TWI410443B - 聚(炔基噻吩)及由它形成之電子裝置 - Google Patents
聚(炔基噻吩)及由它形成之電子裝置 Download PDFInfo
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- TWI410443B TWI410443B TW096112013A TW96112013A TWI410443B TW I410443 B TWI410443 B TW I410443B TW 096112013 A TW096112013 A TW 096112013A TW 96112013 A TW96112013 A TW 96112013A TW I410443 B TWI410443 B TW I410443B
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- poly
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- dielectric layer
- alkynylthiophene
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- -1 poly(methacrylate) Polymers 0.000 claims description 101
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- 239000006096 absorbing agent Substances 0.000 claims description 10
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims description 7
- 229910052737 gold Inorganic materials 0.000 claims description 7
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- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 6
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- 229920000620 organic polymer Polymers 0.000 claims description 5
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- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 4
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- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052804 chromium Inorganic materials 0.000 claims description 3
- 239000011651 chromium Substances 0.000 claims description 3
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- BDVZHDCXCXJPSO-UHFFFAOYSA-N indium(3+) oxygen(2-) titanium(4+) Chemical compound [O-2].[Ti+4].[In+3] BDVZHDCXCXJPSO-UHFFFAOYSA-N 0.000 claims description 2
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- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 3
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- 125000003118 aryl group Chemical group 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
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- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 235000019439 ethyl acetate Nutrition 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 3
