフェンピラジンユニットを含有するフルオレン類共重合体は、チオフェンユニット(Ar1)を含むので、適度なバンドギャップ、広いスペクトル応答範囲及び良好な熱安定性、環境安定性を有する。しかも、前記共重合体は、フルオレン基ユニットを含有する。フルオレン基ユニット及びチオフェンユニットは何れも非常に優れた供与体材料であるが、該共重合体中のチオフェンーチオフェンピラジンユニットは非常に優れた受容体材料である。これらのユニットにより構成されるポリマーは、強い供与体−受容体構造を形成する。これにより、材料の安定性が向上されるだけでなく、材料のバンドギャップが狭くなり、該共重合体の太陽光に対する吸収範囲が一層拡大され、光電の変換効率が向上した。より詳細には、チエノ[3,4−b]ピラジンは、優れた平面構造を有し、五員環及び六員環の骨格を含有する受容体ユニットであり、分子内での電荷移転性能及び優れた電気化学的還元性能を持ち、且つ常用のキノキサリン等のユニットに比べて、より強い電子吸引能力を有する。また、前記チエノ[3,4−b]ピラジンは、強い可修飾性を有し、簡便な方法で該チエノ[3,4−b]ピラジンに電子供与基及び電子受容基を導入することにより、その電子吸引能力を調節することができる。以下の実施例において、フルオレンユニット及びチオフェンユニットを導入する。
ステップS02において、触媒、アルカリ溶液及び有機溶剤の条件下で、前記化合物A、B、CをSuzuki重合反応させて、下記一般式(I)で表される共重合体を得る。
本実施例1に係るチオフェンピラジンユニットを含有するフルオレン類共重合体において、R1及びR2はメチルであり、R3及びR10はHである。その構造は、下記一般式(VI)で表される。
(実施例2)
本実施例2に係るチオフェンピラジンユニットを含有するフルオレン類共重合体において、R1、R2、R9、R10はメチルであり、R3〜R8はHである。その構造は下記一般式(X)で表される。
本実施例3に係るチオフェンピラジンユニットを含有するフルオレン類共重合体において、R1、R2、R3及びR4はメチルであり、R5〜R10はHである。その構造は下記一般式(XIII)で表される。
本実施例3に係る化合物Cの製造方法は、以下のステップを含む。
本実施例4に係るチオフェンピラジンユニットを含有するフルオレン類共重合体において、R1、R2、R3、R4、R9及びR10はC8H17であり、R5〜R8はHである。その構造は下記一般式(XVI)で表される。
本実施例5に係るチオフェンピラジンユニットを含有するフルオレン類共重合体において、R1、R2、R3、R4、R5、R8、R9及びR10はC20H41であり、R6及びR7はHである。その構造は下記一般式(XXV)で表される。
Claims (12)
- チオフェンピラジンユニットを含有するフルオレン類共重合体であって、
前記チオフェンピラジンユニットを含有するフルオレン類共重合体は、下記一般式(I)で表される共重合体を含む。
- 前記R1及びR2は同じアルキル基であり、R3及びR4は同じアルキル基であり、R5及びR6は同じアルキル基であり、R7及びR8は同じアルキル基であることを特徴とする請求項1に記載のチオフェンピラジンユニットを含有するフルオレン類共重合体。
- 前記R1、R2、R5、R6、R7及びR8はC8以上のアルキル基であり、前記R3及びR4はC8以上のアルキル基、C8以上のアルコキシ基、フェニル基又はフェノキシ基であることを特徴とする請求項1に記載のチオフェンピラジンユニットを含有するフルオレン類共重合体。
- 前記Ar1は、下記の一般式(1)〜(7)で表される基であることを特徴とする請求項1に記載のチオフェンピラジンユニットを含有するフルオレン類共重合体。
- 下記一般式で表される化合物A、B、Cをそれぞれ提供するステップと、
触媒、アルカリ溶液及び有機溶剤の条件下で、前記化合物A、B、CをSuzuki重合反応させて、下記一般式(I)で表される共重合体を得るステップと、
を含むことを特徴とするチオフェンピラジンユニットを含有するフルオレン類共重合体の製造方法。 - 前記Suzuki重合反応は、無酸素の条件下で、前記化合物A、B、Cを1.0:a:bのモル比率に基づいて混合して、触媒、アルカリ溶液及び有機溶剤を添加し、50℃〜150℃まで加熱して2日間〜7日間を反応させて、ブロモベンゼンを添加し12時間〜24時間を反応させた後、さらにフェニルボロン酸を添加し続けて12時間〜24時間を反応させ、ここで、a>0,b>0,a+b=1.0であることを特徴とする請求項5に記載のチオフェンピラジンユニットを含有するフルオレン類共重合体の製造方法。
- 前記Suzuki重合反応の生成物に対して、反応が終わった後、生成物を取ってメタノールで何回も沈下させ、濾過し、真空乾燥させて、固体生成物を得るという精製工程をさらに行うことを特徴とする請求項5に記載のチオフェンピラジンユニットを含有するフルオレン類共重合体の製造方法。
- 前記化合物Aは、無酸素の条件下で、アルキル基リチウム溶液を2,7−ジブロモ−9,9−ジアルキル基フルオレン及び有機溶剤の中に入れて、0.5時間〜4時間を撹拌した後、2−イソプロポキシ−4,4,5,5−テトラメチル−1,3,2−ジオキサボロランを添加し、反応させてから、室温まで回復して、続けて24時間〜48時間を撹拌することによって得られる、ことを特徴とする請求項5に記載のチオフェンピラジンユニットを含有するフルオレン類共重合体の製造方法。
