TWI523884B - 以交替式供體受體共聚物為主之高效溶液可加工半傳導性聚合物 - Google Patents
以交替式供體受體共聚物為主之高效溶液可加工半傳導性聚合物 Download PDFInfo
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- TWI523884B TWI523884B TW098122448A TW98122448A TWI523884B TW I523884 B TWI523884 B TW I523884B TW 098122448 A TW098122448 A TW 098122448A TW 98122448 A TW98122448 A TW 98122448A TW I523884 B TWI523884 B TW I523884B
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- Prior art keywords
- semiconductor
- thin film
- copolymer
- composite material
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- 229920001577 copolymer Polymers 0.000 title claims description 26
- 229920000642 polymer Polymers 0.000 title description 16
- 239000004065 semiconductor Substances 0.000 claims description 27
- 239000000463 material Substances 0.000 claims description 22
- -1 n-hexadecyl Chemical group 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 11
- 239000000758 substrate Substances 0.000 claims description 8
- 239000010409 thin film Substances 0.000 claims description 8
- 230000005669 field effect Effects 0.000 claims description 6
- 230000003287 optical effect Effects 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 238000004528 spin coating Methods 0.000 claims description 4
- 239000010408 film Substances 0.000 claims description 3
- 238000007639 printing Methods 0.000 claims description 3
- 239000004020 conductor Substances 0.000 claims description 2
- 238000000151 deposition Methods 0.000 claims description 2
- 238000003618 dip coating Methods 0.000 claims description 2
- 239000007772 electrode material Substances 0.000 claims description 2
- 239000002131 composite material Substances 0.000 claims 5
- 239000007788 liquid Substances 0.000 claims 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 239000010410 layer Substances 0.000 description 21
- 239000000243 solution Substances 0.000 description 17
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 11
- 239000002800 charge carrier Substances 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 9
- 239000000178 monomer Substances 0.000 description 8
- 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 8