- 229910052732 germanium Inorganic materials 0.000 description 3
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000002960 margaryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
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- 150000003577 thiophenes Chemical class 0.000 description 3
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- UEHHXMPCTKFUKR-UHFFFAOYSA-N 2,5-dibromo-3-(4-pentylphenyl)thiophene Chemical compound C1=CC(CCCCC)=CC=C1C1=C(Br)SC(Br)=C1 UEHHXMPCTKFUKR-UHFFFAOYSA-N 0.000 description 2
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- 125000001204 arachidyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
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- 239000004020 conductor Substances 0.000 description 1
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 1
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- YBMRDBCBODYGJE-UHFFFAOYSA-N germanium oxide Inorganic materials O=[Ge]=O YBMRDBCBODYGJE-UHFFFAOYSA-N 0.000 description 1
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- 239000010439 graphite Substances 0.000 description 1
- 229910000449 hafnium oxide Inorganic materials 0.000 description 1
- WIHZLLGSGQNAGK-UHFFFAOYSA-N hafnium(4+);oxygen(2-) Chemical compound [O-2].[O-2].[Hf+4] WIHZLLGSGQNAGK-UHFFFAOYSA-N 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
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- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
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- 239000000203 mixture Substances 0.000 description 1
- QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 description 1
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- BPUBBGLMJRNUCC-UHFFFAOYSA-N oxygen(2-);tantalum(5+) Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[Ta+5].[Ta+5] BPUBBGLMJRNUCC-UHFFFAOYSA-N 0.000 description 1
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- NJCBUSHGCBERSK-UHFFFAOYSA-N perfluoropentane Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F NJCBUSHGCBERSK-UHFFFAOYSA-N 0.000 description 1
- 125000005008 perfluoropentyl group Chemical group FC(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
