JP2013503236A - ポリマー半導体、デバイス、および関連する方法 - Google Patents
ポリマー半導体、デバイス、および関連する方法 Download PDFInfo
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- JP2013503236A JP2013503236A JP2012526691A JP2012526691A JP2013503236A JP 2013503236 A JP2013503236 A JP 2013503236A JP 2012526691 A JP2012526691 A JP 2012526691A JP 2012526691 A JP2012526691 A JP 2012526691A JP 2013503236 A JP2013503236 A JP 2013503236A
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- 229920000642 polymer Polymers 0.000 title claims abstract description 252
- 239000004065 semiconductor Substances 0.000 title claims abstract description 38
- 238000000034 method Methods 0.000 title claims description 35
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 31
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 10
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 6
- 229910052711 selenium Inorganic materials 0.000 claims abstract description 5
- 239000000758 substrate Substances 0.000 claims description 38
- 239000000203 mixture Substances 0.000 claims description 37
- 239000010409 thin film Substances 0.000 claims description 23
- 125000004429 atom Chemical group 0.000 claims description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 239000007787 solid Substances 0.000 claims description 8
- 125000000304 alkynyl group Chemical group 0.000 claims description 7
- 150000001412 amines Chemical class 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
- 150000001408 amides Chemical class 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 5
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 claims description 5
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 5
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 5
- 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 claims description 3
- 238000001035 drying Methods 0.000 claims description 3
- UUIQMZJEGPQKFD-UHFFFAOYSA-N Methyl butyrate Chemical compound CCCC(=O)OC UUIQMZJEGPQKFD-UHFFFAOYSA-N 0.000 claims 1
- 239000010410 layer Substances 0.000 description 72
- 239000000243 solution Substances 0.000 description 50
- 239000000523 sample Substances 0.000 description 46
- -1 carbonate ester Chemical class 0.000 description 40
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 39
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- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 26
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- 239000000463 material Substances 0.000 description 23
- 238000013086 organic photovoltaic Methods 0.000 description 19
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- 230000015572 biosynthetic process Effects 0.000 description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- 239000000178 monomer Substances 0.000 description 15
- 238000003786 synthesis reaction Methods 0.000 description 15
- 230000008569 process Effects 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 229910004298 SiO 2 Inorganic materials 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- 238000004770 highest occupied molecular orbital Methods 0.000 description 10
