CN107266680A - 晶体管及其制造方法 - Google Patents
晶体管及其制造方法 Download PDFInfo
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- CN107266680A CN107266680A CN201710437185.6A CN201710437185A CN107266680A CN 107266680 A CN107266680 A CN 107266680A CN 201710437185 A CN201710437185 A CN 201710437185A CN 107266680 A CN107266680 A CN 107266680A
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- 238000000034 method Methods 0.000 title claims abstract description 67
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 21
- 239000000203 mixture Substances 0.000 claims abstract description 181
- 229920000642 polymer Polymers 0.000 claims abstract description 139
- 239000004065 semiconductor Substances 0.000 claims abstract description 87
- 229920003026 Acene Polymers 0.000 claims abstract description 32
- 239000000853 adhesive Substances 0.000 claims abstract description 23
- 230000001070 adhesive effect Effects 0.000 claims abstract description 23
- 238000000576 coating method Methods 0.000 claims abstract description 18
- 239000011248 coating agent Substances 0.000 claims abstract description 17
- -1 oxyl Chemical group 0.000 claims description 81
- 125000003118 aryl group Chemical group 0.000 claims description 40
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 33
- 125000000217 alkyl group Chemical group 0.000 claims description 32
- 229910052740 iodine Inorganic materials 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 16
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- 238000000151 deposition Methods 0.000 claims description 6
- 238000006116 polymerization reaction Methods 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 238000003682 fluorination reaction Methods 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 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 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 288
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 172
- 239000007787 solid Substances 0.000 description 167
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 117
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 116
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 112
- 239000000463 material Substances 0.000 description 100
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 94
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 92
- 239000010410 layer Substances 0.000 description 90
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 84
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 82
- 239000000243 solution Substances 0.000 description 80
- 150000001875 compounds Chemical class 0.000 description 69
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 63
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 61
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 60
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 58
- 125000004093 cyano group Chemical group *C#N 0.000 description 50
- 239000000376 reactant Substances 0.000 description 50
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 49
- 239000000706 filtrate Substances 0.000 description 49
- 239000000178 monomer Substances 0.000 description 47
- QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 description 45
- 239000000047 product Substances 0.000 description 43
- 229920001167 Poly(triaryl amine) Polymers 0.000 description 42
- 238000005160 1H NMR spectroscopy Methods 0.000 description 41
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- 238000002360 preparation method Methods 0.000 description 40
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- 238000006467 substitution reaction Methods 0.000 description 38
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 37
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 36