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- 239000001294 propane Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
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- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
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- 238000004544 sputter deposition Methods 0.000 description 1
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- VEALVRVVWBQVSL-UHFFFAOYSA-N strontium titanate Chemical compound [Sr+2].[O-][Ti]([O-])=O VEALVRVVWBQVSL-UHFFFAOYSA-N 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 229920000576 tactic polymer Polymers 0.000 description 1
- MZLGASXMSKOWSE-UHFFFAOYSA-N tantalum nitride Chemical compound [Ta]#N MZLGASXMSKOWSE-UHFFFAOYSA-N 0.000 description 1
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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
- H10K85/10—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
- 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
-
- 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
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Thin Film Transistor (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Electrodes Of Semiconductors (AREA)
Description
此電子裝置及其特定組件係由National Institute of Standards and Technology(NIST)獎勵之美國政府合作協定第70NANBOH3033號資助。美國政府具有關於以下描述之裝置及特定半導體組件的特定權利。
本揭示大致關於聚(3-炔基噻吩)、經取代聚(3-炔基噻吩)、及其用途。更特別地,具體實施例之揭示係關於一種選擇作為溶液可處理且實質上安定之有機電子裝置(如薄膜電晶體)中通道半導體的聚(經炔基取代噻吩)。
現在希望有以溶劑溶解度優良之聚(3-炔基噻吩)(其可為溶液可處理性)製造之有機裝置,如薄膜電晶體(TFT);及此裝置呈現機械耐久性與結構撓性,其為在塑膠基板上製造撓性TFT所需之特性。撓性TFT可設計具結構撓性與機械耐久性特性之電子裝置。將塑膠基板與聚(3-炔基噻吩)成分一起使用可將傳統硬矽TFT轉變成機械上較耐久且結構上撓性之TFT設計。其對如大面積影像感應器、電子文件及其他顯示媒體之大面積裝置有特定之價值。對低階微電子之積體電路邏輯元件(如智慧卡、無線頻率識別(RFID)標籤、及記憶/儲存裝置)選擇聚(3-炔基噻吩)TFT可增強其機械耐久性,因此其使用壽命延長。
據信許多種半導體材料在暴露於空氣時不安定,因為其被周圍氧氧化地摻雜而造成導電度增加。結果為由這些材料製造之裝置的關電流大,因此開/關電流比例小。因而對許多種這些材料在材料處理及裝置製造期間通常特別嚴密地防備以排除環境氧,以避免或使氧化性摻雜最小。這些防備手段增加製造成本,因此抵消尋求特定半導體TFT作為對非晶矽技術之經濟性替代方案,特別是用於大面積裝置。在本揭示之具體實施例中避免或使這些及其他缺點最小化。
此外真空沉積亦可能涉及對大面積格式達成一致薄膜品質之困難。聚合物TFT,如藉溶液法由立體規則性成分(例如立體規則性聚(3-烷基噻吩-2,5-二基))製造者,雖然提供某種流動性,其因在空氣中氧化摻雜之傾向而受害。據信由這些材料製造之TFT在周圍條件通常關電流大,開關電流比例非常小,及其性能特性快速地降低。因此對於特性優良之低成本TFT設計,安定且為溶液可處理性,其中其性能不受周圍氧負面地影響之半導體材料有價值,例如以在此描述之聚(3-炔基噻吩)形成之TFT。