- 前記化合物Bは、氷水の中で光を避けて、臭化剤をAr1単体及び有機溶剤の中に数回に分けて添加し、4時間〜48時間を撹拌することによって得られる、ことを特徴とする請求項5に記載のチオフェンピラジンユニットを含有するフルオレン類共重合体の製造方法。
- 前記化合物Cは、光を避ける条件下で、臭化剤を5,7−ビス(3,4−ジアルキル基チオフェン−2−基)−2,3−ジアルキル基チオフェン[3,4−b ]ピラジン及び有機溶剤の中に数回に分けて添加し、12時間〜48時間を反応させることによって得られる、ことを特徴とする請求項5に記載のチオフェンピラジンユニットを含有するフルオレン類共重合体の製造方法。
- 前記Suzuki重合反応において、前記触媒は、有機パラジウム触媒、或いは有機パラジウム触媒と有機ホスフィンリガンドとの混合物であり、その用量が前記化合物Aのモル用量の0.1%〜20%であり、前記アルカリ溶液は、金属水酸化物又は金属炭酸塩の水溶液及びアルキル基水酸化アンモニウムの水溶液であり、その用量が前記化合物Aのモル用量の1倍〜10倍であり、前記有機溶剤は、弱極性又は極性非プロトン性の有機溶剤又は両者の混合溶剤である、ことを特徴とする請求項5に記載のチオフェンピラジンユニットを含有するフルオレン類共重合体の製造方法。
- 有機光起電材料、ポリマー太陽電池素子、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ス素子、有機光学式記憶素子、有機非線形材料又は有機レーザー素子分野における、請求項1〜4の何れか一項に記載のチオフェンピラジンユニットを含有するフルオレン類共重合体の使用。
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JP5914069B2 (ja) * | 2011-03-17 | 2016-05-11 | 住友化学株式会社 | 金属複合体組成物及びその混合物 |
CN111925506B (zh) * | 2020-07-10 | 2022-06-28 | 华南理工大学 | 三苯胺-芴-苯并咪唑低带隙三元共聚物、电存储器件及其制备 |
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CN113831515B (zh) * | 2021-10-13 | 2022-07-08 | 福州大学 | 悬挂芴基小分子受体的聚合物半导体及其制备方法 |
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JPN6013055209; Admassie, Shimelis: 'Electrochemical and optical studies of the band gaps of alternating polyfluorene copolymers' Synthetic Metals 156(7-8), 2006, 614-623 * |
JPN6013055211; 'Tailoring of Low Bandgap Polymer and itsPerformance Analysis in Organic Solar Cells' Macromolecular Chemistry and Physics 210, 2009, 1493-1503 * |
JPN6013055212; Xia, Yangjun: 'Novel random low-band-gap fluorene-based copolymers for deep red/near infrared light-emitting di' Macromolecular Chemistry and Physics 207(5), 2006, 511-520 * |
JPN6013055212; Xia, Yangjun: 'Novel random low-band-gap fluorene-based copolymers for deep red/near infrared light-emitting diodes' Macromolecular Chemistry and Physics 207(5), 2006, 511-520 * |
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WO2011130915A1 (zh) | 2011-10-27 |
US8779204B2 (en) | 2014-07-15 |
CN102753599B (zh) | 2014-04-30 |
EP2562198A1 (en) | 2013-02-27 |
CN102753599A (zh) | 2012-10-24 |
JP5612757B2 (ja) | 2014-10-22 |
US20130005932A1 (en) | 2013-01-03 |
EP2562198A4 (en) | 2017-08-02 |
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