- 210000002381 plasma Anatomy 0.000 description 35
- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 description 34
- 235000019439 ethyl acetate Nutrition 0.000 description 33
- 238000003756 stirring Methods 0.000 description 31
- 229910052799 carbon Inorganic materials 0.000 description 30
- 239000000377 silicon dioxide Substances 0.000 description 30
- 229910052786 argon Inorganic materials 0.000 description 29
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 29
- 239000007789 gas Substances 0.000 description 28
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 27
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 25
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 24
- 229920001577 copolymer Polymers 0.000 description 24
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 24
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 23
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 22
- 238000004528 spin coating Methods 0.000 description 22
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 20
- 239000002904 solvent Substances 0.000 description 20
- 239000000725 suspension Substances 0.000 description 20
- 210000003739 neck Anatomy 0.000 description 19
- 229910052757 nitrogen Inorganic materials 0.000 description 19
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 18
- 229910052796 boron Inorganic materials 0.000 description 18
- 150000001721 carbon Chemical group 0.000 description 18
- 229910052760 oxygen Inorganic materials 0.000 description 18
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 18
- 239000012266 salt solution Substances 0.000 description 18
- 239000012141 concentrate Substances 0.000 description 17
- 230000037230 mobility Effects 0.000 description 17
- 125000005259 triarylamine group Chemical group 0.000 description 17
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 16
- 125000004432 carbon atom Chemical group C* 0.000 description 16
- 239000010931 gold Substances 0.000 description 16
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 15
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 15
- 239000001301 oxygen Substances 0.000 description 15
- 238000005406 washing Methods 0.000 description 15
- 125000006306 4-iodophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1I 0.000 description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 14
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 14
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 14
- 239000013078 crystal Substances 0.000 description 14
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- 239000001257 hydrogen Substances 0.000 description 14
- 239000011630 iodine Substances 0.000 description 14
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- 229910052725 zinc Inorganic materials 0.000 description 14
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- 238000004140 cleaning Methods 0.000 description 13
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- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 11
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- 239000010408 film Substances 0.000 description 11
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- 235000011152 sodium sulphate Nutrition 0.000 description 11
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- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- PBAYDYUZOSNJGU-UHFFFAOYSA-N chelidonic acid Natural products OC(=O)C1=CC(=O)C=C(C(O)=O)O1 PBAYDYUZOSNJGU-UHFFFAOYSA-N 0.000 description 10
- FLLOVYUUNCVOQA-UHFFFAOYSA-N indeno[1,2-b]fluorene Chemical class C1=C2C=CC=CC2=C2C1=CC1=C3C=CC=CC3=CC1=C2 FLLOVYUUNCVOQA-UHFFFAOYSA-N 0.000 description 10
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- RXACYPFGPNTUNV-UHFFFAOYSA-N 9,9-dioctylfluorene Chemical class C1=CC=C2C(CCCCCCCC)(CCCCCCCC)C3=CC=CC=C3C2=C1 RXACYPFGPNTUNV-UHFFFAOYSA-N 0.000 description 6