本揭示之一個特點為提供一種半導體聚(3-炔基噻吩),其可用於微電子裝置應用,如TFT裝置。
本揭示之另一個特點為提供一種聚(3-炔基噻吩),其帶隙為約1 eV至約3 eV,如由其薄膜之吸收光譜所測定,而且此聚(3-炔基噻吩)適合作為TFT半導體通道層材料。
本揭示之又一個特點為提供一種聚(3-炔基噻吩),其可作為微電子成分,而且此聚(3-炔基噻吩)在常用有機溶劑(如二氯甲烷、四氫呋喃、甲苯、二甲苯、1,3,5-三甲苯、氯苯等)中呈現例如至少約0.1至約95重量%之溶解度,因此這些成分可藉溶液法(如旋塗、網版印刷、壓印、浸塗、溶液流延、噴墨印刷等)經濟地製造。
亦在本揭示之又一個特點中提供一種新穎聚(炔基噻吩)及其裝置,而且此裝置對氧之負面影響呈現增強之抗性,即據信這些裝置呈現相當高之開/關電流比例,而且其性能實質上不似以立體規則性聚(3-烷基噻吩-2,5-二基)或并苯製造之類似裝置快速地降低。
具體實施例中揭示聚(3-炔基噻吩)及其電子裝置。具體實施例中之炔基(如乙炔基)指例如聚(3-炔基噻吩)中之經取代炔基。具體實施例中之聚(3-炔基噻吩)指例如一種包括重複單元(其為具至少一對選擇性取代炔基(如乙炔基)之噻吩)之聚合物。
更特別地,本揭示關於由式(I)描述或包括之聚(炔基噻吩)
其中R為適當之烴,如烷基、芳基等,及n表示重複單元之數量,例如n為約2至約5,000,更特別是約10至約1,000,或約20至約100之數目。
在具體實施例中,重複單元可視為聚合物之重要循環單元。聚合物中重複單元之連接可相同,如立體規則性聚合物之情況,或者其可不相似,如立體隨機性聚合物之情況,而且主要關於方向方面。在聚合物中有重複單元A及重複單元B時,將重複單元A視為另一個重複單元B之相同型式或不同型式係與方向方面或定義無關。例如將立體隨機性聚(3-炔基噻吩)視為具有僅一型重複單元。
在具體實施例中,指定種類之聚(3-炔基噻吩)係由下式表示。
在具體實施例中揭示依照例如以下反應圖(略圖1)製備聚(3-炔基噻吩)之方法。
更特別地,經由在室溫,約23℃至約26℃,及至多約50℃,於N,N-二甲基甲醯胺中以約2莫耳當量之N-溴琥珀醯亞胺(NBS)將3-碘噻吩(得自Aldrich)溴化而製備2,5-二溴-3-碘噻吩。然後藉由在室溫於三乙胺(Et3
N)中,在觸媒量之二氯貳(三苯膦)鈀(II)(Pd(PPh3
)Cl2
)與碘化銅(I)(CuI)存在下,反應2,5-二溴-3-碘噻吩與對應之乙炔基化合物、小於5%或0至5%之癸炔化合物、或1-乙炔基-4-丁基苯而製備2,5-二溴-3-乙炔基噻吩,如2,5-二溴-3-癸炔基噻吩或2,5-二溴-3-(4-戊基苯基)噻吩。繼而藉由在回流四氫呋喃(THF)中,在[1,3-貳(二苯膦)丙烷]二氯鎳(II)(Ni(dppp)Cl2
)存在下加入約1莫耳當量之格任亞試劑,如氯化環己鎂(C6
H11
MgCl),而產生2,5-二溴-3-乙炔基噻吩,如2,5-二溴-3-癸炔基噻吩或2,5-二溴-3-(4-戊基苯基)噻吩。
R取代基之實例包括具例如約1至約30個,包括約4至約18個碳原子(包括全部在此範圍內之數目,例如4、5、6、7、8、9、10、11、12、13、14、15、16、17、與18),而且進一步包括約6至約16個碳原子之烷基,如乙基、丙基、丁基、戊基、己基、庚基、辛基、壬基、癸基、十一碳基、十二碳基、十三碳基、十四碳基、十五碳基、十六碳基、十七碳基、十八碳基、十九碳基、等二十碳基;具約6至約54個碳原子,約6至約36個碳原子,約6至約24個碳原子之芳基,噻吩基、苯基、甲基苯基(甲苯基)、乙基苯基、丙基苯基、丁基苯基、戊基苯基、己基苯基、庚基苯基、辛基苯基、壬基苯基、癸基苯基、十一碳基苯基、十二碳基苯基、十三碳基苯基、十四碳基苯基、十五碳基苯基、十六碳基苯基、十七碳基苯基、十八碳基苯基等,據信包括未特別地敘述之其他適當烴基。
指定之含雜原子基為已知的且包括例如多醚、三烷基矽烷基、雜芳基等;而且更特別是噻吩基、呋喃基與吡啶二芳基。雜成分可選自許多已知原子,如硫、氧、氮、矽、硒等。
指定之描述性聚(3-炔基噻吩)實例為
其中n表示聚合物中重複單元之數量;及其中n為約20至約100。
具體實施例中之聚(3-炔基噻吩)溶於或實質上溶於常用塗覆溶劑中,例如在具體實施例中其在如二氯甲烷、1,2-二氯乙烷、四氫呋喃、甲苯、二甲苯、1,3,5-三甲苯、氯苯、二氯苯等之溶劑中呈現至少約0.1,而且更特別是約0.5至約95重量%之溶解度。此外本揭示之聚(3-炔基噻吩)或經取代噻吩在製成TFT裝置之半導體通道層時,據信可提供安定之導電性,例如約10-9
S/公分至約10-4
S/公分,而且更特別是約10-8
S/公分至約10-5
S/公分,如由習知四探針導電度測量測定。