- 238000005227 gel permeation chromatography Methods 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- 239000002019 doping agent Substances 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 238000010926 purge Methods 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 4
- 235000019439 ethyl acetate Nutrition 0.000 description 4
- 229930192474 thiophene Natural products 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- FNQJDLTXOVEEFB-UHFFFAOYSA-N 1,2,3-benzothiadiazole Chemical group C1=CC=C2SN=NC2=C1 FNQJDLTXOVEEFB-UHFFFAOYSA-N 0.000 description 3
- PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 3
- 239000005964 Acibenzolar-S-methyl Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 229910004298 SiO 2 Inorganic materials 0.000 description 3
- 238000006069 Suzuki reaction reaction Methods 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 239000012267 brine Substances 0.000 description 3
- 239000004973 liquid crystal related substance Substances 0.000 description 3
- 229920002521 macromolecule Polymers 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 2
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- FEOWHLLJXAECMU-UHFFFAOYSA-N 4,7-dibromo-2,1,3-benzothiadiazole Chemical compound BrC1=CC=C(Br)C2=NSN=C12 FEOWHLLJXAECMU-UHFFFAOYSA-N 0.000 description 2
- 229910020366 ClO 4 Inorganic materials 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 229910018286 SbF 6 Inorganic materials 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- CETPSERCERDGAM-UHFFFAOYSA-N ceric oxide Chemical compound O=[Ce]=O CETPSERCERDGAM-UHFFFAOYSA-N 0.000 description 2
- 229910000422 cerium(IV) oxide Inorganic materials 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000005684 electric field Effects 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000011877 solvent mixture Substances 0.000 description 2
- 150000003577 thiophenes Chemical class 0.000 description 2
- MDCWDBMBZLORER-UHFFFAOYSA-N triphenyl borate Chemical compound C=1C=CC=CC=1OB(OC=1C=CC=CC=1)OC1=CC=CC=C1 MDCWDBMBZLORER-UHFFFAOYSA-N 0.000 description 2
- PQMFVUNERGGBPG-UHFFFAOYSA-N (6-bromopyridin-2-yl)hydrazine Chemical compound NNC1=CC=CC(Br)=N1 PQMFVUNERGGBPG-UHFFFAOYSA-N 0.000 description 1
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 1
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 1