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- WMKGGPCROCCUDY-PHEQNACWSA-N dibenzylideneacetone Chemical compound C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 WMKGGPCROCCUDY-PHEQNACWSA-N 0.000 description 5
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- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
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- GCUVBACNBHGZRS-UHFFFAOYSA-N cyclopenta-1,3-diene cyclopenta-2,4-dien-1-yl(diphenyl)phosphane iron(2+) Chemical compound [Fe++].c1cc[cH-]c1.c1cc[c-](c1)P(c1ccccc1)c1ccccc1 GCUVBACNBHGZRS-UHFFFAOYSA-N 0.000 description 4
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 4
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- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 4
- 230000005611 electricity Effects 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
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- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 4
- 125000002347 octyl 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])[H] 0.000 description 4
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- 235000011056 potassium acetate Nutrition 0.000 description 4
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- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- MUJIDPITZJWBSW-UHFFFAOYSA-N palladium(2+) Chemical compound [Pd+2] MUJIDPITZJWBSW-UHFFFAOYSA-N 0.000 description 1
- JQQSUOJIMKJQHS-UHFFFAOYSA-N pentaphene Chemical compound C1=CC=C2C=C3C4=CC5=CC=CC=C5C=C4C=CC3=CC2=C1 JQQSUOJIMKJQHS-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920005547 polycyclic aromatic hydrocarbon Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920006389 polyphenyl polymer Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000012925 reference material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 238000007650 screen-printing 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
- 239000002094 self assembled monolayer Substances 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical class [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 235000015096 spirit Nutrition 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 229910052714 tellurium Inorganic materials 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M thiocyanate group Chemical group [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
- 150000003613 toluenes Chemical class 0.000 description 1
- BWHOZHOGCMHOBV-BQYQJAHWSA-N trans-benzylideneacetone Chemical compound CC(=O)\C=C\C1=CC=CC=C1 BWHOZHOGCMHOBV-BQYQJAHWSA-N 0.000 description 1
- 238000010023 transfer printing Methods 0.000 description 1
- FMYXZXAKZWIOHO-UHFFFAOYSA-N trichloro(2-phenylethyl)silane Chemical class Cl[Si](Cl)(Cl)CCC1=CC=CC=C1 FMYXZXAKZWIOHO-UHFFFAOYSA-N 0.000 description 1
- 125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- 238000000825 ultraviolet detection Methods 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
- C08L79/02—Polyamines
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- 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
- H01B1/121—Charge-transfer complexes
-
- 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
-
- 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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/02—Polyamines
- C08G73/026—Wholly aromatic polyamines
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D179/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen, with or without oxygen, or carbon only, not provided for in groups C09D161/00 - C09D177/00
- C09D179/02—Polyamines
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/24—Electrically-conducting paints