據信在此描述之聚(3-炔基噻吩)在由溶液製成例如厚約10奈米至約500奈米或約100至約300奈米之薄膜時,在周圍條件可較由如五并苯之并苯或特定聚(烷基噻吩)製造之類似裝置安定。在未保護時,據信上述聚(3-炔基噻吩)材料及其裝置在暴露於周圍氧後可通常安定數週,而非聚(3-烷基噻吩-2,5-二基)情況之數日或數小時,因此本揭示具體實施例中由聚(3-炔基噻吩)製造之裝置可提供較高之開/關電流比例,而且在材料製備、裝置製造及評估期間未嚴密防備以排除周圍氧時,其性能特性實質上不似五并苯或聚(3-烷基噻吩-2,5-二基)快速地改變。在具體實施例中揭示之聚(3-炔基噻吩)對抗氧化性摻雜之安定性通常不必在惰性大氣中處理,特別是對低成本裝置製造,因此其方法較簡單且較節省成本,而且其製造可應用於大型製法。
本揭示之態樣關於一種電子裝置,其包括式(I)之半導體材料其中R為適當之烴或含雜原子基;及n表示重複單元之數量;一種薄膜電晶體裝置,其包括基板、閘極、閘介電層、源極、與吸極,而且接觸源/吸極與閘介電層為式(I)之半導體層其中半導體材料選自式(1)至(8)
其中R,為烷基、芳基等之烴,而且更特別是甲基、乙基、丙基、丁基、戊基、己基、庚基、辛基、壬基、癸基、十一碳基、十二碳基、十三碳基、十四碳基、十五碳基、十六碳基、十七碳基、十八碳基、十九碳基、二十碳基、羥基甲基、羥基乙基、羥基丙基、羥基丁基、羥基戊基、羥基己基、羥基庚基、羥基辛基、羥基壬基、羥基癸基、羥基十一碳基、羥基十二碳基、甲氧基乙基、甲氧基丙基、甲氧基丁基、甲氧基戊基、甲氧基辛基、三氟甲基、全氟乙基、全氟丙基、全氟丁基、全氟戊基、全氟己基、全氟庚基、全氟辛基、全氟壬基、全氟癸基、全氟十一碳基、或全氟十二碳基;及其中n為約2至約200;一種式(I)聚合物一種TFT裝置,其中基板為聚酯、聚碳酸酯或聚醯亞胺之塑膠片;閘極與吸極各獨立地包括金、鎳、鋁、鉑、氧化銦鈦、或導電性聚合物,而且閘介電體為包括氮化矽或氧化矽之介電層;一種TFT裝置,其中基板為玻璃或塑膠片;該閘與吸極各包括金,而且閘介電體包括有機聚合物聚(甲基丙烯酸酯)或聚(乙烯醇);一種裝置,其中藉旋塗、壓印、網板印刷、或噴墨印刷之溶液法形成聚(3-炔基噻吩)層;一種裝置,其中藉旋塗、溶液流延、壓印、網板印刷、或噴墨印刷之溶液法形成閘、源與吸極、閘介電體、及半導體層;一種TFT裝置,其中基板為聚酯、聚碳酸酯或聚醯亞胺之塑膠片,及由有機導電性聚合物摻雜聚苯乙烯磺酸酯之聚(3,4-伸乙二氧基噻吩)、或由銀於聚合物黏合劑之膠體分散液的導電性墨水/漿料化合物製造閘、源與吸極,而且閘介電層為有機聚合物或無機氧化物顆粒-聚合物複合物;及包括如TFT之電子裝置的裝置。第1圖略示地描述一種TFT組態10,其包括基板16,與其接觸為之金屬接點18(閘極),及一層絕緣介電層14,閘極之一部份或全部閘極接觸介電層14,在此層14上沉積兩個金屬接點20與22(源與吸極)。在其上方且於金屬接點20與22間為半導電性聚合物(如聚(3-癸炔基噻吩))層12。閘極可全部包括於基板、介電層等。
第2圖略示地描述另一種TFT組態30,其包括基板36、閘極38、源極40、與吸極42、絕緣介電層34、及聚(3-癸炔基噻吩)半導體層32。
第3圖略示地描述又一種TFT組態50,其包括重度n摻雜矽晶圓56(可作為閘極)、熱成長氧化矽介電層54、聚(3-癸炔基噻吩)半導體層52、及源極60與吸極62;及閘極接點64。
第4圖略示地描述一種TFT組態70,其包括基板76、閘極78、源極80、吸極82、聚(3-癸炔基噻吩)半導體層72、及絕緣介電層74。
又參考例如已知之TFT裝置可預見其他未揭示之裝置,特別是TFT裝置。
在本發明之某些具體實施例中可將選用保護層併入第1、2、3、及4圖之各電晶體組態上方。對於第4圖之TFT組態,絕緣介電層74亦可作為保護層。
在具體實施例中且進一步參考本揭示及圖式,基板層通常視意圖應用可為包括各種適當矽形式之矽材料、玻璃板、塑膠膜或片等。對於結構上撓性裝置可選擇塑膠基板,例如聚酯、聚碳酸酯、聚醯亞胺片等。基板之厚度可為例如約10微米至超過10毫米,特別是對撓性塑膠基板,指定厚度為約50至約100微米,及對硬基板(如玻璃或矽)為約1至約10毫米。
可分離閘極及源與吸極且接觸半導體層之絕緣介電層通常可為無機材料膜、有機聚合物薄膜、或有機-無機複合物薄膜。介電層之厚度為例如約10奈米至約1微米,更指定厚度為約100奈米至約500奈米。適合作為介電層之無機材料的描述性實例包括氧化矽、氮化矽、氧化鋁、鈦酸鋇、鋯酸鈦酸鋇等;介電層用有機聚合物之描述性實例包括聚酯、聚碳酸酯、聚(乙烯酚)、聚醯亞胺、聚苯乙烯、聚(甲基丙烯酸酯)、聚(丙烯酸酯)、環氧樹脂等;及無機-有機複合物材料之描述性實例包括分散於聚合物(如聚酯、聚醯亞胺、環氧樹脂等)中之奈米化金屬氧化物顆粒。絕緣介電層視所使用介電材料之介電常數通常厚約50奈米至約500奈米。更特別地,介電材料具有例如至少約3之介電常數,如此約300奈米之適當介電體厚度可提供所需之電容,例如約10-9