- 229920000301 poly(3-hexylthiophene-2,5-diyl) polymer Polymers 0.000 description 10
- 238000007639 printing Methods 0.000 description 10
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 8
- 239000010408 film Substances 0.000 description 8
- 238000005259 measurement Methods 0.000 description 8
- 238000005859 coupling reaction Methods 0.000 description 7
- 239000012467 final product Substances 0.000 description 7
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- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 125000001424 substituent group Chemical group 0.000 description 7
- RCHUVCPBWWSUMC-UHFFFAOYSA-N trichloro(octyl)silane Chemical compound CCCCCCCC[Si](Cl)(Cl)Cl RCHUVCPBWWSUMC-UHFFFAOYSA-N 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- 239000012043 crude product Substances 0.000 description 6
- 230000005669 field effect Effects 0.000 description 6
- 125000001072 heteroaryl group Chemical group 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 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 6
- 238000000137 annealing Methods 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 239000002094 self assembled monolayer Substances 0.000 description 5
- 239000013545 self-assembled monolayer Substances 0.000 description 5
- 238000010898 silica gel chromatography Methods 0.000 description 5
- 229910052710 silicon Inorganic materials 0.000 description 5
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 4
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidine Chemical compound CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 238000006619 Stille reaction Methods 0.000 description 4
- 238000006069 Suzuki reaction reaction Methods 0.000 description 4
- 239000011149 active material Substances 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 239000002800 charge carrier Substances 0.000 description 4
- 238000010586 diagram Methods 0.000 description 4
- HKNRNTYTYUWGLN-UHFFFAOYSA-N dithieno[3,2-a:2',3'-d]thiophene Chemical group C1=CSC2=C1SC1=C2C=CS1 HKNRNTYTYUWGLN-UHFFFAOYSA-N 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
- 229910052736 halogen Inorganic materials 0.000 description 4
- 239000012528 membrane Substances 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 239000004417 polycarbonate Substances 0.000 description 4
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 238000007650 screen-printing Methods 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000002411 thermogravimetry Methods 0.000 description 4
- 125000005556 thienylene group Chemical group 0.000 description 4
- 235000012431 wafers Nutrition 0.000 description 4
- 0 *c1c[s]c(-c2cc(*)c[s]2)c1 Chemical compound *c1c[s]c(-c2cc(*)c[s]2)c1 0.000 description 3
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- 229920000144 PEDOT:PSS Polymers 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-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