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
- H10K10/40—Organic transistors
- H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
- H10K10/462—Insulated gate field-effect transistors [IGFETs]
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
- H10K10/40—Organic transistors
- H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
- H10K10/462—Insulated gate field-effect transistors [IGFETs]
- H10K10/466—Lateral bottom-gate IGFETs comprising only a single gate
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
- H10K10/40—Organic transistors
- H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
- H10K10/462—Insulated gate field-effect transistors [IGFETs]
- H10K10/484—Insulated gate field-effect transistors [IGFETs] characterised by the channel regions
- H10K10/488—Insulated gate field-effect transistors [IGFETs] characterised by the channel regions the channel region comprising a layer of composite material having interpenetrating or embedded materials, e.g. a mixture of donor and acceptor moieties, that form a bulk heterojunction
-
- 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
- H10K85/115—Polyfluorene; Derivatives thereof
-
- 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
-
- 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
- H10K85/40—Organosilicon compounds, e.g. TIPS pentacene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
- H10K10/40—Organic transistors
- H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
- H10K10/462—Insulated gate field-effect transistors [IGFETs]
- H10K10/464—Lateral top-gate IGFETs comprising only a single gate
Landscapes
- Chemical & Material Sciences (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Wood Science & Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Polymers & Plastics (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Composite Materials (AREA)
- Thin Film Transistor (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
Abstract
Description
Claims (16)
Applications Claiming Priority (9)
Application Number | Priority Date | Filing Date | Title |
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GB1108864.8 | 2011-05-26 | ||
GBGB1108864.8A GB201108864D0 (en) | 2011-05-26 | 2011-05-26 | Transistors and methods of making them |
GBGB1118867.9A GB201118867D0 (en) | 2011-05-26 | 2011-11-01 | Transistors and methods for making them |
GB1118867.9 | 2011-11-01 | ||
GB1120997.0 | 2011-12-07 | ||
GBGB1120997.0A GB201120997D0 (en) | 2011-05-26 | 2011-12-07 | Transistors and methods for making them |
GB1205022.5 | 2012-03-22 | ||
GBGB1205022.5A GB201205022D0 (en) | 2011-05-26 | 2012-03-22 | Transistors and methods for making them |
CN201280025694.3A CN103703581B (zh) | 2011-05-26 | 2012-05-24 | 晶体管及其制造方法 |
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Application Number | Title | Priority Date | Filing Date |
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CN201280025694.3A Division CN103703581B (zh) | 2011-05-26 | 2012-05-24 | 晶体管及其制造方法 |
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CN107266680A true CN107266680A (zh) | 2017-10-20 |
CN107266680B CN107266680B (zh) | 2021-01-15 |
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Application Number | Title | Priority Date | Filing Date |
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CN201280025694.3A Active CN103703581B (zh) | 2011-05-26 | 2012-05-24 | 晶体管及其制造方法 |
CN201710437185.6A Active CN107266680B (zh) | 2011-05-26 | 2012-05-24 | 晶体管及其制造方法 |
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CN201280025694.3A Active CN103703581B (zh) | 2011-05-26 | 2012-05-24 | 晶体管及其制造方法 |
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US (2) | US9431145B2 (zh) |
EP (1) | EP2715820B1 (zh) |
JP (1) | JP6005147B2 (zh) |
KR (1) | KR101987209B1 (zh) |