至約10-7
F/平方公分。
例如位於介電層與源/吸極間且接觸為包括具有在此描述之聚(3-炔基噻吩)的活性半導體層,而且其中此層之厚度通常為例如約10奈米至約1微米,或約40至約100奈米。此層通常可藉由溶液處理本揭示之聚(3-炔基噻吩)而製造。
閘極可為薄金屬膜、導電聚合物薄膜、由導電墨水或漿料形成之導電薄膜、或基板本身(例如重度摻雜矽)。閘極材料之實例包括但不限於鋁、金、鉻、氧化銦錫,導電聚合物,如聚苯乙烯磺酸酯之聚(3,4-伸乙二氧基噻吩)(PSS/PEDOT)),由碳黑/石墨或膠體銀分散液含於聚合物黏合劑組成之導電墨水/漿料,如得自Acheson Colloids Company之Electrodag,及得自Noelle Industries之填銀導電型熱塑性墨水等。閘極可藉金屬或導電性金屬氧化物之真空蒸發、濺射製備,藉旋塗、流延或印刷由導電聚合物溶液或導電墨水或分散液塗覆。閘極層之厚度為例如約10奈米至約10微米,及指定厚度對金屬膜為例如約10至約200奈米,及對聚合物導體為約1至約10微米。
源與吸極層可由對半導體層提供低電阻歐姆接點之材料製造。適合作為源與吸極之典型材料包括如閘極材料者,如金、鎳、鋁、鉑、導電聚合物、及導電墨水。此層之典型厚度為例如約40奈米至約1微米,更指定厚度為約100至約400奈米。TFT裝置含寬W及長L之半導體通道。半導體通道寬度可為例如約10微米至約5毫米,指定通道寬度為約100微米至約1毫米。半導體通道長度可為例如約1微米至約1毫米,更指定通道長度為約5微米至約100微米。
源極接地且對吸極施加通常為例如約0伏特至約-80伏特之偏移電壓,以在對閘極施加通常為例如約+10伏特至約-80伏特之電壓時,收集跨越半導體通道運輸之電荷載子。
對於本揭示TFT裝置之各種組件,在具體實施例中亦可選擇在此未列出之其他已知材料。
雖然不希望受理論限制,據信炔基(如乙炔基)功能主要為使暴露於氧之不安定性最小或避免,因而增加聚(3-炔基噻吩)在周圍條件下於溶液中之氧化安定性,而且R取代基(如烷基)可使這些聚合物溶於常用溶劑(如二氯乙烷、四氫呋喃、甲苯、氯苯、二氯苯等)中。
所產生產物之識別可藉數種已知方法完成,包括於CdCl3
中之HNMR。
1)2,5-二溴-3-碘噻吩在室溫於氬下將3-碘噻吩(4.20克,20毫莫耳)溶於DMF(50毫升)。將溶於DMF(50毫升)之N-溴琥珀醯亞胺(NBS)(7.83克,40毫莫耳)攪拌加入以上溶液。然後將所得混合物在室溫攪拌1小時,及將反應溫度提高至50℃且在此溫度保持又3至4小時。在去除DMF溶劑後,將所得液體溶於乙酸乙酯且以水清洗3次。將形成之有機相以無水硫酸鎂(MgSO4
)乾燥,及將溶劑去除。使用管柱層析術以己烷作為溶析液在矽膠上進行進一步純化。如此得到2,5-二溴-3-碘噻吩如無色液體。產率:7克(95%)。
2)2,5-二溴-3-癸炔基噻吩於氬下在0℃對以上製備之2,5-二溴-3-碘噻吩(3.43克,9.3毫莫耳)與1-癸炔(1.45克,10.5毫莫耳)於三乙胺(50毫升)之溶液加入二氯貳(三苯膦)鈀(II)(0.28克,0.4毫莫耳)與碘化銅(I)(38毫克,0.2毫莫耳)。於氬下將反應混合物在0℃攪拌6小時及在室溫攪拌20小時。在溶劑蒸發後,將產物藉管柱層析術使用己烷作為溶析液在矽膠上純化。如此得到2,5-二溴-3-癸炔基噻吩如無色液體。產率:3.32克(94%)。
1
H NMR(於CDCl3
中):6.88(s,1H),2.41(t,J=7.0 Hz,2H),1.60(m,2H),1.45(m,2H),1.29(br,10H),0.88(t,J=6.4 Hz,3H).
3)聚(3-癸炔基噻吩)(1a)將乾燥100毫升三頸燒瓶裝載以上製備之2,5-二溴-3-癸炔基噻吩(1.89克,5毫莫耳)及無水THF(50毫升)。然後將溶於二***之2M氯化環己鎂(2.5毫升,5毫莫耳)經針筒加入燒瓶。將反應混合物在室溫攪拌30分鐘,繼而加入Ni(dppp)Cl2
(41毫克,0.075毫莫耳)。然後將反應混合物回流12小時。然後將反應混合物冷卻至室溫,沉澱於甲醇(200毫升)中,及過濾。將所得聚合物藉Soxhlet萃取依序以甲醇(48小時)、丙酮(24小時)、及己烷(24小時)純化。最後將殘渣固體以氯仿溶解。在去除溶劑後,將暗紫色固體真空乾燥而產生聚(3-癸炔基噻吩)(1a)。產率:0.50克(46%)。
1
H NMR(於CDCl3
中):7.09-7.33(br),2.56,1.73,1.51,1.29,0.87。
GPC(以聚苯乙烯作為標準品):Mn=10,300;Mw
/Mn
=2.18。
選擇例如第3圖略示地描述之頂部接觸薄膜電晶體組態。此裝置包括具厚約110奈米之熱成長氧化矽層於其上之n摻雜矽晶圓。將此晶圓作為閘極同時將氧化矽層作為閘介電體,而且具有約30 nF/cm2