- DIIIISSCIXVANO-UHFFFAOYSA-N 1,2-Dimethylhydrazine Chemical compound CNNC DIIIISSCIXVANO-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- CELAWAUPJZMNHF-UHFFFAOYSA-N 1-bromo-2,7-dimethyloctane Chemical compound CC(C)CCCCC(C)CBr CELAWAUPJZMNHF-UHFFFAOYSA-N 0.000 description 1
- HNTGIJLWHDPAFN-UHFFFAOYSA-N 1-bromohexadecane Chemical compound CCCCCCCCCCCCCCCCBr HNTGIJLWHDPAFN-UHFFFAOYSA-N 0.000 description 1
- UITASDKJJNYORO-UHFFFAOYSA-N 389-58-2 Chemical compound S1C=CC2=C1C(SC=C1)=C1C2 UITASDKJJNYORO-UHFFFAOYSA-N 0.000 description 1
- 229920001621 AMOLED Polymers 0.000 description 1
- 229910017008 AsF 6 Inorganic materials 0.000 description 1
- WMAZOIVUIWQRKU-UHFFFAOYSA-N C1(=CC=CC=C1)C(C(OCC)(OCC)OCC)CCCCCCCC Chemical compound C1(=CC=CC=C1)C(C(OCC)(OCC)OCC)CCCCCCCC WMAZOIVUIWQRKU-UHFFFAOYSA-N 0.000 description 1
- 229910052693 Europium Inorganic materials 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 229910019800 NbF 5 Inorganic materials 0.000 description 1
- LYXFCGCYJQCSRL-UHFFFAOYSA-N OOSO Chemical compound OOSO LYXFCGCYJQCSRL-UHFFFAOYSA-N 0.000 description 1
- 101150003085 Pdcl gene Proteins 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 229910018287 SbF 5 Inorganic materials 0.000 description 1
- 238000000944 Soxhlet extraction Methods 0.000 description 1
- 238000006619 Stille reaction Methods 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- 229910007926 ZrCl Inorganic materials 0.000 description 1
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 1
- 229960004373 acetylcholine Drugs 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 150000001347 alkyl bromides Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000003990 capacitor Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 238000006880 cross-coupling reaction Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- ZOCHARZZJNPSEU-UHFFFAOYSA-N diboron Chemical compound B#B ZOCHARZZJNPSEU-UHFFFAOYSA-N 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000011532 electronic conductor Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- OJCSPXHYDFONPU-UHFFFAOYSA-N etoac etoac Chemical compound CCOC(C)=O.CCOC(C)=O OJCSPXHYDFONPU-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000000434 field desorption mass spectrometry Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229910052732 germanium Inorganic materials 0.000 description 1
