TWI485145B - P型有機半導體材料與光電元件 - Google Patents
P型有機半導體材料與光電元件 Download PDFInfo
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- TWI485145B TWI485145B TW101139632A TW101139632A TWI485145B TW I485145 B TWI485145 B TW I485145B TW 101139632 A TW101139632 A TW 101139632A TW 101139632 A TW101139632 A TW 101139632A TW I485145 B TWI485145 B TW I485145B
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- 239000000463 material Substances 0.000 title claims description 39
- 239000004065 semiconductor Substances 0.000 title claims description 26
- 230000005693 optoelectronics Effects 0.000 title 1
- -1 alkyl α-cyanoacrylate Chemical compound 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000010409 thin film Substances 0.000 claims description 3
- IJVRPNIWWODHHA-UHFFFAOYSA-N 2-cyanoprop-2-enoic acid Chemical compound OC(=O)C(=C)C#N IJVRPNIWWODHHA-UHFFFAOYSA-N 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-M nitrite group Chemical group N(=O)[O-] IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 125000006575 electron-withdrawing group Chemical group 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- PJANXHGTPQOBST-QXMHVHEDSA-N cis-stilbene Chemical compound C=1C=CC=CC=1/C=C\C1=CC=CC=C1 PJANXHGTPQOBST-QXMHVHEDSA-N 0.000 description 5
- 230000005525 hole transport Effects 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 229930192474 thiophene Natural products 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 229940125782 compound 2 Drugs 0.000 description 3
- 229920000547 conjugated polymer Polymers 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- 229920000144 PEDOT:PSS Polymers 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 229940125904 compound 1 Drugs 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 description 2
- 239000010408 film Substances 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 238000010791 quenching Methods 0.000 description 2
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 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
- SLLFVLKNXABYGI-UHFFFAOYSA-N 1,2,3-benzoxadiazole Chemical compound C1=CC=C2ON=NC2=C1 SLLFVLKNXABYGI-UHFFFAOYSA-N 0.000 description 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 description 1