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- 229940117389 dichlorobenzene Drugs 0.000 description 3
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- 229910052740 iodine Inorganic materials 0.000 description 3
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- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- INHYKPMJJAWZKY-UHFFFAOYSA-N trimethyl-[5-[4-(5-trimethylstannylthiophen-2-yl)-2,1,3-benzothiadiazol-7-yl]thiophen-2-yl]stannane Chemical compound S1C([Sn](C)(C)C)=CC=C1C(C1=NSN=C11)=CC=C1C1=CC=C([Sn](C)(C)C)S1 INHYKPMJJAWZKY-UHFFFAOYSA-N 0.000 description 3
- FNQJDLTXOVEEFB-UHFFFAOYSA-N 1,2,3-benzothiadiazole Chemical compound C1=CC=C2SN=NC2=C1 FNQJDLTXOVEEFB-UHFFFAOYSA-N 0.000 description 2
- ISPCSVXTQFYEQM-UHFFFAOYSA-N 2-bromo-5-[5-bromo-4-(2-octyldodecyl)thiophen-2-yl]-3-(2-octyldodecyl)thiophene Chemical compound S1C(Br)=C(CC(CCCCCCCC)CCCCCCCCCC)C=C1C1=CC(CC(CCCCCCCC)CCCCCCCCCC)=C(Br)S1 ISPCSVXTQFYEQM-UHFFFAOYSA-N 0.000 description 2
- JESXATFQYMPTNL-UHFFFAOYSA-N 2-ethenylphenol Chemical compound OC1=CC=CC=C1C=C JESXATFQYMPTNL-UHFFFAOYSA-N 0.000 description 2
- CRKVMRJSMBQYRV-UHFFFAOYSA-N 3-(2-octyldodecyl)thiophene Chemical compound CCCCCCCCCCC(CCCCCCCC)CC=1C=CSC=1 CRKVMRJSMBQYRV-UHFFFAOYSA-N 0.000 description 2
- 101710134784 Agnoprotein Proteins 0.000 description 2
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- 230000008901 benefit Effects 0.000 description 2
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- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
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- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
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- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
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- 125000003229 2-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
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- XCMISAPCWHTVNG-UHFFFAOYSA-N 3-bromothiophene Chemical compound BrC=1C=CSC=1 XCMISAPCWHTVNG-UHFFFAOYSA-N 0.000 description 1
- DHWADSHFLSDMBJ-UHFFFAOYSA-N 4,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,1,3-benzothiadiazole Chemical compound O1C(C)(C)C(C)(C)OB1C(C1=NSN=C11)=CC=C1B1OC(C)(C)C(C)(C)O1 DHWADSHFLSDMBJ-UHFFFAOYSA-N 0.000 description 1
- XGERJWSXTKVPSV-UHFFFAOYSA-N 4,7-dithiophen-2-yl-2,1,3-benzothiadiazole Chemical compound C1=CSC(C=2C3=NSN=C3C(C=3SC=CC=3)=CC=2)=C1 XGERJWSXTKVPSV-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
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Images
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- 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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- B82Y10/00—Nanotechnology for information processing, storage or transmission, e.g. quantum computing or single electron logic
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- 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
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- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