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 1
- 229920006158 high molecular weight polymer Polymers 0.000 description 1
- 230000005525 hole transport Effects 0.000 description 1
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000012212 insulator Substances 0.000 description 1
- 238000005468 ion implantation Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229910052747 lanthanoid Inorganic materials 0.000 description 1
- 150000002602 lanthanoids Chemical class 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000004377 microelectronic Methods 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000010525 oxidative degradation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- XDRYMKDFEDOLFX-UHFFFAOYSA-N pentamidine Chemical compound C1=CC(C(=N)N)=CC=C1OCCCCCOC1=CC=C(C(N)=N)C=C1 XDRYMKDFEDOLFX-UHFFFAOYSA-N 0.000 description 1
- 229960004448 pentamidine Drugs 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229920000307 polymer substrate Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 150000003623 transition metal compounds Chemical class 0.000 description 1
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
- C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
- C08G61/123—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds
- C08G61/126—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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
- C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
- C08G61/123—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds
- C08G61/124—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds with a five-membered ring containing one nitrogen atom in the ring
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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
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- 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
-
- 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
- H01B1/124—Intrinsically conductive polymers
- H01B1/127—Intrinsically conductive polymers comprising five-membered aromatic rings in the main chain, e.g. polypyrroles, polythiophenes
-
- 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
- H10K99/00—Subject matter not provided for in other groups of this subclass