- UUNIOFWUJYBVGQ-UHFFFAOYSA-N 2-amino-4-(3,4-dimethoxyphenyl)-10-fluoro-4,5,6,7-tetrahydrobenzo[1,2]cyclohepta[6,7-d]pyran-3-carbonitrile Chemical compound C1=C(OC)C(OC)=CC=C1C1C(C#N)=C(N)OC2=C1CCCC1=CC=C(F)C=C12 UUNIOFWUJYBVGQ-UHFFFAOYSA-N 0.000 description 1
- MLIREBYILWEBDM-UHFFFAOYSA-M 2-cyanoacetate Chemical compound [O-]C(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-M 0.000 description 1
- RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical compound C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 description 1
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 1
- FPQUPWCVIWHUIY-UHFFFAOYSA-N COC(CCC)=O.C[C]C Chemical compound COC(CCC)=O.C[C]C FPQUPWCVIWHUIY-UHFFFAOYSA-N 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 1
- 229920000265 Polyparaphenylene Polymers 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- YSLYSRQNLNGHSS-UHFFFAOYSA-N S1N=NC=2C=CC=3N=CC=NC3C21.S2CNCC2 Chemical compound S1N=NC=2C=CC=3N=CC=NC3C21.S2CNCC2 YSLYSRQNLNGHSS-UHFFFAOYSA-N 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 1
- IPWKHHSGDUIRAH-UHFFFAOYSA-N bis(pinacolato)diboron Chemical compound O1C(C)(C)C(C)(C)OB1B1OC(C)(C)C(C)(C)O1 IPWKHHSGDUIRAH-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- ZXIJMRYMVAMXQP-UHFFFAOYSA-N cycloheptene Chemical compound C1CCC=CCC1 ZXIJMRYMVAMXQP-UHFFFAOYSA-N 0.000 description 1
- 238000007405 data analysis Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Natural products CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 1
- 125000000532 dioxanyl group Chemical group 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- RWXCVESEMJNNMF-UHFFFAOYSA-N oxadiazolo[5,4-b]pyridine Chemical compound C1=CN=C2ON=NC2=C1 RWXCVESEMJNNMF-UHFFFAOYSA-N 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 238000010248 power generation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- YEYHFKBVNARCNE-UHFFFAOYSA-N pyrido[2,3-b]pyrazine Chemical compound N1=CC=NC2=CC=CN=C21 YEYHFKBVNARCNE-UHFFFAOYSA-N 0.000 description 1
- ZVJHJDDKYZXRJI-UHFFFAOYSA-N pyrroline Natural products C1CC=NC1 ZVJHJDDKYZXRJI-UHFFFAOYSA-N 0.000 description 1