(奈法拉第/平方公分)之電容,如電容計所測量。首先以異丙醇、氬電漿清潔矽層,及風乾。然後在60℃將清潔基板浸於辛基三氯矽烷(OTS8)於甲苯之0.1 M溶液經20分鐘。繼而將晶圓以甲苯、異丙醇清潔及風乾。使用以0.3重量%之濃度溶於二氯苯之聚(3-癸炔基噻吩)(1a)沉積半導體層。將溶液首先經1微米針筒過濾器過濾,然後在室溫以1,000 rpm旋塗在OTS8矽基板上經120秒而生成厚約20至約50奈米之薄膜。在80℃真空烤箱中乾燥5至10小時後,藉真空沉積經各種通道長度及寬度之遮罩將約50奈米之金源與吸極沉積在半導體層上,如此製造一系列各種尺寸之電晶體。
所形成場效電晶體性能之評估係使用Keithley 4200 SCS半導體特徵化系統在黑盒中於周圍條件完成。依照方程式(1)由飽和體系(閘電壓VG
<源-吸電壓VSD
)之資料計算載子移動率μ ISD
=Ci
μ(W/2L)(VG
-VT
)2
(1)其中ISD
為飽和體系之吸電流,W與L各為半導體通道寬度與長度,Ci
為每單位面積之閘介電層的電容,及VG
與VT
各為閘電壓及臨界電壓。裝置之VT
係由飽和體系之ISD
的平方根與將測量資料外插至ISD
=0之裝置VG
間之關係決定。
場效電晶體之另一個性質為其開/關電流比例。其為累積體系之飽和源-吸電流對耗竭體系之源-吸電流的比例。
裝置之轉移及輸出特性顯示聚(3-癸炔基噻吩)(1a)為p型半導體。評估尺寸為W=5,000微米及L=90微米之約5種電晶體得到約1至約3,而且更特別是0.001至約0.008平方公分/伏特秒(每秒伏特)之移動率。
移動率:0.008 cm2
V-1
s-1
開/關比例:106
。
1)2,5-二溴-3-(4-戊基苯基)乙炔基噻吩在0℃於氬下對2,5-二溴-3-碘噻吩(3.52克,9.57毫莫耳)與1-乙炔基-4-戊基苯(1.65克,9.57毫莫耳)於三乙胺(50毫升)之溶液加入二氯貳(三苯膦)鈀(II)(0.28克,0.4毫莫耳)與碘化銅(I)(38毫克,0.2毫莫耳)。於氬下將所得反應混合物在0℃攪拌6小時及在室溫攪拌20小時。在溶劑蒸發後,將所得產物藉管柱層析術使用己烷作為溶析液在矽膠上純化。其得到2,5-二溴-3-(4-戊基苯基)乙炔基噻吩如無色液體。產率:3克(73%)。
1
H NMR(於CDCl3
中):7.44(d,J=8.3 Hz,2H),7.16(d,J=8.3 Hz,2H),7.00(s,1H),2.61(t,J=7.7 Hz,2H),1.61(m,2H),1.32(m,4H),0.89(t,J=6.8 Hz,3H)。
2)聚(3-(4-戊基苯基)乙炔基噻吩)(2a)將乾燥100毫升三頸燒瓶裝載以上製備之2,5-二溴-3-(4-戊基苯基)乙炔基噻吩(2.06克,5毫莫耳)及無水THF(50毫升)。然後將溶於二***之2M氯化環己鎂(2.5毫升,5毫莫耳)經針筒加入燒瓶。將所得反應混合物在室溫攪拌30分鐘,繼而加入Ni(dppp)Cl2
(41毫克,0.075毫莫耳)。然後將反應混合物回流12小時。然後將反應混合物冷卻至室溫,沉澱於甲醇(200毫升)中,及過濾。將產生之聚合物藉Soxhlet萃取依序以甲醇(48小時)、丙酮(24小時)、及己烷(24小時)純化。最後將殘渣固體以氯仿溶解。在去除溶劑後,將暗紫色固體真空乾燥而產生聚(3-(4-戊基苯基)乙炔基噻吩)(2a)。產率=0.20克(16%)。
1
H NMR(於CDCl3
中):7.41,7.02,2.51,1.56,1.32,0.90。
GPC(以聚苯乙烯作為標準品):Mn=3,600;Mw
/Mn
=1.41。
重複實例I之裝置製造而類似地製造及評估使用聚(3-(4-戊基苯基)乙炔基噻吩)(2a)作為半導體層之OTFT裝置。裝置之轉移及輸出特性顯示聚(3-(4-戊基苯基)乙炔基噻吩)(2a)為p型半導體。評估尺寸為W=5,000微米及L=90微米之五(5)種電晶體得到類似實例I之裝置的所需特性。
移動率:0.001 cm2
V-1
s-1
開/關比例:106
。
10...TFT組態
12...半導體聚合物層
14...絕緣介電層
16...基板
18...閘極
20...源極
22...吸極
30...TFT組態
32...聚(3-癸炔基噻吩)半導體層
34...絕緣介電層
36...基板
38...閘極
40...源極
42...吸極
50...TFT組態
52...聚(3-癸炔基噻吩)半導體層
54...熱成長氧化矽介電層
56...重度n摻雜矽晶圓
60...源極
62...吸極
64...閘極
70...TFT組態
72...聚(3-癸炔基噻吩)半導體層
74...絕緣介電層
76...基板
78...閘極
80...源極
82...吸極
第1至4圖描述本揭示之各種代表性具體實施例,其中選擇聚(3-烷基噻吩),如聚(3-癸炔基噻吩),作為薄膜電晶體(TFT)組態中之通道或半導體材料。
10...TFT組態
12...半導體聚合物層
14...絕緣介電層
16...基板
18...閘極
20...源極
22...吸極