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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
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/14—Macromolecular compounds
- C09K2211/1441—Heterocyclic
- C09K2211/1458—Heterocyclic containing sulfur as the only heteroatom
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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
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/14—Macromolecular compounds
- C09K2211/1441—Heterocyclic
- C09K2211/1483—Heterocyclic containing nitrogen and sulfur as heteroatoms
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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
- 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
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Description
本發明係關於苯并噻二唑-環戊二烯并二噻吩共聚物、其製備方法及其作為半導體或電荷傳輸材料之用途。
在20世紀下半葉期間,微電子器件發展之龐大構建組塊係以無機電極、絕緣體、及半導體為主之場效電晶體(FET)。已證實此等材料可靠、高效並具有遵循著名莫耳定律(Moore's law)週期性增加之性能。而與習用矽技術相比,發現以分子材料及聚合物材料為主之有機FET(OFET)可大規模地應用於低效記憶元件體以及整合光電器件中,例如主動矩陣有機發光二極體顯示器中之像素驅動及開關元件、RFID標籤、智能ID標籤、及感測器。
由於已開發出數種傳導性或半傳導性有機聚合物,因此彼等作為作用層、由此作為半導體在有機薄膜電晶體(OTFT)中之應用已受到越來越多的關注。
迄今為止,在OTFT中使用有機半導體具有優於使用無機半導體之一些優點。其可以自纖維至膜之任一形式加工並展示出高機械撓性,可以低成本製造且重量輕。然而,顯著優點係能夠於大氣壓力下藉由自溶液沈積層於聚合物基板上(例如藉由印刷技術)來製造整個半導體組件,藉此獲得可廉價製造之FET。
電子器件之性能基本上取決於半導體材料中電荷載流子之遷移率及處於導通狀態時與關斷狀態時電流間之比率(導通/關斷比)。因此,理想半導體在關斷狀態時傳導性最小且在導通時電荷載流子遷移率最大(遷移率大於10-3cm2V-1s-1,導通/關斷比大於102)。此外,由於半導體材料之氧化降解會使組件性能降低,故其必須對氧化相對穩定,即必須具有足夠高之電離電位。
EP 1510535 A1闡述了聚噻吩并(2,3-b)噻吩,其遷移率為3×10-3或1.7×10-2cm2V-1s-1且導通/關斷比為約106。WO 2006/094645 A1闡述了具有一或多個硒吩-2,5-二基及一或多個噻吩-2,5-二基之聚合物,而WO 2006/131185揭示了聚噻吩并(3,4-d)噻唑,且US 2005/0082525 A1揭示了苯并(1,2-b,4,5-b')二噻吩。
US 2007/0014939揭示了經C1-C20烷基取代之環戊二烯并二噻吩與苯并噻二唑之共聚物作為半傳導性材料。在實例中,製備了分別經正己基及乙基己基雙取代之環戊二烯并二噻吩之共聚物。該等材料之缺點係其僅具有中等電荷載流子遷移率(在10-3cm2/Vs範圍內)。
Z.Zhu等人(Macromolecules 2007,40(6),1981-1986)揭示了分別經正己基及2-乙基己基取代基雙取代之環戊二烯并二噻吩與苯并噻二唑之共聚物。據報導,由此材料製成之場效電晶體之電洞遷移率為0.015cm2/Vs。
Zhang等人(J. Am. Chem. Soc. 2007,129(12),3472-3473)揭示了分別經正十六烷基或3,7-二甲基辛基取代基雙取代之環戊二烯并二噻吩與苯并噻二唑之共聚物,其數量平均分子量為10.2kg/mol並在FET中展示出0.17cm2/Vs之電荷載流子遷移率。
本發明之目的係提供可用作有機半導體材料之新穎化合物,其易於合成,具有高遷移率及良好之氧化穩定性,且可便於加工。
此目的係藉由苯并噻二唑-環戊二烯并二噻吩共聚物達成,該共聚物包含式(I)之基團作為重複單元:
其中R係正十六烷基或3,7-二甲基辛基,
且其數量平均分子量Mn在30kg/mol至70kg/mol範圍內。
本發明苯并噻二唑-環戊二烯并二噻吩共聚物之優點在於其能顯著增加場效電晶體中電荷載流子之遷移率,此係由於該材料經改良具有更高分子量與高純度所致。