- FYNROBRQIVCIQF-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole-5,6-dione Chemical compound C1=CN=C2C(=O)C(=O)N=C21 FYNROBRQIVCIQF-UHFFFAOYSA-N 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- MABNMNVCOAICNO-UHFFFAOYSA-N selenophene Chemical compound C=1C=C[se]C=1 MABNMNVCOAICNO-UHFFFAOYSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- QKTRRACPJVYJNU-UHFFFAOYSA-N thiadiazolo[5,4-b]pyridine Chemical compound C1=CN=C2SN=NC2=C1 QKTRRACPJVYJNU-UHFFFAOYSA-N 0.000 description 1
- YJSKZIATOGOJEB-UHFFFAOYSA-N thieno[2,3-b]pyrazine Chemical compound C1=CN=C2SC=CC2=N1 YJSKZIATOGOJEB-UHFFFAOYSA-N 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
Classifications
-
- 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
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/655—Aromatic compounds comprising a hetero atom comprising only sulfur as heteroatom
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y10/00—Nanotechnology for information processing, storage or transmission, e.g. quantum computing or single electron logic
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
- H10K30/30—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation comprising bulk heterojunctions, e.g. interpenetrating networks of donor and acceptor material domains
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
- H10K30/50—Photovoltaic [PV] devices
-
- 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
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/20—Carbon compounds, e.g. carbon nanotubes or fullerenes
- H10K85/211—Fullerenes, e.g. C60
- H10K85/215—Fullerenes, e.g. C60 comprising substituents, e.g. PCBM
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
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- Engineering & Computer Science (AREA)
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Nanotechnology (AREA)
- Mathematical Physics (AREA)
- Theoretical Computer Science (AREA)
- Crystallography & Structural Chemistry (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Materials Engineering (AREA)
- Photovoltaic Devices (AREA)
Description
本發明係有關於p型有機半導體材料,以及p型有機半導體材料於光電元件之應用。
有機半導體材料(organic semiconductor material)因具有半導體與光電特性,可應用於許多光電元件上,如有機薄膜電晶體(organic thin-film transistor,OTFT)、有機太陽能電池(organic solar cell)、有機發光二極體(organic light emitting diode,OLED)、與光感測器上。藉由溶液塗佈技術,可將有機半導體材料製成光電元件的主動層薄膜,形成質輕、價格便宜、製程方便以及大面積化的可撓式光電元件。目前有機半導體材料發展之主流以共軛高分子(conjugated polymer)為主,即主鏈以共軛型態相連。一般共軛高分子應用於光電元件上的主要缺點為載子遷移率(carrier mobility)較低,且吸光範圍較窄(400nm~650nm)所以侷限了元件的使用。因此有許多研究團隊相繼投入共軛高分子材料的合成,研發具有高載子遷移及更廣波域吸收的材料,進一步提升光電元件的效能。
