CN102834945A - 稠合的二噻吩共聚物 - Google Patents
稠合的二噻吩共聚物 Download PDFInfo
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- CN102834945A CN102834945A CN2011800173715A CN201180017371A CN102834945A CN 102834945 A CN102834945 A CN 102834945A CN 2011800173715 A CN2011800173715 A CN 2011800173715A CN 201180017371 A CN201180017371 A CN 201180017371A CN 102834945 A CN102834945 A CN 102834945A
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- Prior art keywords
- alkyl
- aryl
- alkoxyl
- interval
- independently
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- 229920001577 copolymer Polymers 0.000 title claims abstract description 39
- 239000000463 material Substances 0.000 claims abstract description 45
- 239000004065 semiconductor Substances 0.000 claims abstract description 44
- 230000005669 field effect Effects 0.000 claims abstract description 20
- 239000002131 composite material Substances 0.000 claims abstract description 8
- 238000013086 organic photovoltaic Methods 0.000 claims abstract description 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 95
- -1 Phenyl Chemical group 0.000 claims description 67
- 229910052739 hydrogen Inorganic materials 0.000 claims description 63
- 229930192474 thiophene Natural products 0.000 claims description 48
- 229910052799 carbon Inorganic materials 0.000 claims description 45
- 229920000642 polymer Polymers 0.000 claims description 45
- 239000001257 hydrogen Substances 0.000 claims description 35
- 125000000217 alkyl group Chemical group 0.000 claims description 33
- 125000005605 benzo group Chemical group 0.000 claims description 31
- 239000002904 solvent Substances 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 26
- 239000000203 mixture Substances 0.000 claims description 26
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 25
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 24
- 229910052760 oxygen Inorganic materials 0.000 claims description 24
- 239000001301 oxygen Substances 0.000 claims description 24
- 238000007639 printing Methods 0.000 claims description 24
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 22
- 238000006243 chemical reaction Methods 0.000 claims description 20
- 229910052736 halogen Inorganic materials 0.000 claims description 19
- 150000002367 halogens Chemical class 0.000 claims description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
- 238000000151 deposition Methods 0.000 claims description 14
- 230000008021 deposition Effects 0.000 claims description 13
- 229910052731 fluorine Inorganic materials 0.000 claims description 11
- 150000002431 hydrogen Chemical class 0.000 claims description 10
- 230000003252 repetitive effect Effects 0.000 claims description 10
- 238000004528 spin coating Methods 0.000 claims description 10
- 239000010409 thin film Substances 0.000 claims description 9
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 239000011737 fluorine Substances 0.000 claims description 8
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 7
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 4
- SKOWZLGOFVSKLB-UHFFFAOYSA-N hypodiboric acid Chemical compound OB(O)B(O)O SKOWZLGOFVSKLB-UHFFFAOYSA-N 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 238000003618 dip coating Methods 0.000 claims description 3
- 230000003287 optical effect Effects 0.000 claims description 3
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 2
- 125000006731 (C1-C8) thioalkoxy group Chemical group 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 claims description 2
- 229910052720 vanadium Inorganic materials 0.000 claims description 2
- 238000007766 curtain coating Methods 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 13
- CRUIOQJBPNKOJG-UHFFFAOYSA-N thieno[3,2-e][1]benzothiole Chemical group C1=C2SC=CC2=C2C=CSC2=C1 CRUIOQJBPNKOJG-UHFFFAOYSA-N 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 41