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- C07D285/14—Thiadiazoles; Hydrogenated thiadiazoles condensed with carbocyclic rings or ring systems
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- C—CHEMISTRY; METALLURGY
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- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/08—Hydrogen atoms or radicals containing only hydrogen and carbon atoms
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- C—CHEMISTRY; METALLURGY
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- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
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- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
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- 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
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- 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
- C08G61/126—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 sulfur atom in the ring
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- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
- H01B1/06—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances
- H01B1/12—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances organic substances
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- H—ELECTRICITY
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- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L29/00—Semiconductor devices specially adapted for rectifying, amplifying, oscillating or switching and having potential barriers; Capacitors or resistors having potential barriers, e.g. a PN-junction depletion layer or carrier concentration layer; Details of semiconductor bodies or of electrodes thereof ; Multistep manufacturing processes therefor
- H01L29/66—Types of semiconductor device ; Multistep manufacturing processes therefor
- H01L29/68—Types of semiconductor device ; Multistep manufacturing processes therefor controllable by only the electric current supplied, or only the electric potential applied, to an electrode which does not carry the current to be rectified, amplified or switched
- H01L29/76—Unipolar devices, e.g. field effect transistors
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Abstract
Description
本出願は、2009年8月28日出願の米国特許仮出願第61/272,182号の恩典および優先権を主張し、その内容全体が参照により本明細書に組み入れられる。
本発明は、全体として半導体材料に関し、具体的には、ポリマー半導体、そのようなポリマー半導体を包含するデバイス、および関連する方法に関する。
位置規則的なポリ(3-ヘキシルチオフェン)(P3HT)またはポリ(クアテルチオフェン)(PQT)は、有機薄膜トランジスタ(OTFT)または有機光(OPV)電池における半導体として使用されている。位置規則的なP3HTまたはPQTは、スピンコーティングで塗布される場合に0.1〜0.2cm2/Vsだが、溶液を用いた印刷プロセスで塗布される場合ではこれよりも著しく低い電荷移動度を示す。さらに、P3HTは約1.9eVという幅広いバンドギャップを有する。より幅広いバンドギャップによって、より高い波長の光の吸光度が限定され、したがって太陽光の電力変換効率(PCE)が限定される。例えば計算により、1.9eVのバンドキャップでは波長650nmの光のわずか約22%しか吸収できないことが示されている。P3HTをベースにしたデバイスのPCEがわずか最大5%であることが報告されている(Ma, W. L. et al., "Thermally stable, efficient polymer solar cells with nanoscale control of the interpenetrating network morphology," Adv. Funct. Mater., 2005, vol. 15, p. 1617(非特許文献1)参照)。ポリマーバンドギャップを狭くすることは、吸収される太陽光の量を増大させることはできるが、OPV電池の等価開回路電圧を減少させることもあることから、電力変換効率を必ずしも改善するわけではない。これは、狭くなったバンドギャップからの利得を相殺する、電力変換効率の減少を招くことがある。公知の低バンドギャップポリマーOPV材料をベースとするデバイスについて報告されるPCEはわずか最大7.73%である(Hsiang-Yu Chen et. al., "Polymer solar cells with enhanced open-circuit voltage and efficiency," Nature Photonics, 2009, vol. 3, pp. 649-653(非特許文献2)参照)。