在有機太陽能電池的應用上,其主動層材料也必需是高遷移率的電子與電洞傳輸材料,否則因為光激或電激生成之電荷會經由複合而消散,而降低有機太陽能電池的光電轉換效率(power conversion efficiency)。至於光吸收的部分,如能有效的增加材料的太陽光譜吸收能力,配合材料
高載子遷移速度的話,將有機會突破性發展有機太陽能電池之轉換效率。有機太陽能電池之發電原理,主要結合電子予體(donor)與電子受體(acceptor)材料,以異質接面的技術配合發展各種高分子當電子予體材料,結合碳60當電子受體材料,例如:聚(3-己烷基噻吩)(P3HT)摻混苯基-碳61-丁酸甲酯(PCBM),其光電轉換效率提升至3.5%。
目前仍需新穎的p型有機半導體材料取代P3HT,使有機太陽能電池具有更佳效能如更高的轉換效率。
本發明一實施例提供一種p型有機半導體材料,其結
構如下:,其中每一Con相同,係共軛寡聚物;以及每一EW相同,係拉電子基團。
本發明一實施例提供一種光電元件,包括主動層,且主動層包括上述之p型有機半導體材料。
本發明一實施例提供一種p型有機半導體材料,其結構如式1:
在式1中,每一Con相同,係共軛寡聚物,且每一EW相同,係拉電子基團。在本發明一實施例中,共軛寡聚物
Con可為下述單元所形成之共軛寡聚物:噻吩、苯、哌喃(Pyrane)、哌咯(Pyrroline)、呋喃(Furan)、苯并呋喃(Benzofuran)、苯并噻吩(Benzothiophene)、苯并噻二唑(Benzothiodiazole)、吡啶(Pyridine)、喹啉(Quinoline)、異喹啉(isoquinoline)、吡嗪(pyrazine)、嘧啶(Pyrimidine)、吡咯(Pyrrole)、吡唑(Pyrazole)、咪唑(Imidazole)、吲哚(Indole)、噻唑(Thiazole)、異噻唑(Isothiazole)、噁唑(Oxazole)、異噁唑(Isoxazole)、苯并噻唑(Benzothiazole)、苯并噁唑(Benzoxazole)、1,2,4-三噁唑(1,2,4-Triazole)、1,2,3-三噁唑(1,2,3-Triazole)、二氮菲(Phenanthroline)、噁二唑吡啶(Oxadiazolopyridine)、吡啶并吡嗪(Pyridopyrazine)、苯并噁二唑(Benzooxadiazole)、噻二唑吡啶(Thiadiazolopyridine)、哂吩(Selenophene)、噻二唑喹噁啉(Thiadiazoloquinoxaline)、噻嗯并吡嗪(Thienopyrazine)、喹噁啉(Quinoxaline)、或二酮吡咯并吡咯(Diketopyrrolopyrrole)。舉例來說,共軛的噻吩寡聚物之結構如式2所示:
在式2中,每一R1
各自獨立,擇自H或C3-10
烷基,且n係2至20之整數。
在本發明一實施例中,拉電子基團EW可為α-氰基丙烯酸烷基酯、乙烯丙二氰、鹵素、亞硝酸基(-NO2
)、或其他合適的拉電子基團。舉例來說,α-氰基丙烯酸烷基酯之
結構如式3所示,而乙烯丙二氰如式4所示。
在式3中,R2
係C3-10
烷基。
在本發明一實施例中,p型有機半導體材料的合成方式如下述。值得注意的是,用以合成本發明之p型有機半導體材料的合成方式並不限於下述步驟,本技術領域中具有通常知識者自可依其設備與起始材料的考量,自行更動合成步驟。
首先如式5所示,取順-二苯代乙烯(cis
-stilbene)的硼化物與共軛寡聚物(如共軛的噻吩寡聚物)反應。值得注意的是,式5中共軛的噻吩寡聚物僅用以舉例,本發明之共軛寡聚物可為其他合適的共軛寡聚物。
在式5中,每一R11
相同,每一R12
相同、每一R13
相同、每一R14
相同、每一R15
相同、且每一R16
相同。上述R11
、R12
、R13
、R14
、R15
、R16
各自獨立,擇自H或C3-10
烷基。
接著如式6所示,取式5產物與拉電子基團(如α-氰基丙烯酸烷基酯)反應。值得注意的是,式6中α-氰基丙烯酸烷基酯僅用以舉例,本發明之拉電子基團可為其他合適的拉電子基團。
在式6中,每一R2
相同,係C3-10
烷基。由上述可知,本發明之p型有機半導體材料具有分子內鏡面的對稱結構,使結構具有規則性而分子間容易整齊排列,使材料更易成膜。若順-二苯代乙烯(cis
-stilbene)兩側分別取代不同的共軛寡聚物及/或拉電子基團,則無法產生較佳的分子堆疊,使其光電特性受限,於光電應用上效果不佳。
本發明之p型有機半導體材料可應用於有機薄膜電晶體裝置之主動層材料、有機發光二極體裝置之主動層材料、或有機太陽能電池裝置之主動層材料。
例如,有機太陽能電池之主動層包含本發明之p型有
機半導體材料,與電子受體材料(acceptor)如苯基-碳61-丁酸甲酯(PC61
BM)或苯基-碳71-丁酸甲酯(PC71
BM)。在一實施例中,p型有機半導體材料與電子受體材料混合比例約為1:0.5至1:2時,其光電轉換效率最佳。