CN (2) | CN103703581B (zh) |
GB (4) | GB201108864D0 (zh) |
HK (1) | HK1245309A1 (zh) |
TW (1) | TWI551624B (zh) |
WO (1) | WO2012160383A1 (zh) |
Families Citing this family (23)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB201108865D0 (en) | 2011-05-26 | 2011-07-06 | Ct For Process Innovation The Ltd | Semiconductor compounds |
GB201108864D0 (en) | 2011-05-26 | 2011-07-06 | Ct For Process Innovation The Ltd | Transistors and methods of making them |
GB2491810B (en) * | 2011-05-31 | 2018-03-21 | Smartkem Ltd | Organic semiconductor compositions |
GB201203159D0 (en) * | 2012-02-23 | 2012-04-11 | Smartkem Ltd | Organic semiconductor compositions |
CN105493303B (zh) * | 2013-08-28 | 2019-02-22 | 斯马特凯姆有限公司 | 聚合物有机半导体组合物 |
EP2846371A1 (en) | 2013-09-10 | 2015-03-11 | Ecole Polytechnique Fédérale de Lausanne (EPFL) | Inverted solar cell and process for producing the same |
EP2989108A1 (en) | 2014-04-29 | 2016-03-02 | SABIC Global Technologies B.V. | Synthesis of new small molecules/oligomers with high conductivity and absorption for optoelectronic application |
EP3032599A1 (en) | 2014-12-12 | 2016-06-15 | Solvay SA | Organic semiconductor composition |
JP2016162961A (ja) * | 2015-03-04 | 2016-09-05 | 東ソー株式会社 | 有機半導体層形成用溶液、有機半導体層、および有機薄膜トランジスタ |
JP2017098489A (ja) * | 2015-11-27 | 2017-06-01 | 東ソー株式会社 | 有機半導体層形成用溶液、有機半導体層、および有機薄膜トランジスタ |
US11258017B2 (en) | 2016-04-27 | 2022-02-22 | Wuhan Xinqu Chuangrou Optoelectronics Technology Co., Ltd | Semiconducting compositions comprising semiconducting polymers |
EP3257849A1 (en) * | 2016-06-14 | 2017-12-20 | Solvay SA | Organic semiconductor composition and semiconducting layer obtained therefrom |
CN106252362B (zh) * | 2016-08-31 | 2019-07-12 | 深圳市华星光电技术有限公司 | 一种阵列基板及其制备方法 |
GB201810710D0 (en) | 2018-06-29 | 2018-08-15 | Smartkem Ltd | Sputter Protective Layer For Organic Electronic Devices |
CN111416039A (zh) | 2019-01-07 | 2020-07-14 | 纽多维有限公司 | 制剂和层 |
CN111808269A (zh) * | 2019-04-12 | 2020-10-23 | 纽多维有限公司 | 新型聚三芳基胺及其用途 |
CN111808270A (zh) * | 2019-04-12 | 2020-10-23 | 纽多维有限公司 | 半导体组合物及其应用 |
GB201919031D0 (en) | 2019-12-20 | 2020-02-05 | Smartkem Ltd | Sputter protective layer for organic electronic devices |
EP4130103A4 (en) * | 2020-03-30 | 2023-10-18 | Teijin Limited | POLYMER WITH EXCELLENT COMPATIBILITY WITH THERMOPLASTIC RESIN |
CN113372536A (zh) * | 2020-04-21 | 2021-09-10 | 杭州领挚科技有限公司 | 三芳胺聚合物及其制备方法与应用 |
CN113321792A (zh) * | 2020-04-21 | 2021-08-31 | 杭州领挚科技有限公司 | 三芳胺聚合物及其应用 |
GB202017982D0 (en) | 2020-11-16 | 2020-12-30 | Smartkem Ltd | Organic thin film transistor |
GB202209042D0 (en) | 2022-06-20 | 2022-08-10 | Smartkem Ltd | An integrated circuit for a flat-panel display |
Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1999032537A1 (en) * | 1997-12-19 | 1999-07-01 | Avecia Limited | POLYMERIC MATERIAL COMPRISING N, P, S, As OR Se AND COMPOSITION FOR CHARGE TRANSPORT MATERIAL |
WO2005055248A2 (en) * | 2003-11-28 | 2005-06-16 | Merck Patent Gmbh | Organic semiconducting layer formulations comprising polyacenes and organic binder polymers |
CN1813343A (zh) * | 2003-05-08 | 2006-08-02 | 3M创新有限公司 | 有机聚合物、电子器件和方法 |
CN101256954A (zh) * | 2006-12-07 | 2008-09-03 | 三星Sdi株式会社 | 半导体元件、包含其的有机发光显示器以及其制造方法 |
CN101346808A (zh) * | 2005-12-28 | 2009-01-14 | 3M创新有限公司 | 底栅电极薄膜晶体管 |
CN101361205A (zh) * | 2006-01-21 | 2009-02-04 | 默克专利股份有限公司 | 包含有机半导体配方的电子短沟道器件 |
CN101657458A (zh) * | 2007-03-07 | 2010-02-24 | 肯塔基大学研究基金会 | 甲硅烷基乙炔化杂并苯和由其制造的电子器件 |
Family Cites Families (47)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AU7256496A (en) | 1995-10-17 | 1997-05-07 | Minnesota Mining And Manufacturing Company | Method for radiation-induced thermal transfer of resist for flexible printed circuitry |