式中、a、b、c、dおよびnは整数であり、aは0〜3であり、bは1〜5であり、cは1〜3であり、dは1〜5であり、nは2〜5000であり;かつR1は第一の側鎖であり;R2は第二の側鎖であり;R3はHまたは第三の側鎖であり;R4はHまたは第四の側鎖であり; かつここで、aが0である場合、R3およびR4は側鎖である。側鎖の少なくとも1つは6〜30個の骨格原子、または8〜20個の骨格原子、例えば12個の骨格原子を有し得る。ポリマーは2,000〜1,000,000g/mol、例えば5,000〜500,000g/molの数平均分子量(Mn)を有し得る。側鎖の少なくとも1つはアルキル、シロキシ、アルケニル、アルキニル、アミン、エーテル、カルボニル、エステル、アミド、スルホニルまたはスルフィニルを含み得る。アルキルは1〜30個の炭素原子、例えば6〜20個の炭素原子、または12〜20個の炭素原子を有し得る。数nは5〜1,000であり得る。数aは1〜3、または0であり得る。R3およびR4はいずれもHであり得る。
式中、a、b、c、d、eおよびnは整数であり、aは1〜3であり、bおよびcはそれぞれ独立して0または1であり、dおよびeはそれぞれ独立して1または2であり、かつnは2〜5000であり;R1は-COOアルキルを除く第一の側鎖であり;R2は-COOアルキルを除く第二の側鎖であり; かつX1、X2およびX3はそれぞれ独立してO、SまたはSeである。側鎖の少なくとも1つは6〜30個の骨格原子、例えば8〜20個の骨格原子を有し得る。ポリマーは2,000〜1,000,000g/mol、例えば5,000〜500,000g/molの数平均分子量(Mn)を有し得る。数nは5〜1,000、例えば10〜1,000であり得る。側鎖の少なくとも1つはアルキル、シロキシ、アルケニル、アルキニル、アミン、エーテル、カルボニル、アミド、スルホニルまたはスルフィニルを含み得る。アルキルは1〜30個の炭素原子を有し得る。X1、X2およびX3はそれぞれSであり得る。
本発明の第一の例示的な態様は、本明細書において式(I)と呼ぶ、図1Aに示される式で表されるポリマー鎖を含むポリマーに関する。
ISD=μCi(VG-VT)2(W/2L)
式中、ISDはドレイン電流であり、Ciはゲート誘電体層の単位面積当たりのキャパシタンスであり(SiO2、200nm、Ci=17.25nF/cm2)、かつVGおよびVTはそれぞれゲート電圧および閾値電圧である。VTは、飽和領域におけるISDの平方根とVGとの間の関係から、測定データをISD=0に外挿することで導出した。WおよびLはそれぞれチャネルの幅および長さである。Iオン/Iオフは、ゲート電圧VGがドレイン電圧VDと等しいかまたはそれより大きい場合の飽和ソース・ドレイン電流の、ゲート電圧VGがゼロである場合のソース・ドレイン電流に対する比である。
式中、P光は、その内容全体が参照により本明細書に組み入れられる、例えばChristoph Winder and Niyazi Serdar Sariciftci, "Low bandgap polymers for photon harvesting in bulk heterojunction solar cells," J. Mater. Chem., 2004, vol. 14, pp. 1077-1086に記載の通り、照射光の電力強度である(AM 1.5グローバル、100mW/cm2)。一般に、Vocは、活性材料中の供与体のHOMOエネルギーレベルおよび受容体のLUMOエネルギーレベルに依存し、Jscは、活性層、および供与体受容体界面において発生する電荷担体の光子吸収、ならびに電極における電荷収集効率に依存する。したがって、本明細書に記載の低バンドギャップポリマーは、強化された光吸収による増大した光電流を提供することができる。本明細書に記載の低バンドギャップポリマーは、より高いVoc、より高いJsc、およびより良いFF、したがってより高いPCEを示し得る。
マグネシウムの削り物1.3g(54mmol)、触媒量のヨウ素および乾燥THF 50mLをフラスコ中で混合し、窒素下で加熱してわずかに還流させた。2-オクチルドデシルブロミド(18.1g、50mmol)および乾燥THF 25mLの溶液を混合物中に滴下により添加した。次に混合物を3時間還流させた。得られた灰色溶液を室温に冷却した後、乾燥滴下漏斗に移し、3-ブロモチオフェン(6.5g、40mmol)およびNi(dppp)Cl2 (160mg、1.2mmol)の乾燥THF溶液に0℃で滴下により添加した。混合物を窒素雰囲気下で終夜加熱還流させた。次に混合物を冷却し、希塩酸水溶液を加えて過剰のグリニャール試薬を反応停止させた。粗生成物を混合物からヘキサンで抽出し、水で洗浄し、ヘキサンで溶出するシリカゲルクロマトグラフィーで精製した。最終生成物は無色油状物7.2g (49%)であった。生成物は、
によって特性決定された。
3-(2-オクチルドデシル)チオフェン(4.90g、13.2mmol)のDMF 300溶液にN-ブロモスクシンイミド(2.58g、14.5mmol)のジメチルホルムアミド(DMF)100mL溶液を-20℃で滴下により添加した。混合物を室温で終夜攪拌した。次にDMFを真空下で除去し、水100mLを加えた。混合物をヘキサンで3回抽出し、有機層を収集した。ヘキサンの除去後、粗生成物を得てカラムにより精製し、無色油状物の形態の最終生成物5.60g(96%)を得た。
2-ブロモ-3-(2-オクチルドデシル)チオフェン(5.32g、12mmol)、PdCl2(PhCN)2(46.5mg、0.12mmol)、フッ化カリウム(1.39mg、24mmol)およびジメチルスルホキシド(DMSO)(60mL)、AgNO3(4.06g、24mmol)を100mLシュレンク管に一度に加えた。得られた混合物を120℃で3時間攪拌した。次にさらなるフッ化カリウム(1.39mg、24mmol)およびAgNO3(4.06g、24mmol)を混合物に加え、混合物を120℃で8時間攪拌した。次に反応混合物を冷却し、セライトパッドに通して黒色固形分を除去した。得られたケーキを酢酸エチルで繰り返し洗浄した。濾液を水で洗浄し、無水硫酸マグネシウムで乾燥させ、減圧下で濃縮して粗生成物を得た。粗生成物をシリカゲルクロマトグラフィーで精製して最終生成物の淡黄色油状物2.54g(48%)を生成した。