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 32
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
- 239000010410 layer Substances 0.000 description 25
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 239000002585 base Substances 0.000 description 20
- 125000003118 aryl group Chemical group 0.000 description 19
- 239000007789 gas Substances 0.000 description 19
- 150000001875 compounds Chemical class 0.000 description 18
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
- 239000000178 monomer Substances 0.000 description 17
- 229910052786 argon Inorganic materials 0.000 description 16
- 238000005160 1H NMR spectroscopy Methods 0.000 description 14
- 238000004458 analytical method Methods 0.000 description 14
- 239000007787 solid Substances 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- 239000000741 silica gel Substances 0.000 description 11
- 229910002027 silica gel Inorganic materials 0.000 description 11
- 150000004816 dichlorobenzenes Chemical class 0.000 description 10
- 239000010408 film Substances 0.000 description 10
- 229910052717 sulfur Inorganic materials 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 238000001704 evaporation Methods 0.000 description 9
- 239000004793 Polystyrene Substances 0.000 description 8
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 8
- 125000000753 cycloalkyl group Chemical group 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- 229920002223 polystyrene Polymers 0.000 description 8
- 229910052710 silicon Inorganic materials 0.000 description 8
- 239000010703 silicon Substances 0.000 description 8
- 125000003342 alkenyl group Chemical group 0.000 description 7
- 125000000304 alkynyl group Chemical group 0.000 description 7
- 238000002425 crystallisation Methods 0.000 description 7
- 230000008025 crystallization Effects 0.000 description 7
- 238000005516 engineering process Methods 0.000 description 7
- 239000000523 sample Substances 0.000 description 7
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 239000003990 capacitor Substances 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 238000007641 inkjet printing Methods 0.000 description 6
- 238000006116 polymerization reaction Methods 0.000 description 6
- 125000003638 stannyl group Chemical group [H][Sn]([H])([H])* 0.000 description 6
- HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 description 6
- 0 CCc1c(C)c(-c2n[s]nc2C2C(*)=C(C)SC22)c2[s]1 Chemical compound CCc1c(C)c(-c2n[s]nc2C2C(*)=C(C)SC22)c2[s]1 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 150000001721 carbon Chemical group 0.000 description 5
- 239000002019 doping agent Substances 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 239000010931 gold Substances 0.000 description 5
- 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 5
- 239000000843 powder Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical class ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 239000012298 atmosphere Substances 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 239000003989 dielectric material Substances 0.000 description 4
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 4
- 229910052737 gold Inorganic materials 0.000 description 4
- YCOZIPAWZNQLMR-UHFFFAOYSA-N heptane - octane Natural products CCCCCCCCCCCCCCC YCOZIPAWZNQLMR-UHFFFAOYSA-N 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- 239000011630 iodine Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- BGHCVCJVXZWKCC-UHFFFAOYSA-N tetradecane Chemical compound CCCCCCCCCCCCCC BGHCVCJVXZWKCC-UHFFFAOYSA-N 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 3
- YMMGRPLNZPTZBS-UHFFFAOYSA-N 2,3-dihydrothieno[2,3-b][1,4]dioxine Chemical compound O1CCOC2=C1C=CS2 YMMGRPLNZPTZBS-UHFFFAOYSA-N 0.000 description 3