US6309763B1 (en) | 1997-05-21 | 2001-10-30 | The Dow Chemical Company | Fluorene-containing polymers and electroluminescent devices therefrom |
KR100697861B1 (ko) | 1998-03-13 | 2007-03-22 | 캠브리지 디스플레이 테크놀로지 리미티드 | 전장 발광 디바이스들 |
EP1196476A1 (en) | 1999-06-18 | 2002-04-17 | Avecia Limited | Process for the isolation of polymer fractions |
CA2401487C (en) | 2000-02-29 | 2011-06-21 | Japan Science And Technology Corporation | Polyacene derivatives and process of producing thereof |
AU2001290332A1 (en) | 2000-10-05 | 2002-04-15 | Teruyoshi Mizutani | Organic electroluminescent devices |
GB0028867D0 (en) | 2000-11-28 | 2001-01-10 | Avecia Ltd | Field effect translators,methods for the manufacture thereof and materials therefor |
TW588105B (en) | 2001-07-19 | 2004-05-21 | Sumitomo Chemical Co | Polymeric fluorescent substance and polymer light-emitting device using the same |
US6690029B1 (en) | 2001-08-24 | 2004-02-10 | University Of Kentucky Research Foundation | Substituted pentacenes and electronic devices made with substituted pentacenes |
EP1459392B1 (en) | 2001-12-19 | 2011-09-21 | Merck Patent GmbH | Organic field effect transistor with an organic dielectric |
DE10203328A1 (de) | 2002-01-28 | 2003-08-07 | Syntec Ges Fuer Chemie Und Tec | Neue Triarylamin-Derivate mit raumfüllenden Flügelgruppen und ihre Einsatz in elektro-fotografischen und organischen elektrolumineszenten Vorrichtungen |
US20060093852A1 (en) | 2002-06-04 | 2006-05-04 | Dirk Marsitzky | Phosphorescent and luminescent conjugated polymers and their use in electroluminescent assemblies |
US20040004433A1 (en) | 2002-06-26 | 2004-01-08 | 3M Innovative Properties Company | Buffer layers for organic electroluminescent devices and methods of manufacture and use |
WO2004009668A1 (ja) | 2002-07-22 | 2004-01-29 | Sumitomo Chemical Company, Limited | 共重合体およびそれを用いた高分子発光素子 |
EP1529317A2 (en) | 2002-08-06 | 2005-05-11 | Avecia Limited | Organic electronic devices |
JP4174391B2 (ja) | 2002-08-30 | 2008-10-29 | キヤノン株式会社 | 電子写真感光体、プロセスカートリッジおよび電子写真装置 |
KR100694364B1 (ko) | 2002-09-03 | 2007-03-12 | 캠브리지 디스플레이 테크놀로지 리미티드 | 광학 디바이스 |
GB0229659D0 (en) | 2002-12-20 | 2003-01-22 | Avecia Ltd | Electronic devices |
US7279777B2 (en) * | 2003-05-08 | 2007-10-09 | 3M Innovative Properties Company | Organic polymers, laminates, and capacitors |
CN100558791C (zh) * | 2003-12-13 | 2009-11-11 | 默克专利有限公司 | 低聚物和聚合物 |
JP2006228935A (ja) | 2005-02-17 | 2006-08-31 | Ricoh Co Ltd | 有機薄膜トランジスタ |
JP2006352083A (ja) | 2005-05-18 | 2006-12-28 | Ricoh Co Ltd | 有機薄膜トランジスタ及びアクティブマトリックス表示装置 |
JP2007013097A (ja) | 2005-06-01 | 2007-01-18 | Sony Corp | 有機半導体材料、有機半導体薄膜及び有機半導体素子 |
US20100165604A1 (en) | 2005-11-30 | 2010-07-01 | Sumitomo Chemical Company, Limited | White organic electroluminescent device |
GB2433509A (en) | 2005-12-22 | 2007-06-27 | Cambridge Display Tech Ltd | Arylamine polymer |
US20070146426A1 (en) | 2005-12-28 | 2007-06-28 | Nelson Brian K | All-inkjet printed thin film transistor |
US7309876B2 (en) | 2005-12-30 | 2007-12-18 | Lucent Technologies Inc. | Organic semiconductor having polymeric and nonpolymeric constituents |
WO2008009343A1 (en) | 2006-07-21 | 2008-01-24 | Merck Patent Gmbh | Copolymers of indenofluorene and thiophene |
GB0617723D0 (en) | 2006-09-08 | 2006-10-18 | Cambridge Display Tech Ltd | Conductive polymer compositions in opto-electrical devices |
GB2442724B (en) | 2006-10-10 | 2009-10-21 | Cdt Oxford Ltd | Light emissive device |
JP5524043B2 (ja) | 2007-04-19 | 2014-06-18 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング | 置換されたペンタセン類の調製方法 |
JP2009003157A (ja) | 2007-06-21 | 2009-01-08 | Ricoh Co Ltd | 画像形成装置、画像形成方法及びプロセスカートリッジ |
JP5326417B2 (ja) | 2007-10-18 | 2013-10-30 | 三菱化学株式会社 | 電荷輸送膜及び有機電界発光素子 |
GB2467498B (en) | 2007-11-21 | 2012-11-28 | Merck Patent Gmbh | Conjugated copolymer |