20mLマイクロ波バイアルに2-(トリブチルスタニル)チオフェン(1.03g、2.77mmol)、5,5'-ジブロモ-4,4'-ビス(2-オクチルドデシル)-2,2'-ビチオフェン(1.11g、1.26mmol)、Pd(PPh3)4(160mg、0.14mmol)およびDMF 15mLを装入した。バイアルをマイクロ波反応器中、180℃で20分間加熱した。反応が完了した後、混合物を水に注ぎ、混合物を3回抽出した。一緒にした有機画分を水、ブラインで順次洗浄した後、硫酸ナトリウムで乾燥させた。溶媒除去後、ヘキサンを溶離液とするシリカゲルクロマトグラフィーで残渣を精製して最終生成物0.84g(黄色油状物、75%)を生成した。
3',4''-ビス(2-オクチルドデシル)-2,2':5',2'':5'',2'''-クアテルチオフェン(840mg、0.94mmol)のDMF(150mL)およびクロロホルム(30mL)溶液にN-ブロモスクシンイミド(351mg、1.97mmol)のDMF 30mL溶液を-20℃で滴下により添加した。混合物を室温で終夜攪拌した。DMFを真空下で除去し、水100mLを混合物に加えた。混合物をヘキサンで3回抽出し、一緒にした有機層を無水MgSO4で乾燥させた。ヘキサンの除去後、粗生成物をシリカゲルカラムクロマトグラフィーで精製して最終生成物986mg(黄色油状物、98%)を得た。
2,6-ビス-トリメチルスタニル-ジチエノ[3,2-b;2',3'-d]チオフェン(96mg、0.184mmol、1当量)、5,5'''-ジブロモ-3',4''-ジ(2-オクチルドデシル)-[2,2';5',2'';5'',2''']クアテルチオフェン(193mg、0.184mmol、1当量)、トリ(o-トリル)ホスフィン(4.5mg、14.7μmol、8mol%当量)、トリス(ジベンジリデンアセトン)ジパラジウム(3.4mg、3.68μmol、2mol%当量)および乾燥クロロベンゼン(20ml)を窒素下でシュレンクフラスコに加えた。フラスコをしっかり封止し、120℃で72時間攪拌した。室温に冷却後、反応混合物をメタノール(200ml)と濃塩酸(15ml)との混合物中に析出させ、混合物を16時間攪拌した。析出物を収集し、エタノール、ヘキサンおよびクロロホルムでそれぞれ48時間、順次ソックスレー抽出した。残りの固体をクロロベンゼンに溶解させ、メタノール溶液中に析出させた。収集した固体を真空下で乾燥させた。この手順によるバルク生成物収率は40%であった。
図4に示す試料OFET(OTFT)を上記の通りに製造した。ゲート層用の基板は、200nmのSiO2 (ゲート誘電体)を上側とするn+-Siまたはp+Siとした。スピンコーティング技術によって有機薄膜(35〜40nm)をSiO2上に成長させた。シャドウマスクを使用して約100nm厚のAu層を薄膜上に堆積させてソース接点およびドレイン接点を形成した。
ISD=μCi(VG-VT)2(W/2L)
式中、ISDはドレイン電流であり、μは電界効果移動度であり、Ciはゲート誘電体層の単位面積当たりのキャパシタンスであり(SiO2、200nm、Ci=17.25nF/cm2)、かつVGおよびVTはそれぞれゲート電圧および閾値電圧である。VTは、飽和領域におけるISDの平方根とVGとの間の関係から、測定データをISD=0に外挿することで導出した。WおよびLはそれぞれチャネルの幅および長さである。Iオン/Iオフは、ゲート電圧VGがドレイン電圧VDと等しいかまたはそれより大きい場合の飽和ソース・ドレイン電流の、ゲート電圧VGがゼロである場合のソース・ドレイン電流に対する比である。
4,7-ジブロモ-2,1,3-ベンゾチアジアゾール(2.94g、10mmol)、ビス(ピナコラト)ジボロン(5.59g、22mmol)、PdCl2(dppf)(490mg、0.6mmol)およびKOAc(2.95g、30mmol)の脱気した1,4-ジオキサン(30mL)中の混合物を80℃で6時間攪拌した。冷却混合物を水で反応停止させ、酢酸エチルで抽出した。有機層を収集し、ブラインで洗浄し、硫酸ナトリウムで乾燥させた。溶媒を除去し、ヘキサン/酢酸エチル勾配で溶出するシリカゲルカラムクロマトグラフィーで残渣を精製して、カーキ色粉末である最終生成物(1.71g、44%)を生成した。
2,2,6,6-テトラメチルピペリジン(TMP)(0.55g、4mmol)の乾燥THF(25mL)の機械攪拌溶液をアルゴン下で-78℃に冷却した。次に、n-ブチルリチウム(3.9mmol)を速やかに溶液に加えた。得られた溶液を室温に昇温した。それを室温に10分間保持し、続いて-78℃に再度冷却した。次に、4,7-ビス(2-チエニル)-2,1,3-ベンゾチアジアゾールの乾燥THF 5mL溶液を冷却溶液に滴下により添加した。得られた溶液は濃紫色を有しており、-78℃で30分間攪拌した。次に塩化トリメチルスズのヘキサン中1M溶液(3.9mL)を加えた。反応混合物を室温に昇温し、終夜攪拌した。水を加えて反応液を反応停止させた。ジエチルエーテルを加え、混合物を0.1M HClで3回洗浄してTMPを除去した。次に溶液をMgSO4で乾燥させた。溶媒を除去し、最終生成物(0.42g、45%)をエタノール中で再結晶させて橙色針状物を得た。
本実施例では図6の合成経路1に従った。
本実施例では図6の合成経路2に従った。
本実施例で使用した合成経路を図7に示す。5,5'-ジブロモ-4,4'-ジ(2-オクチルドデシル)-2,2'-ビチオフェンを5,5'''-ジブロモ-3',4''-ジ(2-オクチルドデシル)-2,2':5',2'':5'',2'''-クアテルチオフェン(190mg、0.181mmol)に置換し、4,7-ビス(2-トリメチルスタニルチエン-5-イル)-2,1,3-ベンゾチアジアゾールの添加量を113.3mg(0.181mmol)に減少させたという変更を伴う、試料ポリマーII-P1bを調製するための実施例Xの手順に従って、ポリマーII-P3を調製した。得られた黒色固体生成物がポリマーII-P3(178mg、83%)であった。
試料ポリマーII-P1aまたはII-P1bとPCBMとを混合してOPV電池および光起電力デバイスを製造した。ポリマー濃度10mg/mlで各試料ポリマーおよびPCBMをジクロロベンゼンに溶解させた(重量比=1:1、1:2、1:4)。パターン形成インジウムスズ酸化物(ITO)コーティングガラスを、ITO 160nmおよび平均シート抵抗14Ω/スクウェアの基板として使用した。ITO/ガラス基板を洗浄剤(30分)、蒸留水(10分、2回)、アセトン(15分)およびイソプロパノール(20分)中で洗浄した。次に基板を60℃でベーキングして残留溶媒を除去した。乾燥した基板を10分間の酸素プラズマ洗浄、次にポリ(3,4-エチレンジオキシチオフェン)ポリ(スチレンスルホネート)(PEDOT:PSS)正孔輸送層40nmのスピンコーティング、続いて120℃で10分間のベーキングに供した。続いて、不活性ガスグローブボックス中、回転速度500rpmで120秒間、ポリマー:PCBMブレンドを含む試料組成物をPEDOT:PSS層上にスピンコーティングした。次にシャドウマスクを通じて圧力8×10-5Paで金属陰極層(Ca/Ag)を蒸着させて、9mm2の作用面積を有するデバイスを得た。電力強度100mW/cm2での誘導AM1.5G太陽光照射下で有機太陽電池を特性決定した。