Claims (7)
- 一種電子裝置,其包括式(2a)或式(2b)之同元聚合物:
- 如申請專利範圍第1項之裝置,其中n表示10至500之數目。
- 如申請專利範圍第1項之裝置,其中n表示20至100之數目。
- 如申請專利範圍第1項之裝置,其中該裝置為薄膜電晶體。
- 一種薄膜電晶體裝置,其包括基板、閘極、閘介電層、 源極、與吸極,而且接觸源/吸極與閘介電層為包括式(2a)或式(2b)之同元聚合物的半導體層:
- 如申請專利範圍第5項之裝置,其中該基板係聚酯、聚碳酸酯或聚醯亞胺之塑膠片,該閘極、源極與吸極各自獨立地包括銀、金、鎳、鋁、鉻、鉑、氧化銦鈦、或導電性聚合物,以及該閘介電層係包括無機氮化物類、無機氧化物類、或有機聚合物類。
- 如申請專利範圍第5項之裝置,其中該基板係玻璃、或塑膠片,該閘極、源極與吸極各自獨立地包括銀、金、 鎳、或鉻,以及該閘介電層係包括聚(甲基丙烯酸酯)、聚矽氧烷、或聚(乙烯醇),以及其中該半導體層藉由旋塗、壓印、網版印刷、或噴墨印刷所沉積。
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US11/398,931 US8049205B2 (en) | 2006-04-06 | 2006-04-06 | Poly(alkynylthiophene)s and electronic devices generated therefrom |
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EP (1) | EP1843409B1 (zh) |
JP (1) | JP5367953B2 (zh) |
KR (1) | KR101376080B1 (zh) |
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CN101952345A (zh) * | 2008-02-13 | 2011-01-19 | 国立大学法人大阪大学 | 聚合物、使用它的有机薄膜以及有机薄膜元件 |
FR2933238B1 (fr) * | 2008-06-27 | 2011-01-14 | Commissariat Energie Atomique | Nouveaux materiaux macromoleculaires semi-conducteurs organiques mesomorphes |
GB2467293B (en) * | 2008-11-28 | 2013-07-10 | Cambridge Display Tech Ltd | Organic semiconductors |
JP2010283072A (ja) * | 2009-06-03 | 2010-12-16 | Sumitomo Chemical Co Ltd | 有機薄膜トランジスタ、面状光源及び表示装置 |
US8304512B2 (en) * | 2010-01-19 | 2012-11-06 | Xerox Corporation | Benzodithiophene based materials compositions |
US8742403B2 (en) | 2011-03-08 | 2014-06-03 | Samsung Electronics Co., Ltd. | Xanthene based semiconductor compositions |
JP2013119589A (ja) * | 2011-12-07 | 2013-06-17 | Sumitomo Chemical Co Ltd | 高分子化合物及び電子素子 |
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CN101050267A (zh) | 2007-10-10 |
JP5367953B2 (ja) | 2013-12-11 |
CA2583020C (en) | 2013-03-26 |
TW200745203A (en) | 2007-12-16 |
KR101376080B1 (ko) | 2014-03-19 |
US8049205B2 (en) | 2011-11-01 |
EP1843409B1 (en) | 2015-05-13 |
US20070235719A1 (en) | 2007-10-11 |
CA2583020A1 (en) | 2007-10-06 |
EP1843409A3 (en) | 2012-09-05 |
KR20070100174A (ko) | 2007-10-10 |
JP2007281475A (ja) | 2007-10-25 |
EP1843409A2 (en) | 2007-10-10 |
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