數量平均分子量Mn較佳係在40kg/mol至60kg/mol範圍內。在一特定實施例中,Mn係在65kg/mol至70kg/mol範圍內。
R係正十六烷基或3,7-二甲基辛基。
「遷移率(Mobility,mobility)」係指由外部刺激(例如電場)產生之電荷載流子(例如,在p型半導體材料之情形下其為電洞(或正電荷之單元)且在n型半導體材料之情形下其為電子)在電場之影響下移動經過材料之速度的量度。
本發明另外提供本發明之共聚物之用途,其用作半導體或電荷傳輸材料(尤其在光學、電光或電子組件中)、作為薄膜電晶體(尤其在平面視覺顯示單元中)、或用於無線射頻辨識標籤(RFID標籤)或用於有機發光二極體(OLED)之半導體組件(例如電致發光顯示器或用於液晶顯示器之背光照明)、用於光電伏打組件或在感測器中、作為電池中之電極材料、作為光波導、用於電子照像術應用(例如電子照像記錄)。
本發明另外提供包含本發明聚合物之光學、電光或電子組件。該等組件可為(例如)FET、積體電路(IC)、TFT、OLED或配向層。
本發明之聚合物尤其適於作為半導體,此乃因其展示出此目的所需之高遷移率。
可藉由如業內已知之數種基團對該等聚合物實施封端。較佳之端基係H、經取代或未經取代之苯基、或經取代或未經取代之噻吩,但不限於該等。
本發明之共聚物可藉由已知方法製備。較佳之合成路線闡述於下文中。
本發明之共聚物可由2,1,3-苯并噻二唑-4,7-雙(4,4,5,5-四甲基-1,3,2-二氧硼-2-基)(BTZ)及2,6-二溴-4,4-二(十六烷基)-4H-環戊二烯并[2,1-b:3,4-b']二噻吩(CDT)來製備。
單體2,6-二溴-4,4-二(十六烷基)-4H-環戊二烯并[2,1-b:3,4-b']二噻吩(CDT)可藉由P. Coppo等人,Macromolecules 2003,36,2705-2711中所述之方法使用下述反應圖來製備:
在此反應圖中,R係正十六烷基或3,7-二甲基辛基。
共單體2,1,3-苯并噻二唑-4,7-雙(4,4,5,5-四甲基-1,3,2-二氧硼-2-基)(BTZ)可由4,7-二溴-2,1,3-苯并噻二唑來製備,如Zhang等人,J. Am. Chem. Soc. 2007,129(12),3472-3473中所闡述。
BTZ/CDT共聚物可經由交叉偶合聚合反應(例如Stille或Suzuki反應)來合成,其中在鹼及少量金屬觸媒(例如四(三苯基膦)鈀(0))之存在下使烷基二鹵化物與有機錫化合物或硼酸二酯/硼酸發生反應。通常,該反應係在溶劑或溶劑混合物中在介於20℃與130℃間之反應下溫度實施。
合成高分子量聚合物之關鍵在於使用Suzuki交叉偶合反應以及純度大於99%之高純度單體,且因此需要所使用單體之適當純化方法。
對先前所獲得之粉色固體狀BTZ單體(Zhang等人,J. Am. Chem. Soc. 2007,129(12),3472-3473)進行多次重結晶,得到無色晶體,經GC測定其純度大於99%。
為獲得所需之純度大於99%的CDT,可使用循環式GPC。
分子量可藉由調節1:1單體混合物之濃度再現地獲得。獲得50kg/mol至60kg/mol數量平均分子量之單體於反應溶液中之最佳總濃度為約60重量%。
本發明包含本發明聚合物之氧化形式及還原形式二者。電子不足或過量皆會導致形成高傳導性離域離子。此可藉由用習用摻雜劑進行摻雜來達成。摻雜劑及摻雜方法已眾所周知且(例如)可自EP-A 0 528 662、US 5198153或WO 96/21659中獲知。適宜摻雜方法包含(例如)用摻雜氣體實施摻雜、在包含摻雜劑之溶液中實施電化學摻雜、藉助熱擴散及藉助離子植入將摻雜劑引入半導體材料中。
在使用電子作為電荷載流子之情形下,較佳使用鹵素(例如I2、Cl2、Br2、ICl、ICl3、IBr及IF)、路易士(Lewis)酸(例如PF5、AsF5、SbF5、BF3、BCl3、SbCl5、BBr3及SO3)、無機酸(例如HF、HCl、HNO3、H2SO4、HClO4、FSO3H及ClSO3H)、有機酸或胺基酸、過渡金屬化合物(例如FeCl3、FeOCl、Fe(ClO4)3、Fe(4-CH3C6H4SO3)3、TiCl4、ZrCl4、HfCl4、NbF5、NbCl5、TaCl5、MoF5、MoCl5、WF5、WCl6、UF6及LnCl3(其中Ln係鑭系元素))、陰離子(例如Cl-、Br-、I-、I3 -、HSO4 -、SO4 2-、NO3 -、ClO4 -、BF4 -、PF6 -、AsF6 -、SbF6 -、FeCl4 -、Fe(CN)6 3-、及不同磺酸之陰離子,例如芳基-SO3 -)。在使用電洞作為電荷載流子之情形下,摻雜劑為(例如)陽離子(例如H+、Li+、Na+、K+、Rb+及Cs+)、鹼金屬(例如Li、Na、K、Rb及Cs)、鹼土金屬(例如Ca、Sr及Ba)、O2、XeOF4、(NO2 +)(SbF6 -)、(NO2 +)(SbCl6 -)、(NO2 +)(BF4 -)、AgClO4、H2lrCl6、La(NO3)3、FSO2OOSO2F、Eu、乙醯膽鹼、R4N+、R4P+、R6As+及R3S+,其中R係烷基。
本發明共聚物之傳導形式可用作有機導體,例如有機發光二極體(OLED)中之電荷注入層及ITO平坦化層、平面螢幕及觸摸式螢幕、抗靜電膜、印刷電路及電容器,但並不限於該等。