為了讓本發明之上述和其他目的、特徵、和優點能更明顯易懂,下文特舉數實施例配合所附圖式,作詳細說明如下:
取50毫升雙頸圓底瓶內置攪拌子與上接迴流管,真空乾燥後通入氮氣。接著將3,7-dibromo-5,5-spirofluorenyl[a,d]cycloheptene(Stif
,如J.Am.Chem.Soc.2007 , 129
,7478.製備而得)(2501毫克,5毫莫耳)、Bis(pinacolato)diboron(2666毫克,10.5毫莫耳)、醋酸鉀(2356毫克,24毫莫耳)、與催化劑Pd(dppf)Cl2
(163毫克,0.2毫莫耳)依序加入圓底瓶中,再以針筒將100mL之去氧二氧陸環注入圓底瓶中。接著加熱反應瓶使其迴流反應18小時,再將反應瓶回溫至室溫並通入氧氣以淬息反應。以二氯甲烷(3×20毫升)萃取反應後之混合物,所得萃取液依序以硫酸鎂乾燥、以矽藻土過濾、再迴旋濃縮得粗產物。接著以甲醇(3×20毫升)清洗粗產物,得到2427毫克(4.08毫莫耳)的白色固體化合物1
如式7,產率82%。白色固體化合物1之
數據分析如下:1
H NMR(CDCl3
,400 MHz,ppm):δ 7.97(d,J
=7.8 Hz,2H),δ 7.73(d,J
=7.6
Hz,2H),δ 7.70(dd,J
=7.5,1.0 Hz,2H),δ 7.38(d,J
=7.3,2H),δ 7.35(t,J
=7.6 Hz,2H),δ 7.23(td,J
=7.7,1.1 Hz,2H),δ 7.01(s,2H),δ 1.19(s,24H);13
C NMR(100 MHz,CDCl3
)δ 152.4,141.2,139.0,138.8,135.3,134.3,133.3,131.4,127.7,127.1,127.0,120.2,83.4,66.0,24.7。
取25毫升雙頸圓底瓶內置攪拌子並接上迴流管,依序加入化合物1
(406毫克,0.35毫莫耳)、碳酸鈉(223毫克,2.1毫莫耳)、5”-(4-溴)-3-3”-二己基-2,2’:5’,2”-三噻吩-5-醛(5"
-(4-bromo)-3,3"
-di-n-hexyl-2,2'
:5'
,2"
-terthiophene-5-carbaldehyde,209毫克,0.77毫莫耳)、與催化劑Pd(PPh3
)4
(35毫克,0.03毫莫耳)後,除去反應裝置內之氧氣並通入氮氣,接著以針筒將10mL已除氧之1,2-二甲氧基乙烷與1mL水注入圓底瓶中,開啟迴流裝置使其反應18小時。反應結束後將圓底瓶回溫至室溫,再將氧氣通入圓底瓶以淬息反應。以二氯甲烷(3×20毫升)萃取反應後之混合物,所得萃取液依序以硫酸鎂乾燥、過濾、及迴旋濃縮,再以管柱層析搭配衝提液(CH2
Cl2
/hexane,1/2)純化濃縮後之粗產物,得384毫克(0.31毫莫耳)的化合物2
如式7所示,產率為89%。化合物式2
之數據分析如下:1
H NMR(CDCl3
,400 MHz,ppm):δ 9.82(s,2H),δ 8.03(d,J
=7.7 Hz,2H),δ 7.80(d,J
=7.5 Hz,2H),δ 7.58(s,2H),δ 7.44(t,J
=7.3 Hz,2H),δ 7.41(dd,J
=8.1,1.6 Hz,2H),δ 7.36(d,J
=7.8 Hz,2H),δ 7.33(t,J
=7.4 Hz,2H),δ 7.23(d,J
=1.4 Hz,2H),δ 7.22(d,J
=3.9 Hz,2H),δ 7.04(d,J
=3.8 Hz,2H),δ 6.96(s,
2H),δ 6.79(s,2H),δ 2.81(t,J
=7.7 Hz,4H),δ 2.68(t,J
=7.6 Hz,4H),δ 1.72-1.55(m,8H),δ 1.43-1.31(m,24H),δ 0.92-0.88(m,12H);13
C NMR(CDCl3
,100 MHz,
ppm):δ182.48,152.18,142.16,141.96,141.16,141.06,140.25,140.18,139.04,139.01,138.32,135.90,134.37,133.60,132.92,132.70,129.49,128.23,127.75,127.53,126.95,126.30,126.05,123.98,120.53,66.01,31.66,31.61,30.28,29.51,29.46,29.16,29.12,22.57,22.57,14.10,14.05。
取50毫升圓底瓶內置攪拌子,將化合物2
(256毫克,0.20毫莫耳)、氰基乙酸辛酯(400毫克,2.1毫莫耳)、無水的20毫升的氯仿溶劑依序加入圓底瓶中,再加入兩滴三乙基胺。上述混合物於室溫下反應18小時,再加入水與二氯甲烷進行萃取,所得萃取液依序以硫酸鎂乾燥、過濾、及迴旋濃縮得粗產物。以管柱層析搭配沖提液(CH2
Cl2
/hexane,1/1)純化粗產物,得284毫克(0.18毫莫耳)的深紅色固體EtStif
如式7所示,產率為90%。EtStif
之數據分析如下:1
H NMR(CDCl3
,400 MHz,ppm):δ8.20(s,1H),δ 8.03(d,J
=7.8 Hz,2H),δ 7.80(d,J