Claims (32)
- 前記側鎖の少なくとも1つが6〜30個の骨格原子を有する、請求項1記載のポリマー。
- 前記側鎖の少なくとも1つが8〜20個の骨格原子を有する、請求項1または請求項2記載のポリマー。
- 前記側鎖の少なくとも1つが12個の骨格原子を有する、請求項1〜3のいずれか一項記載のポリマー。
- 2,000〜1,000,000g/molの数平均分子量(Mn)を有する、請求項1〜4のいずれか一項記載のポリマー。
- Mnが5,000〜500,000g/molである、請求項5記載のポリマー。
- 前記側鎖の少なくとも1つが、アルキル、シロキシ、アルケニル、アルキニル、アミン、エーテル、カルボニル、エステル、アミド、スルホニルまたはスルフィニルを含む、請求項1〜6のいずれか一項記載のポリマー。
- 前記アルキルが1〜30個の炭素原子を有する、請求項7記載のポリマー。
- 前記アルキルが6〜20個の炭素原子を有する、請求項8記載のポリマー。
- 前記アルキルが12〜20個の炭素原子を有する、請求項8記載のポリマー。
- nが5〜1,000である、請求項1〜10のいずれか一項記載のポリマー。
- aが1〜3である、請求項1〜11のいずれか一項記載のポリマー。
- aが0である、請求項1〜11のいずれか一項記載のポリマー。
- R3およびR4がHである、請求項1〜11のいずれか一項記載のポリマー。
- 請求項1〜14のいずれか一項記載のポリマーを含む、半導体。
- 請求項15記載の半導体を含む、電子デバイス。
- 薄膜トランジスタを含む、請求項16記載のデバイス。
- 前記側鎖の少なくとも1つが6〜30個の骨格原子を有する、請求項18記載のポリマー。
- 前記側鎖の少なくとも1つが8〜20個の骨格原子を有する、請求項18または請求項19記載のポリマー。
- 2,000〜1,000,000g/molの数平均分子量(Mn)を有する、請求項18〜20のいずれか一項記載のポリマー。
- Mnが5,000〜500,000g/molである、請求項21記載のポリマー。
- nが5〜1,000である、請求項18〜請求項22のいずれか一項記載のポリマー。
- nが10〜1,000である、請求項18〜請求項22のいずれか一項記載のポリマー。
- 前記側鎖の少なくとも1つが、アルキル、シロキシ、アルケニル、アルキニル、アミン、エーテル、カルボニル、アミド、スルホニルまたはスルフィニルを含む、請求項18〜24のいずれか一項記載のポリマー。
- 前記アルキルが1〜30個の炭素原子を有する、請求項25記載のポリマー。
- X1、X2およびX3がそれぞれSである、請求項18〜26のいずれか一項記載のポリマー。
- 請求項18〜27のいずれか一項記載のポリマーを含む、デバイス。
- 薄膜トランジスタ、光電池、フォトダイオード、発光ダイオード、センサまたはメモリを含む、請求項28記載のデバイス。
- 前記ポリマーとm=61または71であるフェニル-Cm-酪酸メチルエステル(PCBM)との混合物で形成される層を含む前記光電池を含む、請求項29記載のデバイス。
- 前記層における前記ポリマー対前記PCBMの重量比が約2:1〜約1:5である、請求項30記載のデバイス。
- 以下の工程を含む、請求項16、17および28〜31のいずれか一項記載のデバイスを形成するための方法:
前記ポリマーを溶液に溶解させる工程;
該溶液を基板に塗布する工程; および
該溶液を乾燥させて、該ポリマーを含む固体層を形成する工程。
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JP2010018790A (ja) * | 2008-06-13 | 2010-01-28 | Sumitomo Chemical Co Ltd | 共重合体及びそれを用いた高分子発光素子 |
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JP2017503875A (ja) * | 2013-12-26 | 2017-02-02 | レイナジー テック インコーポレイション | 共役ポリマーおよびそれを組み込んでいるデバイス |
JP2019522102A (ja) * | 2016-07-19 | 2019-08-08 | フイリツプス66カンパニー | 非対称ベンゾチアジアゾールに基づくランダムコポリマー |
JP7033590B2 (ja) | 2016-07-19 | 2022-03-10 | フイリツプス66カンパニー | 非対称ベンゾチアジアゾールに基づくランダムコポリマー |
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TWI481639B (zh) | 2015-04-21 |
JP2015096607A (ja) | 2015-05-21 |
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JP5986173B2 (ja) | 2016-09-06 |
US20120156829A1 (en) | 2012-06-21 |
KR20120062847A (ko) | 2012-06-14 |
KR101867784B1 (ko) | 2018-06-15 |
WO2011025453A1 (en) | 2011-03-03 |
KR20170005518A (ko) | 2017-01-13 |
EP2470584A4 (en) | 2014-01-22 |
KR101694917B1 (ko) | 2017-01-23 |
EP2470584A1 (en) | 2012-07-04 |
TWI541267B (zh) | 2016-07-11 |
TW201522413A (zh) | 2015-06-16 |
US9627621B2 (en) | 2017-04-18 |
US20140231784A1 (en) | 2014-08-21 |
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TW201111409A (en) | 2011-04-01 |
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