可使用本發明之共聚物來製造光學、電子及半導體材料,尤其作為場效電晶體(FET)中之電荷傳輸材料,例如作為積體電路(IC)之組件、ID標籤或TFT。或者,其可用於電致發光顯示器中之有機發光二極體(OLED)中或用作背光照明(例如液晶顯示器(LCD)),用於光電伏打應用中或用於感測器、用於電子照像記錄及其他半導體應用。
由於本發明之共聚物具有良好之溶解性,故可將其以溶液形式施加至基板。因此,可使用廉價方法(例如旋塗或印刷)來施加層。
適宜溶劑或溶劑混合物包含(例如)醚、芳香族化合物且尤其氯化溶劑。
FET及其他包含半導體材料之組件(例如二極體)可有利地用於ID標籤或安全標記中以指示真實性並防止諸如鈔票、信用卡、身份證件(例如ID卡或駕照)或其他具有金錢利益之文件(例如橡膠圖章、郵票或票據等)等有價值物品之偽造品。
或者,本發明之聚合物可用於有機發光二極體(OLED)中,例如用於顯示器中或用作液晶顯示器(LCD)之背光照明。通常,OLED具有多層結構。發光層通常係嵌於一或多個電子傳輸層及/或電洞傳輸層之間。當施加電壓時,電子或電洞可在發光層方向上遷移並在發光層中重新結合而產生激發,且隨後使發光層中之發光化合物發光。可根據聚合物、材料及層之電學及光學性質將其用於一或多個傳輸層及/或發光層中。當化合物、材料或層為電致發光或具有電致發光基團或化合物時,其尤其適用於發光層。
與用於OLED中之適宜聚合物之加工一樣,其選擇已眾所周知且其闡述於(例如)Synthetic Materials,111-112(2000),31-34或J. Appl. Phys.,88(2000)7124-7128中。
本文所引用之所有文獻皆以引用方式併入本發明專利申請案中。除非另有說明,否則所有數量數據(百分比、ppm等)皆以重量計(以混合物之總重量計)。
單體2,1,3-苯并噻二唑-4,7-雙(4,4,5,5-四甲基-1,3,2-二氧硼-2-基)(BTZ)與2,6-二溴-4,4-二(十六烷基)-4H-環戊二烯并[2,1-b:3,4-b']二噻吩(CDT)係根據公開程序(Zhang等人,J. Am. Chem. Soc. 2007,129(12),3472-3473;P. Coppo等人,Macromolecules 2003,36,2705-2711)合成。
將4,7-二溴-2,1,3-苯并噻二唑(1g,3.41mmol)、雙(戊醯)二硼(2g,7.8mmol)、PdCl2(dppf)(500mg,0.6mmol)、及KOAc(2g,20mmol)存於脫氣1,4-二噁烷(10ml)中之溶液於80℃下攪拌過夜。藉由添加水來猝滅反應,並將所得混合物用乙酸乙酯(30ml×3)洗滌。將有機層用鹽水洗滌,經Na2SO4乾燥並於真空中濃縮,得到暗紅色固體。利用矽膠層析藉助3%存於己烷中之乙酸乙酯來純化該固體,得到粉色固體狀預期化合物。將粗產物於乙醇中重結晶4小時,產生無色晶體,由此得到300mg BTZ。
FD-MS:m/z=388.0(calcd. 388.1)。1H NMR(250MHz,CD2Cl2):δ8.10(s,2H),1.41(s,24H)。13C NMR(62.9MHz,CD2Cl2):δ157.55,138.11,84.91,25.3。
將4H-環戊二烯并[2,1-b:3,4-b']二噻吩(2.0g,11.2mmol)溶於50mL二甲基亞碸中。分別添加正十六烷基溴或2,7-二甲基辛基溴(22.4mmol),隨後添加碘化鉀(50mg)。混合物用氮沖洗並在冰浴中冷卻,且最後分批添加粉狀氫氧化鉀(2.0g)。於室溫下將所得綠色混合物劇烈攪拌過夜。然後使反應容器於冰浴中冷卻並添加水(50mL)。有機相經乙醚萃取兩次,將其用水、鹽水及氯化銨溶液洗滌並用硫酸鎂乾燥。蒸發掉溶劑,得到黃色油狀標題化合物。利用二氧化矽/己烷進行層析來實施純化,以除去痕量的單烷基化產物及未反應的烷基溴。得到透明油狀標題化合物。產率:85%。
於氮下在黑暗中將4,4-二-正十六烷基-環戊二烯并[2,1-b:3,4-b']二噻吩/4,4-雙-(3,7-二甲基辛基)-環戊二烯并[2,1-b:3,4-b']二噻吩(4,97mmol)溶於50mL經蒸餾DMF中。分批添加NBS(1.8g,9.94mmol)。將所得黃色溶液於室溫下於氮下攪拌過夜。然後添加水(50mL),且有機相經乙醚(100mL)萃取2次,用水及1%的HCl溶液洗滌並用硫酸鎂乾燥。於減壓下去除溶劑,得到黃色油狀標題產物。藉助管柱層析利用二氧化矽/己烷及循環式GPC(4至5次)來去除雜質。得到無色油狀標題化合物(產率為68%)。
BTZ/正十六烷基-CDT共聚物係經由Suzuki偶合反應來合成,將正十六烷基-CDT(300mg,0.382mmol)及BTZ(148mg,0.382mmol)、K2CO3(2mL,2M)及3滴Aliquat 336溶於X mL存於安裝有回流冷凝器之50mL Schlenk燒瓶中之甲苯中。然後使用冷凍/抽氣/吹洗方法實施3次使溶液脫氣,並添加四(三苯基膦)鈀。然後再對溶液實施3次冷凍/抽氣/吹洗,並將其加熱至100℃並保持3天。然後添加0.1mL硼酸苯基酯存於甲苯中之1M溶液並再攪拌12小時,此時添加0.1mL溴苯存於甲苯中之1M溶液以封端反應鏈端。
將所得混合物倒入甲醇與濃鹽酸之混合物(2:1)中並攪拌過夜。將固體過濾並溶於熱氯苯中,然後在甲醇中沉澱並用丙酮實施索式萃取(soxhlet extraction)。隨後將聚合物於己烷、丙酮、及乙酸乙酯中沉澱3次,然後用己烷進行索式萃取,得到190mg(43%)。GPC分析:Mn=5k(X=10mL);14k(X=8mL);51k(X=4mL),D=2.6-4.0。