- AGBXYHCHUYARJY-UHFFFAOYSA-N 2-phenylethenesulfonic acid Chemical compound OS(=O)(=O)C=CC1=CC=CC=C1 AGBXYHCHUYARJY-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- 229920000144 PEDOT:PSS Polymers 0.000 description 3
- 229940049706 benzodiazepine Drugs 0.000 description 3
- 239000002800 charge carrier Substances 0.000 description 3
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- 238000004587 chromatography analysis Methods 0.000 description 3
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- 238000001035 drying Methods 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
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- 125000001072 heteroaryl group Chemical group 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 238000000813 microcontact printing Methods 0.000 description 3
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- 238000000059 patterning Methods 0.000 description 3
- 125000003367 polycyclic group Chemical group 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 238000007650 screen-printing Methods 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 238000010129 solution processing Methods 0.000 description 3
- 239000011877 solvent mixture Substances 0.000 description 3
- 125000001544 thienyl group Chemical group 0.000 description 3
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- HWPRFMCKSFTMHQ-UHFFFAOYSA-N 2-(1-thiophen-2-ylethenyl)thiophene Chemical compound C=1C=CSC=1C(=C)C1=CC=CS1 HWPRFMCKSFTMHQ-UHFFFAOYSA-N 0.000 description 2
- AYBFWHPZXYPJFW-AATRIKPKSA-N 2-[(e)-2-thiophen-2-ylethenyl]thiophene Chemical compound C=1C=CSC=1/C=C/C1=CC=CS1 AYBFWHPZXYPJFW-AATRIKPKSA-N 0.000 description 2
- HYRYQZIGBWDHAD-UHFFFAOYSA-N 2-bromo-5-ethylthiophene Chemical compound CCC1=CC=C(Br)S1 HYRYQZIGBWDHAD-UHFFFAOYSA-N 0.000 description 2
- 229910020366 ClO 4 Inorganic materials 0.000 description 2
- 229910017488 Cu K Inorganic materials 0.000 description 2
- 229910017541 Cu-K Inorganic materials 0.000 description 2
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 2
- 229910018286 SbF 6 Inorganic materials 0.000 description 2
- 238000006619 Stille reaction Methods 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
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- 150000001450 anions Chemical class 0.000 description 2
- 239000002518 antifoaming agent Substances 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical group 0.000 description 2
- 150000005347 biaryls Chemical group 0.000 description 2
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- 230000003197 catalytic effect Effects 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- KWTSZCJMWHGPOS-UHFFFAOYSA-M chloro(trimethyl)stannane Chemical compound C[Sn](C)(C)Cl KWTSZCJMWHGPOS-UHFFFAOYSA-M 0.000 description 2
- 238000007265 chloromethylation reaction Methods 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
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- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 239000011903 deuterated solvents Substances 0.000 description 2
- 125000000950 dibromo group Chemical group Br* 0.000 description 2
- 238000000113 differential scanning calorimetry Methods 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
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- 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 2
- 229910003472 fullerene Inorganic materials 0.000 description 2
- 229910002804 graphite Inorganic materials 0.000 description 2
- 239000010439 graphite Substances 0.000 description 2
- NDJKXXJCMXVBJW-UHFFFAOYSA-N heptadecane Chemical compound CCCCCCCCCCCCCCCCC NDJKXXJCMXVBJW-UHFFFAOYSA-N 0.000 description 2
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 2
- 150000002429 hydrazines Chemical class 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- CBFCDTFDPHXCNY-UHFFFAOYSA-N icosane Chemical compound CCCCCCCCCCCCCCCCCCCC CBFCDTFDPHXCNY-UHFFFAOYSA-N 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- 238000013508 migration Methods 0.000 description 2