=7.4 Hz,2H),δ 7.58(s,2H),δ 7.45(t,J
=7.4 Hz,2H),δ 7.41(dd,J
=7.9,1.7 Hz,2H),δ 7.37-7.32(m,4H),δ 7.27(d,J
=4.0 Hz,2H),δ 7.23(d,J
=1.6 Hz,H),δ 7.05(d,J
=3.9 Hz,2H),δ 6.97(s,2H),δ 6.79(s,2H),δ 4.29(t,J
=6.8 Hz,4H),δ 2.82(t,J
=7.8 Hz,4H),δ 2.69(t,J
=7.5 Hz,4H),δ 1.78-1.57(m,12H),δ 1.41-1.25(m,44H),δ 0.92-0.87(m,18H);13
C NMR
(CDCl3
,100 MHz,
ppm):δ163.09,152.36,145.85,142.18,141.9,141.72,141.2,140.69,140.37,139.02,138.77,135.89,133.91,133.53,32.92,132.82,132.68,129.49,128.23,128.08,127.53,126.94,126.22,126.05,123.96,120.52,115.98,97.59,77.20,66.50,65.99,31.75,31.66,31.58,30.19,30.14,29.55,29.33,29.17,29.15,29.12,28.54,25.78,22.61,22.58,22.55,14.09,14.06,14.04。
本實施例製備如第1圖所示之有機太陽能電池裝置10,其包括氧化銦錫(ITO)陽極11;電洞傳輸層12,材料為聚3,4-乙基二氧噻吩:聚對苯乙烯磺酸Poly(3,4-ethylenedioxythiophene):poly(styrene-sulfonate)(PEDOT:PSS),形成於陽極11上;主動層13,包含本發明之p型有機半導體材料或市售之P3HT,形成於電洞傳輸層12上;以及陰極14為鈣(Ca)/鋁(Al)。
上述之主動層13由實施例1之EtStif
(或市售之P3HT)與苯基-碳-丁酸甲酯([6,6]-phenyl-C-butyric acid methyl ester,PCBM)以1:0.8的重量比例摻混而組成,其中PCBM中的碳可以是碳61或是碳71的衍生物。效率的量測是在AM 1.5的太陽光照度下測量。
製備的步驟如下:
1.於實驗前一天配置主動層溶液(EtStif/PCBM或P3HT/PCBM,10mg/mL),攪拌一晚。
2.氧化銦錫(ITO)玻璃分別用丙酮及異丙醇以超音波震盪清洗15分鐘,以氮氣吹乾後,置於加熱板烘烤5分鐘。
3.將氧化銦錫(ITO)玻璃置於氧氣電漿下5分鐘。
4.以3000rpm/30sec旋轉塗佈聚3,4-乙基二氧塞吩:聚對苯乙烯磺酸(PEDOT:PSS,Baytron P-VP AI4083),之後放置手套箱以150℃加熱烤一小時。
5.在手套箱中以1200rpm/60sec旋轉塗佈主動層(EtStif
/PCBM或P3HT/PCBM)。
6.將ITO玻璃置於140℃加熱板上退火20分鐘,靜置冷卻。
7.放至光罩上,蒸鍍鈣/鋁電極。
8.最後封裝整個元件並進行量測。
表1為本發明實施例1之EtStif
與市售之P3HT應用於有機太陽能電池中的光電轉換效率、短路電流、開路電壓、與填充因子。
與習知之P3HT/PCBM作為主動層的有機太陽能電池相較,含有本發明之p型有機半導體材料EtStif
之主動層的有機太陽能電池,其短路電流較低,開路電壓較高,填充因子較高,且轉換效率較高。
雖然本發明已以數個較佳實施例揭露如上,然其並非用以限定本發明,任何熟習此技藝者,在不脫離本發明之精神和範圍內,當可作任意之更動與潤飾,因此本發明之保護範圍當視後附之申請專利範圍所界定者為準。
10‧‧‧有機太陽能電池
11‧‧‧陽極
12‧‧‧電洞傳輸層
13‧‧‧主動層
14‧‧‧陰極
第1圖係本發明一實施例中,有機太陽能電池的裝置圖。
10‧‧‧有機太陽能電池
11‧‧‧陽極
12‧‧‧電洞傳輸層
13‧‧‧主動層
14‧‧‧陰極
Claims (7)
- 一種p型有機半導體材料,其結構如下:
- 如申請專利範圍第1項所述之p型有機半導體材料,其中Con之結構如下:
- 如申請專利範圍第1項所述之p型有機半導體材料,其中EW係α-氰基丙烯酸烷基酯、乙烯丙二氰、鹵素、或亞硝酸基(-NO2 )。
- 如申請專利範圍第3項所述之p型有機半導體材料,其中α-氰基丙烯酸烷基酯之結構如下:
- 如申請專利範圍第1項所述之p型有機半導體材 料,其結構如下:
- 一種光電元件,包括一主動層,且該主動層包括申請專利範圍第1項所述之p型有機半導體材料。
- 如申請專利範圍第6項所述之光電元件,包括有機太陽能電池、有機發光二極體、或有機薄膜電晶體。
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US8907108B2 (en) | 2014-12-09 |
US20140121386A1 (en) | 2014-05-01 |
TW201416356A (zh) | 2014-05-01 |
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