使用甲苯(X=4mL)以類似方式獲得BTZ/3,7-二甲基辛基-CDT,其數量平均分子量為38k,D=4.5。
藉由凝膠滲透層析(GPC)對照聚苯乙烯標準使用三氯苯作為洗脫劑來測定聚合物之分子量。使試樣經過3個管柱,第一個管柱之孔隙率範圍為106,第二個管柱為104,且最後一個管柱為500。
使用具有150nm SiO2層之高n++摻雜Si晶圓作為電晶體基板。用苯基三乙氧基矽烷對SiO2介電質進行處理。然後將整個基板浸於含有1mg/ml共聚物(溶於氯苯中)之溶液中。藉由以1μm/s之速率緩慢地將試樣取出,聚合物膜經由此浸塗方法「定向地生長」。或者,半傳導性層可藉由旋塗存於氯苯中之0.5重量%溶液進行塗佈,其中厚度為50nm。於氮氣氛中將此聚合物層於200℃下加熱1小時並藉由在此層之頂部蒸鍍50nm金觸點來完成電晶體之製造。
電荷載流子遷移率自飽和轉移曲線得到。
在場效電晶體中所測定之電荷載流子遷移率明顯展示出對分子量之依賴性且較高分子量有利(表1)。
對於旋塗聚合物(Mn為51k)而言,當於氮中量測時,FET展示出0.65cm2/Vs之電洞遷移率及Ion/Ioff=103之電流導通/關斷比。
對於浸塗聚合物而言,當於氮中量測時,FET展示出1.4cm2/Vs之電洞遷移率及Ion/Ioff=105之電流導通/關斷比。在不同閘極電壓VG下之典型輸出曲線闡釋於圖1中。
當於氮中量測時,BTZ/3,7-二甲基辛基-CDT共聚物展示出0.45cm2/Vs之電荷載流子遷移率及Ion/Ioff=105之電流導通/關斷比。
將BTZ(148mg,0.382mmol)、正十六烷基-CDT(300mg,0.382mmol)及K2CO3(12當量,4.584mmol於2M溶液中)及3滴Aliquat 336溶於4mL存於安裝有回流冷凝器之25mL Schlenk燒瓶中之甲苯中。然後使用冷凍/抽氣/吹洗方法對溶液實施3次脫氣,並於氬下添加四(三苯基膦)鈀(0.0191mmol)。然後再對溶液實施3次冷凍/抽氣/吹洗並將其於氬下加熱至100℃並保持24小時。然後將反應冷卻至室溫並再添加4mL甲苯。使用冷凍/抽氣/吹洗方法對混合物實施3次脫氣並再次添加四(三苯基膦)鈀(0.0191mmol),隨後實施3次冷凍/抽氣/吹洗循環。將反應加熱至100℃並保持48小時,且然後添加硼酸苯基酯(0.1M)存於甲苯中之溶液並再攪拌12小時,此時添加溴苯(0.1M)存於甲苯中之溶液。將所得混合物倒入甲醇與濃鹽酸(2:1)之混合物中並攪拌4小時。過濾出固體並將其溶於熱1,2,4-三氯苯中,然後在甲醇中沉澱並用丙酮實施索式萃取。然後將聚合物於己烷、丙酮、及乙酸乙酯中沉澱3次,隨後用己烷實施索式萃取,得到200mg(45%)產物。
GPC分析:由於受溶解性限制,未對此試樣之分子量進行直接比較。然而,在單獨管柱中於130℃下以三氯苯作為洗脫劑之GPC分析得到Mn=6.9×104之外推值,與經量測Mn為5.1×104之試樣相比,其展示出約35%之增加。
將2mg/mL存於鄰二氯苯中之試樣滴鑄於底部接觸FET基板上,該基板保持於100℃下且具有經HMDS功能化之200nm SiO2。通道長度及寬度分別為20μm及1.4mm。經量測,4個電晶體之最低飽和電洞遷移率為μsat=2.5cm2/Vs且最高為μsat=3.3cm2/Vs。平均遷移率為μsat=2.95cm2/VS。導通/關斷比為106(圖4)。加工係於氮氣氛中實施。
圖1顯示旋塗BTZ/正十六烷基-CDT共聚物(Mn=51K)之典型輸出特性。
圖2a及b顯示旋塗BTZ/3,7-二甲基辛基-CDT共聚物(Mn=38K)之典型轉移(a)及輸出(b)特性。
圖3顯示浸塗BTZ/正十六烷基-CDT共聚物(Mn=51K)之典型轉移特性。
圖4a及b顯示正十六烷基-CDT共聚物(Mn=69K)之典型轉移(a)及輸出(b)特性。
Claims (10)
- 一種可用作有機半導體材料之苯并噻二唑-環戊二烯并二噻吩共聚物,其包含式(1)之基團作為重複單元:
- 一種如請求項1之共聚物之用途,其作為半導體或電荷傳輸材料、作為薄膜電晶體(TFT)、或用於有機發光二極體(OLED)之半導體組件中、用於光電伏打組件或感測器中、作為電池中之電極材料、作為光波導或用於電子照像術應用。
- 一種組合物,其包含溶解或分散於液體介質中之一或多種如請求項1之共聚物。
- 一種薄膜半導體,其包含一或多種如請求項1之共聚物。
- 一種複合材料,其包含基板及沈積於該基板上之如請求項4之薄膜半導體。
- 一種製備如請求項5之複合材料之方法,其包含將如請求項1之共聚物溶於液體介質中以形成溶液、將該溶液沈積於基板上、及去除該溶劑以於該基板上形成薄膜半 導體。
- 如請求項6之方法,其中該溶液係藉由旋塗、浸塗或印刷來沈積。
- 一種場效電晶體器件,其包含如請求項4之薄膜半導體或如請求項5之複合材料。
- 一種光電伏打器件,其包含如請求項4之薄膜半導體或如請求項5之複合材料。
- 一種有機發光二極體器件,其包含如請求項4之薄膜半導體或請求項5之複合材料。
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