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- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- RZJRJXONCZWCBN-UHFFFAOYSA-N octadecane Chemical compound CCCCCCCCCCCCCCCCCC RZJRJXONCZWCBN-UHFFFAOYSA-N 0.000 description 2
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- WYURNTSHIVDZCO-SVYQBANQSA-N oxolane-d8 Chemical compound [2H]C1([2H])OC([2H])([2H])C([2H])([2H])C1([2H])[2H] WYURNTSHIVDZCO-SVYQBANQSA-N 0.000 description 2
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- 230000001105 regulatory effect Effects 0.000 description 1
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- 239000013557 residual solvent Substances 0.000 description 1
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- 229910052701 rubidium Inorganic materials 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000004621 scanning probe microscopy Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 238000001338 self-assembly Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 125000004079 stearyl 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])C([H])([H])C([H])([H])C([H])([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 description 1
- 238000003860 storage Methods 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- KBLZDCFTQSIIOH-UHFFFAOYSA-M tetrabutylazanium;perchlorate Chemical compound [O-]Cl(=O)(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC KBLZDCFTQSIIOH-UHFFFAOYSA-M 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- HZPQJLDBYJZHLL-UHFFFAOYSA-N thiophen-2-ylstannane Chemical compound [SnH3]C1=CC=CS1 HZPQJLDBYJZHLL-UHFFFAOYSA-N 0.000 description 1
- AZRUJABJKZWHPR-UHFFFAOYSA-N thiophen-3-ylidenemethanone Chemical compound O=C=C1CSC=C1 AZRUJABJKZWHPR-UHFFFAOYSA-N 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
- 230000001131 transforming effect Effects 0.000 description 1
- XVOARZYNJXNFKO-UHFFFAOYSA-N tributyl-(3-dodecylthiophen-2-yl)stannane Chemical compound CCCCCCCCCCCCC=1C=CSC=1[Sn](CCCC)(CCCC)CCCC XVOARZYNJXNFKO-UHFFFAOYSA-N 0.000 description 1
- 125000002889 tridecyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
- 238000002371 ultraviolet--visible spectrum Methods 0.000 description 1
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 1
- 125000002948 undecyl 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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000004736 wide-angle X-ray diffraction Methods 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- 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
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- 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
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- 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
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B69/00—Dyes not provided for by a single group of this subclass
- C09B69/10—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds
- C09B69/109—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds containing other specific dyes
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L31/00—Semiconductor devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof
- H01L31/04—Semiconductor devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof adapted as photovoltaic [PV] conversion devices
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- 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
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
- H10K85/113—Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
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- 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
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
- H10K30/30—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation comprising bulk heterojunctions, e.g. interpenetrating networks of donor and acceptor material domains