US8956555B2 (en) | 2008-05-30 | 2015-02-17 | 3M Innovative Properties Company | Silylethynyl pentacene compounds and compositions and methods of making and using the same |
WO2010067746A1 (ja) | 2008-12-08 | 2010-06-17 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子、表示装置、及び照明装置 |
US8212243B2 (en) | 2010-01-22 | 2012-07-03 | Eastman Kodak Company | Organic semiconducting compositions and N-type semiconductor devices |
TWI421279B (zh) | 2011-02-01 | 2014-01-01 | Eternal Chemical Co Ltd | 可固化材料及其應用 |
GB201108865D0 (en) * | 2011-05-26 | 2011-07-06 | Ct For Process Innovation The Ltd | Semiconductor compounds |
GB201108864D0 (en) | 2011-05-26 | 2011-07-06 | Ct For Process Innovation The Ltd | Transistors and methods of making them |
GB2491810B (en) * | 2011-05-31 | 2018-03-21 | Smartkem Ltd | Organic semiconductor compositions |
US20140183414A1 (en) | 2011-08-22 | 2014-07-03 | Sumitomo Chemical Company, Limited | Polymer compound and light emitting device using same |
JP5750165B2 (ja) | 2011-10-17 | 2015-07-15 | 住友化学株式会社 | 化合物 |
WO2013114976A1 (ja) | 2012-01-30 | 2013-08-08 | 住友化学株式会社 | 高分子化合物および組成物、並びにこれらを用いた発光素子 |
WO2013114118A2 (en) | 2012-01-31 | 2013-08-08 | Cambridge Display Technology Limited | Polymer |
GB201203159D0 (en) * | 2012-02-23 | 2012-04-11 | Smartkem Ltd | Organic semiconductor compositions |
WO2013156125A1 (de) | 2012-04-17 | 2013-10-24 | Merck Patent Gmbh | Vernetzbare sowie vernetzte polymere, verfahren zu deren herstellung sowie deren verwendung |
-
2011
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2012
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Patent Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1999032537A1 (en) * | 1997-12-19 | 1999-07-01 | Avecia Limited | POLYMERIC MATERIAL COMPRISING N, P, S, As OR Se AND COMPOSITION FOR CHARGE TRANSPORT MATERIAL |
CN1813343A (zh) * | 2003-05-08 | 2006-08-02 | 3M创新有限公司 | 有机聚合物、电子器件和方法 |
WO2005055248A2 (en) * | 2003-11-28 | 2005-06-16 | Merck Patent Gmbh | Organic semiconducting layer formulations comprising polyacenes and organic binder polymers |
TW200529483A (en) * | 2003-11-28 | 2005-09-01 | Avecia Ltd | Improvements in and relating to organic semiconducting layers |
CN101346808A (zh) * | 2005-12-28 | 2009-01-14 | 3M创新有限公司 | 底栅电极薄膜晶体管 |
CN101361205A (zh) * | 2006-01-21 | 2009-02-04 | 默克专利股份有限公司 | 包含有机半导体配方的电子短沟道器件 |
CN101256954A (zh) * | 2006-12-07 | 2008-09-03 | 三星Sdi株式会社 | 半导体元件、包含其的有机发光显示器以及其制造方法 |
CN101657458A (zh) * | 2007-03-07 | 2010-02-24 | 肯塔基大学研究基金会 | 甲硅烷基乙炔化杂并苯和由其制造的电子器件 |
Non-Patent Citations (5)
Title |
---|
JANOS VERES,ET AL.: "Low‐k insulators as the choice of dielectrics in organic field‐effect transistors", 《ADVANCED FUNCTIONAL MATERIALS》 * |
JOHN E. ANTHONY: "Silylethyne-substituted pentacenes", 《MATERIAL MATTERS》 * |
何曼君 等: "《高分子物理》", 31 March 2007, 复旦大学出版社 * |
谢大荣 等: "《电工高分子物理》", 30 June 1990, 西安交通大学出版社 * |
路甬祥 等: "《现代科学技术大众百科 技术卷》", 30 June 2001, 浙江教育出版社 * |
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GB201120997D0 (en) | 2012-01-18 |
US20170005269A1 (en) | 2017-01-05 |
WO2012160383A1 (en) | 2012-11-29 |
CN103703581B (zh) | 2017-06-09 |
CN103703581A (zh) | 2014-04-02 |
TWI551624B (zh) | 2016-10-01 |
GB201118867D0 (en) | 2011-12-14 |
KR20140035434A (ko) | 2014-03-21 |
EP2715820A1 (en) | 2014-04-09 |
TW201319121A (zh) | 2013-05-16 |
EP2715820B1 (en) | 2018-02-14 |
HK1245309A1 (zh) | 2018-08-24 |
GB201108864D0 (en) | 2011-07-06 |
US10121970B2 (en) | 2018-11-06 |
JP6005147B2 (ja) | 2016-10-12 |
US20140175409A1 (en) | 2014-06-26 |
US9431145B2 (en) | 2016-08-30 |
CN107266680B (zh) | 2021-01-15 |
JP2014516210A (ja) | 2014-07-07 |
GB201205022D0 (en) | 2012-05-09 |
KR101987209B1 (ko) | 2019-06-10 |
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