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
- H10K30/50—Photovoltaic [PV] devices
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- 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
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
- H10K85/113—Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
- H10K85/1135—Polyethylene dioxythiophene [PEDOT]; Derivatives thereof
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- 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
- H10K85/20—Carbon compounds, e.g. carbon nanotubes or fullerenes
- H10K85/211—Fullerenes, e.g. C60
- H10K85/215—Fullerenes, e.g. C60 comprising substituents, e.g. PCBM
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Physics & Mathematics (AREA)
- Materials Engineering (AREA)
- Nanotechnology (AREA)
- Medicinal Chemistry (AREA)
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- Computer Hardware Design (AREA)
- General Physics & Mathematics (AREA)
- Power Engineering (AREA)
- Mathematical Physics (AREA)
- Theoretical Computer Science (AREA)
- Crystallography & Structural Chemistry (AREA)
- Electromagnetism (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- Photovoltaic Devices (AREA)
- Thin Film Transistor (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Electroluminescent Light Sources (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP10158584 | 2010-03-31 | ||
| EP10158584.2 | 2010-03-31 | ||
| PCT/EP2011/054787 WO2011120951A1 (en) | 2010-03-31 | 2011-03-29 | Annealed dithiophene copolymers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN102834945A true CN102834945A (zh) | 2012-12-19 |
Family
ID=42263923
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2011800173715A Pending CN102834945A (zh) | 2010-03-31 | 2011-03-29 | 稠合的二噻吩共聚物 |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP2553743A1 (ja) |
| JP (1) | JP2013523931A (ja) |
| KR (1) | KR20130040830A (ja) |
| CN (1) | CN102834945A (ja) |
| WO (1) | WO2011120951A1 (ja) |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103483560A (zh) * | 2013-09-17 | 2014-01-01 | 武汉工程大学 | 一种2,1,3-苯并噻二唑并二噻吩衍生溴代物与咔唑的共轭聚合物及其合成方法 |
| CN104098592A (zh) * | 2013-04-12 | 2014-10-15 | 艾尼股份公司 | 由苯并二噻吩基团二取代的苯并杂二唑化合物的制备方法 |
| CN104119504A (zh) * | 2013-04-25 | 2014-10-29 | 海洋王照明科技股份有限公司 | 含吡咯吲哚并二噻吩-二噻吩并苯并噻二唑共轭聚合物材料及其制备方法和应用 |
| CN104211922A (zh) * | 2013-05-29 | 2014-12-17 | 海洋王照明科技股份有限公司 | 共轭聚合物及其制备方法与应用 |
| CN104211923A (zh) * | 2013-05-29 | 2014-12-17 | 海洋王照明科技股份有限公司 | 共轭聚合物及其制备方法与应用 |
| CN104211916A (zh) * | 2013-05-29 | 2014-12-17 | 海洋王照明科技股份有限公司 | 共轭聚合物及其制备方法与应用 |
| CN106103538A (zh) * | 2014-03-21 | 2016-11-09 | 株式会社Lg化学 | 聚合物和包含其的有机太阳能电池 |
| US9896536B2 (en) | 2014-02-28 | 2018-02-20 | Corning Incorporated | Dihydropyrrolo[2,3-F] indole-diketopyrrolopyrrole semiconducting materials, and methods and uses thereof |
| CN114560869A (zh) * | 2022-03-07 | 2022-05-31 | 青岛农业大学 | 4-溴苯并[1,2-b:3,4-b`]二噻吩-2,7-二甲醛及其制备方法 |
| CN115558412A (zh) * | 2022-10-12 | 2023-01-03 | 深圳市华之美科技有限公司 | 一种聚酰亚胺复合材料及其制备方法和应用 |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8557987B2 (en) * | 2010-09-10 | 2013-10-15 | Ocean's King Lighting Science & Technology Co., Ltd. | Benzodithiophene organic semiconductive material and its preparation method and use |
| KR102158583B1 (ko) * | 2012-12-04 | 2020-09-23 | 주식회사 클랩 | 전자 응용을 위한 관능화 벤조디티오펜 중합체 |
| KR101676904B1 (ko) | 2013-11-04 | 2016-11-29 | 주식회사 엘지화학 | 공중합체 및 이를 포함하는 유기 태양 전지 |
| JP6419838B2 (ja) * | 2014-03-27 | 2018-11-07 | エルジー・ケム・リミテッド | 共重合体およびこれを含む有機太陽電池 |
| JP5951839B1 (ja) | 2015-03-24 | 2016-07-13 | 株式会社東芝 | ポリマーとそれを用いた太陽電池 |
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| CN101415715A (zh) * | 2006-03-10 | 2009-04-22 | 住友化学株式会社 | 稠环化合物及其制造方法、聚合物、含有它们的有机薄膜以及具备该有机薄膜的有机薄膜元件及有机薄膜晶体管 |
| WO2009101982A1 (ja) * | 2008-02-13 | 2009-08-20 | Osaka University | 縮合環化合物及びその製造方法、重合体、これらを含む有機薄膜、並びに、これを備える有機薄膜素子及び有機薄膜トランジスタ |
| WO2009105041A1 (en) * | 2008-02-21 | 2009-08-27 | Nanyang Technological University | Dithienothiophene derivatives |
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| JPH0794538B2 (ja) * | 1986-11-11 | 1995-10-11 | 株式会社リコー | 新規な重合体およびその製造方法 |
| US5198153A (en) | 1989-05-26 | 1993-03-30 | International Business Machines Corporation | Electrically conductive polymeric |
| JP3224829B2 (ja) | 1991-08-15 | 2001-11-05 | 株式会社東芝 | 有機電界効果型素子 |
| JPH07188399A (ja) * | 1993-12-27 | 1995-07-25 | Unitika Ltd | 光照射部が導電性に変化する成形性またはフィルム形成性組成物 |
| WO1996021659A1 (en) | 1995-01-10 | 1996-07-18 | University Of Technology, Sydney | Organic semiconductor |
| JP3898063B2 (ja) * | 2002-02-01 | 2007-03-28 | 凸版印刷株式会社 | 有機発光材料 |
| JP4889085B2 (ja) * | 2005-10-07 | 2012-02-29 | 株式会社リコー | ベンゾジチオフェン化合物 |
| JP4712514B2 (ja) * | 2005-10-19 | 2011-06-29 | 株式会社リコー | ベンゾジチオフェン重合体 |
-
2011
- 2011-03-29 JP JP2013501804A patent/JP2013523931A/ja active Pending
- 2011-03-29 EP EP11710512A patent/EP2553743A1/en not_active Withdrawn
- 2011-03-29 CN CN2011800173715A patent/CN102834945A/zh active Pending
- 2011-03-29 KR KR1020127027110A patent/KR20130040830A/ko not_active Application Discontinuation
- 2011-03-29 WO PCT/EP2011/054787 patent/WO2011120951A1/en active Application Filing
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN101415715A (zh) * | 2006-03-10 | 2009-04-22 | 住友化学株式会社 | 稠环化合物及其制造方法、聚合物、含有它们的有机薄膜以及具备该有机薄膜的有机薄膜元件及有机薄膜晶体管 |
| WO2009101982A1 (ja) * | 2008-02-13 | 2009-08-20 | Osaka University | 縮合環化合物及びその製造方法、重合体、これらを含む有機薄膜、並びに、これを備える有機薄膜素子及び有機薄膜トランジスタ |
| WO2009105041A1 (en) * | 2008-02-21 | 2009-08-27 | Nanyang Technological University | Dithienothiophene derivatives |
| WO2010000669A1 (en) * | 2008-07-02 | 2010-01-07 | Basf Se | Poly(5,5'bis(thiophen-2-yl)-benzo[2,1-b;3,4-b']dithiophene) and its use as high performance solution processable semiconducting polymer |
Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104098592B (zh) * | 2013-04-12 | 2018-11-09 | 艾尼股份公司 | 由苯并二噻吩基团二取代的苯并杂二唑化合物的制备方法 |
| CN104098592A (zh) * | 2013-04-12 | 2014-10-15 | 艾尼股份公司 | 由苯并二噻吩基团二取代的苯并杂二唑化合物的制备方法 |
| CN104119504A (zh) * | 2013-04-25 | 2014-10-29 | 海洋王照明科技股份有限公司 | 含吡咯吲哚并二噻吩-二噻吩并苯并噻二唑共轭聚合物材料及其制备方法和应用 |
| CN104211922A (zh) * | 2013-05-29 | 2014-12-17 | 海洋王照明科技股份有限公司 | 共轭聚合物及其制备方法与应用 |
| CN104211923A (zh) * | 2013-05-29 | 2014-12-17 | 海洋王照明科技股份有限公司 | 共轭聚合物及其制备方法与应用 |
| CN104211916A (zh) * | 2013-05-29 | 2014-12-17 | 海洋王照明科技股份有限公司 | 共轭聚合物及其制备方法与应用 |
| CN103483560B (zh) * | 2013-09-17 | 2015-12-02 | 武汉工程大学 | 一种2,1,3-苯并噻二唑并二噻吩衍生溴代物与咔唑的共轭聚合物及其合成方法 |
| CN103483560A (zh) * | 2013-09-17 | 2014-01-01 | 武汉工程大学 | 一种2,1,3-苯并噻二唑并二噻吩衍生溴代物与咔唑的共轭聚合物及其合成方法 |
| US9896536B2 (en) | 2014-02-28 | 2018-02-20 | Corning Incorporated | Dihydropyrrolo[2,3-F] indole-diketopyrrolopyrrole semiconducting materials, and methods and uses thereof |
| US10100143B2 (en) | 2014-02-28 | 2018-10-16 | Corning Incorporated | Dihydropyrrolo[2,3-F]indole-diketopyrrolopyrrole semiconducting materials, and methods and uses thereof |
| US10144800B2 (en) | 2014-02-28 | 2018-12-04 | Corning Incorporated | Dihydropyrrolo[2,3-F] indole-diketopyrrolopyrrole semiconducting materials, and methods and uses thereof |
| CN106103538A (zh) * | 2014-03-21 | 2016-11-09 | 株式会社Lg化学 | 聚合物和包含其的有机太阳能电池 |
| CN106103538B (zh) * | 2014-03-21 | 2018-09-25 | 株式会社Lg化学 | 聚合物和包含其的有机太阳能电池 |
| CN114560869A (zh) * | 2022-03-07 | 2022-05-31 | 青岛农业大学 | 4-溴苯并[1,2-b:3,4-b`]二噻吩-2,7-二甲醛及其制备方法 |
| CN115558412A (zh) * | 2022-10-12 | 2023-01-03 | 深圳市华之美科技有限公司 | 一种聚酰亚胺复合材料及其制备方法和应用 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP2553743A1 (en) | 2013-02-06 |
| JP2013523931A (ja) | 2013-06-17 |
| WO2011120951A1 (en) | 2011-10-06 |
| KR20130040830A (ko) | 2013-04-24 |
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